Diverse Directions Cycling Tours
Self-Guided Bike Tours in Vermont & Neighboring States

Vermont Cycling Tour Itineraries

Historic River Valleys 4-Stage Tour

General Information

Location & Tour Highlights

Tour Dates

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

4-stage circuit tour requires a minimum of 4 days / 5 nights. Spend as many days as you like in overnight destination.


Predominantly easy to moderately challenging. However, there are stretches of the ride that will test your climbing mettle, particularly in Stage 3, which involves a long, though not terribly steep section of climbing.


106 miles in 4 stages plus miles of optional cycling. Average of 27 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.


  • Overnight destinations: Brattleboro, Chester, Grafton, & Bellow Falls
  • Gorgeous scenery
  • 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.

Daily Itinerary
Arrival Day: Free day in Brattleboro. Sightsee, Canoe, Kayak, Dine, Relax. Spend 1 or more nights. photo

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 of motels. View Brattleboro's accommodation options.

Stage 1: Cycle from Brattleboro, VT to Bellows Falls, VT - Distance: 27 miles. Spend 1 or more nights.

photoFollowing 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.

photoWe 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 Chocolates.

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.

photoLeaving 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 Grafton, VT - Distance: 20 miles. Spend 1 or more nights.

photoBecause today's ride takes you on a long climb into the Green Mountains on your way to Grafton, we've kept the mileage low so that you can relax and enjoy the scenery. Though l ong, the climb is fairly gradual, and you will want to stop frequently at any rate to enjoy the views of pristine forested hills. This portion of the ride is pure nature -- just lovely scenery and few reminders that you have not left the 21st century for a more peaceful time. In fact, the second half of today's ride is along an unpaved state highway! How often do you encounter those? This second half of the ride is virtually all downhill to Grafton, so your legs will have a chance to recover before you arrive at the day's destination.

Grafton is one of Vermont's most beautiful villages and is like a trip back to a simpler time. Its setting amidst the hills and river is magnificent, as is the restoration of its historic structures. Accommodation options for your stay in Grafton include one very historic inn and two B&Bs in the neighboring village of Saxtons River. View Grafton's accommodation options.

Optional Free Day(s) in Grafton

photoShould you decide to spend two nights in Grafton we offer for your second day 2 very different cycling circuits. One is a 25-mile loop over quiet, wooded back roads, passing small farms, a covered bridge, and quaint villages like Cambridgeport and  Saxtons River.

The second cycling option is a 27-mile loop that takes you south to the pretty village of Townshend in the West River Valley. Adjacent to Townshend are two wonderful parks for hiking: Townshend State Park and Townshend Lake and Dam Recreational Area. On this loop, you also visit the Scott Covered Bridge, the longest wooden span covered bridge in Vermont.

Should you need a break from the saddle however, you may choose to stay closer to home, just soaking in Grafton's beauty, or taking the short half-mile ride to the Grafton Village Cheese Company, the Grafton covered bridge, and Grafton Ponds Outdoor Center.

Stage 4: Cycle from Grafton, VT to Brattleboro, VT - Distance: 32 miles. Spend 1 or more nights.

photoToday's ride is another of exceptional beauty along quiet back roads. From Grafton you follow the valleys of the Saxtons River, Bull Creek, and Grassy Brook on your way to the tiny village of Brookline, with its historic one-room, round schoolhouse. 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 West Dummerston 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.

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