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Road cycling routes
United States
Vermont
Bennington County

Manchester

The best road cycling routes around Manchester

By Fede from komoot

·

Updated June 4, 2026

If you've ever tried to plan road cycling around Manchester, you know the struggle: endless routes, conflicting advice, and no clear way to tell which ones are genuinely worth your precious time and effort. It's easy to get lost in the sheer volume of options, wondering if you're truly hitting the highlights or just spinning your wheels on filler. That's where we come in. Our komoot community has meticulously mapped, ridden, and reviewed these routes, cutting through the noise to bring you a curated shortlist of the best road cycling routes Manchester has to offer. We're here to save you the guesswork.

Road cycling around Manchester is a surprisingly diverse experience. You'll find everything from urban sections and canal-side paths to rolling hills and challenging ascents as you head towards the Pennine foothills. The landscape shifts quickly from cityscapes to open countryside, passing picturesque water features like ponds and lakes. It’s a region that truly offers something for every ability, with routes ranging from easy spins to demanding climbs.

If you're looking for a solid, popular ride to start with, the Chiselville Covered Bridge loop from Manchester Center is a fantastic choice, offering 23.1 miles (37.2 km) of moderate terrain that’s a local favorite. For those craving a bigger challenge and significant elevation, the Lyons Pond – The Mill Pond loop from Manchester delivers a rewarding 63.5 miles (102.2 km) with plenty of climbing. More than 160 road cyclists have already used komoot to explore Manchester's varied terrain, so dive in and discover your next favorite ride!

If you only do 3 of these routes

  1. 1

    Chiselville Covered Bridge loop from Manchester Center
  2. 2

    South Village Pond – Emerald Lake loop from Lye Brook Falls Trailhead
  3. 3

    Chiselville Covered Bridge loop from Manchester Center

Compare these routes at a glance

Trail

Distance

Elevation

Difficulty

Chiselville Covered Bridge loop from Manchester Center

37.2 km

360 m

Moderate

South Village Pond – Emerald Lake loop from Lye Brook Falls Trailhead

73.6 km

740 m

Moderate

Chiselville Covered Bridge loop from Manchester Center

101 km

1,060 m

Hard

Lyons Pond – The Mill Pond loop from Manchester Center

102 km

1,370 m

Hard

Emerald Lake – South Village Pond loop from Manchester Center

91.9 km

840 m

Moderate

Equniox Mt Trailhead loop from Manchester Center

30.5 km

280 m

Easy

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1.

Chiselville Covered Bridge loop from Manchester Center

37.2km

01:51

360m

360m

If you're looking for a quintessential Vermont road cycling experience, the Chiselville Covered Bridge loop from Manchester Center delivers a scenic journey through rolling countryside. This moderate 23.1-mile (37.2 km) route, which you can complete in about 1 hour and 51 minutes, takes you past the historic 1870 Chiselville Covered Bridge, a true highlight spanning the Roaring Branch of the Batten Kill. You'll navigate varied terrain, from gentler stretches along the river to more demanding climbs, all while soaking in the picturesque views between the Taconic and Green Mountains. Expect around 1180 feet (360 metres) of elevation gain, making it a rewarding ride for those with good fitness.

Starting from Manchester Center, this loop is best enjoyed when the weather is clear to fully appreciate the rural Vermont landscapes. While specific parking information isn't detailed, Manchester Center provides a convenient base for beginning your ride. Be prepared for a mix of paved and potentially unpaved segments, and ensure your bike is equipped for varied road conditions. This route is ideal for cyclists who enjoy a blend of natural beauty and a moderate physical challenge.

The Chiselville Covered Bridge itself is a significant landmark, a 117-foot Town lattice truss bridge notable for its impressive height and the quirky "One Dollar Fine" sign. This historic structure, built in 1870, offers a fantastic photo opportunity and a glimpse into 19th-century engineering. The route provides a great way to explore the charming Southern Vermont countryside, offering a memorable road cycling experience that combines history with stunning natural beauty.

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2.

