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Routes
Running Trails
United States
New York
Dutchess County

Dover Plains

The best running trails around Dover Plains

17

runners

4

runs

Jogging around Dover Plains offers diverse terrain across rolling hills, extensive wooded areas, and natural rock formations. The region provides a varied environment for runners, with elevations like Cobble Mountain and numerous forested paths. Rivers and ponds contribute to the natural setting, creating a serene backdrop for outdoor exercise.

Best jogging routes around Dover Plains

  • The most popular jogging route is Cobble Mountain Summit View loop from Macedonia Brook State Park, a 6.7 miles (10.8 km) trail that takes…

Last updated: June 26, 2026

8

runners

#1.

Bulls Bridge loop from Bull's Bridge

14.9km

01:33

80m

80m

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

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Moderate

3

runners

8.04km

00:51

80m

80m

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

Moderate
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2

runners

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

Hard

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Popular around Dover Plains

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Tips from the Community

Caro "Bandit"
January 24, 2024, Housatonic River

With its spring in Massachusetts the Housatonic River flows for 149 miles to southern Connecticut into Long Island Sound. The Appalachian Trail follows the river from the covered wooden Bulls Bridge to Falls Village. The river is also a popular whitewater paddling destination with mostly Class I to Class III rapids.

1

0

Caro "Bandit"
February 24, 2022, Bulls Bridge

This is one of three old covered wooden bridges spanning over the Housatonic River. While the one at Cornwall is still intact, the original Old Covered Bridge in Sheffield was destroyed by fire and had to be rebuilt.

0

0

This is part and beyond is part of the Appalachian trail and is recreational part that is open to bicycles. It is a dead end tho!

2

0

Frequently Asked Questions

How many running routes are available in the Dover Plains area?

There are 5 curated running routes around Dover Plains featured in this guide, offering a variety of distances and difficulties to suit different preferences.

What kind of terrain can I expect on jogging routes near Dover Plains?

Runners in Dover Plains can enjoy a diverse landscape, from rolling hills and extensive wooded areas to natural rock formations. You'll find paths through serene forests, along rivers like the Ten Mile River, and even trails with unique 'white sands' due to eroding Stockbridge Marble. The region offers both relatively flat sections, ideal for a steady jog, and more challenging climbs with rewarding views.

Are there any rail trails suitable for running in Dover Plains?

Yes, the Harlem Valley Rail Trail is an excellent option for runners seeking a generally flat and accessible surface. Rail trails provide a consistent and scenic route, often away from vehicle traffic, making them ideal for a relaxed jog or longer runs.

Are there any challenging running routes in the area for experienced runners?

Absolutely. For those seeking a challenge, routes like the Cobble Mountain Summit View loop from Macedonia Brook State Park offer significant elevation gain and rewarding views. Another demanding option is the Bulls Bridge – Schaghticoke Mountain loop from Bull's Bridge, which features substantial climbs and longer distances.

Can I find circular jogging routes around Dover Plains?

Yes, many of the routes in the area are designed as loops, allowing you to start and finish at the same point. Examples include the Bulls Bridge loop from Bull's Bridge and the Running loop from Kent, providing convenient options for your run.

Are there any scenic points of interest or natural features to see while running?

Dover Plains is rich in natural beauty. A notable highlight is the Dover Stone Church Preserve, where you can find a unique natural rock formation and beautiful waterfalls cascading into a pool. The region also features picturesque ponds like Fuller Pond and the serene Ten Mile River, providing lovely backdrops for your run.

Are the running trails in Dover Plains dog-friendly?

Many trails in the Dover Plains area are suitable for running with dogs, provided they are kept on a leash. It's always a good idea to check specific preserve or park regulations before heading out, but generally, the natural trails welcome well-behaved, leashed canine companions.

What are some good options for longer distance running or endurance training?

For longer runs, consider routes that cover more ground and offer varied terrain. The Bulls Bridge – Schaghticoke Mountain loop from Bull's Bridge, at nearly 20 kilometers, is an excellent choice for endurance training. Another substantial option is the Housatonic River loop from Kent, which also provides a significant distance.

Is there dedicated parking available near the running routes?

While specific parking details vary by trailhead, many popular running areas and preserves in Dover Plains, such as the Dover Stone Church Preserve and J.H. Ketcham Memorial Park, offer designated parking facilities. For routes starting from specific locations like Macedonia Brook State Park or Bull's Bridge, parking is typically available nearby.

Can I access running trails in Dover Plains using public transport?

Yes, Dover Plains is accessible via the Metro-North train station, which is conveniently located near some trailheads, including the Dover Stone Church Preserve. This makes it possible to reach certain running routes without a car, especially those closer to the village center.

Are there any easy or beginner-friendly running routes?

While this guide features mostly moderate to difficult routes, the Harlem Valley Rail Trail offers a generally flat and accessible surface that is ideal for beginners or those looking for an easier, less strenuous run. Additionally, parts of the Dover Stone Church Preserve trails are mild and suitable for a scenic jog.

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