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Routes
Road cycling routes
United States
Connecticut
Northwest Hills Planning Region

Lakeville

The best road cycling routes around Lakeville

4.5

(8)

224

riders

45

rides

Road cycling around Lakeville features a landscape characterized by rolling hills, forested areas, and watershed regions. The terrain includes moderate climbs and descents, offering varied challenges for road cyclists. Routes often traverse through areas like the Centennial Watershed State Forest, providing a mix of natural scenery and paved roads. The region's topography supports both longer distance road cycling routes and shorter, more accessible options.

Best road cycling routes around Lakeville

  • The most popular road cycling route is Babes Hill –…

Last updated: July 2, 2026

3.5

(2)

37

riders

#1.

Wassiac Rail Station – Wassiac Bridge over a Creek loop from Millerton

36.8km

01:57

170m

170m

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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Easy

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
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Popular around Lakeville

Hiking around Lakeville

Cycling around Lakeville

Tips from the Community

Alex Tray
July 15, 2024, Rail Trail North Start

Started here to go south to Wassiac

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Near and artist commune

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Wonderful food and rest stop at the end of the trail

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Train goes to and from NYC

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View of a pond and wildlife

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Scott
March 6, 2024, Ore Hill Park

The name stems from the nearby Ore Hill Mine, once the last active goethite mine in Connecticut. Operating from the 18th century until 1923, the mine extracted iron ore, contributing to the state's industrial development. Encompassing roughly 11 acres, Ore Hill Park provides a serene setting for a relaxing ride.

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Scott
February 27, 2024, Scoville Library

Established in 1803, it holds the distinction of being the first free, public library in the United States. This pioneering accomplishment paved the way for public libraries across the nation.

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Scott
February 27, 2024, Lakeville

Nestled in the Litchfield Hills of Connecticut, Lakeville is a charming small town known for its scenic beauty. The town is surrounded by rolling hills, forests, and several lakes, including Lake Wononscopomuc, which is the largest natural lake in the state.

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Frequently Asked Questions

What kind of terrain can I expect on road cycling routes in Lakeville?

Lakeville's road cycling routes feature rolling hills, forested sections, and watershed areas. You'll encounter moderate climbs and descents, offering a varied and engaging ride through the region's natural scenery.

How many road cycling routes are available around Lakeville?

There are over 20 road cycling routes around Lakeville, catering to various skill levels from easy to difficult.

Are there any easy road cycling routes suitable for beginners in Lakeville?

While most routes are moderate, there is at least one easy road cycling route available. For those looking for a gentle introduction, consider exploring routes that stick to flatter sections or shorter distances.

What are some longer distance road cycling routes near Lakeville?

For longer rides, consider routes like the Rudd Pond – Rail trail bridge loop from Centennial Watershed State Forest, which covers about 40 miles (65 km) and passes by Rudd Pond. Another option is the Babes Hill – Reed Hill loop from Centennial Watershed State Forest, a 37-mile (59.6 km) route with rolling hills.

Are there challenging road cycling routes for experienced cyclists in Lakeville?

Yes, Lakeville offers routes with more significant climbs and descents for experienced cyclists. While most are moderate, there is at least one difficult route available to test your endurance and skill.

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

The area is highly rated by the komoot community, with an average score of 4.4 stars. Reviewers often praise the varied terrain, which includes forested hills and watershed areas, providing a scenic and engaging ride.

Are there circular road cycling routes in Lakeville?

Many of the popular road cycling routes in Lakeville are designed as loops, allowing you to start and finish at the same point. Examples include the Scoville Library – Lakeville loop from Centennial Watershed State Forest and the Wassiac Bridge over a Creek – Wassiac Rail Station loop from Centennial Watershed State Forest.

What are some scenic viewpoints or attractions along road cycling routes in Lakeville?

While cycling, you might find opportunities to see natural landmarks. Nearby attractions include Lion's Head, Sage's Ravine, and Great Falls Reservoir. Some routes also pass through the Centennial Watershed State Forest, offering beautiful forested sections.

When is the best time of year for road biking in Lakeville?

The best time for road biking in Lakeville is typically during the spring, summer, and fall months when the weather is mild and the roads are clear. Autumn offers particularly scenic rides with vibrant fall foliage.

Are there any hidden gem road cycling routes in Lakeville?

For a route that offers a mix of terrain and local charm, consider the King Hill Road – Scoville Library loop from Centennial Watershed State Forest. It's a moderate 42 km ride that provides a good sense of the region's varied landscape.

What facilities are available at road biking trailheads in Lakeville?

While specific facilities like restrooms or cafes at trailheads are not detailed, many routes start or pass through areas near towns like Lakeville, where amenities such as cafes and shops can be found.

Most popular routes around Lakeville

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