“Reading with Rebel” at First Fridays at Five
2025-09-05 17:00 - 19:00 (America/New_York) | Witch Slapped, 78 North Street, Pittsfield, MA, 01201, United States
Witch Slapped, 78 North Street, will host “Reading with Rebel” from 5 to 7 pm. Drag queen, Miz Rebel Progress, has teamed up with Witch Slapped to promote literacy at this storytelling event. All children who attend will leave with a free book. The event is free, but donations to the Witch Slapped Community Fund are welcomed.

“Art in the Park” with Carly Holmes at First Fridays at Five
2025-09-05 17:00 - 20:00 | Palace Park, 116 North Street, Pittsfield, MA, 01201, United States
Downtown Pittsfield, Inc. and First Fridays Artswalk are pleased to announce the September “Art in the Park” artist at First Fridays at Five is Carly Holmes.
Carly will be popped up in Palace Park (near 122 North Street), inviting the community to watch her paint live and discussing her process with all who are interested.
Carly is a lifelong resident of Pittsfield and describes herself as an emerging artist with a passion for creating art. “I have always loved creating art,” Carly says. “As a child, I was constantly drawing and crafting. I have explored drawing, ceramics, and 3-dimensional design. But painting with acrylics is where my true passion lies. I view my work as a reflection of my ever-evolving interests, and as a personal outlet for self-expression.”
Carly is the City of Pittsfield’s inaugural artist-in-residence and is currently working out of studio space in the Lichtenstein Center for the Arts. Carly also recently unveiled her new mural “DOWNTOWN BOUND” on the train platform at the Berkshire Regional Transit Authority Intermodal Center located at 1 Columbus Avenue in Pittsfield. “DOWNTOWN BOUND” was created alongside mentor artist Jesse Tobin McCauley as part of the Let It Shine! Public Art Partnership.
In the case of inclement weather, “Art in the Park” with Carly Holmes will be inside the Lichtenstein Center for the Arts at 28 Renee Avenue.
“Art in the Park” is supported by the Feigenbaum Foundation.

Jim Horsford Pottery Demonstration at First Fridays at Five
2025-09-05 17:00 - 20:00 | Lichtenstein Center for the Arts, 28 Renne Avenue, Pittsfield, MA, 01201, United States
Jim Horsford will be in his studio at the Lichtenstein Center for the Arts at 28 Renee Avenue 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.

Family Fun Zone at First Fridays at Five
2025-09-05 17:00 - 20:00 | Downtown Pittsfield, Pittsfield, MA, 01201, United States
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 lawn games in the center of North Street, and Balloon Ben will be crafting free balloon creations.

“Where’s Winston?” Scavenger Hunt at First Fridays at Five
2025-09-05 17:00 - 20:00 | Downtown Pittsfield, Pittsfield, MA, 01201, United States
Downtown Pittsfield, Inc. will present a one-night-only Back-to-School edition of “Where’s Winston?” during the September 5th First Fridays at Five. This Back-to-School themed scavenger hunt for images of Officer Winston, the Pittsfield Police Department’s comfort dog, will take place on Friday, September 5, from 5 to 7:45 pm. Game Cards will be available at the Downtown Pittsfield, Inc. tent in Dunham Mall at 100 North Street starting at 5 pm. The last Game Card will be redeemed at 7:55 pm. “Where’s Winston?” is for children aged 3 to 18 years old, and young children participating must be accompanied by a parent or guardian.
Every Winston will have a unique Back-to-School themed word with him. Find the hidden Winstons, write the words on the Where’s Winston? Game Card, and bring the Game Card to the Downtown Pittsfield, Inc. tent in Dunham Mall at 100 North Street to redeem for prizes.
All participants will get a Winston Sticker.
Children who find any 5 words will win a Winston Drawstring Bag while supplies last.
The first 10 children who find all 6 words and turn in their completed Game Card to the Downtown Pittsfield, Inc. tent in Dunham Mall will win a Winston plushie!

