Bicycle tour of the Berkshires, Lenox, Great Barrington, and Stockbridge
A six day tour of the beautiful southern Berkshires
for intermediate and advanced cyclists

North Shore CyclistsThis mix of beautiful valleys, mountains and farmlands in the Berkshires makes it one of the most popular cycling destinations in the American Northeast. Our six day tour take us to the Berkshires' most popular attractions , with 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 .

Request this Tour:
Available by special request only by groups of six or more from Bike New England, $1295 /per person .

Lenox Mountain overlookDay 1: Great Barrington. We enjoystaying at the charming Windflower Inn in Great Barrington, Massachusetts, near the South Egremont town line. A convenient and affordable option is the Day's Inn in Great Barrington.   After checking in,  set out on a gentle 15 mile "Get Acquainted" ride through North Egremont or Alford. .  Dinner each night ican be at one of the great restaurants in South Egremont and Great Barrington. 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 cyclingDay 2 Umpachenee Falls :Today's ride takes you along the flat flood plain of the Housatonic River through Sheffield farmland to Umpachenee Falls. Stop for sandwiches at the Mill River General Store. On your return, enjoy an exhilarating downhill ride back to the Housatonic Riverbefore returning to Sheffield , and stop by the oldest covered bridge in Massachusetts.  Rreturn by bike to the inn.  route map   cue sheet

Day 3 : West Stockbridge and Shaker Village Head out through North Egremont 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. 35- 50 miles with rolling hills. cue sheet  map

View from Mount Everett in the BerkshiresDay 4: (advanced cyclists) 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 short tour at Twin Lakes. This full day 55 mile ride is for advanced cyclists who enjoy climbs.  Cue sheet   map

Barthomews Cobble and Twin Lakes (intermediate cyclists)
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 . We'll ride past the Colonel John Ashley House built in 1735 and said to be the oldest complete house in the Berkshires. We return to the inn for a free afternoon. Relatively flat 30 miles with extra mileage options . Cue Sheet   map

Bicycle ride near Sheffield, MADay 5: Tyringham and  Stockbridge  Today's ride takes you past Butternut Ski Basin to Monterey, then descending to Tyringham and Lee.  An option is to turn on Monument Valley Road  in Great Barrington for a shortcut to popular Stockbridge, MA where 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.  Cue sheet  map

Friday, Day 6: Sheffield We set out early for a flat and beautiful 15 mile loop along back roads to Sheffield, staying in sight of Mount Everett, the state's highest mountain. Our retuirn brings us back to the inn in time for checkout..

Request this Bike New England Tour for your group

Cycling near Jiminy Peak in the BerkshiresPrice $1295 / person. Add$350 for single occupancy for groups of six or more. A $100 deposit is required to hold each reservation. Full payment is due two months before start date. You may cancel up to one month before the start date with full refund minus deposit. Partial refunds afterwards minus our obligations to inns.

Lodging: 5 nights at the Windflower Inn in Great Barrington, Massachusetts. Meals: Continental breakfasts and full dinners at local restaurants. We pay for our own lunches.

Rides: Rides generally start about 9 am. You will be led by Bike New England owner Gordon Harris and Berkshire guide Barbara Lampron. Maps and cue sheets are provided for each ride. . Both guides generally ride out from the inn with participants, offering a short and long version each day. Van support is provided only when necessary

Cycling North Egremont MassachusettsBike Rentals: Jamis Coda hybrid roadbikes with straight handlebars are available for $100 /week.

Other 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 Bicycle Shipping and rental: Assembly, transportation of your bikes is available for an additional charge. 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. Pickup and return to Logan Airport in Boston is available for a $100 extra charge

To Register: Email Bike New England or speak to tour director Gordon Harris, (978) 979-6598

Register for cycling tourDownload pdf tour signup form