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United States
New York
Dutchess County

Dover Plains

The best walks and hikes around Dover Plains

5.0

(2)

110

hikers

18

hikes

Hiking around Dover Plains, NY, offers a variety of trails through a landscape characterized by hills, natural rock formations, and wooded areas. The region features elevations such as Cobble Mountain and Tenmile Hill, providing viewpoints and varied terrain. Natural features like Fuller Pond and the Dover Stone Church are accessible via established routes.

Best hiking trails around Dover Plains

  • The most popular hiking route is Cobble Mountain Cliff Face – Cobble Mountain Summit View loop from Flanders Historic District,…

Last updated: June 23, 2026

5.0

(3)

27

hikers

#1.

Macedonia Ridge Trail

11.1km

04:06

450m

460m

Moderate hike. Good fitness required. Mostly accessible paths. Sure-footedness required.

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Moderate

2

hikers

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

1.85km

00:29

10m

10m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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Tips from the Community

Kniebolek
August 16, 2025, Cobble Mountain Summit View

Nice Lookout westwards

0

0

Can be slippery with leaves and water or ice. Take your time. Easier to climb up than slide down imho

1

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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.

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A narrow steel bridge spans the Tenmile River just before it joins the much wider Housatonic River. Right next to it is a campsite with easy access.

2

0

360 awesome summit view with little scrambling.

0

0

Frequently Asked Questions

How many hiking trails are available in Dover Plains?

Dover Plains offers around a dozen hiking routes, catering to various preferences. You'll find a good mix of easy, moderate, and challenging trails to explore the region's natural beauty.

What kind of terrain can I expect on hikes in Dover Plains?

The hiking terrain in Dover Plains is characterized by rolling hills, natural rock formations, and extensive wooded areas. Notable elevations include Cobble Mountain and Tenmile Hill, which provide varied landscapes and viewpoints. Trails often lead through forests and past features like Fuller Pond and the Dover Stone Church.

What are the difficulty levels of hiking trails in Dover Plains?

The trails around Dover Plains offer a range of difficulty levels. You can find 2 easy routes, 9 moderate routes, and 1 difficult route, ensuring options for hikers of all experience levels.

Are there any easy, family-friendly hiking options in Dover Plains?

Yes, there are easy routes suitable for families. For example, the Fuller Pond – Calebs Peak loop from Macedonia Brook State Park is an easy 7 km trail. Another accessible option is The Stone Church loop from Dover Plains, which is about 5.5 km long.

What do other hikers say about the trails in Dover Plains?

The hiking routes in Dover Plains are highly regarded by the komoot community, holding an average rating of 5.0 stars from 5 reviews. Hikers often praise the varied terrain and scenic viewpoints, especially from summits like Cobble Mountain.

Are there any circular hiking routes in Dover Plains?

Many of the trails in Dover Plains are designed as loops, offering a complete experience without retracing your steps. Examples include the Cobble Mountain Cliff Face – Cobble Mountain Summit View loop from Flanders Historic District and the Tenmile Hill – Bulls Bridge loop from Wingdale.

What are some notable natural features or landmarks to see while hiking?

Hikers can explore natural features such as the Dover Stone Church, a unique rock formation, and Fuller Pond. Many routes also offer panoramic views from elevated points like Cobble Mountain and Tenmile Hill.

What is the best time of year to go hiking in Dover Plains?

While specific seasonal information for Dover Plains is limited, generally, spring and fall offer pleasant temperatures and beautiful scenery for hiking. Fall foliage can be particularly stunning in wooded areas. Summer can be warm, and winter hiking is possible but may require appropriate gear for snow and ice.

Are there any trails that offer significant elevation gain or challenging climbs?

Yes, some trails in Dover Plains feature notable elevation gains. For instance, the Cobble Mountain Cliff Face – Cobble Mountain Summit View loop from Flanders Historic District involves over 450 meters of ascent, providing a good workout and rewarding views from the summit.

Is there parking available at the trailheads in Dover Plains?

While specific parking details for every trailhead are not available, it is common for hiking areas in the region to have designated parking lots or roadside parking near popular access points. It is advisable to check individual route descriptions for precise parking information before your hike.

Can I bring my dog on the hiking trails in Dover Plains?

Many hiking trails in natural areas typically allow dogs, often requiring them to be on a leash. However, specific regulations can vary by park or preserve. It's recommended to check local signage or official park websites for the most current dog policies before heading out.

Are there any long-distance hiking opportunities or connections to other trails?

While the provided routes are primarily day hikes, the region's landscape suggests potential connections to longer trail systems. The Appalachian Trail is known to pass through parts of Dutchess County, which may offer opportunities for extended hikes or sections of a larger trail network near Dover Plains.

Most popular routes around Dover Plains

Easy hikes around Dover Plains

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