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.
Last updated: May 16, 2026
3.0
(1)
51
riders
94.2km
04:22
1,110m
1,110m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
44
riders
51.3km
02:32
740m
740m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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9
riders
95.3km
04:39
1,280m
1,280m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
15
riders
28.9km
01:16
290m
290m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
11
riders
31.9km
01:48
650m
650m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
8
riders
62.3km
03:17
520m
520m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
5
riders
55.4km
02:19
410m
410m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4
riders
71.9km
03:12
500m
500m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
10
riders
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
11
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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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 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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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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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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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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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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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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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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