Great Barrington (37 min) | Lee (22 min) | Lenox (15 min) | North Adams & Williamstown (39/33 min) | Stockbridge (26 min)

*Average drive times from Pittsfield to other town centers

Famous For...

• Largest city in Berkshires

• Home to renowned museum and performing arts center

• Host of First Fridays Artswalk

• Cinemas, theaters and studios

• Diverse downtown storefronts, galleries and shops  

About Pittsfield

Pittsfield enjoys the distinction as the "City of Festivals." Perfectly placed in the heart of the Berkshires, this surprising haven bustles with cultural and recreational amenities. The first county agricultural fair in America was held here in 1810, perhaps portending its current-day reputation for celebrations. You'll discover many and varied concert series, art, culture, night life, fine and fun dining, charming lodgings, a professional baseball team, a multitude of parks and plenty of hometown celebrations and parades. Pittsfield embraces summer with an exciting Third Thursday celebration each month. The celebration includes countless arts and crafts, food vendors, Arts exhibitions, and other attractions. Among other venues are top-quality exhibitions at the Berkshire Museum, which houses American landscape paintings and an inspiring collection of Americana; and historical and cultural programming at Arrowhead, headquarters of the Berkshire County Historical Society and former home of author Herman Melville.

Find in Pittsfield

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    Food & Drink

    Browse the many Food & Drink options in Pittsfield more

  • shoes


    Browse the diverse shops in Pittsfield more

  • family fun in the berkshires

    Family Fun

    Browse the many family friendly activities to do in Pittsfield more

Stay & Plan

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    Drink, Dine, Decompress

    What better way to end your long day than with a cocktail and appetizer... in bed! the Courtyard by Marriott Lenox offers every convenience under one roof! more

  • Courtyard Marriott Lenox Girlfriend Getaway

    Girlfriend Getaway

    The Berkshires is the perfect place for a girlfriends notch shopping, amazing restaurants and comfortable lodging. more

  • Yankee Suites Extended Stays Pittsfield Ma

    Extended Stays

    Looking to stay a week? Month? Year? Yankee Suites Extended Stays offers fully equipped condo-style living in downtown Pittsfield. more

  • Yankee Inn

    Book an in-room massage

    Upgrade your next stay with the ultimate indulgence- an in room massage at the Yankee Inn more

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