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Cycling routes
United States
Connecticut
Northwest Hills Planning Region

Watertown

The best cycling routes around Watertown

4.8

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Touring cycling around Watertown features routes characterized by rolling hills and varied natural landscapes. The area's terrain includes significant elevation changes, with many routes gaining several hundred meters. Cyclists can expect to navigate through areas near state parks and nature reserves, suggesting a mix of wooded sections and open spaces. This provides a diverse environment for touring cyclists seeking both moderate and challenging rides.

Best touring cycling routes around Watertown

  • The most popular touring cycling route is Quassy – Caleb Hill loop from Middlebury, a 23.7 miles (38.1 km) trail that takes 2 hours 33 minutes to complete. This difficult route features substantial elevation gain through the region's hilly terrain.
  • Another top favourite among local touring cyclists is Quassy – Cox Nature Reserve loop from Bethlehem, a difficult 24.4 miles (39.3 km) path. This route offers scenic views and challenging climbs, passing through natural reserve areas.
  • Local touring cyclists also love the Larkin State Park Trail – Whittemore Glen State Park loop from Whittemore Glen State Park, a 8.5 miles (13.7 km) trail leading through state park landscapes, often completed in about 1 hour 19 minutes.
  • Touring cycling around Watertown is defined by rolling hills, state park trails, and natural reserves. The network offers options for different ability levels, from moderate paths to more difficult routes with significant climbs.
  • The routes in Watertown are highly rated by the komoot community with an average score of 4.5 stars from over 3 reviews. More than 56 touring cyclists have used komoot to explore Watertown's varied terrain.

Last updated: June 28, 2026

5.0

(1)

15

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#1.

Quassy – Cox Nature Reserve loop from Bethlehem

39.5km

02:39

620m

620m

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

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Hard

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

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

Moderate

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
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Popular around Watertown

Hiking around Watertown

Running Trails around Watertown

Road Cycling Routes around Watertown

Tips from the Community

J.D.
September 2, 2025, Larkin State Park Trail

Southbury to Oxford still closed as of 9/1/25 due to flooding washout. Road detours possible.

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This section of the Middlebury Greenway near Chase Road is an especially scenic bit of riding on this popular, paved multi-use path. You ride on the raised trail above a pretty stream, then pass through an interesting rock notch east of Chase Road. This is a great bit of riding that is also away from cars.

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This historic home offers guided tours for a fee. The gardens are nice, especially in the spring with the flowers in bloom. The property also joins the 81-acre Bellamy Preserve.

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Alex
February 8, 2024, Larkin State Park Trail

Stretching about 10 miles, the Larkin State Park Trail in Connecticut meanders through wooded terrain, open expanses, and scenic meadows. Renowned for its diverse plant and animal life, it attracts nature lovers seeking to immerse themselves in the area's vibrant natural beauty.

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This woodland just off Tuttle Road is a natural reserve of trees and land. There is no public access into the reserve, but you get a good feel for the natural beauty of the area when riding down the road.

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Javi Jaavii
January 31, 2024, Bird Pond

This pond was created in the early 19th century to provide water for the fulling mill on Woodcreek Road, even before Long Meadow Pond was constructed.

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Marzahl Refuge, also known as Frederick W. Marzahl Memorial Refuge, is a very small patch of woods with two short trails that backs up to Camel Hill Brook. Step off the bike and take a walk if you would like a closer look.

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Whittemore Glen State Park is a 242-acre wilderness park across Route 63 from Hop Brook Dam and is known for housing a portion of the Larkin State Park Trail.

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Frequently Asked Questions

How many touring cycling routes are available in Watertown?

There are over 10 touring cycling routes available in Watertown, offering a diverse range of experiences for cyclists. These routes are highly rated by the komoot community, with an average score of 4.5 stars.

What are the difficulty levels of touring cycling routes in Watertown?

Touring cycling routes in Watertown range from moderate to difficult. You'll find 4 moderate routes and 6 difficult routes, many featuring significant elevation changes and rolling hills. For example, the Quassy – Caleb Hill loop from Middlebury is a difficult route with over 589 meters of elevation gain.

