Bicycle tour of the south Berkshires of Massachusetts
Six rides in the Berkshires for intermediate to advanced cyclists

Lenox Mountain overlookThe Berkshires are the cultural center in the mountains and hills of western Massachusetts. We suggest this tour with six days of cycling to the Berkshires' most popular attractions. 5 nights, 6 days based in Great Barrington, Massachusetts. Daily Ride options are 35-50 miles, with rolling hills and a few good climbs, designed for upper intermediate to advanced cyclists. Road or light hybrid bikes are required, and all roads are paved. Our rides are on safe quiet country roads with very little traffic. To fully enjoy this tour, participants should be capable of riding the short or long loop each day

Location: Great Barrington, MA . We suggest staying at the Days Inn if you prefer to be near downtown in popular Great Barrington, Massachusetts. During your free time this week, you'll enjoy walking along this charming town's tree-lined streets. Make sure to spend one evening at the Mahaiwe Theater Performing Arts Center


Mill River Store cyclingRide 1: Umpachenee Falls : Today's ride takes you along the flat flood plain of the Housatonic River through Sheffield farmland to Umpachenee Falls. We'll stop for sandwiches at the Mill River General Store. On the return, enjoy an exhilarating downhill ride back to the Housatonic River before returning to Sheffield , where we'll stop by the oldest covered bridge in Massachusetts . Return by bike to Great Barrington. route map cue sheet

Cycling North Egremont MassachusettsRide 2: Stockbridge, West Stockbridge and Hancock Shaker Village: Today's rides take you along the edge of the Taconic Mountains and through tiny Alford to West Stockbridge where you'll have time to visit Baldwin's General Store and Hoffman Pottery. You may wish to continue farther for a visit to fascinating Hancock Shaker Village our Richmond, with a stop at Bartlett's Apple Orchard. In popular Stockbridge, MA you may wish to visit the Norman Rockwell Museum. and Chesterwood, the studio of Lincoln Monument sculptor Daniel Chester French. Our return is along the rapids of the Housatonic River to Great Barrington. 30 miles with extra loop options. This could be turned into two good rides. 35- 50 miles with rolling hills. Cue sheet map

View from Mount Everett in the BerkshiresRide 3: Bartholomew's Cobble and Twin Lakes This easy ride take us along back roads to Sheffield and Ashley Falls , where we'll visit 'Bartholomew's Cobble , an unusual limestone formation with plants and ferns that are generally found several hundred miles north of this area . Ride past the Colonel John Ashley House built in 1735 and said to be the oldest complete house in the Berkshires. Return to the inn for a free afternoon. Relatively flat 30 miles with extra mileage options. Cue sheet map

Advanced cyclists version: Mount Everett , New York State, Connecticut. For the "climbers", we have a 5 mile ascent toward the second highest mountain in Massachusetts, 'Mount Everett. After reaching rural Mount Washington, you'll have a great descent to Copake in New York State, riding near Bash Bish Falls. Continue a few miles on the 'Harlem Valley Rail Trail and cross into Connecticut, then join the above tour at Twin Lakes. This full day 55 mile ride is for advanced cyclists. cue sheet map

Bicycle ride near Sheffield, MARide 4: Beartown State Forest and Tyringham  This 40 mile ride takes you by the Berkshire Fish Hatchery in Hartsville and on to Monterey, MA, where you have the option to turn back through Beartown State Forest with a challenging quarter mile climb and easy descent--for a shorter ride. The full ride continues with a sweeping descent into Tyringham, continuing to Lee, South Lee, and Tyringham, then following the Housatonic River rapids back to Great Barrington .   cue sheet map



Cycling near Jiminy Peak in the BerkshiresOther Activities: You may wish to take time to visit other Berkshire cultural highlights: The Mount in Lenox, the Massachusetts Museum of Contemporary Art, (MassMOCA) in North Adams, and Kripalu yoga center next in Lenox

Getting There:
Great Barrington is at the intersection of Rts. 7 and 23 in the southwest corner of Massachusetts, approximately 150 miles from New York City and Boston.


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