Historic River Valleys 3-Stage Tour with Chester
Location & Tour Highlights
You may schedule your tour to begin on any date during our tour season, which extends from May 1 through October 31. See
Scheduling Your Bike Tour for scheduling considerations. Length & Format
3-stage circuit tour requires a minimum of 3 days / 4 nights. Spend as many days as you like in overnight destination.
This is the least challenging of our Vermont circuit tours. The terrain is mostly easy to moderately challenging. However, there are stretches of the ride that will test your climbing mettle.
88 miles in 3 stages plus miles of optional cycling. Average of 29 miles per day.
Southeastern Vermont's lovely and historic Windham and Windsor Counties, and small portions southwestern New Hampshire. The tour starts and ends in Brattleboro, Vermont. See
Getting to Brattleboro for
transportation options to the tour's starting point. Highlights
Overnight destinations: Brattleboro, Grafton, & Bellow Falls
Mostly easy-to-moderate cycling along river valleys
Visits to quintessential Vermont and New Hampshire villages, including Grafton, Chester, Walpole (NH) and Newfane, among New England's most beautiful
Opportunities to supplement your cycling with hiking, swimming, or canoeing
Historic covered bridges
*The route map is only a close approximation of the tour's route and is not intended for navigation purposes. It
is provided to show the area covered by this tour's itinerary.
Arrival Day: Free day in Brattleboro. Sightsee, Canoe, Kayak, Dine, Relax. Spend 1 or more nights.
You may arrive in
Brattleboro 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 wonderful New England town.
Brattleboro is a lively southern Vermont arts and cultural center, ideal for window shopping, gallery
hopping, people watching, participating in a walking tour, canoeing on the Connecticut River, hiking the trails of the Brattleboro Retreat or visiting the Retreat's Petting Farm, buying Vermont handcrafts,
relaxing over a locally brewed beer, catching a movie or some live music, and of course, enjoying any one of a variety of exciting eateries and fine restaurants.
Accommodation options for your stay in Brattleboro include a downtown 1930's art deco style hotel, several lovely bed and breakfasts, and for the budget-minded, a variety
View Brattleboro's accommodation options.
Stage 1: Cycle from Brattleboro, VT to Bellows Falls, VT - Distance: 27 miles. Spend 1 or more nights.
Following breakfast you'll attend a brief orientation at your hotel or B&B, test
ride your bicycle, and then begin your first day's journey from Brattleboro to Bellows Falls.
Today's route follows the mighty Connecticut River, which forms the border between Vermont and New Hampshire. Though cycling in the fertile, orchard-studded valley carved by the river, the terrain is
gently rolling, with occasional rises providing beautiful views of the mountains just across the river. You arrive shortly in the quintessentially Vermont village of
Putney, known as a Mecca for arts and crafts, and a wonderful opportunity to break and refuel.
Beyond Putney, your route takes you down to the riverside for wooded cycling on a quiet dirt road before reaching Westminster. In Westminster you
cross the river to the New Hampshire side for the day's final riverside stretch. Just ahead, the mountains begin to close in on you, creating Bellows Falls' dramatic setting. Crossing back into Vermont, you
reach the day's final destination, Bellows Falls.
Bellows Falls was a manufacturing powerhouse in the 19th century, putting to use the massive energy of the falls for which it is
named. The old factories are mostly gone now, but the vestiges of that prosperous era remain in the Victorian mansions that comprise the town's
registered historic district. (You can even overnight in one, if you wish.) Bellows Falls is a wonderful place for strolling and soaking in the New England atmosphere.
The village even provides a walking tour of the historic district.
Accommodation options for your stay in Bellows Falls include two B&Bs and an economy motel. If you prefer to stay in a smaller village, you also have the option of staying
at one of two B&Bs in nearby Saxtons River, VT.
View Bellows Fall's accommodation options.
Optional Free Day(s) in Bellows Falls Area with Optional Cycling.
We encourage you to spend at least two nights in the Bellows Falls area to
take advantage of additional cycling in the area. You have the choice of two day-trip rides: (1) a moderately challenging 29-mile ride through deep forests and sleepy New Hampshire villages, which includes
the opportunity to visit historic Charlestown, NH and a restored
18th century fort; and (2) an easy 11-mile ride to Walpole, one of New Hampshire's most beautiful villages and home to locally renowned Burdick's
In addition to these cycling options, you can make the short, scenic ride along the Saxtons River to the quaint village of Saxtons River. Or you can take a break from
cycling altogether and spend the day looking at Indian petro graphs by the river, browsing in the local shops, or strolling the streets to become more familiar with the charms of Bellows Falls.
Stage 2: Cycle from Bellows Falls to Chester, VT - Distance: 27 miles. Spend 1 or more nights.
Leaving the relative bustle of Bellows Falls you quickly return to quiet, wooded cycling along the Vermont side of the Connecticut River. Here the river cuts right
through the more rugged landscape, providing occasional vistas of the narrow river valley. Bidding adieu to the Connecticut, you 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. Like Bellows Falls, Springfield was also a manufacturing powerhouse in the 19th century, and you can still see its Industrial Revolution era factories that once
harnessed the river's power. Beyond Springfield your route takes a long, challenging 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 a village full of charm and good-natured Vermonters looking to share their
portion of paradise with you. You'll definitely want to spend some time exploring Chester's artisan and retail shops, marveling at the grand Victorian
homes, and perhaps swing by Chester's "Stone House Village," named for the pre-Civil War houses constructed from locally quarried stone. Accommodation
options for your stay in Chester include one historic inn, six B&Bs, and one economy motel. View Chester's accommodation options.
Optional Free Day(s) in Chester
With its quaint shops, cafes, and beautiful setting, it would be a shame not to spend at least one day relaxing and becoming better acquainted with this charming quintessentially Vermont village.
Stage 3: Cycle from Chester, VT to Brattleboro, VT - Distance: 34 miles. Spend 1 or more nights.
Your final cycling stage is one of exceptional beauty along quiet back roads.
After leaving Chester, you return to the shaded canopy of the forest for a relaxing, rolling, and gorgeous ride into Grafton. Grafton
is one of Vermont's most beautiful villages and is like a trip back to a simpler time. The restoration of its historic structures is magnificent, as is its setting.
From Grafton most of your route is downhill, so you'll have nothing to distract you from the picturesque farms and maple sugaring shacks you'll pass as you follow the south branch of the Saxtons
River to the pretty village of
Townshend, your introduction to the beautiful West River Valley. Then it's on to Newfane, the loveliest of Windham
County's so-called 18th Century "White Villages." (Virtually all of Newfane's buildings and homes are white, from the grand, Federal-style courthouse to the smallest private home.) Newfane is the
ideal place to stop for lunch and explore the beautiful buildings along the village green.
Beyond Newfane, your route follows the West River, where you have a number of opportunities to take a
dip with the locals in one of several pristine swimming holes. At the
Covered Bridge, Vermont's longest covered bridge still open to traffic, you have the option of continuing your flat route back to
Brattleboro along the West River, or taking an exceptionally beautiful, but more challenging ride through the mountains for some incredible vistas of the West River Valley.
In Brattleboro, you'll have a final opportunity to shop for keepsakes made by Vermont artisans and enjoy at least one more evening of fine dining before heading home.
To Main Menu