Downtown Pittsfield Western Massachusetts The Berkshires

Downtown Pittsfield Summer Music Series - Free!
2024-09-06 17:00 - 20:00 (America/New_York) | Persip Park, 175 North Street, Pittsfield, MA, 01201, United States
The Downtown Pittsfield Cultural Association, with partners the City of Pittsfield, MassDevelopment’s Transformative Development Initiative (TDI), and Downtown Pittsfield, Inc. (DPI), are presenting a free Downtown Pittsfield Summer Music Series on Fridays, Saturdays, and Sundays (and select Thursdays) through early September.

Fridays will feature a variety of local musicians and performers live at Persip Park, 175 North Street, from 5 to 8 pm. Saturdays will feature live Jazz in collaboration with Berkshires Jazz from 2 to 5 pm at Persip Park; and Sundays will feature Latin Dance Instruction in Dunham Mall, 100 North Street, from 5 to 7 pm.

Friday, July 26, 5 to 8 pm: Moe Greene in Persip Park
Moe Greene is a singer songwriter from the Upper Hudson Valley who performs original material along with tasteful interpretation of blues, Americana, and rock covers.

Friday, August 2, 5 to 8 pm: First Fridays at Five in Persip Park with the Wandering Dance Society: Swing Dance with Rushelle Bowie and Step & Dance with Youth Alive
Persip Park, 175 North Street, will feature interactive performances presented by the Wandering Dance Society as part of the August 2 First Fridays at Five and the free Downtown Pittsfield Summer Music Series. Dancers of all ages and abilities are encouraged to participate throughout the evening.
East Coast Swing Lesson with Rushelle Bowie: 5 to 6:15 pm
Step, Dance, and Drumline with Youth Alive: 6:30 to 8 pm
Featuring guests: R.O.P.E. member Abby Percy and James Ryan
Rushelle Bowie will be teaching a basic lesson in East Coast Swing from 5 to 6:15 pm. East Coast Swing is a fun, upbeat dance guaranteed to bring a smile to your face. The lesson will be followed by a short demo and open dancing.
Rushelle has been sharing her passion for dancing for over 15 years, offering group and private lessons in East Coast Swing, Rumba, Cha-Cha, Foxtrot, and Waltz. She also provides personalized dance instruction for weddings, parties, and other special events. Her dance studio is located in Dalton, MA, where it is always ‘Time to Dance’.
There will be a performance of Step, Dance, and Drumline with Youth Alive from 6:30 to 8 pm. Youth Alive, Inc. (YA) is a multi-cultural, community-based organization founded in 1995 by two teenagers, Akilah Edgerton and Erica Young, in Pittsfield, MA. The purpose of YA is to teach life skills to youth aged six to eighteen using performance arts as the teaching vehicle. YA performs at major cultural institutions such as Jacob’s Pillow, MASS MoCA, and Williams College, and YA has performed and been recognized at the Massachusetts State House for their impact. YA has impacted hundreds of young people’s lives in the Berkshires, who are now contributing adult citizens – some in key leadership positions locally and beyond. The New Era of YA steppers, dancers, and drummers are being coached by YA phenomenal alumnus: Step Coach Chyenne VanBramer, Dance Coach Serina Saunders, and Musical Director, Percussionist and Spoken Word Artist Jerome Edgerton Jr.
In the case of inclement weather, the Wandering Dance Society performances will be at the Lichtenstein Center for the Arts, 28 Renne Avenue.

Friday, August 9, 5 to 8 pm: Dave Brown in Persip Park
Pittsfield native Dave Brown has been performing for decades, both backing up and leading bands of all different types in the Berkshires and beyond. He’ll be performing his solo set at Persip Park consisting of primarily classic rock covers.

Friday, August 16, 5 to 8 pm: The Whinin’ Boys in Persip Park
The Whinin’ Boys, featuring Jeff Gonzales and Mike Mercier, are a finger picking blues based acoustic duo who perform The Music of Hot Tuna along with blues, folk and rock covers from the 60’s and 70’s.

Friday, August 23, 5 to 8 pm: DJ Young Champ in Persip Park
New Jersey born and raised in Pittsfield, Massachusetts, DJ Champ has been lighting up the dance floor since 2008 – doing everything from celebrity events to the smallest of venues. He is the founder of Young Champ Foundation which helps the community with back-to-school supplies and Christmas gifts as well as providing mentoring for our youth. There’s nothing DJ Champ hasn’t touched in Berkshire County. One thing you can be sure of is that when he is around the vibe with be great!

Friday, August 30, 5 to 8 pm: Christine Bilé with full band in Persip Park
Christine Bilé is a singer-songwriter and multi-instrumentalist from Pittsfield, MA, known for her acoustic pop-folk original music and covers. Influenced by artists like John Mayer, Tracy Chapman, and Beyoncé, Christine’s performances are captivating and emotionally engaging, featuring her wide vocal range and skills on guitar and ukulele. Her music is designed to empower, make you smile, laugh, groove, and maybe even cry. Christine will be playing at the Downtown Pittsfield Summer Music Series on August 30th with a full band including Tony Berkley (Guitar), Zen Reinhardt (Bass), and John Harris (Drums).

Friday, September 6, 5 to 8 pm: Housie Shakers in Persip Park (First Fridays at Five)

While the Housie Shakers are a new band on the Berkshire music scene, its members have deep local roots and have been playing music in the area for decades. All four members grew up in the Berkshires, and after various adventures living around the country and the world, returned here to raise their families. Having played together informally for various short-term projects in recent years, they decided the time was ripe to solidify the lineup and start playing out more.
The Housie Shakers bring a variety of styles to the mix, with wide-ranging covers and original music spanning rock, blues, pop, bluegrass, reggae, Americana, and improvisational groove. They don’t take themselves too seriously and have no ambitions to go on the road (as if the 12 kids they have collectively would make that possible anyway)… they’re just out to play local gigs and give people a chance to hang out, let loose, dance, and have a good time! The band’s name is a nod to their home community and the people and places that have shaped their musical journeys.
The Housie Shakers are Simeon Bittman (drums & vocals), Noah Cook-Dubin (guitar, cavaquinho & vocals), Jonathan Denmark (guitar & vocals), and Colin Ovitsky (bass).

