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

Vermont Cycling Tour Itineraries

The Bridges of Windham County 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

3-stage circuit tour requires a minimum of 3 days / 4 nights. Spend as many days as you like in overnight destination.


With the exception of a very challenging 3-mile climb in stage 2 with an average grade of 6.2%, this tour's cycling itinerary is moderately challenging to challenging. There are long stretches of moderately rolling terrain, often on quiet dirt roads. You may forego the most difficult 3-mile climb in favor of a shuttle with your bikes. There is no additional charge for this when you rent bikes from us.


80 miles in 3 stages plus miles of optional cycling. Average of 27 miles per day.


Southeastern Vermont's lovely and historic Windham County. Tour starts in Brattleboro, Vermont's southern gateway. See Getting to Brattleboro for transportation options to the tour's starting point.


  • Overnight destinations: Brattleboro, Jamaica, & Wilmington
  • The five historic covered bridges of Windham County
  • Gorgeous scenery
  • Winery tour & free wine tasting
  • Sugar maple house tour
  • Visits to quintessentially Vermont villages
  • Opportunities to supplement your cycling with hiking, swimming, or canoeing

*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.

photoYou 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 to Jamaica - Distance: 26 miles. Spend 1 or more nights in Jamaica.

photoFollowing 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 Jamaica.

Following the crystal clear waters of the West River, you'll pass cascading waterfalls and the historic West Dummerston Covered Bridge, the first of five historic covered bridges you'll see on this tour and Vermont's longest covered bridge still in use. As you continue northward, you'll visit Newfane, the loveliest of Windham County's so-called 18th Century "White Villages;" Townshend;  the Scott Covered Bridge; and the Townshend Lake and Dam.

Along your way to Jamaica, you'll be tempted to stop (and we encourage you to do so) to sample locally grown produce and, of course, our world famous Vermont cheeses and maple products.  But save time for dipping your feet into the rushing waters of the West River below the Dummerston Bridge, shopping at the world famous Mary Meyer's Teddy Bear Shop in Townshend, and outdoor fun in Jamaica State Park.

Accommodation options for your stay in Jamaica include several lovely inns and two country bed & breakfasts. View Jamaica's accommodation options.

Optional Free Day(s) in Jamaica with Opportunities for Additional Cycling, Hiking, Swimming, Sunbathing, Shopping, or Just Relaxing.

photoIf you choose to have a second night in Jamaica, you'll have a variety of options from which to choose. We highly recommend an easy to moderate 5-mile roundtrip hike to Hamilton Falls, Vermont's highest waterfall, or hiking the easy riverside trails in Jamaica State Park -- with plenty of spots ideal for a refreshing afternoon swim.

Or you can return to the saddle and cycle the short distance to Ball Mountain Dam Recreational Area for more spectacular scenery. Or you may choose simply to explore the tiny village of Jamaica with its craft and antique shops.

Stage 2: Cycle from Jamaica to Wilmington - Distance: 27 miles. Spend 1 or more nights in Wilmington.

photoYour journey from Jamaica to Wilmington will take you far off-the-beaten path into dense forests on tiny, dirt roads. For many miles, you'll be surrounded by the sights, sounds and aromas of unspoiled woodlands interrupted only by the babbling streams and brooks running through them.

As you leave the forest, you'll begin to climb into the Green Mountains where you'll cycle passed some of Vermont's most well known ski resorts. Passing through the Mount Snow and Haystack resorts, you'll be challenged by several lengthy climbs but always rewarded with stunning vistas and exhilarating descents.

Finally, you'll coast into the fun and lively village of Wilmington where you'll find a myriad of boutiques, coffee shops, brew pubs with live music, and lots of wonderful restaurants!

Accommodation options for your stay in Wilmington include several very well-appointed inns, two charming bed & breakfasts and two unique motels. View Wilmington's accommodation options.

Optional Free Day(s) in Wilmington with Opportunities for Additional Cycling, Hiking, Swimming, Sunbathing, Kayaking, Shopping, or Just Relaxing.

photoIf you choose to have a second night in Wilmington, you'll have a variety of options from which to choose, including an awe-inspiring, optional 28-mile roundtrip cycling excursion featuring quiet, breathtakingly scenic roads, visits to several quintessential Vermont villages, including Dover, and the discovery of your third historic covered bridge, the tiny Williamsville Covered Bridge.

Should you need a break from the saddle, you may choose instead to visit nearby Lake Whitingham (also known as the Harriman Reservoir) with its crystal clear waters -- an idyllic location for swimming, sunbathing, kayaking, enjoying a picnic, and/or hiking along its pristine shoreline. Or you may find that a visit to a local winery for a free tour and wine-tasting and/or a visit to a local Sugar Maple House is in order.

However you choose to spend your free day in Wilmington, be sure to set aside some time to relax -- many accommodations offer pools and spa facilities -- and to explore Wilmington's eclectic mix of shops, boutiques, and fun places to eat and drink!

Stage 3: Cycle from Wilmington to Brattleboro - Distance: 26 miles. Spend 1 or more nights in Brattleboro.

photoFor your journey from Wilmington back to Brattleboro, you'll have two distinctively beautiful routes from which to choose (your route instructions includes additional information for selecting the route that's best for you.)

Our southern route is a bucolic delight featuring quiet, winding, dirt roads through rich woodlands and working farms (many of them organic). You'll cycle under the canopy of magnificent maple trees and follow the path of the meandering Green River until you reach the romantic Green River Covered Bridge. Entering Brattleboro via its foothills, you'll pass through the fifth historic covered bridge of your tour, the old-world Creamery Bridge.

On the other hand, our northern route features sights that fill the pages of classic Vermont wall calendars! From the quintessential Vermont town of Dover to the colorful wooded hillsides of your long and thrilling descent back into the West River Valley, these final images of the Vermont countryside will stay with you for a lifetime.

In Brattleboro, you'll return your bicycle, shop for keepsakes made by Vermont artisans and enjoy a final evening of fine dining and entertainment before heading home the next day.

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