September 5 First Fridays at Five
2025-09-05 17:00 - 20:00 | Downtown Pittsfield, Pittsfield, MA, 01201, United States
The final First Fridays at Five of the 2025 season will be held on Friday, September 5th from 5 to 8 pm with an Afterparty from 8 to 11 pm. The event presented by the City of Pittsfield, Downtown Pittsfield, Inc., and Mill Town Foundation will feature live music, art, dance, family fun, shopping, food, a beer garden, 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.

Live Music at Persip Park, 175 North Street (5-8PM):

Live performance by The Wolves. Beer Garden with Hot Plate Brewing Co.

The Wolves bring you a nostalgic and eclectic mix of songs spanning genres – from the 80s, 90s, and beyond.

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

Entertainment Zone at the south end of North Street near Hot Harry’s (5-8PM):

Opal Raven Cirque will perform a Scarf Routine at 5 pm and a Fire Show at 7:30 pm in the Entertainment Zone.

Stunt Comedian WackyChad! will perform 45-minute shows at 5:30 pm and 6:30 pm in the Entertainment Zone.

Opal Raven Cirque is a circus and sideshow performer based in Western Massachusetts. She’s known across New England and the Tri-State area for her “Danger Dame of the Flame” variety show.

WackyChad!’s award-winning, action-packed, and interactive stunt comedy show will blow your mind. With his extreme pogo stick stunts and big tricks, WackyChad! delivers a delightful entertainment experience that will leave you roaring with laughter and applauding in amazement.

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

In the case of inclement weather, Opal Raven Cirque’s Scarf Routine will be at the Lichtenstein Center for the Arts at 28 Renee Avenue.

Dance Party on Dunham Mall, 100 North Street (5-8PM):

Dunham Mall will feature a “Solid Gold” Dance Party with DJ Pup Daddy from 5 to 8 pm. DJ Pup Daddy will spin vinyl records of the 60s, 70s, and 80s, along with 90s party jams.

In the case of inclement weather, the Dance Party with DJ Pup Daddy will be at WANDER Berkshires, 34 Depot Street, Suite 101, from 5 to 7 pm.

Mural Unveilings at Dunham Mall, 100 North Street (6:15PM):

Downtown Pittsfield, Inc. will hold a Ribbon Cutting in Dunham Mall for Robert Markey’s Mosaic Mural and Emily Elizabeth Bunnell’s Map of Downtown Pittsfield at 6:15 pm.

“Art in the Park” at Palace Park, 122 North Street (5-8PM):

Carly Holmes and Sadiya Quetti-Goodson will be popped up in Palace Park inviting the community to watch them create art live!

In the case of inclement weather, “Art in the Park” with Carly Holmes and Sadiya Quetti-Goodson will be inside the Lichtenstein Center for the Arts at 28 Renee Avenue.

Pottery Demo at the Lichtenstein Center for the Arts, 28 Renee Avenue (5-8PM):

Jim Horsford will be in his studio at the Lichtenstein Center for the Arts hosting a free live pottery demonstration where he will be inviting individuals to help him make pots on the potter’s wheel.

Makers Market and Food Vendors, North Street (5-8PM):

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.

Check out a variety of food vendors including BB’s Hot Spot, Cravins Ice Cream, D’s Island Food Truck, Just Kickin It Bar B Que, and Upstreet Smoke.

Family Fun Zone and Balloon Ben, North Street (5-8PM):

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

The Berkshire County Sheriff’s Office will be offering the Child ID Project at the September 5 First Fridays at Five. This free service creates a digital ID with fingerprints, photo, physical description, and emergency contacts, which is stored in a secure national database. If a child ever goes missing, this information can help law enforcement respond quickly and effectively, nationwide. The process only takes a few minutes and gives families added peace of mind.

There will be lawn games in the center of North Street, and Balloon Ben will be crafting free balloon creations.

“Where’s Winston?” starts at Dunham Mall, 100 North Street (5-7:45PM):

Downtown Pittsfield, Inc. will present a one-night-only Back-to-School edition of “Where’s Winston?” during the September 5th First Fridays at Five. This Back-to-School themed scavenger hunt for images of Officer Winston, the Pittsfield Police Department’s comfort dog, will take place on Friday, September 5, from 5 to 7:45 pm. Game Cards will be available at the Downtown Pittsfield, Inc. tent in Dunham Mall at 100 North Street starting at 5 pm. The last Game Card will be redeemed at 7:55 pm. “Where’s Winston?” is for children aged 3 to 18 years old, and young children participating must be accompanied by a parent or guardian.