Follow along with @downtownpittsfield on Facebook for updates including cancellations due to weather.

Housie Shakers at First Fridays at Five!
2024-09-06 17:00 - 20:00 | Persip Park, 175 North Street, Pittsfield, MA, 01201, United States
Persip Park, 175 North Street, will feature a live performance by the Housie Shakers as part of the September 6 First Fridays at Five and the free Downtown Pittsfield Summer Music Series.
While the Housie Shakers are a new band on the Berkshire music scene, its members have deep local roots and have been playing music in the area for decades. All four members grew up in the Berkshires, and after various adventures living around the country and the world, returned here to raise their families. Having played together informally for various short-term projects in recent years, they decided the time was ripe to solidify the lineup and start playing out more.
The Housie Shakers bring a variety of styles to the mix, with wide-ranging covers and original music spanning rock, blues, pop, bluegrass, reggae, Americana, and improvisational groove. They don’t take themselves too seriously and have no ambitions to go on the road (as if the 12 kids they have collectively would make that possible anyway)… they’re just out to play local gigs and give people a chance to hang out, let loose, dance, and have a good time! The band’s name is a nod to their home community and the people and places that have shaped their musical journeys.
The Housie Shakers are Simeon Bittman (drums & vocals), Noah Cook-Dubin (guitar, cavaquinho & vocals), Jonathan Denmark (guitar & vocals), and Colin Ovitsky (bass).
In the case of inclement weather, the Housie Shakers will be at the Lichtenstein Center for the Arts, 28 Renne Avenue.

Downtown Pittsfield Summer Music Series - Free!
2024-09-07 14:00 - 17:00 | Persip Park, 175 North Street, Pittsfield, MA, 01201, United States
The Downtown Pittsfield Cultural Association, with partners the City of Pittsfield, MassDevelopment’s Transformative Development Initiative (TDI), and Downtown Pittsfield, Inc. (DPI), are presenting a free Downtown Pittsfield Summer Music Series on Fridays, Saturdays, and Sundays (and select Thursdays) through early September.

Fridays will feature a variety of local musicians and performers live at Persip Park, 175 North Street, from 5 to 8 pm. Saturdays will feature live Jazz in collaboration with Berkshires Jazz from 2 to 5 pm at Persip Park; and Sundays will feature Latin Dance Instruction in Dunham Mall, 100 North Street, from 5 to 7 pm.

CANCELLED DUE TO WEATHER: Saturday, August 3, 2 to 5 pm: Jazz in Persip Park with the Peggy Stern Trio
Peggy Stern Trio: Peggy Stern, Maryann McSweeney, and Conor Meehan

Saturday, August 10, 2 to 5 pm: Jazz in Persip Park with Charlie Tokarz and Paul Arslanian
Charlie Tokarz plays saxophone, flute, and clarinet. He has worked as an accompanist for modern dance at the Institute For Contemporary in Boston, Contact Improvisation in New England, and for The American Tap Dance Foundation in New York directly as a result of being introduced to the group by Paul Arslanian. He has played in the pit band for musicals for local theatre groups, high schools, the Colonial Theatre, and Arena Stage in Washington, DC. He continues to freelance with various jazz groups and teaches primarily at Hotchkiss School.
Paul Arslanian has been playing professionally since 1970, first in the San Francisco Bay Area as a freelance jazz pianist, bandleader, composer and dance accompanist and then, since 1984, in New England where he now resides.
Paul was a Senior Lecturer in Dance at UMass, Amherst from 1999-2018 until retiring, teaching “Music for Dancers” and accompanying classes in ballet, modern and tap dance. From 2010 to the present, Paul has been pianist with the Green Street Trio and coordinator of the Northampton Jazz Workshop, a weekly concert and jam session series. He has been a producer for the Northampton Jazz Festival, in Northampton, MA, since 2015.
Throughout his long career, Paul has had the opportunity to play with, and learn from, many great jazz artists such as Pharoah Sanders, Houston Person, Freddie Hubbard and Gary Smulyan and with many vocalists including Karrin Allyson, Rebecca Parris, and Giacomo Gates.

Saturday, August 17, 2 to 5 pm: Katherine Winston in Persip Park
From the rolling hills of New England, Katherine Winston is a Singer/Songwriter whose music is a blend of country, folk/rock, and pop. Inspired by musical icons like Stevie Nicks, Brandi Carlile, and Dolly Parton, Katherine’s powerhouse vocals and raw emotional power have captivated audiences all over the country and beyond.
Katherine’s deeply relatable songwriting explores the intricate layers of human emotion and experience. Her live shows are a testament to her ability to connect with audiences on a profound level, leaving fans spellbound with each heartfelt lyric and impassioned melody. https://katherinewinston.com

Saturday, August 24, 2 to 5 pm: Jazz in Persip Park with The Lucky 3
The Lucky 3 is a slimmed down version of the quintet ’The Lucky 5’. While a smaller outfit than their mainstay band, the trio has more room to explore the music all the while maintaining their signature swing. Consisting of Jonathan Talbott on violin, Matt Downing on bass, and Kip Beacco on guitar, The Lucky 3 plays everything from old hot jazz and swing to Parisian gypsy jazz and eastern European styles. The trio runs the gamut of the sounds their quintet is known for in the region and beyond.

Saturday, August 31, 2 to 5 pm: Jazz in Persip Park with Luke Franco
Guitarist Luke Franco purveys the rich tradition of jazz guitar by gleaning from the masters, both past and present. Formative years spent with John Abercrombie—his main influence and one of the great guitar innovators—led Franco to develop his own style and compositional voice. While pursuing a Doctorate of Musical Arts at the University of Miami, he was Teachers Assistant in John Hart’s talented and ambitious guitar studio, and performed as a featured soloist with the award winning Concert Jazz Band led by Grammy winner Jon Daversa alongside guest artists including Gonzalo Rubalacaba and Alan Ferber. He was featured as lead guitarist at the world premiere of Michael Tilson Thomas’s “Four Preludes on Playthings of the Wind” along with the New World Symphony in 2016. Presently, Franco has been performing in the Berkshires, Hudson Valley, and NY Capital Region presenting his own music both as a leader and as an in-demand sideman, notably in trio with Tarik Shah and Jimmy Madison. As a counterpoint to his musical career, he and his wife founded Tiny Hearts Farm in Copake, NY in 2011 and manage the 35-acre farm with their two young boys, growing cut flowers and playing music at the foothills of the Berkshire Mountains.

