Bespoke Bike Tours New England

The Art of Cycling

Launch Photo Gallery
World-class museums and music add an artsy spin to summertime biking in the Berkshires! Our Western Massachusetts bike tour visits celebrated venues as well as some hidden treasures in this sophisticated mecca of art, music, literature, and dance. Your imagination will be in high gear as we tour Chesterwood, where sculptor Daniel French created the Lincoln Memorial; admire Shaker ingenuity at Hancock Village; and savor a concert under the stars at the Tanglewood Music Festival.

The biking is as varied as the artistry. We'll ride past forested wilderness and flowering meadows, Colonial-era houses and Gilded Age mansions, and villages immortalized by iconic illustrator (and cyclist) Norman Rockwell. Discover the Berkshires’ unique mix of cycling, art, and nature!

Watch our Biking in New England video

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
  • Experience a Boston Symphony Orchestra concert under the stars
  • Visit Hancock Shaker Village, the Norman Rockwell Museum, and the Clark Art Institute
  • Tour Chesterwood, Daniel Chester French’s home and studio
  • Historic Gilded Age mansions and spectacular summer gardens
  • 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: Mid-morning rendez-vous at Boston Logan Airport for our transfer to the Windflower Inn for a two-night stay in Great Barrington. Take an afternoon warmup spin past classic New England farms and Simon’s Rock College, then relax with a wine and cheese reception back at our inn. Tonight’s dinner at The Old Mill is set in an atmospheric chestnut-beamed gristmill. (8 or 15 mi.)

Day 2: Bike a scenic loop to Sheffield and its fine antique shops, with a longer option into Connecticut for mountain lakes and a historic iron-smelting furnace. En route we’ll visit a contemporary metal artist at Butler Sculpture Park, and picnic at Bartholomew’s Cobble, a quartzite knoll rich with ferns and flora. Nearby is the Colonel Ashley House, from where enslaved African American Mum Bett Freeman sued for her freedom, helping to end slavery in Massachusetts. (23, 35, or 59 mi.)

Day 3: Spin through the 18th-century hamlets of Alford and Housatonic to Chesterwood, where we’ll tour the home and studio of Daniel Chester French (sculptor of the Lincoln Memorial). Your choice in the afternoon of visiting the Norman Rockwell Museum, strolling the garden paths at Berkshires Botanical Gardens, or a hike through the ancient Ice Glen. After we regroup, the home stretch of our ride to Lenox takes in picturesque horse ranches and sweeping mountain views. The Victorian-styled Rookwood Inn is located in the heart of town, close to tempting restaurants, galleries, and shops. (25 or 35 mi.)

Day 4: Pedal up to Olivia’s Overlook for birds-eye vistas, then on to Hancock Shaker Village to tour its 19th-century Meetinghouse, communal Brick Dwelling, and unusual round stone barn. Afterwards, loop back to Lenox, with a stop at a Calder-inspired mobile gallery in West Stockbridge. The longer ride options wind through New York’s Rensselaer County, then on to Williamstown and the impressive galleries of the Clark Museum. Tonight’s grand finale at Tanglewood is a feast for the senses: a gourmet picnic dinner followed by a concert under the stars! (31, 40, or 64 mi.)  )

Day 5: Free morning in Lenox to browse local art galleries, tour Edith Wharton’s palatial Gilded Age “cottage,” or hike in the Pleasant Valley Wildlife Sanctuary. Early afternoon departure for Logan Airport, rriving at around 5:00 p.m. (0-11 mi.)

Trip Feedback

“The Berkshires trip was amazing. The B&B's were unique, the food was outstanding, and I also enjoyed the museums and hiking. I would definitely recommend this trip to anyone who is interested in cycling and wants to meet new friends...”
– K.H., California

“I was, and always have been, impressed with the care and attentiveness of the guides in meeting our every need. We look forward to doing more trips with Easy Rider.”
–R.S. & C.S., Michigan

“Excellent reviews online and helpful office staff made me decide to sign up. This was a much-needed vacation, and I was able to relax and escape completely. Thank you!”
– E.L., Georgia

“A very enjoyable, well-organised tour, with excellent cycling equipment.”
– K.S. & S.S., Austraila

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

What's Included

  • 4 nights accommodations in historic country inns (double occupancy, private bath)
  • 3 dinners, 2 picnic lunches, and all breakfasts
  • Use of a top-quality 27-speed Trek hybrid or Cannondale road bicycle
  • Detailed maps, written directions, and background information
  • Daily choice of mileage options; total mileage of 87-184 miles
  • Two experienced guides
  • Support van to carry luggage, provide snacks, and offer assistance and lifts
  • Admission to Chesterwood, Hancock Shaker Village, and the Tanglewood Music Festival
  • 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$2750 pp for
5 day/4 night guided bike tour.
Single supplement: $550.

Bespoke Private Tour: Minimum group of 10 required.

2022 Season
July, August

Activity Level: 2, 3. Moderate to hilly terrain. Wide range of options for all riders.

See more New England bike tours.