Find Adventurous Things to do For Travelers of All Ages

Berkshire visitors quickly find that this rural vacation area — long known as a cultural Mecca of museums, historic sites and performing arts venues — offers a year-round assortment of adventurous things to do for travelers of all ages and inclinations.

Scenic Driving Itineraries
Explore the beautiful countryside and historic towns of the Berkshires on these three driving routes.  

North Central Berkshire - Approximately 50 miles View Map 

  1. Begin at historic Park Square in the center of Pittsfield on Route 7, just a block north from where Route 20 bears off     westbound towards New York.
  2. Driving north from here on Route 7, pass by the beautiful mountain panorama surrounding Pontoosuc Lake. There are several beaches open to the public as well as rentals for sail boats, jet skis and canoes.
  3. Once in Lanesborough, turn right onto the Berkshire Mall Road and follow to its connection with Route 8 North. 8 North winds through the town of Cheshire before it arrives in Adams. A favorite pastime for locals and visitors is to bicycle on along the Ashuwillticook Rail Trail which runs parallel with Route 8. The Trail offers great scenic vistas of lake and mountains and places to stop for refreshments.
  4. Approaching the center of Adams, turn right onto Route 116 East, leaving behind this charming town while entering the rural beauty of the area’s farmlands and forests. Route 116 winds upward in elevation.
  5. After entering Savoy, look for River Road on the right leading to the Windsor Jambs, Windsor State Forest. This is a popular area for hiking and camping and is operated by the Department of Environmental Management. River Road passes by a cascading waterfall of spring water at the “jambs” next to Windsor Pond.
  6. Upon leaving the forest, River Road will meet Route 9 in Windsor; turn right onto 9 South. Follow through the old towns of Windsor and Dalton before returning to Pittsfield, via the busy Allendale Center and back to historic Park Square.

Central Berkshire - Approximately 78 miles  View Map 

  1. Historic Park Square, Pittsfield marks the central point in Berkshire County where all directional roads meet: North, East, South and West.
  2. Follow Route 7 South from Park Square one block and turn right onto Route 20 West. This scenic roadway passes by Clapp Park where sports and recreational activities take place in summer, fall, winter and spring. Leave the neighborhoods of Pittsfield behind and enter the rural countryside of old farming communities.
  3. Turn left at the intersection with Route 41 and follow south along one of the prettiest Berkshire roads reflecting old New England. The town of Richmond paints a charming picture of white, clapboard homes and old family cemeteries. Route 41 South soon enters the village of West Stockbridge where its center focuses on clusters of shops and restaurants, the Town Hall, and Library. Crossing through the center of this busy area is the Williams River, adding more to the sites to be seen here. In a short distance, Route 41 intersects with Route 102 East.
  4. Follow 102 East into Stockbridge to Route 183 North – a left turn at a yellow blinking light. This area is full of attractions, rich with history and popular with locals as well as visitors. Continue along Route 183 North into the center of Lenox. Notice the colorful Victorian Inns and attractive galleries that fill the town’s center.
  5. Stay on Route 183 North until it meets Route 20 East – a right turn. 20 East travels just minutes into Lee, ducking under the Massachusetts Turnpike. 20 East soon enters rural Becket. Once inside the town of Becket, look for the left turn onto Route 8 North. Winding through the hilltowns of Becket, Washington and Hinsdale, with an off-shoot into Peru, Route 8 North eventually leads into Dalton. Stately church steeples and colonial style architecture describe this old town of the Berkshires.
  6. Nearing the end of this tour, Route 8 North intersects with Route 9 South in the Allendale section of Pittsfield. 9 South guides drivers to the conclusion of this tour at Park Square in central Pittsfield.

South Central Berkshire - Approximately 44 Miles  View Map 

  1. This tour highlights so much of what the Berkshires is famous for – its scenic beauty and it cultural and performing arts venues.
  2. Begin on Main Street in Great Barrington and follow Route 7 North and cross over the Housatonic River to meet Route 23 East. Route 23 East leads to the mountains and wooded terrain often sought by hikers and explorers. Enter the small town of Monterey, where the General Store still operates catering to residents and second-homeowners alike.
  3. From the center of Monterey, turn left onto Tyringham Road and pass by Lake Garfield towards Tyringham. Upon arriving in Tyringham, notice the contrasting architecture; from an artist’s residence and studio to colonial farmhouses.
  4. Continue along the Tyringham Road until it intersects with Route 102 in Lee and turn left onto 102 West. In just five miles, enter the famous Main Street of Stockbridge immortalized through the painting by its’ own resident, Norman Rockwell. The Main Street of Stockbridge is the place to watch people while relaxing in a rocking chair or on a park bench. Walking in the area invites people to explore an ancient deposit of boulders from the Ice Age and the interesting Sedgewick family plot in the Stockbridge Cemetary. Opposite the historic Red Lion Inn on Main Street, turn right onto Pine Hill and then left at the fork to Prospect Hill Road. This area reflects the wealth of families from the Gilded Age who selected choice spots to build their 50 room “summer cottages".
  5. Return to Main Street, turning right onto Route 102 West and follow to the intersection with Route 183 South.
  6. Turn left onto 183 South. Notice the wonderful Berkshire attractions. A scenic ride along Route 183 and the Housatonic River passes through the picturesque villages of Glendale, Housatonic and Risingdale. Soon, the road re-enters the center of Great Barrington, concluding this tour.

Museums Gardens & Historical Sites
From the beloved paintings of Norman Rockwell to the public displays at Berkshire Botanical Gardens, immerse yourself in the cultural beauty of the Berkshires. For additional information, visit the Berkshire Visitors Bureau.

Theatre, Dance & Music
The Berkshires are unparalleled when it comes to offering a combination of exciting theatre, award-winning dance and world-renown music. Visit the Berkshire Visitors Bureau for complete information.

Galleries, Shopping & Antiques
The Berkshires are an antique lover's dream and our galleries have exquisite local and world-renown art. Plus, you'll love shopping in all the stylish boutiques in Lenox and other towns throughout the area. For additional information, visit the Berkshire Visitors Bureau.

Outdoor Sports & Recreation
You'll need more than one visit to the Berkshires to take in all the exciting activities available throughout Western Massachusetts. Visit the Berkshire Visitors Bureau for complete information on outdoor sports and recreational activities in the area. 

Family Fun in the Berkshires
The Berkshires are the ideal location for your next family vacation, offering an array of family activities for all ages. Many Berkshire museums and cultural attractions offer free admission for children and student discounts.

For a full list of family activities, visit the Berkshire Visitors Bureau.

Culinary Experiences
From farmers markets to wineries, let your palette explore the Berkshires. Visit the Berkshire Visitors Bureau for information and sTaste Berkshire on Facebook for the latest culinary news in the Berkshires, including "Edible Berkshires."

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Cranwell Resort, Spa and Golf Club

Exterior at Cranwell Resort, Spa and Golf Club, Lenox, MA

55 Lee Road, Lenox, MA 01240

Shakespeare & Company