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United States
Vermont
Windsor County

Ascutney

The best cycling routes around Ascutney

By Fede from komoot

·

Updated June 1, 2026

If you've ever tried to plan touring cycling around Ascutney, you know how overwhelming the options can be. With so many roads and trails, it's hard to tell which routes are genuinely worth your time and effort, and which are just filler. That's where komoot comes in. Our community has ridden, mapped, and reviewed countless routes, and we've distilled that collective wisdom into a curated shortlist of the very best, saving you the guesswork.

Touring cycling around Ascutney is defined by the dramatic presence of Mount Ascutney, rising from the Connecticut River Valley. You'll find a fantastic mix of terrain here, from challenging ascents up forested slopes to more gentle routes along scenic backroads and river valleys. It’s a region that truly captures the essence of rural New England by bike, offering something for every ability level. While beautiful year-round, the fall foliage makes for particularly stunning rides.

If you're looking for a gentle introduction to the area, we'd start with the Sugar River Trail, a moderate 27.6 miles (44.4 km) route that offers a wonderfully scenic journey along the river. For those ready to explore more of the region's charm, the Plainfield loop from Cornish, at 20.4 miles (32.8 km), is a local favorite, winding through rolling hills and pastoral views. With more than 39 touring cyclists having already explored Ascutney with komoot, you're in good company.

If you only do 3 of these routes

  1. 1

    Sugar River Trail
  2. 2

    Plainfield loop from Cornish
  3. 3

    Bellows Falls & the Connecticut River loop from Claremont

Compare these routes at a glance

Trail

Distance

Elevation

Difficulty

Sugar River Trail

44.4 km

290 m

Moderate

Plainfield loop from Cornish

32.8 km

290 m

Moderate

Bellows Falls & the Connecticut River loop from Claremont

75.3 km

600 m

Hard

Woodstock Middle Covered Bridge loop from Windsor Trail

100.0 km

2,060 m

Hard

Taftsville Covered Bridge – Carriage Barn Visitor Center loop from Windsor Trail

66.0 km

1,260 m

Hard

Bowers Covered Bridge loop from Brownsville

10.3 km

150 m

Moderate

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1.

Sugar River Trail

44.4km

03:54

290m

290m

The Sugar River Trail offers a delightful touring cycling experience, winding through south-central Wisconsin's varied landscapes. This former railroad line treats you to a journey past farmlands, dense woods, and scenic meadows, often following the Sugar River. You'll cross fourteen trestle bridges, providing unique perspectives, and encounter a charming replica covered bridge near Brodhead, making it a great option for scenic viewpoints on Sugar River Trail for cyclists.

This moderate 27.6-mile (44.4 km) route, with a gentle 957 feet (292 metres) of elevation gain, typically takes around 3 hours and 54 minutes. The trail is predominantly flat with a compacted limestone surface, though some sandy spots might challenge bikes with thinner tires. Starting or ending in New Glarus, known as "Little Switzerland," provides access to cafes, pubs, and accommodation, while a connection to New Glarus Woods State Park offers camping.

Beyond its natural beauty, the Sugar River Trail is notable for its rail-to-trail conversion and its connection to other regional paths like the Badger State Trail and the Ice Age National Scenic Trail. Wildlife sightings, including deer and various birds, are common along the route, especially as it traverses the Albany Wildlife Area. This makes it a popular choice for those seeking a relaxed ride through diverse scenery and a chance for wildlife sightings Sugar River Trail cycling.

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2.

Plainfield loop from Cornish

32.8km

01:59

290m

290m

Embark on a touring cycling journey through the scenic Plainfield and Cornish regions of New Hampshire, where you'll discover a charming blend of rural landscapes and historic architecture. This route weaves through picturesque forests and open fields, offering a refreshing escape into New England's natural beauty. Expect a mix of paved roads and gravel sections, providing a varied and engaging ride for those who enjoy diverse terrain.

This moderate touring cycling route covers 20.4 miles (32.8 km) with an elevation gain of 949 feet (289 metres), typically taking around 1 hour and 58 minutes. While specific parking for this loop isn't detailed, general access points are available in the towns of Plainfield and Cornish. The area is particularly beautiful for cycling from spring through fall, with autumn providing stunning fall foliage views.

One of the highlights of this area is the chance to pass by the historic Cornish-Windsor Covered Bridge, a notable landmark that adds character to your ride. The region's country roads are well-suited for touring, offering a glimpse into New Hampshire's heritage and natural attractions. This route is perfect for cyclists seeking a balanced ride with both paved and unpaved sections, allowing you to explore the unique features of Plainfield and Cornish.

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3.

Bellows Falls & the Connecticut River loop from Claremont

75.3km

04:33

600m

600m

Embark on a challenging touring cycling adventure through the picturesque Connecticut River Valley with the Bellows Falls & the Connecticut River loop from Claremont. This difficult 46.8-mile (75.3 km) route features a significant 1975 feet (602 metres) of elevation gain, winding through rolling hills and river valleys. You'll experience classic Vermont farmland, serene riverside idylls, and continuous water views, especially along the peaceful Old Connecticut River Road. Expect a demanding ride that showcases the diverse beauty of the New England landscape over approximately 4 hours and 32 minutes.

Planning your visit to this challenging route is straightforward, as it begins in Claremont, a recognized Bicycle Friendly Community. While the trail offers a mix of paved and some unpaved sections, it requires very good fitness, so it's best suited for experienced cyclists rather than beginners or families. Ensure you carry enough water and supplies for the full duration, and check local weather conditions, as the New England climate can be unpredictable.

This loop provides an immersive exploration of the scenic Connecticut River Valley, connecting historic towns like Claremont and Bellows Falls. It stands out for its diverse cycling experience, moving beyond typical rail trails with varied elevations and terrain. The route offers a unique opportunity to discover hidden gem cycling routes along the Vermont and New Hampshire border, providing continuous river views and a true sense of regional character.