All participants will get a Winston Sticker. Children who find any 5 words will win a Winston Drawstring Bag while supplies last. The first ten children who find all 6 words and turn in their completed Game Card to the Downtown Pittsfield, Inc. tent in Dunham Mall will win a Winston plushie!

Reading with Rebel” at Witch Slapped, 78 North Street (5-7PM):

Drag queen, Miz Rebel Progress, has teamed up with Witch Slapped to promote literacy at this storytelling event. All children who attend will leave with a free book.

First Fridays Artswalk, Downtown Pittsfield (5-8PM):

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, Marketplace Cafe, NUarts gallery + studios, Ralph Froio Senior Center, Roots and Dreams and Mustard Seeds, and the Soda Chef. Follow a virtual walking tour on the free Downtown Pittsfield App and enjoy opening receptions with the artists.

Free Drop-In Art Making at Berkshire Art Center, 141 North Street (5:30-7:30PM):

Enjoy a rotating set of art projects for individuals and families to participate in at their own pace with the guidance and support of a Faculty Artist. All children must be accompanied by an adult.

Original Concert Series with Job Creators at Hot Plate Brewing Co., 1 School Street (7PM):

Job Creators is a psychedelic math rock based out of Boston/Brooklyn. The dynamic pair consists of Blaise Lucey on bass guitar and audio samples and Tim Winslow on drums and synthesizer.

“Depot After Dark”: The Official First Fridays Afterparty (8-11PM):

Downtown Pittsfield, Inc., Tito’s Mexican Bar & Grill, and Wander Berkshires will present “Depot After Dark” outside on Liberty Street (the alleyway between Tito’s/Wander and Crawford Square).

The vibe for the evening will be a Glow Party! Who says you can’t wear white after Labor Day? Dress in white and be ready to dance! Joe Wheaton will be bringing BIG black lights and Missy VonBowtie will be doing neon and glow in the dark face paint. There will be neon markers and an interactive sheet “mural” for everyone to decorate.

The DJ for the evening is Brooklyn-born and East Coast-based, DJ Bengey, who 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.

Beverages including beer, wine, and margaritas will be available from Tito’s, and non-alcoholic “zero proof” cocktails and other specialty drinks will be available from Wander. Attendees are invited to bring their own food or order takeout from Tito’s.

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, Mill Town Foundation, MountainOne, and Guardian.

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

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

Free Drop-In Art Making at First Fridays at Five
2025-09-05 17:30 - 19:30 | Berkshire Art Center, 141 North Street, Pittsfield, MA, 01201, United States
The Berkshire Art Center (BAC), 141 North Street, will host Free Drop-In Art Making during First Fridays at Five on Friday, September 5 from 5:30 to 7:30 pm.
Enjoy a rotating set of art projects for individuals and families to participate in at their own pace with the guidance and support of a Faculty Artist. All children must be accompanied by an adult.

Rhythmscape: Sandra Zarate teaches Zumba®
2025-09-14 18:00 - 20:00 | Dunham Mall, 100 North Street
“Rhythmscape” on Dunham Mall highlights a different rhythm and instructor from our local community each session, reflecting the many identities that make Pittsfield home.
Rhythmscape is free and open to all and encourages everyone to experience the joy of movement and the beauty of cultural exchange. No experience is necessary to participate. Dunham Mall can be located by entering 100 North Street on your GPS.
At the Sunday, September 14 session, enjoy a free Zumba® class with Sandra Zarate open to all ages and fitness levels. Beginners are welcome!
Sandra Zarate is a Colombian Zumba® instructor with over 10 years of experience sharing her passion for dance and fitness with people of all ages and skill levels. Since 2013, she has been teaching Zumba® and holds multiple certifications.
Sandra loves what she does and finds great joy in helping her students reach their goals while having fun along the way. She believes that in today’s fast-paced and hyper-connected world, it’s essential to create moments to disconnect and focus on ourselves. Her classes are designed to be that space — a place to move, laugh, sweat, and feel alive.
Her mission is to cultivate a fun, energetic, and welcoming environment where everyone feels inspired to dance, express themselves, and enjoy the journey to better health.

