My tour

Autumn in the Berkshires


Autumn Berkshires1

Historic inns, country lanes, and autumn colors combine for the best foliage cycling in New England. The routes lead through idyllic farmlands, forested hillsides, and quintessential New England villages.

Recreational, Road bike
6 days
367 km / 228 mi
$ 2,795.-
  • Bespoke Private Tour: Minimum group of 10 required.
  • Excellent meals and accommodations with a local character.
  • 5 Nights accommodations in historic country Inns and a Victorian Mansion (double occupancy, private bath).
  • Meals included: all breakfasts, 2 picnic lunches, 4 dinners.
  • Snacks and sport-drinks during the day.
  • Experienced cycling guides and support van.
  • Including guided tours of selected attractions.
  • Option to shorten or extend the daily distances.
  • Admission to the Rockwell Museum, Chesterwood, and Hancock Shaker Village.
  • Deposit for this tour is $500.-pp



Recreational, Road bike
6 days
Easy = untrained, normal physical condition
Moderate = regular cyclist, good condition
Challenging = experienced, well trained
Guided = with cycling guide(s) - support van
Self Guided = individual - directions+maps
Daily distance
60-80 km / 37-50 mi
Total distance
367 km / 228 mi
Deluxe = 4-5 star hotel or excellent B&B
Basic = 1-2 star hotel/motel or B&B
Camping = tent, sports hall or campus
Deluxe, half board
Luggage transport
Daily luggage transfers
01 Sep 2020 - 31 Oct 2020
Private tour minimum 10 riders in one booking
Gr. Barrington (12.00)
Lenox (14.00)
Logan Airport, Boston
Airport at start
Boston Logan Int. Airport (BOS)
Airport at finish
Boston Logan Int. Airport (BOS)


Price per person
The tour price per person
$ 2,795.-
Single supplement
If you travel alone a single supplement is charged. With some group tours you can avoid a single supplement by sharing a room with another rider.
$ 550.-


Day 1:

Meeting with the tour company representative at noon at Boston Logan Airport. Transfer to the tour start. Tour instruction and optional short ride. We’ll relax around the fireplace before our welcome dinner.

Day 2:

Serene pasturelands and majestic mountain views line our route to Bartholomew’s Cobble for a picnic overlooking the Housatonic River. Our afternoon loop ride discovers Berkshires’ village gems: Sheffield’s covered bridge, the classic town green in Alford, and Great Barrington’s shops and galleries.

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 stay at Devonfield in Lee.

Day 4:

Enjoy the “art of cycling” on our loop visiting the Rockwell Museum, Gilded Age mansions, and Chesterwood. Continue to the Tanglewood grounds or take a short hike through the ancient Ice Glen gorge. Arrival in Lenox.

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.

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 in Boston

Map & Routes



bikes-easyrider - Trek or Marin hybrid or Cannondale 27 speed road bike. All bicycles come equipped with handlebar bag, lock, and water bottle.
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