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
$ 2,895.-
  • Spectacular peak-season foliage display.
  • Visit the Norman Rockwell Museum, Hancock Shaker Village, and the Clark Art Institute.
  • Historic Gilded Age mansions, and Berkshires’ village gem: Sheffield’s covered bridge.
  • Option to visit Umpachene Falls and follow a pristine whitewater river.
  • Short hikes in Bartholomew’s Cobble, Pleasant Valley Audubon Sanctuary, and the Ice Glen Gorge
  • Optional challenging tri-state ride to New York and Vermont.
  • Bespoke Private Tour: Minimum group of 10 required.
  • 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 Oct 2022 - 31 Oct 2022
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)

Prices *Please note the prices are subject to change depending availability*

Price per person / please note the prices are subject to change depending availability
The tour price per person
$ 2,895.-
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.
$ 600.-


Included / Not Included – lodging

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

* Moderate to hilly terrain. Challenging options for strong riders.

* This is a general itinerary. Tour itineraries are subject to change based on the group, available accommodations and other unforeseen circumstances such as the weather, local conditions, government intervention, that may affect the quality of the trip and/or safety of the participants. Please view this itinerary as an outline as to what to expect on this tour.


Transfers to and from Boston Logan Airport at specified times
5 nights accommodations in historic country inns and a Victorian mansion (double occupancy, private bath)
4 dinners, 2 picnic lunches, and all breakfasts
Gratuities for all accommodations and group meals
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
Comprehensive tour preparation information and training tips
Tour operators cycling jersey and water bottle

Not included

Airfare is not included.
Night before and after the tour
Gratuities for the guides


Historic country inns and a Victorian mansion

Map & Routes



bikes-easyrider All trip prices include the use of a top-quality bike for the duration of the tour. Our bicycle fleet consists of custom-equipped 24- and 27-speed Trek, Cannondale, and Marin hybrid and road bikes. Our hybrids are light enough to be efficient on paved roads, yet have the sure-footedness and low gearing of mountain bikes, with flat handlebars and sturdy wheels to take on the occasional dirt-road option.
Our leaders will adjust your bike to fit you properly and offer friendly coaching on shifting and riding technique. If you ride with a clipless pedal-shoe system, you're welcome to bring your own pedals and we'll install them.
This website uses cookies to save your search preferences on this website, thereby improving your user experience. In addition, we place cookies for measuring and tracking visitor statistics. By clicking Accept, or continuing to use this site, you agree with this.