4.5
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36
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If you've ever tried planning hiking around Winchester, you know how quickly the options can feel overwhelming. With so many trails to choose from, it's tough to tell which routes are genuinely worth your time and effort. That's where we come in: komoot's community has explored, mapped, and reviewed these trails, so we've done the legwork to bring you a curated shortlist of the best hiking routes around Winchester.
Hiking around Winchester means immersing yourself in dense woodlands, rolling hills,…
Last updated: May 31, 2026
1
hikers
18.4km
07:01
520m
480m
Embark on the MA NET: Section 18, a difficult 11.5-mile (18.4 km) hiking adventure that plunges you into the heart of northern Massachusetts's wild woodlands. This route, taking around 7…
35.4km
09:06
180m
120m
The Ashuelot Rail Trail offers a unique hiking experience, following the Ashuelot River through varied terrain from Keene to Hinsdale. You'll traverse everything from smooth asphalt to packed gravel and…

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2.15km
00:46
210m
0m
Mount Grace offers an easy 1.3-mile (2.1 km) hike with 702 feet (214 metres) of elevation gain, typically taking about 46 minutes. The route climbs through northern hardwood forests, leading…
6.40km
01:45
90m
90m
The Old Chesterfield Road, Broad Brook Road, & Doolittle Trail Loop offers a pleasant journey through Pisgah State Park's diverse forests, blending natural beauty with historical intrigue. You'll wander along…
10.2km
02:55
250m
250m
The Chestnut Hill, Reservoir and North Ponds Loop offers a dynamic hiking experience, transitioning from the wide-open, paved paths of the historic Chestnut Hill Reservoir with its expansive water views…
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Popular around Winchester
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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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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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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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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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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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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