Rhythmscape: SíncoPaz, Raíces y Ritmos (Roots & Rhythm)
2025-09-21 18:00 - 20:00 | Dunham Mall, 100 North Street
“Rhythmscape” on Dunham Mall highlights a different rhythm and instructor from our local community each session, reflecting the many identities that make Pittsfield home.
Rhythmscape is free and open to all and encourages everyone to experience the joy of movement and the beauty of cultural exchange. No experience is necessary to participate. Dunham Mall can be located by entering 100 North Street on your GPS.
At the final Sunday, September 21 session, enjoy a free interactive event, where you can build your own instruments to use in collaborative music-making and dancing.
What happens when rhythm becomes a language of belonging?
SíncoPaz, Raíces y Ritmos (Roots & Rhythm), is a new community-based music project that invites people of all ages and backgrounds to create sound together.
Part workshop and jam – and definitely a celebration – SíncoPaz is less about performance and more about what emerges when we listen and respond to find resonance with one another.
SíncoPaz explores the power of síncopa (syncopation) and paz (peace) as metaphors for collective life: How might we hold tension and release?
How do we find the pulse between difference and unity? How can rhythm become a bridge across language, cultures, and experiences?
Participants will have the chance to build their own instruments — cajóns, rattles, drums — and use them in collaborative music-making and dancing that emphasizes connection over perfection. SíncoPaz’s intention is to create a space where finding the beat together and coming into sync is an act of community.

Annual Country Fair at Hancock Shaker Village
2025-09-27 10:00 - 17:00, 2025-09-28 10:00 - 17:00 | Hancock Shaker Village, 1843 West Housatonic Street, Pittsfield, MA, 01201, United States
Spend the weekend celebrating what makes the Berkshires special: fine artisanship, local food, breathtaking beauty, exploring the trail, and family fun. This year’s fair includes live music, workshops and demonstrations, family activities, farm animals, a farmer’s market, craft beer, antique tractors, quilt show, and dozens of craft vendors.
Included in admission/free to Hancock Shaker Village members.

Downtown Pittsfield… It’s Alive! Kids’ Zone
2025-10-18 10:00 - 13:00 | Lawn of St. Joseph’s Church, 414 North Street, Pittsfield, MA, 01201, United States
Downtown Pittsfield… It’s Alive! Kids’ Zone: Saturday, October 18, 10 am to 1 pm
The Downtown Pittsfield… It’s Alive! Kids’ Zone will be held on the St. Joseph’s Church lawn. The Kids’ Zone will feature a bounce house, Halloween-themed arts & crafts, games, face painting, balloon twisting, giveaways, live entertainment, and more! All Kids’ Zone activities are free, and costumes are encouraged.
There will be free Face Painting and Balloon Twisting by BTC Family Entertainment (Bowey the Clown and Magic Brushes); a live DJ, and Opal Raven Cirque will perform a variety show at 11 am and 12 pm. Downtown Pittsfield, Inc. will host a Halloween Paint & Sip activity.
Berkshire Art Center will be there with a spooky ghost pull art project for all ages; and Berkshire Museum will be there with their Mobile Museum Unit and Large Dinosaur Bone Blocks for kids to make their own dinosaurs!
There will be additional free activities provided by the Berkshire Athenaeum, Berkshire County Head Start/Pittsfield CFCE, Berkshire District Attorney’s Office, Berkshire Music School, Foster MA/Adopt MA, Susan B Anthony Birthplace Museum, and The Berkshire County Kids’ Place.
Downtown Pittsfield… It’s Alive! Kids’ Zone is presented by Downtown Pittsfield, Inc. in partnership with Mill Town Foundation, the City of Pittsfield, St. Joseph’s Church, and Carr Hardware.
For more information on Downtown Pittsfield… It’s Alive!, call Downtown Pittsfield, Inc. at 413-443-6501.

