September 5 First Fridays at Five

The City of Pittsfield, Downtown Pittsfield, Inc. (DPI), and the Downtown Pittsfield Cultural Association (DPCA) have announced details for the final First Fridays at Five of the 2025 season. The event on Friday, September 5th presented by 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.

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

The Wolves bring you a nostalgic and eclectic mix of songs spanning genres – from the 80s, 90s, and beyond. Led by Kara Wolf on vocals (Eavesdrop) and Darby Wolf on keys (Matt Schofield, Reckoners, Eavesdrop), they are joined by a variety of players from Western Massachusetts. This performance will feature Jared Quinn on guitar and vocals (Eavesdrop, John Cruz, Live on the Planet w/ Kim Zombik) and Andrew Ricketts on drums (Eavesdrop, Mary McAvoy).

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

New for September, enjoy an Entertainment Zone at the south end of North Street near Hot Harry’s featuring performances by WackyChad! and Opal Raven Cirque.

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

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. As his own witty master of ceremonies, WackyChad! improvises and banters with the audience, making the show even more engaging and interactive.

WackyChad!’s pogo stick skills, charmingly funny jokes, and wild antics have earned him appearances on America’s Got Talent (twice!), The Gong Show, Das SuperTalent (Germany), ESPN2 for PogoPalooza (World Championship of Pogo Competition), and even a performance at the Super Bowl. With his talent and experience, WackyChad! has wowed audiences in 26 different countries, making him a true global sensation. Be warned, if you don’t like laughing, this isn’t the show for you!

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

Opal Raven Cirque will perform a Scarf Routine at 5 pm and a Fire Show at 7:30 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. Also known as the Sword Queen of Gypsy Layne, Opal showcases masterful sword spinning and daring prop tricks.

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.

Dunham Mall, 100 North Street, 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.

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. The three mosaic mural panels by Markey are intended to beautify downtown as part of the Reimagine Dunham Mall effort, and the map is the first of several wayfinding efforts being introduced in the Downtown in partnership with Downtown Pittsfield, Inc., MassDevelopment’s Transformative Development Initiative (TDI), and the City of Pittsfield.

Downtown Pittsfield, Inc. and First Fridays Artswalk will feature Carly Holmes at the September “Art in the Park” artist.

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 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.

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

There will also be a bonus “Art in the Park” artist popped up alongside Carly: Sadiya Quetti-Goodson.

Sadiya is a 21-year-old artist from Pittsfield who holds a B.A. in Afro-American Studies with a minor in African Studies from Howard University, which grounds her artistic practice. Her work centers on people of the African Diaspora, emphasizing everyday rituals through a variety of media including acrylics, fabric and bleach painting, photography, crochet, and printmaking.

At this demonstration, prints will be available for sale, and Sadiya will focus on jean painting and portraiture drawing – two methods she uses to explore identity and share her core message: “Make More Art, Create More Joy!”

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.

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.

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.

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.

Participating organizations include the Alzheimer’s Association, Barrington Stage Company, BART Charter Public School, Berkshire Athenaeum, Berkshire Coalition for Suicide Prevention, Berkshire County Board of Realtors, Berkshire County Head Start/CFCE, Berkshire County Kids Place, Berkshire District Attorney’s Office, Berkshire Family YMCA, Berkshire Medical Center, Berkshire Regional Planning Commission – SPARK Coalition, Child Care of the Berkshires (ParentChild+ program), CleanSlate Centers, Department of Community Development, Elizabeth Freeman Center, Foster MA/Adopt MA, Living in Recovery, Pittsfield Little League, Susan B. Anthony Birthplace Museum, United States Air Force & Space Force, Western Massachusetts Labor Action, and Xtreme Wrestling Alliance.

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.

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!

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.

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.

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.

Hot Plate Brewing Co. and Potency will feature the Job Creators during the next installment of their Original Concert Series on Friday, September 5 at 7 pm inside their taproom at 1 School Street.

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. For 10 years they have been plying their own high-energy improvisational music across the Northeast. Releasing their 2nd full LP, Love Monster, in October of 2023 has made big waves for the band. Venerable online music magazine Fecking Bahamas has said they are, “Embedding new-wave texture and groove with math rock, indie, and psychedelic prog, it’s a ship on a current all its own.”

After the event, join the free afterparty at “Depot After Dark” with DJ Bengey from 8 to 11 pm!

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.

North Street will be closed from Park Square to Columbus Avenue on Friday, September 5 from 3 to 8:30 pm. Drivers are asked to seek alternate routes during this timeframe and follow appropriate detours. In addition, a parking restriction will be in place on North Street between Park Square and Columbus Avenue starting at 2 pm on Friday.