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Road cycling routes
United States
New York
Dutchess County

Millerton

The best road cycling routes around Millerton

4.4

(7)

180

riders

47

rides

Road cycling around Millerton, New York, offers routes through the scenic Hudson Valley, characterized by rolling hills and the backdrop of the Taconic and Berkshire Mountain ranges. The region features dedicated paved paths, including sections of the Harlem Valley Rail Trail, which provide smooth surfaces with minimal traffic. Beyond the rail trail, local paved country roads present scenic views, though these routes typically lack shoulders. The terrain provides options ranging from gentle gradients to more challenging climbs.

Best road cycling…

Last updated: June 28, 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 Millerton

Hiking around Millerton

Cycling around Millerton

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

How many road cycling routes are available around Millerton?

There are over 45 road cycling routes around Millerton, offering a variety of options for different skill levels and preferences.

What kind of terrain can I expect when road cycling in Millerton?

Road cycling in Millerton features a mix of terrain. You'll find dedicated paved paths like sections of the Harlem Valley Rail Trail, known for their smooth surfaces. Beyond the rail trail, local paved country roads wind through picturesque rolling hills and offer views of the Taconic Mountains. While scenic, these country roads typically lack shoulders.

What do other cyclists enjoy most about road cycling in Millerton?

The komoot community highly rates road cycling in Millerton, with an average score of 4.4 stars from 7 reviews. Cyclists often praise the varied scenery, from the smooth rail trail sections to the challenging climbs through rolling hills and the Taconic Mountains.

Is the Harlem Valley Rail Trail suitable for road bikes?

Yes, the Harlem Valley Rail Trail is a prime attraction for road cyclists. It's a paved trail known for its smooth surface and minimal traffic, making it ideal for a pleasant ride. It currently spans 26 miles south from Millerton to Wassaic, with an 8-mile extension north nearing completion.

Are there any easy road cycling routes for beginners or families in Millerton?

Yes, Millerton offers several easy road cycling routes suitable for beginners or families. An excellent option is the Wassiac Rail Station – Wassiac Bridge over a Creek loop from Village of Millerton, an easy 22.9-mile path with gentle elevation changes that passes by the Wassaic Rail Station.

Where can I find more challenging road cycling routes with significant elevation gain?

For more challenging rides, explore routes that venture into the rolling hills and Taconic Mountains surrounding Millerton. The Babes Hill – Reed Hill loop from Centennial Watershed State Forest is a popular 37.0-mile route leading through rolling hills with notable elevation changes.

What natural features or landmarks can I see while cycling around Millerton?

While cycling, you'll encounter the scenic Taconic Mountains and rolling hills. Nearby attractions include Stissing Mountain, offering panoramic views from its fire tower, and Brace Mountain, Dutchess County's highest point. You might also pass by Taconic State Park - Rudd Pond, or the internationally acclaimed Innisfree Gardens, known for their unique design.

Are there any circular road cycling routes in the Millerton area?

Yes, many of the road cycling routes around Millerton are designed as loops. For example, the popular Rudd Pond – Rail trail bridge loop from Centennial Watershed State Forest is a 30.6-mile circular route that incorporates sections of the rail trail.

Where can I park my car when starting a road cycling route in Millerton?

For routes utilizing the Harlem Valley Rail Trail, you can often find parking in downtown Millerton or near the Wassaic Metro North Station at the southern end of the trail. For other country road routes, look for designated parking areas at trailheads or public access points, though specific parking details may vary by route.

Is public transport available to access road cycling routes in Millerton?

Yes, the Harlem Valley Rail Trail connects directly to the Wassaic Metro North Station, making it accessible via public transportation from New York City. This allows cyclists to take a train to Wassaic and begin their ride on the rail trail, which extends north towards Millerton.

Are there any cafes or pubs near the road cycling routes in Millerton?

Millerton and nearby towns offer various cafes and pubs where you can refuel. The town of Millerton itself has options for refreshments. For more information on local establishments, you can visit visitmillertonny.com.

What is the best time of year for road cycling in Millerton?

The best time for road cycling in Millerton is typically from spring through fall, when the weather is mild and the scenery is vibrant. Summer offers warm temperatures, while spring and autumn provide cooler rides and beautiful foliage. Always check local weather conditions before heading out.

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