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Routes
Road cycling routes
United States
Vermont
Windsor County

South Woodstock

The best road cycling routes around South Woodstock

26

riders

16

rides

Road cycling routes around South Woodstock, Vermont, traverse a landscape characterized by rolling hills, verdant forests, and the Ottauquechee River valley. The region, nestled within the Green Mountains, offers varied terrain suitable for road cyclists, from gentle ascents to more challenging climbs. Historic covered bridges and picturesque village settings are common features along these routes. The area provides a network of paved roads that wind through scenic vistas and rural environments.

Best road cycling routes around South Woodstock

  • The most…

Last updated: July 8, 2026

20

riders

#1.

Woodstock Middle Covered Bridge – Taftsville Covered Bridge loop from Quechee

66.6km

03:11

770m

770m

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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Moderate

Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

Hard
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Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

Hard

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate
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Tips from the Community

Natalie
January 29, 2024, Billings Farm & Museum

Billings Farm is an outdoor museum and dairy farm and a hidden gem of Vermont. It is an especially good place to come if you're cycling with children who will love seeing the farm animals up close, especially the herd of Jersey cows with their beautiful big brown eyes.

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Alex
January 29, 2024, Sheep Cemetery

A lovely old cemetery surrounded by a stone wall. Jump off the bike to take a closer look on foot.

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This road is a joy to ride whilst it travels through the woods with stunning hills such as Mount Tom providing the backdrop.

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Alex
January 23, 2024, Woodward Reservoir

Woodward Reservoir in Plymouth, Vermont, offers a calm setting for cyclists. With its quiet reservoir and rural surroundings, riders can take a leisurely break. The reservoir's laid-back atmosphere and practical amenities, like picnic areas, provide a straightforward spot for cyclists to relax amidst Vermont's natural scenery.

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It is worth pedaling through Lincoln Bridge to truly appreciate the design and craftsmanship that went into its creation. Built in 1877, it was restored in the 1980s to ensure its survival for years to come.

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On the north side of the river there is a viewing spot where you can have a closer look at the Mill ponds and old dam waterfall. In the winter, the water freezes; a spectacular sight.

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Built recently in 2012, Hurricane Irene had damaged the previous structure so badly that it didn't reach the river bank on either side. It has been sympathetically redesigned to complement the other covered bridges in the area.

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Taftsville Covered Bridge was opened in 1836 and is very well maintained. You can also walk down onto the river bank to get a lovely view of the river crossing from below. There are information boards which provide further information about the wooden bridge's history.

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Frequently Asked Questions

What kind of terrain can I expect on road cycling routes around South Woodstock?

Road cycling routes in South Woodstock feature a diverse landscape of rolling hills, verdant forests, and the picturesque Ottauquechee River valley. While many routes offer gentle ascents, the region, nestled within the Green Mountains, also presents more challenging climbs for experienced cyclists. You'll find a network of paved roads winding through scenic vistas and rural environments.

Are there road cycling routes suitable for different difficulty levels in South Woodstock?

Yes, South Woodstock offers road cycling routes for various ability levels. The guide includes options ranging from moderate loops to more difficult climbs. For instance, the Woodstock Middle Covered Bridge – Carriage Barn Visitor Center loop from George Perkins Marsh Boyhood Home is classified as difficult, while the Woodstock Middle Covered Bridge – Silver Lake loop from Lincoln Covered Bridge is a moderate option.

What notable landmarks or natural features can I see along the road cycling routes?

Many routes pass by historic covered bridges, such as the Taftsville Covered Bridge, and offer views of natural features like the Ottauquechee River and Lake Runnemede. You might also spot prominent features like Mount Tom in the distance. The Carriage Barn Visitor Center – Taftsville Covered Bridge loop from George Perkins Marsh Boyhood Home, for example, leads past the historic Taftsville Covered Bridge (Taftsville Covered Bridge).

Are there any scenic viewpoints along the road cycling routes in South Woodstock?

While specific viewpoints are not always marked on every route, the entire region is known for its scenic beauty. Many routes offer stunning vistas of rolling hills and forests. For panoramic views, consider exploring areas around Mount Tom (Mount Tom), which often provides excellent perspectives of the surrounding landscape, such as the View from Faulkner Trail on Mount Tom.

Where can I find parking for road biking in South Woodstock?

While specific parking areas for each route are not detailed in the guide, many routes start from locations that typically offer public parking, such as visitor centers or village areas. For example, the Carriage Barn Visitor Center – Taftsville Covered Bridge loop starts near the Carriage Barn Visitor Center, which is a common starting point for outdoor activities and likely has parking facilities.

What is the best time of year for road cycling in South Woodstock?

The region is particularly beautiful during the fall when the landscape transforms with stunning autumn foliage, enhancing any outdoor excursion. Spring and summer also offer pleasant conditions for cycling, with lush greenery and comfortable temperatures. It's always advisable to check local weather conditions before heading out.

Are there any long-distance road cycling routes available?

Yes, South Woodstock offers routes of varying lengths. For a longer ride, consider the Lake Runnemede – Martin's Mill Covered Bridge loop from Breeze Hill, which is approximately 41.6 miles (67.0 km) long. Another option is the Woodstock Middle Covered Bridge – Carriage Barn Visitor Center loop, covering about 44.3 miles (71.2 km).

Can I find loop road cycling trails in South Woodstock?

Yes, many of the road cycling routes in South Woodstock are designed as loops, allowing you to start and end at the same point. Examples include the Woodstock Middle Covered Bridge – Silver Lake loop from Lincoln Covered Bridge and the Lake Runnemede – Martin's Mill Covered Bridge loop from Breeze Hill.

Are there any challenging road bike climbs in the South Woodstock area?

The Green Mountains backdrop means that challenging climbs are definitely part of the road cycling experience in South Woodstock. Routes like the Woodstock Middle Covered Bridge – Carriage Barn Visitor Center loop feature significant elevation gains, with over 930 meters of ascent, making them suitable for cyclists looking for a demanding ride.

What are some popular road cycling routes in South Woodstock?

Among the local favorites are the Woodstock Middle Covered Bridge – Silver Lake loop from Lincoln Covered Bridge, known for its historic covered bridges and scenic lake views. Another popular choice is the Lake Runnemede – Martin's Mill Covered Bridge loop from Breeze Hill, offering views of Lake Runnemede and another historic covered bridge.

Are there any cafes or pubs near the road cycling routes for a break?

South Woodstock village and nearby towns offer various local establishments where cyclists can take a break. The South Woodstock Country Store, a local landmark, has served the community for over 200 years and is a great spot for local charm and goods. While specific cafes directly on routes are not listed, the charming village settings along the routes provide opportunities to find refreshments.

How many road cycling routes are available around South Woodstock?

There are several road cycling routes available around South Woodstock, with this guide featuring 7 distinct routes. These routes have been explored by over 40 road cyclists using komoot, highlighting the area's popularity for cycling.

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