Nightlife+Arts
The Outdoors
Food+Drink
Shopping
PITTSFIELD, MA
So Much To Love!
There is truly something for everyone in Pittsfield – world class theaters, live music, art shows, museums, unique shopping and a vibrant restaurant scene – all just minutes from spectacular four-season recreation and scenic beauty.
Don’t Miss Events
First Fridays at Five Festival
Get ready for another unforgettable summer in downtown Pittsfield. Join us for First Fridays at Five, happening on May 1, June 5, August 7, and September 4 from 5pm – 8pm.
Solve puzzles, fight monsters, and adopt little guys in role-play adventures. Pittsfield High School’s Dungeons & Dragons Club meets at the library! Players of all experience are welcome. You do[...]
There’s something special about a room full of people brave enough to share a piece of themselves. Whether it’s a song, a poem, a story, or something beautifully unexpected—this is[...]
Debra Jo Rupp and Ray Anthony Thomas star in this beloved Pulitzer Prize-winning play that explores the life-changing relationship between two people bridging societal divides. Set in 1948 Georgia, Daisy,[...]
Pup Daddy Productions & Thistle & Mirth team up to bring you a Thursday night game of SPINDLE (music bingo) w/ DJ Pup Daddy. The music theme for the May[...]
The Buzz About Pittsfield
“As beautiful as I expected … Pittsfield is a walkable, former mill city with a lively music scene and a growing number of bars, coffee shops and restaurants.”
“Whether you’re looking for gourmet farm-to-table dining, boutique hotels, endless hiking trails, or world-class theater, Pittsfield offers it all just a short train right away from NYC.”
“Very recently, I’d heard that the city was experiencing a rebirth and drove in to see it for myself…this Western Massachusetts city has its own art scene.”
“Pittsfield creates ultimate vacation weekend. … an excellent escape for those of us living in New York City”
“It is truly remarkable all that Pittsfield has to offer. The incredible natural surroundings are just a small part of it. The showcase of culture is outstanding.”








Recent Instagram and TikTok Love
Click on a social image above to visit its post, video, or reel.