South Village Pond – Emerald Lake loop from Lye Brook Falls Trailhead

73.6km

03:36

740m

740m

The South Village Pond – Emerald Lake loop offers a quintessential Vermont road cycling experience, winding through the scenic valleys and rolling hills of Danby. You'll encounter picturesque landscapes, from expansive panoramas to glimpses of distant peaks like Dorset Mountain, making for a truly engaging ride. This moderate route spans 45.8 miles (73.6 km) with 2438 feet (743 metres) of elevation gain, typically taking about 3 hours and 35 minutes, perfect for cyclists seeking a substantial challenge.

Starting near the Lye Brook Falls Trailhead, this loop is a local favorite, known for its varied terrain. While mostly paved, some sections might be unpaved, requiring adaptability and good bike handling skills. It's best to plan for a morning start, especially on weekends, to enjoy the tranquility of the roads and avoid any potential traffic. Always carry enough water and be prepared for changing conditions.

This route is notable for showcasing the diverse elevations and natural beauty nestled between the Taconic and Green Mountains. It's a fantastic way to experience the region's character, passing through areas that highlight features like Dutch Hill and offering views towards Woodlawn Mountain. The loop is a testament to why Danby is a beloved spot for road cyclists, providing both a workout and stunning scenery.

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3.

Chiselville Covered Bridge loop from Manchester Center

101km

06:04

1,060m

1,060m

The Chiselville Covered Bridge loop from Manchester Center offers a truly immersive road cycling experience through Southern Vermont's rolling countryside. You'll pedal past classic rural scenery, with sections along Sunderland Hill Road and River Road providing serene views. The highlight is undoubtedly the historic Chiselville Covered Bridge, a beautifully preserved 1870 structure that crosses high above the Roaring Branch of the Batten Kill, making for a perfect photo opportunity.

This is a difficult road cycling route, covering 62.8 miles (101.1 km) with a substantial 3463 feet (1055 metres) of elevation gain, and typically takes around 6 hours and 3 minutes to complete. It's best suited for experienced cyclists looking for a long, challenging day in the saddle. Plan to start early from Manchester Center to make the most of the daylight and ensure you carry ample water and snacks for the duration.

The Chiselville Covered Bridge itself is a fascinating piece of local history, famous for its humorous "One Dollar Fine for Driving Faster Than a Walk on This Bridge" sign and its appearance in the 1987 film *Baby Boom*. This route is a favorite among local cycling groups and offers a deep dive into the region's charm, combining natural beauty with significant historical landmarks like the bridge and the Historic Equinox Hotel.

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5.

Emerald Lake – South Village Pond loop from Manchester Center

91.9km

04:19

840m

840m

The Emerald Lake – South Village Pond loop from Manchester Center offers a captivating road cycling experience through Southern Vermont's diverse landscape. You'll wind through rolling hills and expansive valley panoramas, with the Taconic Mountains to your west and the Green Mountains to your east, providing a stunning backdrop. The route takes you past the famed Emerald Lake, whose waters shimmer with an emerald-green hue, and offers picturesque views of the Battenkill, Otter Creek, and Mettawee River valleys. This moderate 57.1-mile (91.9 km) ride, featuring 2756 feet (840 metres) of elevation gain, typically takes around 4 hours and 19 minutes, making it a rewarding challenge. It's a fantastic option for cyclists with good fitness looking to explore the region's natural beauty.

Starting from Manchester Center, this popular route features a mix of well-paved roads and some unpaved segments, so be prepared for varied surfaces. Given the significant distance and elevation, ensure you're well-hydrated and have the necessary supplies for a substantial ride. While specific parking information isn't detailed, the area is well-known for outdoor activities, suggesting accessible starting points. This loop is best suited for intermediate to advanced riders who appreciate a dynamic and scenic cycling adventure.

This loop is a standout among local cyclists, showcasing the best of the

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Tips from the Community

Natalie
February 6, 2024, Lyons Pond

Lyons Pond can be seen glistening between the tall pine trees. Many years ago, ice from the pond was stored in ice houses for use in food preservation during the summer. The ice was packed into the houses with sawdust and it was surprisingly effective. If done well, it could remain frozen for several years.

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This is a stunning covered bridge. It is also known as the East Arlington Covered Bridge. It was built in 1870 and spans over the Roaring Branch of the Batten Kill on Sunderland Hill Road in the town of Sunderland, Vermont. There is a sign on the bridge that states you will get fined $1 if you drive over the bridge faster than a walking man.