Saturday, September 7, 2 to 5 pm: Jazz in Persip Park with the Peggy Stern Trio
Peggy Stern – piano
Paul Ostermayer – sax
Dave Christopolis – bass
Peggy Stern has composed, played, recorded, and toured in a wide variety of situations: from solos to octets to jazz choruses. Her compositions range from highly original pieces to reharmonized jazz standards. “Everything she writes wants to dance,” says Ken Dais of Jazziz.
Peggy’s background would account for her varied musical tastes. She began playing classical piano at an early age, continuing her studies at the Eastman School of Music, and finishing a master’s degree, still in Classical music, at the New England Conservatory. And then she began to improvise. While living in San Francisco, she played in salsa bands, notably Azteca and Supercombo with Benny Vallarde. She did a stint in an R&B band (called Cat’s Cradle) with singer Linda Tillery and was “instructed” by Paul Jackson (bass) and Mike Clark (drums) of Herbie Hancock’s Headhunter band.
Subsequently, Peggy moved to New York, absorbing the piano stylings of the greats, such as Jimmy Rowles and Tommy Flanagan. Peggy has worked and toured with many wonderful musicians: Lee Konitz, Diane Schuur, David “Fathead” Newman, Jay Clayton, Gary Peacock, Gene Bertoncini, Bud Shank, Red Holloway, Thomas Chapin, Machito, Puck Fair, Bobby Shew, Stanley Turrentine, Gerry Mulligan, Eddie Henderson, and Emily Remler, to name a few.
Peggy has toured throughout Europe, the US, Canada, Australia, and Japan. In addition, Peggy has worked as an educator for the past 20 years, at colleges in the US. She has given workshops throughout Europe (Switzerland, Sweden, Denmark, Italy), and the US. peggystern.com

Follow along with @downtownpittsfield on Facebook for updates including cancellations due to weather.

Hispanic Heritage Month Celebration in Downtown Pittsfield!
2024-09-07 17:00 - 19:00, 2024-09-15 17:00 - 19:00, 2024-09-22 17:00 - 19:00, 2024-09-27 17:00 - 19:00, 2024-10-02 19:00 - 21:00, 2024-10-04 17:00 - 19:00, 2024-10-12 19:00 - 21:00 | MA
Partners including The Funk Box Dance Studio, Dance with Luana, THECOLLAB, Katunemo Art Collective, Hot Plate Brewing Co., Panchos Mexican Restaurant, Latinas413, Tito’s Mexican Bar & Grill, and MassDevelopment’s Transformative Development Initiative (TDI) are thrilled to announce the first-ever Hispanic Heritage Month Celebration in Downtown Pittsfield. This celebration will honor the stories, cultures, and contributions of community members of the Berkshires who have heritage from Spain, Mexico, the Caribbean, and Central and South America.
Events include:
Sunday, September 8, 5 to 7 pm: Dance class and performance in Dunham Mall lead by Andres Ramirez, owner of The Funk Box Dance Studio
Sunday, September 15, 5 to 7 pm: Cumbia music at Hot Plate Brewing Co., 1 School Street, with “Media Noche,” a Berkshire-based Cumbia band
Sunday, September 22, 5 to 7 pm: Salsa and Bachata classes with Luana Dias in Dunham Mall
Friday, September 27, 5 to 7 pm: An art workshop in Spanish led by Katunemo Art Collective and information about Latinas413 programming at THECOLLAB, 163 North Street
Wednesday, October 2, 7 to 9 pm: Storytelling and open mic in Spanish hosted by Melchor Cine at Hot Plate Brewing Co., 1 School Street
Friday, October 4, 5 to 7 pm: Reception for Open Exhibition with Katunemo Art Collective at Downtown Pittsfield, Inc. and Framework, 437 North Street
Saturday, October 12, 7 to 9 pm: Tornado Musical Music Performance at Tito’s Mexican Bar and Grill, 34 Depot Street
Berkshire County’s Latin American and Hispanic immigrant population is growing. This celebration aims to honor, recognize, and support the contributions of the Hispanic population in the district and county by sharing music, dance, and food with the community. It also seeks to foster a sense of belonging and create opportunities for new immigrant business owners and artists.
This celebration is part of MassDevelopment’s TDI for Gateway Cities which is working to revitalize North Street by promoting cultural and economic growth. Special thanks to Downtown Pittsfield, Inc. and the City of Pittsfield for their support in organizing this event.

Jazz in Persip Park with the Peggy Stern Duo
2024-09-15 14:00 - 16:00 | Persip Park, 175 North Street, Pittsfield, MA, 01201, United States
Peggy Stern – piano
Michael Junkins – guitar
Peggy Stern has composed, played, recorded, and toured in a wide variety of situations: from solos to octets to jazz choruses. Her compositions range from highly original pieces to reharmonized jazz standards. “Everything she writes wants to dance,” says Ken Dais of Jazziz.
Peggy’s background would account for her varied musical tastes. She began playing classical piano at an early age, continuing her studies at the Eastman School of Music, and finishing a master’s degree, still in Classical music, at the New England Conservatory. And then she began to improvise. While living in San Francisco, she played in salsa bands, notably Azteca and Supercombo with Benny Vallarde. She did a stint in an R&B band (called Cat’s Cradle) with singer Linda Tillery and was “instructed” by Paul Jackson (bass) and Mike Clark (drums) of Herbie Hancock’s Headhunter band.
Subsequently, Peggy moved to New York, absorbing the piano stylings of the greats, such as Jimmy Rowles and Tommy Flanagan. Peggy has worked and toured with many wonderful musicians: Lee Konitz, Diane Schuur, David “Fathead” Newman, Jay Clayton, Gary Peacock, Gene Bertoncini, Bud Shank, Red Holloway, Thomas Chapin, Machito, Puck Fair, Bobby Shew, Stanley Turrentine, Gerry Mulligan, Eddie Henderson, and Emily Remler, to name a few.
Peggy has toured throughout Europe, the US, Canada, Australia, and Japan. In addition, Peggy has worked as an educator for the past 20 years, at colleges in the US. She has given workshops throughout Europe (Switzerland, Sweden, Denmark, Italy), and the US. peggystern.com

Hispanic Heritage Month Block Party
2024-10-12 19:00 - 21:00 | Tito’s Mexican Bar & Grill, 34 Depot Street, Pittsfield, MA, 01201, United States
Hispanic Heritage Month Block Party: Saturday, October 12, 7 to 9 pm (Alleyway between Tito’s Mexican Bar & Grill and Crawford Square)

Tornado Musical will perform outside from 7 to 9 pm. Tornado Musical is a Latin Music Band made up of members from two different Latin American countries: Mexico and Guatemala. These talented artists came together with one common goal—to share with the world how wonderful Latin rhythms in Spanish are!

