Great Barrington, Massachusetts Travel Information

A Southern Berkshire Loop Many residents of eastern Massachusetts head north each autumn without ever having visited the Berkshires. Located in western Massachusetts, the Berkshire Hills extend from Vermont south to the Connec... Tyringham, MA

Beartown State Forest Campground Beartown State Forest is a beautiful, intimate campground set along the shores of Benedict Pond, a good-sized pond ready to accept anglers, swimmers, and paddlers. There are only 12 sites, but if ther... Monterey, MA

Lakeville, Canaan, and Winsted, Connecticut, and the Albany Turnpike In the days before railroads and superhighways, Hartford and Albany, New York, were linked by a rutted roadway called the Albany Turnpike. This highway of sorts was the main route through the rugged n... Canaan, CT

Monterey, Great Barrington, and the Massachusetts Southern Berkshires Winding country roads make it impossible not to double back on your tracks around here, but you won’t mind in this scenic New England of yesteryear, composed of farms, ponds, meadows of Queen Anne’s l... Great Barrington, MA

North Litchfield Hills Scenic Drive A 56-mile loop drive that wanders across wooded hills and up the Housatonic River in northwestern Connecticut’s scenic Litchfield Hills. The North Litchfield Hills scenic drive explores the rural nort... Canaan, CT

Other Activities

• Boston Area & Eastern Massachusetts Weekend Getaways and Day Trips
• Central and Western Massachusetts Weekend Getaways and Day Trips
• New York City Weekend Getaways and Day Trips
• Western Massachusetts and the Berkshires Off the Beaten Path Travel
• Trips from New York City (outside New York) Weekend Getaways and Day Trips
• Trips from Boston (in Massachusetts) Weekend Getaways and Day Trips
• Berkshires of Massachusetts Romantic Getaways and Places
• Bridgeport, Waterbury, and Western Connecticut Off the Beaten Path Travel

Housatonic River: Bridge Street to Brookside Road (Distance: 0.2 mi) This trip takes you down a lovely stretch of river filled with lots of privacy and past farm fields and the historic Great Barrington Fairgrounds. The river floats through the remains of the debris fi...

Great Barrington, MA - Flatwater Paddling & Canoeing - length:1.8 mi

Great Barrington Cruise (Distance: 0.3 mi) The Great Barrington Cruise is adapted from the Great Josh Billings RunAground, a triathlon run every fall. This ride follows the triathlon's cycling course almost to Stockbridge. It then turns sout...

Great Barrington, MA - Road Biking - length:28.9 mi

Monument Valley Ramble (Distance: 0.4 mi) Centering on the Housatonic River Valley, winding across its plain and rolling along the foothills this ride is virtually flat its entire first half, once you climb the initial mile-long hill. Passin...

Great Barrington, MA - Road Biking - length:37 mi

Housatonic River: Brookside Road to Old Covered Bridge (Distance: 1.2 mi) The Nature Conservancy calls the southern Berkshires home to “one of the most globally significant ecosystems in New England.” The combination of calcareous bedrock, alkaline soils, pure water, and la...

Great Barrington, MA - Flatwater Paddling & Canoeing - length:4.8 mi

Housatonic River: Division Street to Bridge Street (Distance: 2.6 mi) It is sometimes difficult to admire the scenery while floating down quickwater, but if you do glance about you will see tall sycamore and cottonwood trees clustered along the shore. The sycamore trees...

Great Barrington, MA - Flatwater Paddling & Canoeing - length:4.2 mi

>> See all Trails near Great Barrington, Massachusetts

Wyantenuck Wyantenuck Country Club Private Equity, 18 holes 6403 yards, par 72 1.7 miles from center of Great Barrington, Massachusetts

Egremont Egremont Country Club Public, 18 holes 6036 yards, par 71 3.0 miles from center of Great Barrington, Massachusetts

Stockbridge Stockbridge Golf Club Private Equity, 18 holes 6567 yards, par 71 6.6 miles from center of Great Barrington, Massachusetts

Greenock Greenock Country Club Public, 18 holes 3080 yards, par 35 9.3 miles from center of Great Barrington, Massachusetts

Cranwell Cranwell Resort, Spa & Golf Club Public, 18 holes 6204 yards, par 70 11.3 miles from center of Great Barrington, Massachusetts

>> See all Golf Courses near Great Barrington, Massachusetts