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.

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SAVE THE DATE! The 10×10 Winter Festival is coming Feb 16-26

The 10×10 Upstreet Arts Festival is a collaboration between more than a dozen arts and cultural organizations. It brings more than 10,000 people downtown for 10 days in the heart of the winter. Stay tuned for a full lineup of events.

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Feb 05

Domingo Brunch w/Dave Bartley & Pete Toigo

Every first Sunday of the month, join us for a delightful morning of music; soulful jazz and blues. Pete Toigo on bass, Dave Bartley on piano & vocals. live music: […]

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Feb 10

WordxWord Story Slam Heart of the Matter

Heart of the Matter story slam at Dottie's! Just in time for Valentines Day, the theme is Heart of the Matter. The stories are yours. Admission is free. Dottie’s will […]

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Feb 11

Pittsfield Farmers Market

Join us for the Pittsfield Farmers Market indoor season! Local vendors showcase the bounty of our community one Saturday a month during the indoor season, from 9AM - 1PM at […]

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Free

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Feb 12

Domingo Brunch w/Jason Ennis and Natalia Bernal

Welcome back local favorites, Jason Ennis and Natalia Bernal. Stop by for their magical and soothing sounds (vocals and guitar). live music: 10am-12pm our full menu available and coffee bar […]

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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.”

“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.”

“the best spot to enjoy summer activities in the Berkshires. … it’s home to award-winning restaurants, world-class performance venues, fascinating historical properties, great retail shops, a vibrant music and art scene, plus incredible outdoor recreation.”

Experience The Downtown Cultural District

Head downtown to North Street, a Massachusetts-designated Cultural District, boasting year-round live music, dance, performances, community celebrations, including two award-winning professional theaters and a dynamic visual arts scene.

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Find your happy place
outdoors!

Year-round outdoor beauty and adventures await! Enjoy hiking with breathtaking vistas, boating and water sports on pristine lakes, snowshoeing, downhill and cross-country skiing and more – all just minutes from downtown.

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