There will be beer and wine available outside from 7 to 9 pm and outside dining. There will be a dance after-party with DJ inside from 10 pm to 1:30 am.

More about Tornado Musical:

Band Members:
Citlalli Rodríguez from MEXICO
José García from GUATEMALA
Lorenzo Cruz from GUATEMALA
José Cruz from GUATEMALA
Antonio Chávez from MEXICO
Erik Urizar from GUATEMALA
Xavier Urizar from USA

Tornado Musical was formed in February 2022, near North Plain Road in the town of Great Barrington, MA. This versatile group aims to bring the Mexican and Guatemalan heritage to this country, especially to Berkshire County, and share the beauty of Spanish-language songs. This story began as a dream, and with each performance, it is becoming a reality. Tornado Musical has performed in various parts of Berkshire County, including Pittsfield, Great Barrington, Lee, and other places like Copake Falls, New York. Their vision is to become the best Latin Music Band in the BERKSHIRES… and for this type of music to transcend borders and language barriers.

This celebration is part of MassDevelopment’s TDI for Gateway Cities which is working to revitalize North Street by promoting cultural and economic growth. Special thanks to Downtown Pittsfield, Inc. and the City of Pittsfield for their support in organizing this event.

Best of the ‘70s with Dizzyfish and the Uptown Horns
2025-03-22 19:30 - 21:30 | Colonial Theatre, 111 South Street, Pittsfield, MA, 01201, United States
Get ready for a night of unforgettable music with The Best of the ‘70s! This electrifying celebration features the timeless hits of Neil Young, The Beatles, Elton John, Led Zeppelin, The Rolling Stones, Pink Floyd, and many more. The show is brought to life by the dynamic band DizzyFish, joined by the legendary Uptown Horns, creating an experience that will have you singing and dancing along to every song.
Led by powerhouse vocalist and guitarist Eric Herbst, DizzyFish has wowed audiences alongside icons like ZZ Top and Steve Miller. With world-class backup singers Angela Clemmons, Sharon Jerry-Collins, and Emily Bindiger, whose collective credits include collaborations with Aretha Franklin, Carole King, and Michael Jackson, this group delivers unparalleled performances. Adding to the magic, The Uptown Horns, famed for their work with Bruce Springsteen and James Brown, elevate the music to new heights.
Audiences are raving: “This is the best show I’ve ever seen!” “We sang every song—it was incredible!” “Amazing from start to finish!”
Don’t miss this spectacular trip back to the greatest decade of music!
Click here to purchase tickets!

Berkshire Music School's 85th Year Community Celebration
2025-03-26 18:00 - 20:00 | Barrington Stage Company, Sydelle and Lee Blatt Performing Arts Center, 36 Linden Street, Pittsfield, MA, 01201, United States
Come celebrate Berkshire Music School’s 85th year with a night of music provided by Berkshire Music School students, faculty, and alums!
Click here to purchase tickets!

May 2 First Fridays at Five!
2025-05-02 17:00 - 20:00 | Downtown Pittsfield, Pittsfield, MA, 01201, United States
The City of Pittsfield, Downtown Pittsfield, Inc. (DPI), and the Downtown Pittsfield Cultural Association (DPCA) have announced details for the May 2nd First Fridays at Five sponsored by AccessPlus. The event will feature live music, art, dance, family fun, shopping, food, and entertainment throughout downtown Pittsfield. Attendees are encouraged to bring their own chairs so they can sit and enjoy a variety of food, beverages, and entertainment!

Persip Park, 175 North Street, will feature a live performance by Futon Lasagna from 5 to 8 pm. Enjoy a beer garden from Hot Plate Brewing, Co. and local food vendors within the vicinity.

Futon Lasagna is ska comfort food made with love since 2021. Hailing from Boston, this high-energy, female-fronted LGBTQ+ band blends the melodic vocals of pop punk with the infectious rhythms of punk ska—think Bouncing Souls meets Less Than Jake, but hold the horns. Their catchy, relatable songs are perfect for dancing your feelings out. What started as four friends jamming at parties quickly turned into a beloved act lighting up stages across New England.

In the case of inclement weather, Futon Lasagna will be at Price Memorial A.M.E. Zion Church, 27 East Street.

Dunham Mall, 100 North Street, will feature Dance on Dunham with Latin Dance Lessons from Luana Dias David and Prashad Abeysinghe. Luana and Prashad will host two 30-minute dance lessons at 5:30 pm and 6:30 pm, with open dance space before, between, and after to keep the energy flowing and allow for community interaction. Enjoy a beer garden from Hot Plate Brewing, Co. on Dunham Mall. Dance on Dunham is presented in partnership with Mill Town Foundation.

In the case of inclement weather, Dance on Dunham with Luana and Prashad will be at the Lichtenstein Center for the Arts, 28 Renne Avenue.

Downtown Pittsfield, Inc. and First Fridays Artswalk will feature a different “Art in the Park” artist each month of the First Fridays at Five Season. On May 2 from 5 to 8 pm, Shelsy Rodriguez (Stephx) will be popped up in Palace Park (near 122 North Street), inviting the community to join her in creating an original painting. “Art in the Park” is supported by the Feigenbaum Foundation.

Shelsy Rodriguez is a 22-year-old student from Bogota, Colombia. She came to the United States almost four years ago in search of her own well-being and development as a person. She is an environmental science student at BCC and has a creative baking business with her mother. Shelsy’s first mural can be seen on the Intermodal Center in Pittsfield.