Downtown Pittsfield… It’s Alive! Night Circus
2025-10-18 15:00 - 18:00 | Dunham Mall, 100 North Street
Downtown Pittsfield… It’s Alive! Night Circus: Saturday, October 18, 3 to 6 pm, on Dunham Mall, School Street, and the portion of North Street that connects the two.
The Downtown Pittsfield… It’s Alive! Night Circus will feature live ska and punk rock bands presented by 413ska; a fire show with Last Ember; free Tarot Readings by Emily Dunsay Wild at 90 North Studio; a beer garden with Hot Plate Brewing Co.; specialty alcoholic beverages from HAND CRAFTED Catering; food from Flavourful Bites, HAND CRAFTED Catering, and Cookie’s Cupcakes; and vendors curated by Jake Seeley of Bomb Shack Vintage.
Last Ember will bring two fire performances to School Street at 4 and 5 pm!
Jesse M. Thomas (Last Ember) has dedicated much of his life to the mastery of prop manipulation and fire-spinning. Jesse has a variety of 10+ acts (from flaming staves to fire eating to knife juggling) and over 15 years professional training.
413ska will present 3 bands on Dunham Mall.
CARSON DALY CITY TRAIN (3 to 4 pm):
A supergroup featuring members of Futon Lasagna, The Agonizers, ghost tones, So Many Dangers, and Steppin Razor Blades – playing covers from the Carson Daly TRL era and your favorite punk songs from the 90’s!
Datura (4:15 to 5 pm):
Datura is a Punk Rock Band from Pittsfield with Lead singer and rhythm guitarist Paxton miller, Lead guitarist Zach Farina, Drummer Brody Barnes, and semi temporary Bassist Jack Bradway. Datura’s style is inspired by Greenday, blink-182, The Ramones, and other punk classics, attempting to provide a comical, fun experience and music an audience can relate to.
HardCar (5:15 to 6 pm):
HardCar is a four-piece alternative punk rock band from Western MA. They combine elements of The Ramones, The Vandals, and The Muppets to create a frenetic cartoon fight cloud of three chord mischief with more catchy hooks than a fishing derby. They released the EP, “Cars of Hardness” in 2024.
The band schedule is subject to change.
Enjoy free 3 Card Tarot Readings with master psychic, alchemist, life coach, and poet Emily Dunsay Wild inside 90 North Studio (90 North Street). The readings are free, but tips are appreciated.
“My methods are vast, I am a channel for nature magic, spirit realms, angelic messages, beauty, art, inspiration, sacred ceremony, expert tarot oracle interpretation,” says Emily. “My specialties, seeing the past present & future. Releasing trauma & psychic wounds. Creating breathtaking original spells & manifesting what your heart truly yearns for. I use a plentitude of skills & tools woven in a master tapestry to give each client the most accurate & thorough transformation possible of body mind & soul. My clients include celebrities, fellow master healers & everyone else in between.” Learn more about Emily at thejewelsofknowing.com.
Downtown Pittsfield… It’s Alive! Night Circus is presented by Downtown Pittsfield, Inc. in partnership with Mill Town Foundation, the City of Pittsfield, Bomb Shack Vintage, 413ska, HAND CRAFTED Catering & Events, Hot Plate Brewing Co., and 90 North Studio.
For more information on Downtown Pittsfield… It’s Alive!, call Downtown Pittsfield, Inc. at 413-443-6501.

Free Kids’ Harvest Paint & Sip
2025-11-07 17:00 - 19:00 | St. Stephen’s Episcopal Church, 67 East Street, Pittsfield, MA, 01201, United States
Downtown Pittsfield, Inc. and St. Stephen’s Episcopal Church will host a Free Kids’ Paint & Sip on Friday, November 7, from 5 to 7 pm, in the auditorium at St. Stephen’s Episcopal Church, 67 East Street.
This free Harvest-themed Paint & Sip is best suited for ages 5 to 12, although younger and older children are welcome. All materials, instruction, snacks, and juice will be provided. Children are welcome to drop in anytime over the course of the event, and all children must be accompanied by an adult. The auditorium is on the second floor of the parish house, and the entrance is on Allen Street.

