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Running Trails
United States
Maryland
Carroll County

New Windsor

The best running trails around New Windsor

44

runners

6

runs

Jogging around New Windsor offers diverse landscapes, from riverfront paths along the Hudson River to wooded trails and expansive parkland. The region features varied terrain, including gentle paths and routes with significant elevation gain in areas like the Hudson Highlands. These running paths in New Windsor provide opportunities for different fitness levels, set against a backdrop of natural features.

Best jogging routes around New Windsor

  • The most popular jogging route is Wakefield Valley Pond loop from Carroll County, a…

Last updated: June 27, 2026

16

runners

#1.

Wakefield Valley Pond loop from Carroll County

8.65km

00:54

70m

70m

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

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Moderate

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

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

Moderate

4

runners

Easy run. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy

4

runners

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

Hard

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Popular around New Windsor

Road Cycling Routes around New Windsor

Tips from the Community

Lisa
February 20, 2024, Fenby Farm Pond

This little pond makes nice eye candy from the road, or you can cycle the paved trail loop around the pond, which is accessible from the road to the south of the lake.

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Frequently Asked Questions

How many jogging routes are available in New Windsor?

Komoot features 6 diverse jogging routes around New Windsor. These paths offer a range of experiences, from moderate loops to more challenging trails, catering to different fitness levels.

What kind of terrain can I expect on New Windsor's running paths?

New Windsor offers a variety of terrains for runners. You'll find everything from riverfront paths along the Hudson River to wooded trails and expansive parkland. Some routes feature gentle, accessible paths, while others, particularly in areas like the Hudson Highlands, include significant elevation gain.

Are there any challenging running trails for experienced runners in New Windsor?

Yes, for those seeking a challenge, New Windsor and the surrounding Hudson Valley offer trails with significant elevation gain. For example, the Fenby Farm Pond loop from Westminster is rated as difficult, covering 9.4 miles with notable ascents. The region also features trails that can reach up to 1000 feet or more in elevation.

Where can I find scenic running routes with good views in New Windsor?

Many routes in New Windsor offer stunning views. The town's location along the Hudson River provides opportunities for panoramic vistas of the river and the majestic Hudson Highlands. The Wakefield Valley Pond loop from Carroll County offers pleasant views of the valley and pond. Additionally, areas like Kowawese Unique Area at Plum Point feature a rare Hudson beach, perfect for scenic jogs along the water's edge.

Are there any circular jogging routes in the New Windsor area?

Yes, several popular running routes in New Windsor are circular, allowing you to start and end at the same point. Examples include the Wakefield Valley Pond loop from Carroll County and the Splash Pad loop from Carroll Community College, both offering convenient loop experiences.

What are some unique natural features or landmarks I might see while running in New Windsor?

New Windsor is rich in natural beauty and unique landmarks. You can jog along the Hudson River, explore the Kowawese Unique Area at Plum Point with its rare Hudson beach, or ascend Snake Hill for spectacular views of the Hudson Highlands. While not a traditional running trail, the Storm King Art Center also offers an expansive landscape of meadows and large sculptures for a visually stimulating experience.

Is parking available near the running trails in New Windsor?

Yes, many running routes in New Windsor, especially those in parks and designated trailheads, offer convenient parking options. For example, routes starting from Carroll Community College or within Kristi Babcock Park typically have accessible parking facilities.

What is the best time of year to go jogging in New Windsor?

The Hudson Valley region, including New Windsor, is beautiful year-round. Spring and fall offer pleasant temperatures and vibrant foliage, making them ideal for running. Summer can be warm, but early mornings or evenings are great. Winter running is also possible, with trails often offering serene, snowy landscapes, though conditions may vary.

How long do the running routes typically take to complete?

The duration of jogging routes in New Windsor varies depending on the distance and your pace. For instance, the Wakefield Valley Pond loop, at 5.4 miles, typically takes about 54 minutes. Longer routes like the Fenby Farm Pond loop, which is 9.4 miles, can take around 1 hour and 36 minutes.

What do other runners say about jogging in New Windsor?

Runners using komoot have explored New Windsor's varied terrain over 39 times, indicating a strong interest in the area's trails. The routes are generally well-regarded for their diverse landscapes, from riverfront paths to wooded areas, offering options for different ability levels.

Are there any accessible running paths in New Windsor?

Yes, New Windsor offers accessible options. Kristi Babcock Park, for example, features paths with a poured-rubber surface, which is easy on joints and wheelchair-friendly, making it suitable for a comfortable and accessible jogging experience.

Are there any 'hidden gem' running spots in New Windsor?

Snake Hill is often considered a 'hidden gem' in New Windsor. This 95-acre area features a 1.5-mile woodland trail that ascends to a 700-foot summit, rewarding runners with spectacular, less-trafficked views of the Hudson Highlands and the river.

Most popular routes around New Windsor

Road Cycling Routes around New Windsor

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