Jim Horsford will also be in Palace Park hosting a free live pottery demonstration from 5 to 8 pm where he will be inviting individuals to help him make pots on the potter’s wheel. Jim spent 30 years as an art teacher at Herberg Middle School from 1978 to 2008. Currently, he teaches pottery on the wheel at the Lichtenstein Center for the Arts where he has been since 2000. His creations will be available for purchase.

In the case of inclement weather, “Art in the Park” with Shelsy Rodriguez and Pottery with Jim Horsford will be inside the Lichtenstein Center for the Arts at 28 Renee Avenue.

The Big Air Bike Jam hosted by Berkshire Bike and Board and Berkshire Mountain Bike Training Series will be in the Palace Park Parking Lot on May 2 from 5 to 8 pm (weather permitting). Enjoy this freestyle bike demo right in downtown Pittsfield!

DJ Bengey will be the featured First Fridays at Five DJ for May and will be stationed on North Street closer to Park Square along with the Makers Market. (In the case of inclement weather, the DJ will be at the Hot Harry’s pavilion.)

Brooklyn-born and East Coast-based, DJ Bengey brings over two decades of experience creating unforgettable musical moments. A veteran of New York City’s vibrant music scene, Bengey is known for his genre-defying mixes that perfectly match any event’s energy.

The Makers’ Market at First Fridays at Five will feature a dozen local vendors selling handmade products such as crafts, clothing and accessories, candles, art, custom gift items, self-care items, and packaged foods and sweets.

The Family Fun Zone at First Fridays at Five will expand onto North Street this year and will feature free, interactive activities from local non-profit organizations including face-painting, arts & crafts, games, and more. Participating organizations include the Albany Berkshire Ballet/Cantarella School of Dance, Barrington Stage Company, BART Charter Public School, Berkshire Athenaeum, Berkshire Coalition for Suicide Prevention, Berkshire County Head Start/CFCE, Berkshire County Kids Place, Berkshire Family YMCA, Berkshire Medical Center, Elizabeth Freeman Center, Pittsfield Little League, Susan B. Anthony Birthplace Museum, The Berkshire Eagle, and Xtreme Wrestling Alliance, Inc.

There will also be a self-guided Animal Scavenger Hunt for families presented by the Berkshire Natural Resources Council (BNRC) beginning at Palace Park, and Balloon Ben will be crafting free balloon creations!

First Fridays Artswalk will showcase artists at venues throughout downtown Pittsfield from 5 to 8 pm including Berkshire Art Center, Clock Tower Artists, Framework by Downtown Pittsfield, Inc., Hotel on North, Lichtenstein Center for the Arts, Living in Recovery, Marie’s North Street Eatery and Gallery, Marketplace Cafe, Ralph Froio Senior Center, Soda Chef, and the Unitarian Universalist Church of Pittsfield. Follow a virtual walking tour on the free Downtown Pittsfield App and enjoy opening receptions with the artists.

A free ART BUS provided and operated by RSVP Volunteers will take you to a half dozen locations throughout downtown during the First Fridays at Five on May 2nd. The ART BUS will make stops at City Hall, The Berkshire Carousel, Clock Tower Artists, the Framework by DPI Gallery at the corner of North and Linden Streets, Hotel on North, and Persip Park at the corner of North Street and Columbus Avenue. The ART BUS will depart City Hall every half hour starting at 5 pm with the last ride departing City Hall at 7:30 pm. Visit downtownpittsfield.com for the ART BUS schedule.

Berkshire Art Center, 141 North Street, will feature Free Drop-in Art Making from 5:30 to 7:30 pm. All ages are welcome to stop by to participate in a free art activity with the guidance and support of a faculty artist.

Hot Plate Brewing, Co., 1 School Street, will celebrate the return of First Fridays with a two-band lineup featuring two Northampton-based bands: Gentle Hens and The Fawns starting at 7 pm.

WANDER Berkshires, 34 Depot Street, Suite 101, will feature Roadhouse Gospel Revival with Misty Blues from 7 to 9 pm. Misty Blues pays tribute to the bold and brassy women of early blues while honoring the legendary male artists of the 1920s–1940s. Rooted in reverence and joy, this evening promises deep grooves, raw emotion, and pure blues energy. $20 advance tickets or pay at the door.

Berkshire Theatre Group will present “Henry Cho: The Empty Nest Tour 2025” at The Colonial Theatre, 111 South Street, at 7:30 pm. Known for his clean, clever humor and unique comedic style, Henry has been entertaining audiences across the country with his hilarious observations on life, family and culture. With numerous appearances on late-night TV, Comedy Central, and his own Comedy Central special, Henry has established himself as one of the most beloved comedians in the industry.

First Fridays at Five is led by the City of Pittsfield and Downtown Pittsfield, Inc. and will take place in downtown Pittsfield on May 2, June 6, August 1, and September 5. A portion of North Street will be closed during the event.

Season partners and sponsors include AccessPlus, MountainOne, and Guardian Life Insurance Company of America.

For more information and a full event listing, visit https://lovepittsfield.com/first-fridays.

First Fridays at Five: Futon Lasagna
2025-05-02 17:00 - 20:00 | Persip Park, 175 North Street, Pittsfield, MA, 01201, United States
Persip Park, 175 North Street, will feature a live performance by Futon Lasagna from 5 to 8 pm. Enjoy a beer garden from Hot Plate Brewing, Co. and local food vendors within the vicinity.

Futon Lasagna is ska comfort food made with love since 2021. Hailing from Boston, this high-energy, female-fronted LGBTQ+ band blends the melodic vocals of pop punk with the infectious rhythms of punk ska—think Bouncing Souls meets Less Than Jake, but hold the horns. Their catchy, relatable songs are perfect for dancing your feelings out. What started as four friends jamming at parties quickly turned into a beloved act lighting up stages across New England.

In the case of inclement weather, Futon Lasagna will be at Price Memorial A.M.E. Zion Church, 27 East Street.