Are there any circular touring cycling routes in Watertown?

Yes, many touring cycling routes in Watertown are designed as loops, allowing you to start and end at the same point. Examples include the Quassy – Caleb Hill loop from Middlebury and the Larkin State Park Trail – Whittemore Glen State Park loop from Whittemore Glen State Park.

What kind of landscapes can I expect on touring cycling routes in Watertown?

The touring cycling routes in Watertown (CT) are characterized by rolling hills and varied natural landscapes, including sections near state parks and nature reserves. If you're exploring other Watertowns, you might find urban scenery and waterfront views along the Charles River in Watertown, MA, marshy and tree-lined areas along the Rock River in Watertown, WI, or scenic views around glacial lakes like Lake Kampeska in Watertown, SD.

What are some notable attractions or landmarks along the touring cycling routes in Watertown?

Along the touring cycling routes in Watertown, you can explore natural and man-made attractions. Consider visiting Hop Brook Lake, the unique Hogpen Hill Farms, or the scenic Black Rock State Park. The Middlebury Greenway (Chase Road Section) also offers a pleasant cycling experience.

Are there any touring cycling routes that pass through state parks or nature reserves?

Yes, several routes in Watertown pass through or near state parks and nature reserves. The Larkin State Park Trail – Whittemore Glen State Park loop from Whittemore Glen State Park is a great example, leading directly through state park landscapes. Another option is the Quassy – Cox Nature Reserve loop from Bethlehem, which offers scenic views and challenging climbs through natural reserve areas.

What do other touring cyclists say about the routes in Watertown?

The komoot community highly rates the touring cycling routes in Watertown, with an average score of 4.5 stars from over 3 reviews. Cyclists often praise the varied terrain, the challenge of the rolling hills, and the scenic beauty of the state parks and natural reserves encountered along the way.

Are there any specific trails for touring cyclists in Watertown, WI?

In Watertown, WI, a notable trail for cyclists is the Watertown/Oconomowoc Interurban Trail. This seven-mile paved path follows a former electrical rail line, offering views of marshy areas, tree-lined spots, and the Rock River. It also provides amenities like restrooms, parking, and a bike repair station at the Clark Street trailhead.

Where can I find bike-friendly infrastructure in Watertown, MA?

Watertown, MA, is actively developing its cycling infrastructure. You can utilize the Bluebikes bike-sharing system and explore routes like the Charles River Bike Path, the Watertown Community Bike Path, and the Watertown-Cambridge Greenway. These paths offer connections to Boston and surrounding areas, with some providing physical barriers from traffic. More information can be found on the Watertown-MA website.

What kind of cycling experiences can I find in Watertown, NY?

Watertown, NY, offers a range of cycling experiences, including options for mountain biking with 40 dedicated trails. For touring cyclists, routes vary in length and elevation, often featuring scenic views along the Black River and opportunities to ride through historic neighborhoods. Thompson Park also provides scenic biking and walking trails. For local attractions, visit the Watertown-NY website.

Are there any easy touring cycling routes for beginners in Watertown?

While many routes in Watertown (CT) feature significant elevation and are rated moderate to difficult, the Larkin State Park Trail – Whittemore Glen State Park loop from Whittemore Glen State Park is a moderate option at 8.5 miles (13.7 km) with less elevation gain compared to the more challenging routes, making it a good starting point for those looking for a less strenuous ride.

What is the best time of year for touring cycling in Watertown?

The best time for touring cycling in Watertown generally depends on the specific region. In areas with significant elevation changes like Watertown (CT), spring and fall offer pleasant temperatures and vibrant scenery. For regions like Watertown, SD, around Lake Kampeska, warmer months are ideal for enjoying the lake views. Always check local weather conditions before your ride.

Are there any long-distance touring cycling routes near Watertown?

Many routes in Watertown are designed for day tours, with some extending up to 24.4 miles (39.3 km), such as the Quassy – Cox Nature Reserve loop from Bethlehem. These routes provide substantial distances and elevation for a fulfilling long-distance touring experience within the region.

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