4.5
(4)
109
riders
33
rides
Touring cycling routes in Rutland County, Vermont, traverse a landscape characterized by the Green Mountains, serene lakes, and extensive trail networks. The region features challenging climbs and rolling country roads, offering varied terrain for cyclists. Key natural features include parts of the Green Mountains, with peaks like Killington Mountain, and tranquil waters such as Chittenden Reservoir and Lake Bomoseen. Forests like Aitken State Forest and the Green Mountain National Forest also contribute to the diverse cycling environment.
Last updated: June 28, 2026
10
riders
76.4km
05:04
1,120m
1,120m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
7
riders
45.5km
04:17
870m
870m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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5.0
(1)
5
riders
19.7km
01:18
140m
140m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
5
riders
54.2km
03:34
760m
760m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
15
riders
16.9km
01:39
290m
290m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
5
riders
17.3km
01:10
130m
130m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
3.0
(1)
1
riders
19.7km
01:13
210m
210m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
6
riders
23.6km
02:26
460m
460m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
6
riders
72.2km
06:50
1,220m
1,220m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3
riders
37.5km
03:20
640m
640m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Rutland County
Cycling in Robert T. Stafford White Rocks National Recreation Area

Cycling around East Poultney

Cycling around Middletown Springs

Cycling around Poultney
Cycling around Killington Village

Cycling in Jim Jeffords State Forest
The Long Trail — America's oldest long-distance path
Hiking in Rutland County
Road Cycling Routes in Rutland County
MTB Trails in Rutland County
Forest Dale is a small community with a church, post office, and historic early-1800s ironworks, the ruins of which can be found on the northeast side of town. The Junction Store & Deli is open 7am-7pm most days if you want to grab a bite before continuing on your ride.
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Extremely hilly, sounds of nature, lot's to see & experience. Downhills are well worth the climbs. You definitely need to have some rides/climbing in your season. Update 7/26/25 Still crazy hilly & and punchy. However, the downhill runs are amazing..😉
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Brandon Gap is a tall mountain pass in the green mountains on Gap Road. This is a challenging climb in a beautiful area in the green mountains. The Long Trail crosses the road right at the summit of the pass, so be on the lookout for thru-hikers as you ride past!
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Middlebury Gap is a mountain pass in Vermont's Green Mountains and a great, very challenging climb for any rider. It divides two different drainage areas with the Robbins Branch flowing southeast into the White River, and the South Branch into Middlebury River, which into Otter Creek, connecting to Lake Champlain. The Long Trail, a 272-mile hiking route traversing Vermont, runs through here, passing between Worth Mountain and Boyce Mountain. The Breadloaf Wilderness lies to the north, while Middlebury College Snow Bowl and Joseph Battell Wilderness are nearby to the south.
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Hapgood Pond is a 12-acre pond that is 12 feet deep at its deepest point. This pond is within a recreation area of the same name. The recreation area has a campground, restrooms, picnic tables, and a swimming beach.
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Gifford Woods State Park is a popular destination for outdoor enthusiasts and Appalachian Trail through-hikers. The park has a wooded picnic area, two camping loops with water and restrooms, and one of Vermont's few remaining old-growth hardwood tree stands. The stand is home to grand-sized trees like sugar maple, beech, yellow birch, white ash, and hemlock, and the park's understory is rich with beautiful native wildflowers.
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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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Rochester welcomes visitors with its quintessential New England charm. Nestled amid picturesque mountains, the town offers outdoor adventures, artisan shops, and local eateries. Explore the scenic Green Mountain National Forest, discover charming boutiques, and savor the hospitality of this Vermont gem.
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Rutland County offers a diverse selection of over 30 touring cycling routes. These routes cater to various skill levels, from easy loops to challenging mountain climbs, allowing cyclists to explore the region's unique landscapes.
You can expect a varied terrain that includes challenging climbs through the Green Mountains, serene stretches around lakes, and rolling country roads. The region is characterized by its mountainous landscape, tranquil waters, and extensive trail networks, providing a mix of experiences for touring cyclists.
Yes, Rutland County has 5 easy touring cycling routes. A great option for beginners or families is the Pine Hill Park loop from Rutland City, which is a 4.7-mile easy loop through the park, typically taking about 45 minutes to complete.
For those seeking a challenge, Rutland County offers 16 difficult touring cycling routes. One such route is the SVT Ringmaster loop from Middletown Springs, a demanding 28.3-mile path with significant elevation gain, taking approximately 4 hours and 17 minutes to complete.
Many routes in Rutland County are designed as loops. For instance, the Lake Bomoseen – Scotch Hill Road loop from Fair Haven offers a scenic 12.2-mile circular ride around Lake Bomoseen, which can be completed in about 1 hour and 13 minutes.
Rutland County is rich in natural beauty. Near many routes, you can find attractions like the majestic Killington Peak Summit, the scenic Deer Leap Overlook, and the tranquil Little Rock Pond. These offer great opportunities for exploration off the bike.
Absolutely. The mountainous terrain of Rutland County provides numerous opportunities for stunning views. Highlights like the Deer Leap Overlook and the summit of Pico Peak are accessible near some touring routes, offering panoramic vistas of the Green Mountains and surrounding valleys.
Yes, Rutland County is home to several beautiful lakes. The Lake Bomoseen – Scotch Hill Road loop from Fair Haven is a prime example, leading you through the scenic area around Lake Bomoseen. Other routes may pass by Chittenden Reservoir, Half Moon Pond, and Lake St. Catherine, offering picturesque waterside cycling.
Many popular trailheads and starting points for touring cycling routes in Rutland County offer designated parking. For example, the SVT Ringmaster loop from SVT Fairgrounds Trailhead parking indicates a specific parking area for convenience. It's always a good idea to check the route details on komoot for specific parking information.
The touring cycling routes in Rutland County are highly rated by the komoot community, with an average score of 4.3 stars. Cyclists often praise the diverse terrain, from challenging mountain climbs to serene lakeside paths, and the stunning natural beauty of the Green Mountains and tranquil lakes.
The best season for touring cycling in Rutland County is typically from late spring through early fall. During these months, the weather is generally pleasant, and the natural landscapes, including the Green Mountains and various lakes, are at their most vibrant. Fall foliage offers a particularly spectacular backdrop for cycling.
Yes, Rutland County's extensive forests, such as Aitken State Forest and the Green Mountain National Forest, provide habitats for various wildlife. Cyclists often report sightings of deer, various bird species, and other small animals, especially on quieter routes away from urban areas. Early mornings or late afternoons are often the best times for wildlife viewing.
Certainly. The Gifford Woods State Park loop from Giffords Woods State Park is a moderate 11.2-mile route that takes you through the beautiful state park. Additionally, routes like the Pine Hill Park loop from Rutland City offer cycling within dedicated parkland, providing a mix of natural scenery and maintained trails.


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