The Berkshires Travel Guide

USA  #7 in Best Weekend Getaways in New England

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The Berkshires Area Map


The Berkshires is made up of a variety of towns, each offering different activities and cultural experiences. In the northern Berkshires, travelers will find the towns of Adams and Williamstown, which are home to two of the region's top art museums. Pittsfield, Lenox and Stockbridge sit in the central region of the Berkshires. These towns are known for their performing arts centers, bed-and-breakfasts and popular restaurants. The southern section of the Berkshires is home to Great Barrington, a charming town with antique shops and trendy cafes. Whether you are looking to immerse yourself in the arts, culinary experiences, history or the outdoors, you'll find just what you're looking for in the many towns that comprise the Berkshires.

This cozy town lined with boutique shops is also home to some of the area's most iconic properties, including the luxury wellness retreat Canyon Ranch Lenox, the historical country house and garden landmark The Mount, and comforting rustic restaurants like Nudel. What's more, staying in this town means being within easy reach of the Tanglewood performance venue and Shakespeare & Company.

For a diverse array of reasonably priced restaurants (more than 70 options) and intimate bars, quaint antique shops, and an impressive annual farmers market, visit Great Barrington. Its main street draws hipsters and families alike into its unique stores. Every corner offers an unexpected and exciting browsing opportunity and the town features the newly renovated Mahaiwe Performing Arts Center. For informational guided hikes and historic tours, sign up for one of the town's Housatonic River Walks, which are free in the summer. If you're looking to explore on your own, there are many locations with scenic trails varying in length and difficulty at Great Barrington's Alford Springs.

A visit to Stockbridge is not complete without stopping for a meal with live music at The Red Lion Inn. This is one of the oldest hotels in the Berkshires and is a great overnight stay as it is filled with on-site restaurants and nightly entertainment. There are many other famed restaurants, cafes and wine cellars on this countryside destination. Visitors also enjoy a visit to Stockbridge for its cultural attractions, like the Norman Rockwell Museum.

Lovers of the arts will enjoy this town's Clark Art Institute and Williamstown Theatre Festival. What's more, Williamstown is not far from the state's highest peak, Mount Greylock. Lodging options in Williamstown vary from austere mountain farmhouses to enchanting lodges.

This town, considered the heart of the Berkshires, is brimming with cultural experiences. Arrowhead Museum, the country estate where Herman Melville once wrote "Moby Dick," calls this town home. Renowned performers can be found at the 20th-century Colonial Theatre, which is part of the Berkshire Theatre Group. Travelers also recommend visiting Guido's Fresh Marketplace, which has its own pasta shop, sushi bar and large display of local meats and fishes.

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