September 5 First Fridays at Five

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.