1

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Jamie S.
December 30, 2023, The Mill Pond

The Mill Pond is a small pond off of the scenic West River in Londonderry, Vermont. It is just east of downtown Londonderry where you can get a bite to eat on your ride.

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0

Natalie
November 29, 2023, Lyons Pond

Lyons Pond can be seen glistening between the tall pines trees. Many years ago, ice from the pond was stored in icehouses for use in food preservation during the summer. The ice was packed into the houses with sawdust and it was surprisingly effective. If done well, it could remain frozen for several years.

0

0

Frequently Asked Questions

How many road cycling routes are available around Manchester?

There are over 20 road cycling routes around Manchester documented on komoot, offering a diverse range of experiences for cyclists of all levels. These routes traverse varied landscapes, from urban environments to the rolling hills and river valleys surrounding the city.

Are there easy road cycling routes suitable for beginners in Manchester?

Yes, Manchester offers several easy road cycling routes perfect for beginners. You can find 6 routes specifically graded as easy, often following flatter sections like canal paths or disused railway lines. An example is the Equniox Mt Trailhead loop from Manchester, which is a manageable 30.5 km ride.

Where can I find challenging road cycling routes with significant climbs near Manchester?

For experienced cyclists seeking a challenge, Manchester's routes extend towards the Pennine foothills, offering more demanding ascents. There are 6 routes graded as difficult. A notable option is the Lyons Pond – The Mill Pond loop from Manchester, a 102.2 km route with over 1300 meters of elevation gain.

Are there options for long-distance road cycling around Manchester?

Yes, Manchester provides several routes suitable for longer rides. The Lyons Pond – The Mill Pond loop from Manchester is a substantial 102.2 km, while the South Village Pond – Emerald Lake loop from Lye Brook Falls Trailhead covers 73.6 km, both offering significant distances for endurance cyclists.

What kind of scenery can I expect on road cycling routes around Manchester?

Road cycling routes around Manchester offer a mix of urban sections, picturesque canal-side paths, and rolling hills. You'll encounter open countryside, suburban areas, and natural water features such as ponds and lakes. Routes extending towards the Pennine foothills provide more dramatic landscapes and elevated views.

What do other road cyclists enjoy the most about road cycling in Manchester?

The komoot community highly rates road cycling in Manchester, with an average score of 5.0 stars. Cyclists often praise the varied terrain, which includes both flat sections and challenging climbs, as well as the opportunity to explore both urban and natural environments.

Are there any circular road cycling routes available in Manchester?

Yes, many of the road cycling routes around Manchester are designed as circular loops, allowing you to start and finish at the same point. Examples include the popular Chiselville Covered Bridge loop from Manchester and the Equniox Mt Trailhead loop from Manchester.

What interesting landmarks or natural features can I see along the road cycling routes?

Many routes pass by notable landmarks and natural features. You might cycle past the historic Chiselville Covered Bridge, enjoy views from Lookout Rock, or see the serene Equinox Pond. Some routes also lead near the Lye Brook Falls Trail or offer panoramic vistas from the Mount Equinox and St. Bruno Scenic Viewing Center.

Are there routes that pass by water features like ponds or lakes?

Yes, several road cycling routes around Manchester incorporate natural water bodies into their scenery. For instance, the South Village Pond – Emerald Lake loop from Lye Brook Falls Trailhead passes by multiple natural water features, and the Lyons Pond – The Mill Pond loop from Manchester also features ponds.

What is the typical elevation gain on road cycling routes in Manchester?

The elevation gain varies significantly depending on the route's difficulty and length. Moderate routes like the Chiselville Covered Bridge loop from Manchester have around 360 meters of elevation, while more challenging routes, such as the Lyons Pond – The Mill Pond loop from Manchester, can feature over 1300 meters of climbing.

Can I find routes that combine urban cycling with countryside exploration?

Absolutely. Manchester's road cycling network is characterized by its blend of urban sections and transitions into open countryside. Many routes allow you to start within or near the city and quickly find yourself cycling through suburban areas, along canal paths, and into the more rural landscapes surrounding Manchester.

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