The Three B’s Jazz Combo
2025-06-06 17:00 - 18:30 | Lichtenstein Center for the Arts, 28 Renne Avenue, Pittsfield, MA, 01201, United States
The Lichtenstein Center for the Arts, 28 Renee Avenue, will present The Three B’s Jazz Combo from 5 to 6:30 pm. The Three B’s Jazz Combo is the top jazz ensemble at Pittsfield High School. They have won three awards at the Clark Terry Jazz Festival, one being an Honorable Mention for overall group. They have performed live at Shire Tavern in Dalton and WANDER in Pittsfield. Members are Aiden Hyatt – keyboard, Anna Newell – tenor sax, Maverick Roberts – guitar, James Smith – alto sax, and Isabella Williams – drums.
The Lichtenstein will also host an opening reception for “Mixed Bag” by JJ Tobin, an abstract art show featuring paintings and sculptures from the past and present, on Friday, June 6, 5 to 8 pm. JJ Tobin will be present.

June 6 First Fridays at Five
2025-06-06 17:00 - 20:00 | Downtown Pittsfield, Pittsfield, MA, 01201, United States
The June 6 First Fridays at Five sponsored by MountainOne will feature live music, art, dance, family fun, shopping, food, two beer gardens, and entertainment throughout downtown Pittsfield. Attendees are encouraged to bring their own chairs so they can sit and enjoy a variety of food, beverages, and entertainment!
6/6 UPDATE: RAIN LOCATIONS ARE IN EFFECT

Housie Shakers at Persip Park (5 to 8 pm)

Persip Park, 175 North Street, will feature a live performance by the Housie Shakers from 5 to 8 pm. Enjoy a beer garden from Hot Plate Brewing, Co. and local food vendors within the vicinity.
In the case of inclement weather, the Housie Shakers will be at Price Memorial A.M.E. Zion Church, 27 East Street.

Dance on Dunham (5 to 8 pm)

Dunham Mall, 100 North Street, will feature Dance on Dunham with Aimee Gelinas, the Berkshire Rhythm Keepers, and Noel Staples-Freeman from 5 to 8 pm.

In the case of inclement weather, Dance on Dunham will be at WANDER Berkshires, 34 Depot Street, Suite 101.

“Art in the Park” with Isabel Rosenthal (5 to 8 pm)

On June 6 from 5 to 8 pm, Isabel Rosenthal will be popped up in Palace Park (near 122 North Street), inviting the community to watch her paint and alter recycled clothing. She will be discussing her process with all who are interested.

Live Pottery Demo with Jim Horsford (5 to 8 pm)

Jim Horsford will also be in Palace Park hosting a free live pottery demonstration from 5 to 8 pm where he will be inviting individuals to help him make pots on the potter’s wheel.

In the case of inclement weather, “Art in the Park” with Isabel Rosenthal and Pottery with Jim Horsford will be inside the Lichtenstein Center for the Arts at 28 Renee Avenue.

DJ BFG (5 to 8 pm) Cancelled

Albany Berkshire Ballet Performance (5:30 pm)

The Albany Berkshire Ballet will perform at 5:30 pm on North Street close to Park Square. The ABB Junior Company and Academy dancers of the Cantarella School of Dance, along with the senior dance team of the Cantarella School of Dance, will perform excerpts from the ballet Cinderella and a contemporary piece by ABB dancer Ruslan Sprague.

In the case of inclement weather, the performance will be at Price Memorial A.M.E. Zion Church, 27 East Street.

Snippet from BTG’s Magic Tree House: Pirates Past Noon (6:30 pm)

Berkshire Theatre Group will perform a snippet from the Magic Tree House: Pirates Past Noon at 6:30 pm on North Street close to Park Square.

In the case of inclement weather, the performance will be at Price Memorial A.M.E. Zion Church, 27 East Street.

Makers’ Market (5 to 8 pm)

The Makers’ Market at First Fridays at Five will feature over a dozen local vendors selling handmade products such as crafts, clothing and accessories, candles, art, custom gift items, self-care items, and packaged foods and sweets.

Family Fun Zone (5 to 8 pm)

The Family Fun Zone at First Fridays at Five will be on North Street and will feature free, interactive activities from local non-profit organizations including face-painting, arts & crafts, games, and more.

There will be an ADA and Disability Awareness Celebration presented by the Pittsfield Commission on Disabilities, offering a fun and interactive educational experience. There will be a braille activity, ASL information, and more.

Reading with Rebel (5 to 7 pm)

Come join your favorite Drag queen Miz Rebel Progress as she teams up with Witch Slapped at 78 North Street to promote literacy at this free event.

First Fridays Artswalk (5 to 8 pm)

First Fridays Artswalk will showcase artists at venues throughout downtown Pittsfield from 5 to 8 pm including Berkshire Art Center, Berkshire Theatre Group, Clock Tower Artists, Dottie’s Coffee Lounge, Framework by Downtown Pittsfield, Inc., Hotel on North, Lichtenstein Center for the Arts, Living in Recovery, Marketplace Cafe, Ralph Froio Senior Center, Roots and Dreams and Mustard Seeds, Soda Chef, and TKG Real Estate. Follow a virtual walking tour on the free Downtown Pittsfield App and enjoy opening receptions with the artists.

Art Shuttle (5 to 8 pm)

A free Art Shuttle provided and operated by RSVP Volunteers will take you to five locations throughout downtown during the First Fridays at Five on June 6. The Art Shuttle will make stops at City Hall, Berkshire Carousel, Clock Tower Artists, the Framework by DPI Gallery at the corner of North and Linden Streets, and Hotel on North. The Art Shuttle will depart City Hall every half hour starting at 5 pm with the last ride departing City Hall at 7:30 pm. (This is the updated route as of JUNE 6)

Free Drop-in Art Making (5:30 to 7:30 pm)

Berkshire Art Center, 141 North Street, will feature Free Drop-in Art Making from 5:30 to 7:30 pm. All ages are welcome to stop by to participate in a free art activity with the guidance and support of a faculty artist.

Sing Out Loud: A Berkshire Pride Karaoke Fundraiser (5 pm)
Hot Plate Brewing Co., 1 School Street, will feature Sing Out Loud: A Berkshire Pride Karaoke Fundraiser starting at 5 pm. Every song submission requires a small donation to Berkshire Pride, and you can raise your voice and your donation by competing to climb higher on the song list. The more you donate, the higher you’ll be on the list to showcase your favorite tunes, and thanks to Temescal Wellness, $1 will be donated to Berkshire Pride for every beer poured at the event.

