Covered Bridges of Windsor 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

86.5 to 106.5 miles in 4 cycling stages with miles of optional 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 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. On days with challenging climbs, we’ve kept the required cycling distances relatively short.
The area known as the Upper Valley in southeastern Vermont’s Windsor County. The tour starts and ends in Windsor with overnight stops in White River Junction, Quechee, and Woodstock / South Woodstock. 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, shorten the itinerary to fit into a long weekend or, replace one or two cycling stages with shorter walking stages.
Gorgeous scenery; Visits to the most popular summertime destinations in Central Vermont … Quechee and Woodstock. Historic sites. Quechee Gorge. Marsh-Billings Rockefeller National Park (Vermont’s only National Park). Billings Farm and Museum. And of course, the beautiful, historic covered bridges of Windsor County (from six to ten).
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 Windsor. Visit the Windsor-Cornish Covered Bridge and explore the Old Constitution House and the Precision Museum, Dine, Shop, Relax. Spend 1 night.

You may arrive in Windsor 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 historic town on the Connecticut River.Known as the birthplace of the “free and independent State of Vermont” Windsor’s Historic District includes its “Old Constitution House,” the American Precision Museum (birthplace of the interchangeable parts concept for the machine tool trades), numerous historically noted homes and markers, and of course, the grand-daddy of all covered bridges.

Stage 1

Cycle from Windsor to White River Junction – Distance: 25 miles. Spend 1 night.

The ride on this day includes a wide variety of cycling terrains as you traverse beautiful Vermont landscapes. You’ll depart the Windsor area by way of gentle rolling hills dotted by horse farms and family-owned farms. Once you’ve had the opportunity to warm-up, your cycling mettle will be slightly challenged for several miles but, your efforts will be rewarded with gorgeous panoramic views.

About a third of the way into your ride, the terrain flattens, you’ll visit the picturesque Ottauquechee Twin Covered Bridges and then, begin your trek into White River Junction to enjoy the sights and charms of this “on the rise” hip gateway to the Upper Valley. White River Junction gets its name from its bygone heyday as a major junction of north-south and east-west railroad lines. In addition, the town sits at the confluence of the White and Connecticut Rivers. Today, commerce in WRJ has taken on a different form which has attracted a young, hip crowd looking for trendy restaurants, lively bars, chic boutiques, theater, and music. You’ll stay downtown in the historic Coolidge Hotel.

Stage 2

Cycle from White River Junction to Woodstock via Quechee – Distance: 22.4 miles with hiking, and / or swimming options. Spend 1 or 2 nights.

Your ride on this day begins with a relatively long stretch of flat leisurely cycling paralleling the White River. As you head west, you’ll enjoy the tranquil sights and sounds of riverside meadows with grazing livestock and fertile farmland. About halfway through your ride, you’ll begin your trek to the delightful village of Quechee via the verdant rolling hills of the Upper Valley.

As you cycle this day, you’ll pass through the Quechee Covered Bridge, the Taftsville Covered Bridge and Woodstock’s Center Bridge.

For those choosing to overnight in Quechee before heading to Woodstock, there’s plenty to do including a visit to the majestic Quechee Gorge, VINS (Vermont Institute of Natural Science) and you’ll be able to traverse your way between sights by way of the Ottauquechee River Trail and the Quechee State Park Trail System.

Recommended (Optional) Layover Day in Woodstock

Woodstock is a magnificently preserved New England village, offering an historic village green, beautiful riverside estates, a covered bridge, the Marsh-Billings Rockefeller National Park with miles of pristine hiking trails and guided tours of the Rockefeller Mansion, the award-winning Marsh-Billings Farm and Museum, tons of wonderful shops (may we suggest the Vermont Flannel Company) and a variety of exciting eateries to enjoy. Woodstock is an ideal destination for a mid-trip layover day.

Also available is lovely riverside cycling offering the opportunity to pass through yet another historic covered bridge, the Lincoln Bridge or, we can arrange day hike on the Appalachian Trail which passes through the region.

Stage 3

Cycle from Woodstock to South Woodstock via Barnard – Distance: 25.2 miles. Spend 1 night.

Departing Woodstock, you’ll head northward passing the Marsh-Billings Rockefeller National Park and soon after you’ll enjoy effortless cycling with expansive views through South Pomfret. As your trek turns north again toward Barnard, you’ll enjoy gently rolling hills with idyllic scenes of grazing cows on lush green hills lined with ancient stone walls.

Midway through your ride, you’ll encounter the sparkling waters of Silver Lake in Barnard where you can enjoy a refreshing dip and picnic alongside its banks (the Barnard General Store across the road prepares wonderful sandwiches to go).

The remainder of trek includes a long descent back into the Woodstock area where you’ll continue south into the idyllic Kedron Valley known for its tranquil horse farms and the Green Mountain Riding Association. You’ll stay at the Kedron Inn which includes a swimming pond for those warm summer afternoons.

Stage 4

South Woodstock to Windsor- Distance: 18.5 to 28.5 miles. Spend 1 night.

You’ll begin the day cycling further south along slightly rolling hills shaded by this forest on either side of the road. For much of the way, you will also enjoy the gurgling of the stream to your right. As the forest gives way to open pastures and farmland, you’ll begin to glimpse Mount Ascutney and soon, as you begin to head east, you’ll cycle in its shadow for many miles along quiet dirt roads, through two covered bridges and later the village of Brownsville.

For those wishing to do more cycling, there is an optional loop midway through the route which will take you back in time through three additional covered bridges which blend beautifully into the bucolic scenery. Finally, you’ll begin your descent back into the Connecticut River Valley.

Client Views

  • 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
  • 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
  • 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
  • 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

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