Bridges of Windham County 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

128 miles in 4 cycling stages with miles of optional loops, available upon request. 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 an easy to slightly challenging circuit tour. From several long flat stretches and rolling hills to a couple of climbs which may test your cycling mettle, this tour offers a wide variety of terrains.
Southeastern Vermont’s Connecticut River Valley. The tour starts and ends in Brattleboro with overnight stops in Newfane, Grafton, and Chester. In addition to being the birthplace of Vermont, Windsor County is home to more covered bridges than any other Vermont county.
4 Days / 4 Nights. Note: You may begin AND end your tour on the date of your choosing. You may add as many “layover days” to your itinerary as you desire or shorten the itinerary to fit into a long weekend. For layover days, cycling loops from your overnight destination are available upon request.
Gorgeous scenery; Brattleboro, the “Gateway to Southern Vermont. The iconic beauty of Newfane, Grafton and Chester, three of southern Vermont’s most beloved small villages and of course, eight of Windham County’s 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. Canoe on the Connecticut River, hike the trails of the Brattleboro Retreat, visit the Grafton Village cheese-making facility. Dine, Shop, Relax. Spend 1 night.

You may arrive in Brattleboro at the time of your choosing, as there are no activities planned for your arrival day. Brattleboro is a lively southern Vermont arts and cultural center, ideal for window shopping, gallery hopping, people watching, 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 to Newfane via Weatherhead Hollow – Distance: 35.2 miles. Spend 1 night.

This very bucolic ride with easy-to-slightly challenging cycling takes you west to Brattleboro’s Creamery Covered Bridge, before turning south for some wonderful cycling in the hollows between the mountain ridges south of Brattleboro. The route takes you briefly into Massachusetts by way of a shaded, unpaved road that parallels a beautiful cascading river; and then brings you back into Vermont through beautifully rolling areas mixed with forests and dairy farms. Back in Brattleboro, you will pass the uniquely designed buildings that comprise the former Estey Organ factory. Leaving Brattleboro, you cycle northward following the course of the West River from its mouth in Brattleboro to the quintessentially Vermont village of Newfane, one of New England’s most beautiful villages. On your way to Newfane, you’ll visit the magnificent Dummerston Covered Bridge, Vermont’s longest covered bridge still in use.

Stage 2

Cycle from Newfane to Grafton via Townshend’s Scott Covered Bridge. – Distance: 21.5 miles (optional side trips available). Spend 1 night.

Departing Newfane, you will continue traversing northward through the scenic West River valley. After serval miles, you’ll veer westward through a densely forested area along tranquil shaded roads making your way toward and then across the Townshend Dam and soon after, you will visit the recently refurbished, pedestrian only, Scott Covered Bridge.

Soon after, you’ll pass through the sleepy village of Townshend, Newfane’s sister village and begin your trek into Grafton, often described as one of New England’s most beautiful small towns. As you reach the village center, you’ll pass the tiny Grafton Ponds Covered Bridge.

When you reach Grafton, don’t be surprised if you find yourself wanting only to drink-in the lovely setting (if that’s the case, the swimming pond at the Grafton Inn is the perfect place to do so). However, you may also wish to visit the village’s art galleries, the local Nature Museum, the original Grafton Village Cheese Company or perhaps, engage in a variety of outdoor recreational activities at the Grafton Ponds Outdoor Center.

Stage 3

Cycle from Grafton to Chester via Bellows Fall & Springfield – Distance: 38.5 miles. Spend 1 night.

On this third day of cycling, you will experience an impressive variety of Vermont landscapes. Your route begins with a visit to the Kidder Hill Covered Bridge and continues with an easy stretch of quiet cycling out of Grafton as you parallel the meandering Saxtons River. On your way to Bellows Falls, you’ll pass through the tiny village of Saxtons River passing the Hall Covered Bridge. Once a hub of industry, Bellows Falls is home to the nation’s first man-made canal. As you pass through its downtown, a quick side-trip to the Vilas Bridge which is now closed to traffic will provide you with a great view of the magnificent falls for which the town is named.

Leaving the relative bustle of Bellows Falls you’ll return to quiet, wooded cycling along the mighty Connecticut River and soon after, turn westward onto the Toonerville Rail Trail which you’ll follow into Springfield. There you’ll have an opportunity to have lunch and enjoy strolling the picturesque streets of its nicely preserved downtown. Beyond Springfield your route takes a long, gradual climb before plunging down to the Williams River, the course of which you will follow via a tranquil, scenic road, known as the Green Mountain Turnpike, leading you to the ever-so-charming town of Chester.

Stage 4

Cycle from Chester to Brattleboro - Distance: 35.5 miles. Spend 1 night.

On your final day of cycling, you’ll return to the scenic beauty of the Green Mountain Turnpike paralleling the Williams River, crossing it via the Bartonsville Covered Bridge and not long after, crossing it again via the Worall Covered Bridge. As you leave the Williams River corridor, you’ll enjoy a long stretch of quiet, back-road cycling through a lush valley of working farms, later jogging eastward toward the town of Putney through gently rolling hills dotted with orchards, vineyards and dairy farms.

In Putney, you’ll stop for lunch and explore the eclectic mix of shops before beginning the final leg of your journey following the Connecticut River back to Brattleboro.

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
  • 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
  • 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
  • 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

Read our reviews on:

Read our reviews on:


7 Miles from Ludlow - A Documentary

Enjoy this video:

Tour Customization to Meet Your Needs

Dear Diverse Directions, I am beginning to research a bike trip for my mother, sister and I in Vermont for the Fall. We did our own trip in Europe per-Covid and rode 25 to 30 miles / day(mom on an ...

Transportation Advice for Getting to Vermont

Dear Diverse Directions, For the cycling tour we're planning to do in June, we will most likely fly into Boston (perhaps Hartford or Burlington) and would prefer not to rent a car.  We see tha...


1547 Route 131
Springfield VT 05156
This email address is being protected from spambots. You need JavaScript enabled to view it.

© Copyright , Diverse Directions
All rights reserved.