Southern Vermont River Valleys Tour

A Tip from a Repeat Customer:

“Before ordering your tour, jot down the towns you’ll be staying in then, go to the Accommodations page and jot down which inns you like most in those towns. Doing so will make completing your order fast and easy.”


At a Glance

106 miles in 4 stages, plus miles of optional cycling 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.
This is one of the lesser challenging of our Vermont circuit tours. Overall, the terrain is relatively easy (long, flat stretches on Stages 1 and 4) to moderate terrain (gently rolling hills); However, portions of Stages 2 and 3 may test your cycling mettle (for example, there is a long gradual climb out of Springfield’s Black River Valley on Stage 2).
Southeastern Vermont’s Windham and Windsor Counties. The tour starts and ends in Brattleboro, with overnight stops in Bellows Falls, Chester and Grafton.
Min 4 Days / 4 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, Chester, and Newfane; Historic covered bridges.
Base Price
$349.00 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). Hybrid Bike Rental Fee: $35 per day / Electric Assist Bike Rental Fee: $75 per day.

Daily 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.

Stage 1

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

Following breakfast you will 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.

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, 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 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.

Stage 3

Cycle from Chester, VT to Grafton, VT – Distance: 20 miles. Spend 1 or more nights.

Because 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 long, 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. The restoration of its historic structures is magnificent, as is its setting.

Stage 4

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

Today’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.

Client Views

  • Wow! David is remarkable! Whatever seemed to go awry, whether a flat, another flat, rain or even support when I had to leave early, David had a back-up plan already developed when he sent a quick reply and made it happen! He was patient, kind and professional at all times. I recommend Diverse Directions Cycling Tours and would select them again in a heartbeat. So glad we found them.

    - Jill from the Biker Chicks on Google
  • Did a four day cycling trip in Southern Vermont, roughly 30 miles a day, through quaint small towns. We stayed at a charming local inn each night. David, the owner, provided us the routes to follow each day which were super. Roughly half on backroads and the other half on dirt roads which were quiet and picturesque. They collected our bags each morning to transport and were in communication each day with tips, weather and to check-in. We highly recommend to cyclists that love to get out on the bike but don't want to be bothered with logistics, planning the route and don't want to be a part of a group. Was perfect for us!

    - Michelle on Google
  • We had a terrific Trip! Thank you, David, for the excellent service. The cycling itinerary, accommodations, and dining recommendations were all fabulous. It was a lovely experience and we would highly recommend it!

    - Annemarie on Google
  • Booking with David saved our vacation! Perfect in every way. I can't recommend David and his services more. This isn't the kind of trip you want to go it alone! David thought of all the details to ensure we had the perfect bike routes and maximized our time. His selection of inns was spot-on -- a variety of properties all different but all special (and with FANTASTIC food and amenities). Can't say enough great things.

    - CatherineP on TripAdvisor

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