XWA Superstars of Wrestling return to Pittsfield
2025-11-22 17:00 - 19:00 | Masonic Temple, 116 South Street, Pittsfield, MA, 01201, United States
Get ready, Pittsfield! XWA Wrestling is back with another night of high-impact, family-friendly action you won’t want to miss!
Advance Ticket Special:
Kids 10 & under – ONLY $10
Adults – ONLY $15
All tickets are $25 at the door. Buy early and save! All tickets are General Admission seating. Sit where you like – first come first serve!
Buy tickets online at XWATIX.COM or at the entrance (while seats last).
Concession Stand available! Meet & Greet with the wrestlers during intermission!

Bell Time 5 pm
Doors open at 4:30 pm

Festive Frolic: Free Hot Chocolate and Photo Ops with the Grinch
2025-12-05 17:00 - 20:00 | Otto’s Kitchen & Comfort, 95 East Street, Pittsfield, MA, 01201, United States
Otto’s Kitchen & Comfort, 95 East Street, will be providing free hot chocolate and photo ops with the Grinch from 5 to 8 pm on Friday, December 5.
Stop by before or after the Park Square Tree Lighting Ceremony!
This event is a part of the Festive Frolic which is happening on Friday, December 5 and Saturday, December 6.

Festive Frolic: Free Drop-in Crafts at The Berkshire Athenaeum
2025-12-06 12:00 - 15:30 | Berkshire Athenaeum, 1 Wendell Avenue, Pittsfield, MA, 01201
The Berkshire Athenaeum, Pittsfield’s Public Library, 1 Wendell Avenue, will offer free drop-in activities for all ages from 12:30 to 3 pm on Saturday, December 6. The Children’s Library will host a fun winter craft, the Young Adult Department will offer a button-making craft, and there will be festive bookmark making for adults and teens in the Blake Room.

Free Ride Day at The Berkshire Carousel
2025-12-06 12:00 - 17:00 | The Berkshire Carousel, 50 Center Street, Pittsfield, MA, 01201, United States
It’s Donkey Day on Saturday, December 6! There will be free rides in celebration of Missy the Donkey sponsored by author Kevin O’ Hara. Kevin will introduce and sign his latest book, “A Christmas Journey, Volume Two”, and there will be a special dance performance by the Scoil Rince Breifne O Ruairc Dancers at 2 pm.

Festive Frolic: Kids’ Paint & Sip
2025-12-06 12:30 - 15:00 | St. Stephen’s Episcopal Church, 67 East Street, Pittsfield, MA, 01201, United States
Downtown Pittsfield, Inc. and St. Stephen’s Episcopal Church will host a Free Kids’ Paint & Sip on Saturday, December 6, 12:30 to 3 pm, in the auditorium at St. Stephen’s Episcopal Church, 67 East Street.
This free holiday-themed Paint & Sip is best suited for ages 5 to 12, although younger and older children are welcome. All materials, snacks, and juice will be provided. Children will be provided with a small canvas and wooden ornament for painting.
The Berkshire Museum will be joining in on the fun with a free yarn snowflake ornament craft.
Children are welcome to drop in anytime over the course of the event, and all children must be accompanied by an adult. The auditorium is on the second floor of the parish house, and the entrance is on Allen Street.
This event is a part of the Festive Frolic which is happening on Friday, December 5 and Saturday, December 6.

Festive Frolic: Photo Ops with Santa
2025-12-06 12:30 - 15:00 | Dunham Mall, 100 North Street
NOW INSIDE!! Downtown Pittsfield, Inc. will host Photo Ops with Santa on Saturday, December 6, 12:30 to 3 pm, inside Hand Crafted at 26 Dunham Mall.
Santa will be welcoming children and families to visit with him and take photos. Please bring your own camera or cell phone to capture your own photos of this special moment. There will not be a photographer on site.
Hand Crafted will be handing out free hot chocolate and cider to all in attendance, and Downtown Pittsfield, Inc. will be handing out free Winston Ornaments while supplies last.
Berkshire Community Action Council, Inc. (BCAC) invites you to help support the Elf Children’s Warm Clothing Program by bringing a NEW winter coat or pair of boots for a child in need. If you do, you’ll earn an entry into a raffle to win a luxurious one-night stay at Hotel on North.
BCAC will also be giving away free cookies to all. The raffle drawing will be at 3 pm. You do not need to be present to win.
Hand Crafted will also host “Reading with Rebel” from 12:30 to 3 pm. Drag queen, Miz Rebel Progress, has teamed up with Hand Crafted to promote literacy at this holiday storytelling event. All children who attend will leave with a free book.

