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Cycling routes
United States
Vermont

Rutland County

The best cycling routes in Rutland County

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.

Best touring cycling…

Last updated: June 28, 2026

10

riders

#1.

Rochester – Brandon Gap loop from Lions Club Picnic Area

76.4km

05:04

1,120m

1,120m

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Hard

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard
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5.0

(1)

5

riders

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

5.0

(1)

5

riders

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

3

riders

37.5km

03:20

640m

640m

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard
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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

Other adventures in Rutland County

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

Hiking Collection by

Jamie S.

Tips from the Community

Zachary
June 25, 2025, Forest Dale

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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Jamie S.
February 26, 2024, Brandon Gap

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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Jamie S.
February 26, 2024, Middlebury Gap

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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AverieOutside
February 6, 2024, Hapgood Pond

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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Sue
February 5, 2024, Gifford Woods State Park

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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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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Alex
January 22, 2024, Rochester

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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Frequently Asked Questions

How many touring cycling routes are available in Rutland County?

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.

What kind of terrain can I expect on touring cycling routes in Rutland County?

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.

Are there easy touring cycling routes suitable for beginners or families in Rutland County?

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.

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

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.

Are there any circular touring cycling routes in Rutland County?

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.

What natural attractions can I explore near the touring cycling routes in Rutland County?

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.

Can I find routes that offer scenic viewpoints?

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.

Are there touring cycling routes that pass by lakes or water bodies?

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.

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

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.

What do other touring cyclists enjoy about the routes in Rutland County?

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.

When is the best season for touring cycling in Rutland County?

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.

Can I expect to see wildlife while touring cycling in Rutland County?

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.

Are there any routes that explore specific parks or forests?

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.

Most popular routes in Rutland County

Hiking in Rutland County

Most popular attractions in Rutland County

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Didn’t find what you were looking for?

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

Robert T. Stafford White Rocks National Recreation AreaPoultneyEast PoultneyMiddletown SpringsJim Jeffords State ForestKillington Village

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