Cycling tour of Western Massachusetts

Nine Day Bike Tour of Western Massachusetts.

Overview: This cycling trip begins with a ride from Northampton, MA to Great Barrington MA. You’ll stay three nights at the Days Inn in Great Barrington, then will ride from Great Barrington to the Maple Terrace Motel in Williamstown, MA. From there you ride back to Lenox MA, and Northampton. There are recommendations for two rest days as well during the ride.

Day 1: Ride from Northampton, MA to Great Barrington, MA. 57 miles, map and cue sheet provided. Suggested inn: Days Inn, Great Barrington.

Cue sheets and maps

Cue Sheet

Cue sheets and maps

Route Map

Day 2: Waterfalls Loop from Great Barrington. 40-50 mile options, with stops at Bartholomew’s Cobble and one or two waterfalls. Recommended stops: Bartholomew’s Cobble, Umpachenee Falls, Campbell's Falls, Buggy Whips Antiques.

Cue sheets and maps

Cue Sheet

Cue sheets and maps

Route Map

Day 3: Mount Washington / Bash Bish Falls climb from Great Barrington: 40 miles. Recommended stop: Bash Bish Falls.

Cue sheets and maps

Cue Sheet

Cue sheets and maps

Route Map

Day 4: Monterey-Tyringham-Lee- Stockbridge loop from Great Barrington, miles. Recommended stop: Chesterwood, home of sculptor Daniel Chester French, Norman Rockwell Museum, Berkshire Botanical Garden

Cue sheets and maps

Cue Sheet

Cue sheets and maps

Route Map

Recommended Great Barrington Restaurants: Bizen Japanese Restaurant , Castle Street Cafe , Old Mill

Day 5: Great Barrington to Williamstown via Alford, West Stockbridge, Hancock, and Pittsfield. Recommended stop: Hancock Shaker Village . Restaurant: Café Pomo d’Oro. Suggested inn: Maple Terrace Motel in Williamstown .

Cue sheets and maps

Cue Sheet

Cue sheets and maps

Route Map

(Recommended rest day in Williamstown, MA)

Recommended visits: Clark Art Museum, Williams College Museum of Art, Mass MOCA

Day 6: Bennington Loop from Williamstown: 45 miles. Option for extra 8 mile Petersburg Pass loop. Recommended stop: Hemmings Motor News old car museum. , the Bennington Fish Hatchery , ride under three covered bridges. having lunch at All Days and Onions in Bennington

Cue sheets and maps

Cue Sheet

Cue sheets and maps

Route Map

Day 7: Deerfield River loop from Williamstown, 55 miles . Recommended stop: Natural Bridge State Park.

Cue sheets and maps

Cue Sheet

Cue sheets and maps

Route Map

Recommended restaurants in Williamstown and North Adams Freightyard Restaurant & Pub , Hobson's Choice, Jae's Inn , Mezze Bistro & Bar. You might also enjoy hiking the great trails on Mount Greylock!

Day 8: Cycle to Lenox, MA via Adams, Ashuwillticook Rail Trail, Pittsfield. Suggested inn: Apple Tree Inn in Lenox.

Cue sheets and maps

Cue Sheet

Cue sheets and maps

Route Map

Rest day in Lenox, MA. Recommended nearby day off activities: Edith Wharton’s home, The Mount, Tanglewood Music Festival.

Day 9: Begin Huckleberry ride from Lenox to Northampton (Huckleberry ride continues on to Sturbridge.)

Cue sheets and maps

Cue Sheet

Cue sheets and maps

Route Map

Bicycle Shops in the Berkshires: Williamstown: The Spoke , Mountain Goat . Lenox: Arcadian Shop Great Barrington: Berkshire Bike and Board

 

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