Diverse Directions
 Self-Guided Bicycle Tours in Vermont

The Bridges of Windham County Tour Itinerary

Tour Summary

Scheduled Tours: Each week from June 8th thru October 17th.

Length: 3 required cycling days. Spend 1 or more optional free days in each overnight destination..

Distance: 80 miles required. 32 miles optional.

Terrain: Easy to moderately challenging for relatively fit individuals. Long flat stretches often on quiet dirt roads. Some long but gradual climbs. Some short but steep climbs. Many rewarding, lengthy descents.

Location: Southeastern Vermont's lovely and historic Windham County. Tour starts in Brattleboro, Vermont's southern gateway.

Highlights:

* The five historic covered bridges of WIndham County.

* Winery Tour & Free Wine Tasting

* Sugar Maple House Tour

* Visits to quintessential Vermont villages

Daily Itinerary

Arrival Day: Arrive Brattleboro - Sightsee, Attend Orientation, Dine, Relax - Spend 1 or more nights.

We ask all tour participants to arrive in Brattleboro on Sunday by 5:00 pm and to attend an orientation session at 6:15 pm.

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. Click here to view Brattleboro accommodation options.

For more information about the town of Brattleboro, click here.

Required Cycling Day 1: Bike Pick-Up & Fitting - Cycle from Brattleboro to Jamaica - Distance: 26 miles - Spend 1 or more nights in Jamaica.

Following breakfast you will pick up and 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 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 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. Click here to view Jamaica accommodation options.

For more information about the village of Jamaica, click here.

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

If 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.

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

Your 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. Click here to view Wilmington accommodation options.

For more information about the village of Wilmington, click here.

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

If 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 32-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!

Required Cycling Day 3: Cycle from Wilmington to Brattleboro - Distance: 26 miles - Return Bicycle - Spend 1 or more nights in Brattleboro.

For your journey from Wilmington back to Brattleboro, you'll have two distinctively beautiful routes from which to choose (your route instructions will include 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.