First Fridays at Five is led by the City of Pittsfield and Downtown Pittsfield, Inc. and will take place in downtown Pittsfield on May 2, June 6, August 1, and September 5. A portion of North Street will be closed during the event.

Season partners and sponsors include AccessPlus, MountainOne, and Guardian Life Insurance Company of America.

For more information and a full event listing, visit https://lovepittsfield.com/first-fridays.

Thank you to Brick by Brick Markets for day-of vendor coordination.

Housie Shakers at Persip Park (First Fridays at Five)
2025-06-06 17:00 - 20:00 | Price Memorial A.M.E. Zion Church, 27 East Street, Pittsfield, MA, 01201, United States
6/6 UPDATE: The Housie Shakers will be at Price Memorial A.M.E. Zion Church, 27 East Street.

Persip Park, 175 North Street, will feature a live performance by the Housie Shakers from 5 to 8 pm. Enjoy a beer garden from Hot Plate Brewing, Co. and local food vendors within the vicinity.
The Housie Shakers bring a variety of styles to the mix, with wide-ranging covers and original music spanning rock, blues, pop, bluegrass, reggae, Americana, and improvisational groove. They don’t take themselves too seriously and have no ambitions to go on the road (as if the 12 kids they have collectively would make that possible anyway)… they’re just out to play local gigs and give people a chance to hang out, let loose, dance, and have a good time! The band’s name is a nod to their home community and the people and places that have shaped their musical journeys.
The Housie Shakers are Simeon Bittman (drums & vocals), Noah Cook-Dubin (guitar, cavaquinho & vocals), Jonathan Denmark (guitar & vocals), and Colin Ovitsky (bass).
In the case of inclement weather, the Housie Shakers will be at Price Memorial A.M.E. Zion Church, 27 East Street.

The Pitt - Christa Joy and The Honeybees
2025-06-13 18:00 - 20:00 | Dunham Mall, 100 North Street
Hot Plate Brewing Co. has teamed up with Pittsfield-based businesses and organizations including Downtown Pittsfield, Inc. to bring you a free outdoor summer music series in Dunham Mall. They’ll be a beer garden, food vendors, and awesome performers!
We’re kicking off the inaugural season of The Pitt with singer-songwriter Christa Joy and her backing band, The Honeybees.
Christa Joy is the band leader of the Western Mass based, “Christa Joy and the Honeybees.” Americana with a classic country flair, the group includes Lisa Marie Ellingsen (lead guitar), Tim Bowles (pedal steel), Jason Smith (drums), and Tom LeBeau (bass). The songwriter’s fourth full length collection was released in August 2024 at CitySpace in Easthampton, MA. The self-titled project, Christa Joy and the Honeybees, paints a versatile picture of the group’s talents—ranging from kitschy humorous gems like “God Gave Me Two Babies” and “Omens,” to emotional ballads like “Time and Luck” and the sparser indie flavor of “Again and Again.” Also included on the project, Producer Grant Wicks arranged a countrified cover of Pixies “Here Comes Your Man,” a shout out to local hero Black Francis. Christa Joy is expected to release a solo EP of songs written during the early months of the pandemic in early 2025.
Joy is known for her strong sense of melody, resonant storytelling, and charming sincerity. She has played at many notable New England venues, including the Parlor Room, the Iron Horse, and Club Passim. She has opened for some of her heroines, including Lucy Wainwright Roche, Meg Hutchinson, The Sweetback Sisters, Loudon Wainwright III, and Antje Duvekot. Perhaps more importantly, she is a Mom of three and a Forest Kindergarten Teacher in Western Massachusetts. You can follow her more closely on Substack and IG as Momsongwriter.
Originally from rural Massachusetts, Christa grew up in a teacher preacher truck-driving kind of family. Joy spent the earliest years of her songwriting telling stories of her rural upbringing, the illness and death of her mother, and the brokenhearted years that followed this loss. Impermanence, separation, and the fragility of human life were themes that figured prominently in her early collections of songs, Ready or Not (2012) and Daughter of Your Lost Art (2014). Then she became a Mom in 2015. That new little being demanded her presence, and Joy turned her attention back toward this most precious world. She saw it all again for the first time and experienced it all through the soft constant awareness of her first child. In becoming a parent, Joy rediscovered her own inner magic. She began to lighten up, to laugh again, and took notes for the whole ride. These are the moments that brought together her third collection of songs, Get On, Heart! (2019). This album was highlighted by No Depression’s “Crowdfunding Campaigns of the Week,” and later released to a sold out Parlor Room in Northampton, MA. Most notably played on Signature Sounds Jim Olsen’s “The Back Porch” radio show, Jim Neill’s Jukebox, Texas Highway Radio Show, Blue Moon Kentucky, Keepin’ It True Country, Nine Volt Heart, Vizaural Music, Country Routes News, and others.

The Pitt - Alester
2025-06-20 18:00 - 20:00 | Dunham Mall, 100 North Street
Hot Plate Brewing Co. has teamed up with Pittsfield-based businesses and organizations including Downtown Pittsfield, Inc. to bring you a free outdoor summer music series in Dunham Mall. They’ll be a beer garden, food vendors, and awesome performers!
Hailing from the frigid landscapes of the east coast, Alester marries electric performances with passionate lyrics and icy sonics.
Click here to listen to Alester on Spotify

Historic Songs of the American Revolution
2025-06-25 17:30 - 19:00 | Herman Melville’s Arrowhead, 780 Holmes Road, Pittsfield, MA, 01201, United States
Live music and storytelling with award winning singer/songwriters Cosby Gibson and Tom Staudie.
The history of the American Revolution is detailed with many battles, conferences, and personalities. But it was also a time of patriotism, inspiration, and song. This program presented by award winning singer/songwriters Cosby Gibson and Tom Staudie includes a variety of historic songs performed with a variety of instruments. The duo will provide a brief narrative and anecdotes of the history of the songs as well as of the war of American independence.

