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Routes
Road cycling routes
United States
Vermont

Rutland County

The best road cycling routes in Rutland County

4.4

(17)

465

riders

42

rides

Road cycling routes in Rutland County traverse a varied landscape within the Green Mountains of Vermont. The region features a mix of challenging mountain passes, rolling country roads, and scenic routes alongside several lakes and ponds. Elevations range from lower valleys to significant peaks, offering diverse terrain for road cyclists. The area is characterized by extensive forests, including old-growth stands, and varied topography from the Green Mountains to the Taconic Mountains.

Best road cycling routes in Rutland County

  • The most…

Last updated: May 16, 2026

3.0

(1)

51

riders

#1.

Billings Farm & Museum – Woodstock Middle Covered Bridge loop from Killington Resort

94.2km

04:22

1,110m

1,110m

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

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Hard

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

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

Hard

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy

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

Moderate

8

riders

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

Moderate

5

riders

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

Moderate

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

Moderate

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

Hard

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

Moderate
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Popular around Rutland County

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The Long Trail — America's oldest long-distance path

Hiking Collection by

Jamie S.

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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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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Jamie S.
December 29, 2023, Summit Pond

Summit Pond is a small freshwater pond at the base of West Hill on Killington Road. The Foundry at Summit Pond located on its southern side is a great place to grab a bite to eat on your ride.

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Scott
December 14, 2023, Pine Hill Park

Spanning 325 acres, this haven boasts 17 miles (ca. 27 km) of top-notch single-track trails. Ideal for mountain biking, and other outdoor sports in central Vermont. Explore old logging roads amid stunning forests and scenic vistas.

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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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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 touring 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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Natalie
December 13, 2023, Westerly Bridge

Woodstock Middle Covered Bridge has spanned the Ottauquechee River since 1969 and was supposedly constructed without the use of any nails.

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Frequently Asked Questions

How many road cycling routes are available in Rutland County?

Rutland County offers a diverse selection of over 40 road cycling routes. These routes cater to various skill levels, with options ranging from moderate to difficult, allowing cyclists to explore the region's varied terrain.

What do other road cyclists enjoy most about road cycling in Rutland County?

The road cycling experience in Rutland County is highly rated by the komoot community, with an average score of 4.3 stars. Cyclists frequently praise the region's varied terrain, which includes challenging mountain passes and scenic routes alongside lakes, all set within the beautiful Green Mountains.

When is the best time of year for road cycling in Rutland County?

The warmer months, typically from late spring through early autumn, offer the best conditions for road cycling in Rutland County. During this time, the Green Mountains are lush, and the weather is generally pleasant for exploring the diverse landscapes, from rolling country roads to challenging mountain ascents.

Are there easy road cycling routes in Rutland County suitable for beginners?

Yes, Rutland County has several road cycling routes suitable for beginners. Out of the 42 available routes, 8 are classified as easy, offering gentler terrain and less demanding ascents, perfect for those new to road cycling or looking for a more relaxed ride.

Where can I find challenging road cycling routes in Rutland County?

For experienced cyclists seeking a challenge, Rutland County offers 8 difficult routes with significant elevation gains. Routes like the Billings Farm & Museum – Woodstock Middle Covered Bridge loop from Killington Resort and the Hadley Hill – Spruce Knoll loop from Mountain Green Resort traverse mountainous terrain, providing demanding climbs and rewarding views.

Are there many loop road cycling routes in Rutland County?

Many of the road cycling routes in Rutland County are designed as loops, allowing you to start and end your ride in the same location. Examples include the West Hill – Spruce Knoll loop from Mountain Green Resort and the Pine Hill Park – Pine Hill Park loop from Rutland, which offer varied distances and elevations.

What kind of scenery can I expect on road cycling routes in Rutland County?

Road cycling in Rutland County offers incredibly diverse scenery. You'll ride through extensive forests, including old-growth stands, alongside picturesque lakes and ponds such as Chittenden Reservoir and Lake Bomoseen, and experience the dramatic backdrop of the Green Mountains, with elevations ranging from lower valleys to significant peaks.

Are there viewpoints or scenic overlooks along the road cycling routes?

Yes, Rutland County's mountainous terrain provides numerous opportunities for stunning views. While cycling, you might encounter vistas towards peaks like Killington Peak Summit and Pico Peak, or discover scenic spots like Deer Leap Overlook, offering panoramic views of the surrounding landscape.

Can I find routes that pass by lakes or water bodies?

Absolutely. Rutland County is dotted with beautiful lakes and ponds, and many cycling routes incorporate these scenic water bodies. You can find routes that pass by Chittenden Reservoir, Lake Bomoseen, Half Moon Pond, Lake St. Catherine, and Emerald Lake, offering tranquil waterside views.

Are there family-friendly road cycling options in Rutland County?

For families, the 8 easy-rated routes in Rutland County are generally the most suitable. These routes feature less challenging terrain and elevation, making them more enjoyable for cyclists of varying ages and abilities. Consider routes that stick to quieter country roads away from heavy traffic.

Where can I find parking for road cycling routes in Rutland County?

Many road cycling routes in Rutland County start from towns or recreational hubs that offer parking. For example, routes often begin near resorts like Killington Resort or Mountain Green Resort, or from state parks such as Gifford Woods, Bomoseen, or Emerald Lake State Park, which typically provide parking facilities.

Are there cafes or places to stop for refreshments along the routes?

While specific cafes are not listed for every route, many road cycling routes in Rutland County pass through or near small towns and villages. These communities often have local cafes, general stores, or diners where you can stop for refreshments, especially on longer loops that connect different areas.

What wildlife might I encounter while cycling in Rutland County?

Cycling through Rutland County's extensive forests and natural areas, you have a good chance of encountering various wildlife. Keep an eye out for deer, wild turkeys, and a variety of bird species. If you're lucky, you might even spot a black bear or a moose, especially in the more secluded sections of the Green Mountain National Forest.

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Didn’t find what you were looking for?

Check out more Road cycling routes throughout Rutland County below and find the perfect route in your destination.

CastletonRobert T. Stafford White Rocks National Recreation AreaRutlandPoultneyPittsfordBrandonProctorNorth ClarendonEast PoultneyWallingfordWest RutlandMiddletown SpringsJim Jeffords State ForestPawletCastleton Four CornersKillington VillageTaconic Mountains Ramble State ParkBomoseen State ParkDanbyWest PawletWellsFair HavenAitken State Forest

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