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Routes
Hikes
United States
New Hampshire
Cheshire County

Winchester

The best walks and hikes around Winchester

4.5

(2)

36

hikers

7

hikes

Hiking around Winchester offers access to varied natural landscapes, primarily characterized by dense woodlands, rolling hills, and serene water features within Pisgah State Park. The terrain includes moderate ascents and descents, with paths winding through forests and alongside ponds and reservoirs. This region provides opportunities for both shorter, easier walks and longer, more challenging hikes. The area's natural features include tranquil ponds and moderate elevation changes.

Best hiking trails around Winchester

  • The most popular hiking route is MA NET: Section…

Last updated: April 30, 2026

1

hikers

#1.

MA NET: Section 18

18.4km

07:01

520m

480m

Hike the difficult 11.5-mile MA NET: Section 18 through Warwick State Forest, featuring Mayo Hill and Royalston Falls.

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Hard

35.4km

09:06

180m

120m

Hike the Ashuelot Rail Trail, a difficult 22.0-mile route along the Ashuelot River, featuring covered bridges and diverse wildlife.

Hard
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2.15km

00:46

210m

0m

Mount Grace offers an easy hiking experience through varied woodlands, where you will encounter northern hardwood forests. This short route covers 1.3 miles (2.1 km) and involves a manageable elevation…

Easy

Embark on an easy 4.0-mile (6.4 km) hike through the scenic woodlands of Pisgah State Park on the Old Chesterfield Road, Broad Brook Road, & Doolittle Trail Loop. This route…

Easy

Embark on the Chestnut Hill, Reservoir and North Ponds Loop for a refreshing hike through varied New Hampshire forestry and serene waters. You will experience a moderate 6.3-mile (10.2 km)…

Moderate
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Popular around Winchester

Running Trails around Winchester

Cycling around Winchester

Road Cycling Routes around Winchester

Tips from the Community

Zachary
September 22, 2023, Lily Pond Trail

The Lily Pond trail takes you on a beautiful pond walk that is especially stunning in the autumn. Keep an eye out for beaver dams!

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Zachary
September 22, 2023, Parker Trailhead

The Parker Trailhead is only accessible via ATV. Normal vehicles can park on Old Chesterfield Road before it turns to dirt or at Horseshoe Road. From here you can easily hike to Fullam Pond, Chestnut Hill, Lily Pond, and Broad Brook.

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Zachary
September 22, 2023, Doolittle Trail

The Doolittle Trail is a hiking trail that winds through the woods and across the wide and scenic Broad Brook. Keep an eye out for Trillium and beaver dams!

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Zachary
September 22, 2023, Old Chesterfield Road

The road is closed to traffic, and makes for a nice easy hike through the woods. You cross Snow Brook near the north end of this segment.

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You park along Old Chesterfield Road, which becomes gravel near the trailhead. The trail from here has historical markers that spruce up the hike.

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The road runs alongside the chain of reservoirs and ponds connected by Pisgah Brook. The path is easy, and especially beautiful in fall. Because of all the ponds and reservoirs you will want bug spray during the warmer months of the year.

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Fragrant trees, colorful wildflowers and quiet trails await you at Mount Grace State Forest. It's especially beautiful from spring through fall, when winter takes a break. Atop the 1,621-foot summit is a fire tower with prime views.

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Frequently Asked Questions

What kind of terrain can I expect on hiking trails around Winchester?

Hiking around Winchester, particularly within Pisgah State Park, features dense woodlands, rolling hills, and serene water features like ponds and reservoirs. Trails often involve moderate ascents and descents, winding through forests and alongside these water bodies.

Are there any easy hiking trails suitable for beginners or a relaxed stroll?

Yes, there are easy trails available. For example, the Kilburn Pond and John Summers Trail loop — Pisgah State Park is an easy 3-mile (4.8 km) path, perfect for a less strenuous outing.

Can I find circular hiking routes in the Winchester area?

Many of the trails around Winchester are designed as loops, offering circular routes. Examples include the Pisgah Ridge and Reservoir loop — Pisgah State Park and the Kilburn loop — Pisgah State Park, allowing you to start and end at the same point.

What are the most popular natural features or viewpoints on these trails?

The trails often provide views of the reservoirs and lead through tranquil woodlands. The Pisgah Ridge and Reservoir loop — Pisgah State Park specifically features views of the reservoir and follows Pisgah Ridge, offering scenic perspectives of the park's natural beauty.

Are there any landmarks or attractions to see near the hiking trails?

While hiking in Pisgah State Park, you can explore several natural and recreational highlights. These include the Fort Hill Recreational Trail, Mount Grace State Forest, Hubbard Hill Trail, and Lily Pond Trail.

What is the typical difficulty level of hikes around Winchester?

The hikes around Winchester offer a range of difficulty levels. You'll find easy trails for leisurely walks, moderate routes that involve some elevation changes, and a few more challenging options for experienced hikers. The majority of routes are moderate, providing a good balance for most abilities.

What do other hikers say about the trails in Winchester?

The hiking routes in Winchester are highly regarded by the komoot community, with an average rating of 4.5 stars. Hikers often praise the quiet woodlands, serene water features, and the well-maintained paths within Pisgah State Park.

Are there any longer, more challenging hikes in the area?

Yes, for those seeking a longer and more challenging experience, the Pisgah Ridge and Reservoir loop — Pisgah State Park is a moderate 8-mile (12.9 km) trail with nearly 300 meters of elevation gain, offering a more demanding hike.

Are the trails around Winchester suitable for families with children?

Many trails, especially the easy and shorter moderate loops, are suitable for families. The varied terrain within Pisgah State Park, with its woodlands and ponds, offers an engaging environment for children to explore. Consider routes like the Kilburn Pond and John Summers Trail loop for a family-friendly outing.

What are the common natural features I'll encounter on a hike?

You will primarily encounter dense woodlands, tranquil ponds, and reservoirs. The trails often follow natural contours, offering a peaceful immersion in the forest environment with occasional water views.

How many hiking trails are available in the Winchester area?

There are several hiking trails around Winchester, with at least 4 routes detailed in this guide, all located within Pisgah State Park. These include a mix of easy, moderate, and difficult options.

Is there parking available at the trailheads?

As the trails are primarily located within Pisgah State Park, designated parking areas are typically available at various trailheads and access points within the park. It's always advisable to check specific park information for detailed parking instructions.

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