The best walks and hikes around Winchester
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, and serene water features. The terrain offers a good mix, from moderate ascents and descents to paths winding alongside ponds and reservoirs. You'll find everything from easy strolls to more demanding, longer hikes, making it a great spot for all skill levels.
If you're looking for a solid moderate day out that local hikers love, we'd start with the Chestnut Hill, Reservoir and North Ponds Loop, a 6.3 miles (10.2 km) route that takes you through woodlands and past tranquil water bodies. For those ready for a challenge and significant elevation gain, the MA NET: Section 18 is a popular choice at 11.5 miles (18.4 km). Dive in and discover your next favorite trail with komoot.
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 hours to complete, guides you through diverse terrain, from quiet pine and hemlock forests to the scenic shoreline of Richards Reservoir. You'll navigate natural singletrack and old woods roads, with the highlight being the ascent of Mayo Hill, offering a true sense of immersion in nature.
Planning your visit requires a few considerations. Dogs are welcome but should be kept on a leash, particularly within Warwick State Forest. Given the 1701 feet (518 metres) of elevation gain and the trail's length, ensure you carry plenty of water or a reliable filtration system, as natural sources can be limited and sometimes murky. The trail is best enjoyed in spring, summer, or fall, with autumn providing a spectacular display of colors.
This section is an integral part of both the New England National Scenic Trail and the Metacomet-Monadnock Trail, offering a taste of these longer routes. For those seeking an extra adventure, a roughly 2-mile round trip side trail leads to Royalston Falls, a dramatic 45-foot waterfall plunging into a cylinder-shaped gorge. The unbroken woodland character of the trail provides a deep sense of wilderness, making it a rewarding experience for confident hikers.
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 dirt, with continuous riverside views and glimpses of historic covered bridges like the 1864 Ashuelot Covered Bridge. This difficult 22.0-mile (35.4 km) route, with 602 feet (184 metres) of elevation gain, provides a rich blend of natural beauty and industrial heritage, taking approximately 9 hours and 5 minutes to complete.
When planning your trip, be aware that the Ashuelot Rail Trail terrain changes significantly along its length. The northern sections near Keene are smoother, while areas south of Pine Street can be rougher and muddier, especially after rain. The trail is accessible year-round for various activities, but good footwear is recommended due to the varied surfaces. Multiple access points along the route allow you to customize your hike.
What makes the Ashuelot Rail Trail truly special is its blend of history and nature. As a former railway corridor, it's dotted with old granite mile markers and abandoned mill buildings, telling the story of the region's past. It's also part of the larger East Coast Greenway, connecting several towns and offering opportunities to spot wildlife, including moose in certain areas, making it a significant recreational pathway.
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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 to a summit where a 68-foot steel fire tower provides exceptional 360-degree views. While the forest itself is pleasant, the tower is the main draw, offering vistas across Massachusetts and into southern New Hampshire and Vermont on a clear day.
To make the most of your visit, plan to hike on a clear day to fully appreciate the panoramic views from the fire tower. The trail can be moderately rocky in parts, and conditions like snow, mud, or leaf cover can increase the difficulty, so check the weather before you go. Parking is available at the trailhead, and starting early can help you avoid crowds, especially on weekends.
Mount Grace is a significant landmark, being the third-highest point in Massachusetts east of the Connecticut River. It's also part of the longer Metacomet-Monadnock Trail, connecting it to a wider network for those seeking extended adventures. Beyond hiking, the Mount Grace State Forest offers multi-use trails for various activities, making it a versatile recreational hub in Franklin County.
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 old roads and designated trails, passing through mixed hardwood and conifer woodlands. Keep an eye out for historic agricultural sites along the Doolittle Trail, which add a unique touch to the natural surroundings of this New Hampshire gem. The terrain is generally gentle, making it a relaxing experience for most hikers.
This easy 4.0-mile (6.4 km) hiking loop involves a modest 309 feet (94 metres) of elevation gain and can typically be completed in about 1 hour and 44 minutes. It's a fantastic option for families and those looking for a less strenuous outing. Parking is generally available at the trailhead, but be mindful that sections of Old Chesterfield Road are multi-use, so conditions can vary. Dogs are permitted on leash, so feel free to bring your furry friend along.
Nestled within Pisgah State Park, the largest property in the New Hampshire State Park system, this loop provides an accessible way to explore the region's rugged forested terrain and glacially formed landscapes. The park protects numerous streams, wetlands, and ponds, contributing to the area's rich biodiversity. This trail is a great introduction to the park's offerings, providing a taste of its natural and historical character without demanding a full day's commitment.
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 and glimpses of Boston College, to the more secluded, forested trails of Hammond Pond Reservation. Here, you'll navigate moderately challenging terrain with roots and rocks, winding past tranquil smaller bodies of water like Cat Pond and Bare Pond, providing a refreshing escape into nature within an urban setting.
This moderate 6.3-mile (10.2 km) route, with 809 feet (247 metres) of elevation gain, typically takes around 2 hours and 54 minutes to complete. The area is well-served by public transport via the MBTA Green Line, and parking is available nearby, though it can be busy. For the best experience, plan your visit during the spring or fall when the weather is mild and the natural scenery is at its peak.
What makes this loop particularly notable is its blend of historical significance and ecological diversity. The Chestnut Hill Reservoir itself is a historic district, and the entire area functions as a vital green space within a densely populated urban environment. It offers a unique opportunity to experience varied landscapes, from open waterfront to dense woodland, all within easy reach of the city.
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Popular around Winchester
Tips from the Community
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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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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