Berkshire Bicycle Touring

Six days of cycling the southern Berkshires in western Mass.

This 6 day tour of the popular Berkshires in western Massachusetts is available by special group request from Bike New England. takes us into neighboring Connecticut and New York State, with 5 nights at the Windflower Inn in Great Barrington, MA. Daily rides are 30-45 miles, with a nice mixture of a few flat roads and rolling hills, designed for intermediate to advanced cyclists. Our fully supported rides take safe quiet country roads with very little traffic and a mix of beautiful valleys, farmland and mountain views in one of the most popular cycling destinations in the American Northeast.

Sunday, Day 1: Umpachenee Falls Ride This classic Berkshire ride starts out with some easy cycling along the flat flood plain of the Housatonic River through Sheffield farmland to Umpachenee Falls. The return includes an exhilarating downhill ride back to the Housatonic River before returning to Sheffield, where you may want to stop by the oldest covered bridge in Massachusetts. The distance is approximately 35 miles with the option to ride to Southfield for a total of 45 miles. We'll have dinner at the Old Mill Restaurant in nearby South Egremont. View Ride

Monday, Day 2: Twin Lakes This beautiful 46 mile ride take us past Twin Lakes and continues to Falls Village, Connecticut where we'll stop for lunch at the Toymakers Cafe for their great sandwiches, English banger platters or sweet potato waffles. The entire route is on quiet back roads and is relatively gentle, with just a couple of short climbs. On our return we'll stop to visit Bartholomew's Cobble, an unusual limestone formation with plants and ferns that are generally found several hundred miles north of this area. View Ride

Tuesday, Day 3: West Stockbridge and Stockbridge Today we ride north along the edge of the Taconic Mountains and through tiny Alford to West Stockbridge, where you can visit Baldwin's General Store and Hoffman Pottery. The ride continues on to Stockbridge, MA home of 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 and back to the inn, 35 miles with extra loop options. View Ride

Wednesday, Day 4: Mount Everett, New York State You'll have the option today of an easier start with van support or taking on the 5 mile ascent toward Mount Everett, the second highest mountain in Massachusetts. After reaching rural Mount Washington, you'll enjoy the steep descent to Copake in New York State, near Bash Bish Falls. We'll stop for lunch in the town of Copake Falls before continuing on the Harlem Valley Rail Trail. Our ride takes us through upstate New York farm land before returning along a mountain pass to the inn. (Left: a view of Mount Everett as we climb to the community of Mount Washington.) Cue Sheet and Map . There is also an alternative 19 mile ride without the Mount Everett climb. View Ride with climb. Note: Van support is provided the entire distance of this ride

Thursday Day 5, The Tyringham Valley: Today we head east from Great Barrington on a 40 mile ride to visit three of the Berkshire "hill towns". In Hartsville we'll stop for a short visit at the Berkshire National Fish Hatchery, then continue on to Monterey where we'll stop for a break at the Monterey General Store, continuously operated since 1780. We'll continue a steady but gradual climb, and then an exhilarating descent to Tyringham, where we'll stop to view Santarella, the "gingerbread house" built by sculptor Henry Hudson Kitson, known for the Lexington Minuteman and Plymouth Rock Maiden statues. Our return offers us a second visit to Stockbridge on our way back to Great Barrington. View ride

Friday Day 6: North Egremont: for our last morning together we'll enjoy up to 20 miles along the foot of the Taconic Mountains in North Egremont before saying our farewells. View ride

This tour is available by request. Please email Gordon at Bike New England to inquire about leading this tour for your group or family.

Lodging: 5 nights in Great Barrington , MA.

Meals: Continental breakfasts and dinners are included in the tour price. We pay for our own lunches.

Rides: Rides generally start about 9 am. Maps and cue sheets are provided for each ride, but routes are not arrowed. Your guide will ride at a moderate pace with participants, with occasional stops for scenery, photos, visiting towns etc. Shorter rides and/or van support are provided as needed or on request. Note: The Berkshires have a hilly terrain. Participants must be able to ride up to 40 miles per day at a minimum average pace of 12-13 mph.

Bikes: Road or fast hybrid bikes are required for this tour. Jamis Coda hybrid road bikes are available for $100 /week.

Other Activities: During our tour, You may wish to take time to visit other Berkshire cultural highlights including The Mount and Kripalu yoga center in Lenox. While in the area, see what's happening at the Mahaiwe Theater Performing Arts Center in downtown Great Barrington. Catamount Adventure Park just a few miles from our inn offers an exciting aerial forest adventure, training participants to navigate their chosen treetop courses with the safety of harnesses. Monument Mountain between Great Barrington and Stockbridge offers an outstanding lookout after a modest climb. The Appalachian Trail passes nearby, and there is excellent canoeing on the Housatonic River.

Bicycle Shipping and rental: Assembly, transportation and reshipping of your bike is available for a $100 additional charge, plus shipping costs. Pickup and return to Logan Airport in Boston is available for a $100 extra charge.

Price: $1450 / person for groups of 6 or more. Add $350 single occupancy.