This event is a part of the Festive Frolic which is happening on Friday, December 5 and Saturday, December 6.

“Reading with Rebel” at Hand Crafted (Festive Frolic)
2025-12-06 12:30 - 15:00 | Hand Crafted, 26 Dunham Mall, Pittsfield, MA, 01201, United States
Hand Crafted, 26 Dunham Mall, will host “Reading with Rebel” from 12:30 to 3 pm. Drag queen, Miz Rebel Progress, has teamed up with Hand Crafted to promote literacy at this holiday storytelling event. All children who attend will leave with a free book.
This event is a part of the Festive Frolic which is happening on Friday, December 5 and Saturday, December 6.

Festive Frolic: Free DIY dried floral ornaments at SOLARIUM
2025-12-06 12:30 - 15:00 | SOLARIUM Plant Shop, 46 West Street, Pittsfield, MA, 01201, United States
SOLARIUM Plant Shop, 46 West Street, invites children to drop-in to make free dried floral ornaments from 12:30 to 3 pm on Saturday, December 6.

“Reading with Rebel” at Hand Crafted
2025-12-06 12:30 - 15:00 | Hand Crafted, 26 Dunham Mall, Pittsfield, MA, 01201, United States
Hand Crafted, 26 Dunham Mall, will host “Reading with Rebel” from 12:30 to 3 pm. Drag queen, Miz Rebel Progress, has teamed up with Hand Crafted to promote literacy at this holiday storytelling event. All children who attend will leave with a free book.

Festive Frolic: Drag Story Hour with Sativo Green at Indie Readery and Records
2025-12-06 13:00 - 14:30 | Indie Readery and Records, 314 North Street, Pittsfield, MA, 01201, United States
Indie Readery and Records, 314 North Street, and Drag Story Hour Berkshires will present a holiday-themed Drag Story Hour with Sativo Green from 1 to 2:30 pm on Saturday, December 6.

Free Children’s Spring Tea Party and Paint & Sip
2026-04-19 14:00 - 16:00 | WANDER Berkshires, 34 Depot Street, Suite 101., Pittsfield, MA, 01201, United States
Free Children’s Spring Tea Party and Paint & Sip at WANDER on Sunday, April 19, from 2 to 4 pm.
Downtown Pittsfield, Inc. (DPI) will host a free Downtown Celebrates Spring Children’s Tea Party and Paint & Sip on Sunday, April 19, from 2 to 4 pm at WANDER Berkshires, 34 Depot Street, Suite 101 in Pittsfield.
This free Spring-themed Tea Party and Paint & Sip is best suited for ages 3 to 12, although younger and older children are welcome. There will be free lemonade and cookies for the kids, and there will be coffee and tea for the grown-ups available for purchase. All materials for the Paint & Sip will be provided. Children are welcome to drop in anytime over the course of the event, and all children must be accompanied by an adult.
This program is supported by The Feigenbaum Foundation, Downtown Pittsfield, Inc., and WANDER Berkshires.
For a full event listing and additional information on Downtown Celebrates Spring, visit downtownpittsfield.com/2026/04/celebrates-spring or call Downtown Pittsfield, Inc. at 413-443-6501.

Kids’ Spring Fest in Dunham Mall (Celebrates Spring!)
2026-04-21 14:00 - 16:00 | Dunham Mall, 100 North Street
Join Downtown Pittsfield, Inc., the Berkshire Museum, and BeatNest for a Spring gathering outside on Dunham Mall at 100 North Street.
The Berkshire Museum will bring objects from their education collection about the living world blossoming in spring such as plants and bugs, and they will bring a craft relating to spring!
Music will be provided by BeatNest’s Spin Club students as they share their DJ skills that they have been working on this session.
Downtown Pittsfield, Inc. will host kids’ games and hand out free Officer Winston drawstring backpacks!
Children are welcome to drop in anytime over the course of the event, and all children must be accompanied by an adult.
For a full event listing and additional information on Downtown Celebrates Spring, visit downtownpittsfield.com/2026/04/celebrates-spring or call Downtown Pittsfield, Inc. at 413-443-6501.

