Berkshire County Travel Guide

Massachusetts

A historic stone building with a yellow roof, surrounded by a white fence and lush green grass.
A waterfall cascading through a rocky gorge with snow patches on the rocks.
A railway track leading into a stone tunnel surrounded by greenery.
A rural landscape with a large red brick building, a smaller beige structure, and a green field.
A forested area with a waterfall cascading over rocks.

Popular cities in Berkshire County

A town hall with a central dome and columns, surrounded by trees and people.
Lenox
Known for Live music, Entertainment and Museums
A dream destination for those who love all things artistic, this upscale town is known for hosting the world-famous Tanglewood Music Festival.

Reasons to visit

  • Tanglewood Music Center
  • The Mount
  • Wyndhurst Golf & Club
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A historic building with classical architecture, a traffic light, and a yellow taxi.
Pittsfield
Known for Entertainment, Theatres and Sports
Located at a fork in the Housatonic River, this city provides an appealing mix of cultural diversions and outdoor pursuits.

Reasons to visit

  • Hancock Shaker Village
  • Bousquet Ski Area
  • Berkshire Museum
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The Purple Pub with outdoor seating and autumn foliage.
Williamstown
Known for Universities, Museums and Theatres
With culture, small-town charm and beautiful mountain scenery, this lively college town in the Berkshires is a very popular destination.

Reasons to visit

  • Williams College
  • The Clark Art Institute
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A row of parked cars along a street lined with brick buildings, including a sign for 'Vault Studio' and 'Hotpoint'.
Great Barrington
Known for Dining, Hiking and Live music
Enjoy fine dining and antique shopping at this Berkshires hub, along with hiking, biking and skiing in the surrounding countryside.

Reasons to visit

  • Lake Mansfield Park
  • Monument Mountain Reservation
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A nighttime view of a residential area with houses adorned with holiday lights.
Stockbridge
Known for Historical, Museums and Romantic
Get away to relaxing Stockbridge! Enjoy the gardens, camping and monuments.

Reasons to visit

  • Norman Rockwell Museum
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A street lined with historic buildings, including a Morgan House restaurant.
Lee
Known for Shopping, Museums and Scenery
This picturesque town has plenty of family-friendly activities and is ideally placed for exploring the largest forest in the state.

Reasons to visit

  • Goose Pond Reservation
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Stay near popular Berkshire County attractions

A wooden pergola structure with a pathway covered in fallen leaves, surrounded by trees and grass.

Tanglewood Music Center

9.6/10 (457 reviews)
You can make plans for a show at Tanglewood Music Center during your stay in Lenox. While you're in the area, stroll along the lakeside.
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