The Pitt - Ciarra Fragale
2025-06-27 18:00 - 20:00 | Dunham Mall, 100 North Street
The Pitt is Hot Plate Brewing Co.’s brand-new FREE outdoor summer music series in Dunham Mall in Downtown Pittsfield.
On select Fridays, 6 to 8 pm, through August, enjoy a Beer Garden by Hot Plate, food by HAND CRAFTED Catering & Events, and free concerts appropriate for all ages on Dunham Mall.
Bringing your own chairs is recommended!
If there is inclement weather, the show will move inside Hot Plate’s taproom from 6 to 8 pm.
Ciarra Fragale is an indie pop singer/songwriter, producer, and actor from NY’s Hudson Valley. By blending the nostalgic traditions of songwriting with unique new-wave sensibilities, she creates a refreshing sound all her own. In addition to making her own music, Ciarra has also composed many works for theater and film.

Pittsfield Parade Concert featuring the Greater Kensington String Band
2025-07-03 18:00 - 20:00 | The Common, First Street, Pittsfield, MA, 100 First Street, Pittsfield, MA, 01201, United States
Join us for the Pittsfield Parade Concert featuring the Greater Kensington String Band – also known as “The Mummers” – along with special guest the WhoaPhat Brass Band!
Since 1946, the Greater Kensington String Band has been a totally volunteer organization that participates in the world famous Mummers Parade on New Year’s Day in Philadelphia, PA. They will be playing highlights from their foot-tapping music. (Join us at the parade to see them in their famous, colorfully costumed attire.)
WhoaPhat Brass Band specializes in a unique instrumentation, spanning across decades of musical genres including second line, jazz, funk, disco, and rock. WhoaPhat Brass Band has won top honors for musical performances in the Philadelphia Mummers and Saint Patrick’s Day Parades.

Sea Shanties with Alex Harvey and Shinbone Alley
2025-07-10 19:00 - 21:00 | Herman Melville’s Arrowhead, 780 Holmes Road, Pittsfield, MA, 01201, United States
A special concert with Alex Harvey. Harvey is an old-world folklorist who performs street ballads and songs of the sea in a project he calls Shinbone Alley. At his performances listeners learn to celebrate the haunting intercultural exchange of 18th and 19th century maritime music – whose ingredients travelled from the furthest corners of the globe to be remade and stitched anew by sailors of every shade and shape at port and at sea. By teaching the audience to join in on most of the tunes in his concerts, Harvey and his Shinbone Alley builds bridges of time through communal singing. From Sea Shanties to Broadsheet ballads to Come-All-Ye’s to Last Good Nights to Hard Luck Satires to Lovesick Dirges to Whaling Serenades – this music was meant as the earliest form of group therapy. And so it is again – a sepia-toned balm for our topsy-turvy time.

The Pitt - Cold Chocolate
2025-07-11 18:00 - 20:00 | Dunham Mall, 100 North Street
Hot Plate Brewing Co. has teamed up with Pittsfield-based businesses and organizations including Downtown Pittsfield, Inc. to bring you a free outdoor summer music series in Dunham Mall. They’ll be a beer garden, food vendors, and awesome performers!
Cold Chocolate is a genre-bending Americana band that fuses folk, funk, and bluegrass to create a unique sound all their own. Led by Ethan Robbins (vocals/guitar/mandolin) and Ariel Bernstein (vocals/percussion/banjo), the Boston-based duo released their fifth full-length album in the fall of 2023.
Punctuated by tight harmonies and skillful musicianship, Cold Chocolate has quickly gained recognition for their original music and high-energy shows. The band has shared bills with Leftover Salmon, David Grisman, and Angelique Kidjo, and regularly performs at venues and music festivals across the country. Jason Verlinde of The Fretboard Journal, who covered the band’s FreshGrass Festival set, noted “there were plenty of magical moments…I will never forget [watching] Cold Chocolate perform.” Kathy Sands-Boehmer of No Depression raved, “[Ethan] feels the music in his heart and soul and it shows when he plays. Ethan becomes the music on stage. There’s an almost mystical connection between his guitar and the notes that flow out of it.”

The Pitt - The Wolves
2025-07-18 18:00 - 20:00 | Dunham Mall, 100 North Street
Hot Plate Brewing Co. has teamed up with Pittsfield-based businesses and organizations including Downtown Pittsfield, Inc. to bring you a free outdoor summer music series in Dunham Mall. They’ll be a beer garden, food vendors, and awesome performers!
Led by Kara & Darby Wolf (of Eavesdrop, Matt Schofield, and Reckoners), The Wolves features a variety of players from Western MA.

St. Joseph's Polish Picnic
2025-07-20 12:00 - 17:00 | St. Joseph Church Grounds, 414 North Street, Pittsfield, MA, 01201, United States

The Pitt - The Nate Martel Band
2025-07-25 18:00 - 20:00 | Dunham Mall, 100 North Street
Hot Plate Brewing Co. has teamed up with Pittsfield-based businesses and organizations including Downtown Pittsfield, Inc. to bring you a free outdoor summer music series in Dunham Mall. They’ll be a beer garden, food vendors, and awesome performers!
Nate is a singer, songwriter, and guitarist based in the Pioneer Valley of Massachusetts. His solo project is soulful and socially conscious; deep, sometimes dark, but often uplifting.

Hidden Frequency at First Fridays at Five
2025-08-01 17:00 - 20:00 | Persip Park, 175 North Street, Pittsfield, MA, 01201, United States
Persip Park, 175 North Street, will feature a live performance by the band Hidden Frequency during the August 1 First Fridays at Five from 5 to 8 pm. Enjoy a beer garden from Hot Plate Brewing Co. and local food vendors within the vicinity.
Hidden Frequency is an alternative rock trio hailing from the heart of the Berkshires in Pittsfield, MA. Fusing raw emotion with heavy riffs and melodic grit, the band channels the energy of classic rock through a modern, alternative lens.
Longtime friends, Steven Dubuque on guitar and vocals, Mike Morse on bass, and Mitch Gladu on drums, stay committed to bringing good, original music to Western MA.
From stage to studio, Hidden Frequency brings raw presence and passion to a world full of noise and static, they’re the signal you don’t want to miss.
In the case of inclement weather, Hidden Frequency will be at Price Memorial A.M.E. Zion Church, 27 East Street.