Decorate a pot and Plant a flower at Peace Train Tees (Celebrates Spring!)
2026-04-22 15:00 - 17:00 | Peace Train Tees, 2 South Street, Pittsfield, MA, 01201, United States
Peace Train Tees at 2 South Street will present a free, drop-in Decorate a pot and Plant a flower Workshop on Wednesday, April 22 from 3 to 5 pm.
For a full event listing and additional information on Downtown Celebrates Spring, visit downtownpittsfield.com/2026/04/celebrates-spring or call Downtown Pittsfield, Inc. at 413-443-6501.

Wildflower seed bombs and Paper flower Workshop (Celebrates Spring!)
2026-04-24 13:00 - 15:00 | SOLARIUM Plant Shop, 46 West Street, Pittsfield, MA, 01201, United States
SOLARIUM Plant Shop at 46 West Street will present a free, drop-in Wildflower seed bombs and Paper flower Workshop on Friday, April 24 from 1 to 3 pm, open to all ages.
For a full event listing and additional information on Downtown Celebrates Spring, visit downtownpittsfield.com/2026/04/celebrates-spring or call Downtown Pittsfield, Inc. at 413-443-6501.

Free Ride Day at the Berkshire Carousel with UCP (Celebrates Spring!)
2026-04-25 12:00 - 17:00 | The Berkshire Carousel, 50 Center Street, Pittsfield, MA, 01201, United States
The Assistive Technology Department of UCP of Western Massachusetts invites our community to celebrate accessibility, inclusion, and innovation at a special Free Ride Day on Saturday, April 25, from 12 to 5 pm, at the beautiful Berkshire Carousel at 50 Center Street in Pittsfield.
Families, friends, and community members are invited to stop by for an afternoon of free carousel rides and fun for all ages while learning more about the powerful role Assistive Technology plays in many people’s lives.
Assistive Technology includes devices, tools, and systems that help individuals with disabilities live more independently and participate fully in everyday life. From simple tools that make daily tasks easier to advanced technology that enhances communication and mobility, Assistive Technology helps people of all abilities live, work, and engage with their communities.
This free community event is an opportunity to celebrate inclusion, while highlighting how Assistive Technology empowers people to live a life without limits. There will be a variety of tools on display as well as demonstrations on how the tools help people.
For a full event listing and additional information on Downtown Celebrates Spring, visit downtownpittsfield.com/2026/04/celebrates-spring or call Downtown Pittsfield, Inc. at 413-443-6501.

First Fridays: “Art in the Park” with Peter Vacchina
2026-05-01 17:00 - 20:00 | Palace Park, 116 North Street, Pittsfield, MA, 01201, United States
Downtown Pittsfield, Inc. and First Fridays Artswalk will feature Peter Vacchina as the May “Art in the Park” artist.

Peter will be popped up in Palace Park (near 122 North Street) from 5 to 8 pm, inviting the community to add pieces to a “made-on-the-spot” mosaic and discussing his process with all who are interested.

Peter is a sculptor working primarily in marble, mosaic, and the occasional ice sculpture. His art reflects his personal life experiences, particularly his time living and traveling abroad. Before becoming a full-time artist in Pittsfield, Peter lived and taught science in Belgium, Brazil, Mexico, England, Italy, and California. “I appreciate the challenge of working in marble and its potential to last for centuries. In my marble sculptures, I seek to invoke memory in the way a scent or sound might, and in doing so inspire heartfelt stories in the viewer.”

“Art in the Park” is supported in part by the Feigenbaum Foundation.

“Art in the Park” is supported in part by a grant from the Mass Cultural Council, and a grant from the Pittsfield Cultural Council, a local agency which is supported by the Mass Cultural Council, a state agency.

Jim Horsford will also be popped up 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 Peter Vacchina will be inside the Lichtenstein Center for the Arts at 28 Renee Avenue.

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