Grafton-Chester Getaway Circuit Tour

At a Glance …


70 miles in 3 stages (with 27 miles of optional loops). Note: A “stage” is defined as a day in which tour support services are provided and cycling is required from one hotel or B&B to the next.


Overall, the terrain is moderate, consisting mostly of gently rolling hills with some stretches which may test your cycling mettle; so, we’ve kept the required distances relatively short with optional loops to increase overall mileage if desired..


Southeastern Vermont’s Windham and Windsor Counties. The tour starts and ends in Bellows Falls, with overnight stops in Chester and Grafton.


Min 3 Days / 3 Nights.    Note: You may begin AND end your tour on the date of your choosing. You may also add as many “layover days” to your itinerary as you desire.


Gorgeous scenery; Visits to quintessential Vermont villages often cited as among New England’s most beautiful including Grafton and Chester; Historic covered bridges.

Base Price

$225.00 per person (does not include bike rental, vehicle parking fees, if applicable, or charges related to special services such as shuttles or SAGs for non bike rental customers).

Daily Itinerary …

Arrival Day

Bellows Falls Vermont Bike TourFree Day in Bellows Falls. Do the Historic Neighborhood Walking Tour, Dine, Shop, Relax. Spend 1 night.

You may arrive in Bellows Falls at the time of your choosing, as there are no activities planned for your arrival day. Of course, the earlier you arrive, the more time you have to take advantage of the sights and charms of this historic New England mill town.

Bellows Falls Vermont Bike TourBellows Falls is known for its magnificent view of the Connecticut River, the Vilas Bridge Waterfalls, the Mansion District, a quaint downtown offering a variety of antique shops, coffee houses and cafes offering wonderful daytime fare and a growing community of local artisans showing their wares. In the evening, be sure to dine at much praised Popolo and catch a movie a the historic Bellows Falls Opera House.

Stage One

Vermont Bike TourCycle from Bellows Falls to Chester, VT – Distance: 27 miles. Spend 1 night.

Once past the relative bustle of the Bellows Falls area, you’ll descend onto a  road paralleling the magnificent Connecticut River and its scenic fertile shores.. Bidding adieu to the Connecticut River Valley, you’ll then begin a gradual westward ascent on a paved rail trail that parallels the Black River to Springfield, VT. There you’ll have an opportunity to have lunch and enjoy strolling the picturesque streets of its nicely preserved downtown. Springfield was a manufacturing powerhouse through the mid-20th century; beyond the downtown, you’ll observe the renaissance of the old machining factories into offices and medical facilities.

Chester Vermont Bike TourBeyond Springfield your route takes a long, gradual climb before plunging down to the Williams River, the course of which you will follow via tranquil, thickly forested dirt roads the remainder of the way to Chester.

Chester is often cited as one of southern Vermont’s most picturesque villages with its wide village green flanked by historic sites, grand Victorian mansions, and a variety of interesting shops and eateries. Beyond the village green, you’ll find Chester’s “Stone House Village,” named for the pre-Civil War houses constructed from locally quarried stone.

Stage Two

Grafton Vermont Bike TourCycle from Chester, VT to Grafton, VT – Distance: 20 miles (with an optional 16 mile scenic loop from Grafton following your arrival). Spend 1 or more nights.

Because today’s ride takes you on a long climb on your way to Grafton, we’ve kept the mileage low so that you can relax and enjoy the scenery. Though long, the climb is fairly gradual, and you will want to stop frequently at any rate to enjoy the views of pristine forested hills.  The second half of your route is along an unpaved road and is virtually all downhill to Grafton, so your legs will have a chance to recover before you arrive at the day’s destination.

Grafton Ponds Bridge - VermontGrafton is one of Vermont’s most beautiful villages, and like Chester, is often cited in travel publications as being one of New England’s best places to visit and stay. Arriving early, you’ll have plenty of time to visit the Nature Museum, the Grafton Ponds Outdoor Recreation Center, The Grafton Forge Blacksmith, the Grafton Village Cheese Company and the Grafton Covered Bridge. Or, enjoy additional cycling and more bucolic scenery by doing an optional 16 mile scenic loop from Grafton following your arrival.

Stage Three

Grafton Vermont Bike TourCycle from Grafton, VT to Bellows Falls, VT – Distance: 23 miles (with an optional 11 mile loop to the historic village of Walpole, New Hampshire; home of Burdick’s Chocolates).

On this third and final day of required cycling, you’ll be immersed in rural beauty. Your route begins with a long stretch of quiet cycling out of Grafton with gracious country estates and gentleman farms on one side and  a babbling brook on the other. Grafton Vermont Bike TourYou’ll then do a switchback heading back toward Bellows Falls passing through deep forests, and the working farmsteads of Athens. You’ll then meet up with the Saxtons River and follow it to the sleepy village that bears its name. On your final stretch back into Bellows Falls, you’ll see a covered bridge.