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6.

Bowers Covered Bridge loop from Brownsville

10.3km

00:50

150m

150m

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

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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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The road cuts through the Saint-Gaudens Historical National Park. It was once the home of the celebrated sculptor, Augustus Saint-Gaudens. The grounds are peppered with casts of his most famous works. If you have time during your ride to look around, it is well worth it. Take the Saint-Gaudens Road to the northwest. If you're just riding through, you pass Blow-Me-Down Pond, a beautiful wetland right next to the road.

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The Cornish-Windsor Bridge was built in 1866 and is the longest wooden covered bridge in the country. It's an iconic way to cross the Connecticut River and travel between New Hampshire and Vermont. Despite being nearly 160 years old, it still carries traffic every day. There is a pull-out here, where you can stop and take photos.

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Pedalling along Bellows Falls Road, there are fantastic views westwards across the Connecticut River and into Vermont.

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It is worth taking the Old Connecticut River Road to pass through the riverside rural idyll. There are great views of the river all along its length, and a sense of space and calm.

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The covered bridges on the Sugar River Trail are hidden gems on the riverside path. Wright's Covered Bridge was built in 1906, and it's amazing to think it once carried a railroad. There are info boards at the bridge which provide loads more detail about its history and construction.

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Natalie
January 11, 2024, Pier Covered Bridge

This is a real highlight of the Sugar River Trail. The Pier Covered Bridge was built as part of the Boston and Maine Railroad. Dating back to 1907, it is a delight to ride through part of the area's history. There are great views of the bridge as you approach it on the trail.

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Known locally as 'Sunshine Town', Newport is a great place to come if you love being active. Not only are there plenty of cafes to sample before, during or after a ride, there is a comprehensive outdoor recreational centre and winter skating on the Common.

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Frequently Asked Questions

How many touring cycling routes are available around Ascutney?

There are over 10 touring cycling routes around Ascutney, offering a variety of experiences for different skill levels. You'll find options ranging from moderate loops to more challenging, longer routes through the region's diverse terrain.

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

Touring cycling around Ascutney features varied terrain, influenced by the prominent Mount Ascutney monadnock and the Connecticut River Valley. You can expect forested slopes, scenic backroads, and rolling hills. While some routes follow gentler river valleys, others, like the challenging ascent of Mount Ascutney itself, offer significant climbs. The region is also known for its unpaved 'Class 4' roads, providing unique gravel touring opportunities.

Are there any family-friendly touring cycling routes in the Ascutney area?

While specific family-designated routes aren't detailed, many of the region's scenic backroads and state park areas offer a more relaxed cycling experience suitable for families. Routes that follow river valleys, such as the Sugar River Trail, tend to have less elevation gain and can be more enjoyable for a family outing.

What are some notable landmarks or viewpoints I can see along the touring cycling routes?

The Ascutney area is rich with natural beauty and historical landmarks. You can visit the Observation Tower on Mount Ascutney for expansive views, or see the picturesque Cornish-Windsor Covered Bridge, one of the longest wooden covered bridges in the US. The Little Cascade Falls also offers a scenic stop.

Are there any circular touring cycling routes around Ascutney?

Yes, there are several circular routes available. For example, the Plainfield loop from Cornish is a moderate 20.4-mile path that explores rural areas with rolling hills and pastoral views. Another option is the Bellows Falls & the Connecticut River loop from Claremont, a longer 46.8-mile route through the Connecticut River Valley.

What is the best time of year to go touring cycling in Ascutney?

The best time for touring cycling in Ascutney is typically from late spring through early fall. The fall foliage season is particularly vibrant, offering stunning scenic rides. Summers are also popular, though it's wise to check weather conditions. Winters can bring snow and ice, making many routes unsuitable for touring bikes.

Where can I find parking for bike trails near Ascutney?

Mount Ascutney State Park offers parking facilities, which can serve as a convenient starting point for many cycling adventures. Additionally, various trailheads and public access points throughout the region will have designated parking areas. It's always a good idea to check specific route details for recommended parking locations.

What do other touring cyclists enjoy most about cycling in Ascutney?

The touring cycling routes in Ascutney are highly rated by the komoot community, with an average score of 4.0 stars. Cyclists often praise the region's diverse terrain, from challenging ascents to peaceful river valley rides, and the opportunity to explore rural New England's picturesque landscapes.

Are there options for advanced touring cyclists seeking a challenge?

Absolutely. Ascutney offers several challenging routes for experienced touring cyclists. The region is known for its steep climbs, including sections of Mount Ascutney itself. Routes like the Woodstock Middle Covered Bridge – Silver Hill loop from Windsor Trail, spanning over 63 miles with significant elevation gain, provide a demanding and rewarding experience.

Are there any cafes or pubs near the touring cycling routes in Ascutney?

While specific cafes directly on every route are not guaranteed, the towns and villages surrounding Ascutney, such as Windsor, Claremont, and Cornish, offer various dining options, including cafes and pubs where you can refuel and relax after your ride. Planning your route to pass through these towns can ensure convenient stops.

What are some moderate touring cycling routes in the area?

For a moderate experience, the Sugar River Trail is a popular choice, covering 27.6 miles and following the scenic Sugar River. Another excellent moderate option is the Plainfield loop from Cornish, a 20.4-mile path featuring rolling hills and pastoral views.

Is public transport available to access touring cycling routes in Ascutney?

Public transport options directly to specific trailheads in the rural Ascutney area may be limited. Most cyclists typically access the routes by car, parking at designated trailheads or in nearby towns. It's advisable to check local transport services if you plan to rely on public transit.

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