Bespoke Bike Tours New England

Autumn in the Berkshires

Launch Photo Gallery
Rich with color, art, and history, the Berkshire Hills of western Massachusetts make for spectacular fall cycling. Our routes lead through idyllic farmlands, forested hillsides, and quintessential New England villages. We’ll stop to visit the Berkshires’ best-loved cultural landmarks, from the Norman Rockwell Museum to Hancock Shaker Village, whose beautifully preserved buildings and gardens are all that remain of the Shakers’ eighteenth-century “City of Peace.” Artists, authors, and dreamers alike have found inspiration in the Berkshires’ beauty. Many a cyclist has as well!

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Join us "on location" with our latest New England bike tour video. Discover the best of New England cycling, culture, and cuisine from the Atlantic coast to the Berkshire Hills!


  • Bike through quintessential New England countryside and towns
  • Spectacular peak-season foliage display
  • Visit the Norman Rockwell Museum, Hancock Shaker Village, and the Clark Art Institute
  • Tour Chesterwood, Daniel Chester French’s home and studio
  • Historic Gilded Age mansions
  • Browse in art galleries and artisans’ studios
  • Short hikes in Bartholomew’s Cobble, Pleasant Valley Audubon Sanctuary, and the Ice Glen
  • Optional challenging tri-state ride to New York and Vermont


Day 1: Meet at noon at Boston Logan Airport, or drive to the Windflower Inn near Great Barrington for a two-night stay. We’ll relax with wine and cheese around the fireplace before our welcome dinner. (0 or 6 mi.)

Day 2: Serene pasturelands and majestic mountain views line our route to Bartholomew’s Cobble for a picnic overlooking the Housatonic River. Visit a metal sculptor’s studio along the way. Our loop ride discovers Berkshires’ village gems: Sheffield’s covered bridge, the classic town green in Alford, and Great Barrington’s shops and galleries. (22, 35, 46, or 59 mi.)

Day 3: Pedal past alpine views in the Monument Valley and handsome horse farms in the Tyringham Valley, where we’ll cross the Appalachian Trail. Longer options visit pretty Umpachene Falls and follow a pristine whitewater river. Tonight we’ll be welcomed at Devonfield in Lee. (34, 48, or 58 mi.)

Day 4: Enjoy the “art of cycling” on our loop visiting the Rockwell Museum, Gilded Age mansions, and Chesterwood, Daniel Chester French’s home and studio. Continue to the Tanglewood grounds, summer home of the Boston Symphony Orchestra, or take a short hike through the ancient Ice Glen gorge. Two-night stay in Lenox at the Rookwood Inn. (15 or 30 mi.)

Day 5: Ride to Hancock Shaker Village, with time to visit the museum and its unusual round stone barn. A beautiful backroad option continues to Williamstown and the impressive galleries of the Clark Art Institute, or pedal on to inspiring views of the Taconic Crest on a tri-state loop into New York and Vermont! Farewell celebration. (31, 40, or 64 mi.) 

Day 6: Free morning in Lenox to browse in art galleries, tour Edith Wharton’s estate, or hike in the Pleasant Valley Wildlife Sanctuary. Early afternoon departure for Logan Airport. (0-11 mi.)

Trip Feedback

“It's been a whole week and we are still thinking about the great time we had on our Easy Rider Tour through the Berkshires!”
– B.A., California

"This was our first bike tour and it exceeded our expectations. There were riding options for all levels of cyclists and everyone was made to feel welcomed and included. All in all just a great combination of fitness, friendship, food, and fun."
- J.K., Ohio

"I've always wanted to visit the Berkshires. This trip was fantastic; I will definitely be back."
- K.H., California

"Location and timing caused me to investigate...excellent reviews online and helpful office staff made me decide to sign up. It was just what I needed. Thank you!"
- E.L., Georgia

"It was wonderful to see the Berkshires in full color, along with tours to places like Hancock Shaker Village...all this and cycling too"
- M.B. & N.B., Oregon

“I have long-dreamt of seeing the fall colors in new England and this tour is definitely the way to do it!”
– B.C., California

“We have been absolutely delighted with the organization, the knowledge and courtesy of our guides, the sheer and breathtaking beauty of the Berkshires, the optional route distances, the great accommodations, food, and group dynamics. Our expectations were well and truly exceeded!"
– I.S. & J.S., Australia

“Well worth crossing the Atlantic for!” 
– J.R., England

“A perfect blend of invigorating cycling, spectacular countryside, beautiful inns, delicious food, and fun, fun people.”
– J.E., Texas

“I wish I could magically impart to you as much fun and satisfaction on your next tour as we've had on this one!”
– Adventure Cycling Magazine

What's Included

  • 5 nights accommodations in historic country inns and a Victorian mansion (double occupancy, private bath)
  • 4 dinners, 2 picnic lunches, and all breakfasts
  • Use of a top-quality 27-speed hybrid or road bike
  • Detailed maps, written directions, and background information
  • Daily choice of mileage options; total mileage of 102 to 228 miles
  • Two experienced guides
  • Support van to carry luggage, provide snacks, and offer assistance and lifts
  • Admission to the Rockwell Museum, Chesterwood, and Hancock Shaker Village
  • Transfers to and from Boston Logan Airport at specified times
  • Gratuities for all accommodations and group meals
  • Comprehensive tour preparation information and training tips
  • Easy Rider cycling jersey and water bottle
  • Airfare is not included.

Boston Logan Airport

Price: US$2895 pp for
6 day/5 night guided bike tour.
Single supplement: $600.

Bespoke Private Tour: Minimum group of 10 required.


Activity Level: 2, 3. Moderate to hilly terrain. Challenging options for strong riders.

See more New England bike tours.