84
runners
36
runs
Jogging in Cheshire County offers diverse landscapes for runners, characterized by extensive rail trails, forested parks, and riverine paths. The region features a mix of terrain, from the relatively flat and accessible surfaces of former railroad lines to more challenging, uneven paths with elevation changes in its state parks. These natural spaces provide varied running experiences through forests, past water features, and across rolling hills.
Last updated: April 24, 2026
4
runners
7.13km
01:13
490m
490m
If you're looking for a challenging jogging route, the Dublin Trail delivers a demanding experience over 4.4 miles (7.1 km). You'll navigate heavily-worn, rocky, and rooted terrain, with steep sections…
4
runners
6.46km
01:12
540m
540m
If you're looking for a challenging jogging route, the Marlboro Trail delivers a tough ascent to the iconic Mount Monadnock Summit. This difficult 4.0 miles (6.5 km) route will have…

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3
runners
6.19km
01:04
290m
290m
Embark on a challenging jogging adventure along the Wantastiquet Mountain Trail, a difficult 3.8-mile (6.2 km) route that climbs 964 feet (294 metres). This journey, typically completed in about 1…
2
runners
22.2km
02:39
150m
150m
Embark on the Cheshire Recreational Rail Trail for a challenging jogging experience that takes you through diverse New Hampshire landscapes. This difficult route spans 13.8 miles (22.2 km) and involves…
1
runners
4.85km
00:32
50m
50m
Lace up your shoes for an easy jogging experience on the Kilburn Loop, a scenic route that winds around the picturesque Kilburn Pond. This 3.0-mile (4.8 km) trail offers a…
1
runners
6.19km
00:53
240m
240m
Embark on the Parker and Lost Farm Trail Loop for a moderate jogging experience through the varied terrain and forest scenery of Monadnock State Park. This 3.8-mile (6.2 km) route…
9.74km
01:00
30m
30m
Embark on a moderate jogging experience along the Fort Hill Recreational Rail Trail, a 6.1 miles (9.7 km) route that offers varied terrain and scenic views. As you jog, you…
3.90km
00:26
80m
80m
Jog along the picturesque Connecticut River on the Wantastiquet Mountain Natural Area River Trail, where continuous water views accompany you. This easy 2.4-mile (3.9 km) route follows an old dirt…
3.15km
00:21
30m
30m
Lace up for an easy jogging experience on the Gilson Pond Remote Campsites Loop, a scenic route nestled within a natural, forested environment. This 2.0-mile (3.1 km) loop offers a…
2.70km
00:23
90m
90m
Prepare for a challenging jogging experience on the Anne Stokes Loop Trail, a difficult route covering 1.7 miles (2.7 km) with a significant 301 feet (92 metres) of elevation gain.…
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Popular around Cheshire County
Running Trails around Hinsdale
Running Trails in Pisgah State Park
Running Trails in Bear Mountain State Forest
Running Trails in Monadnock State Park

Running Trails around Winchester
Running Trails around Troy

Running Trails around West Swanzey

Running Trails around Marlborough
Running Trails around Jaffrey
Running Trails around Keene
Trailhead with parking that lets you choose whether to take the paths that bring you east to Pisgah State Forest or west to Daniels Mountain. In the high season it can get busy, so make sure to get there early to get a parking spot.
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Nice, quiet spot by Gilson Pond. Good area for a break in a shady spot. There are beautiful views of the woodlands across the water.
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Great view point of the White Mountains. It is named Thoreau's Seat because Henry David Thoreau was speaking at a local college when he was told about this beautiful viewpoint. He was able to go to visit it and ended up including it in some of his writing.
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Mount Monadnock is the highest point in Cheshire County and the most popular peak in New Hampshire. It gives great views of the surrounding mountains. There are many paths that get you to the summit, so there should be a route that suits everyone's ability.
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The pond is great for swimming and the edge is lined with large stones that are perfect for scrambling, picnicking, and enjoying the water.
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Trailhead with parking that lets you choose whether to take the paths that bring you east to Pisgah State Forest or west to Daniels Mountain. In the high season it can get busy, so make sure to get there early to get a parking spot.
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The Cheshire Rail Trail is a 42-mile long multiuse trail. It passes through beautiful wood land. It is completely off-road, so it is a great place for a peaceful run.
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Cheshire County offers a wide variety of running experiences, with over 40 routes documented on komoot. These range from easy loops to challenging mountain trails, catering to all fitness levels.
Yes, Cheshire County has several easy and family-friendly options. The region's extensive rail trails, such as sections of the Cheshire Recreational Rail Trail, offer relatively flat surfaces suitable for all ages. Additionally, the Gilson Pond Remote Campsites Loop in Monadnock State Park is an easy 2.0-mile route with gentle terrain.
You'll find a diverse range of terrain. Many routes, particularly the rail trails like the Fort Hill Recreational Rail Trail, are relatively flat with gravel or dirt surfaces. For those seeking more challenge, trails in parks like Monadnock State Park, such as the Dublin Trail, feature significant elevation changes and uneven paths.
Yes, several circular routes are available for runners. The Kilburn Loop in Pisgah State Park is a popular 3.0-mile option around Kilburn Pond, offering scenic forest and water views. Another great choice is the Parker and Lost Farm Trail Loop, which provides a moderate 3.8-mile run.
Many trails in Cheshire County are dog-friendly, but it's always best to check specific park or trail regulations before heading out. Generally, dogs are welcome on leash on rail trails and in many state parks. For example, the Wantastiquet Mountain Natural Area River Trail is a great option for running with your canine companion.
Cheshire County's trails offer stunning natural beauty and interesting landmarks. You can enjoy views of the Connecticut River from trails like the Wantastiquet Mountain Trail, or experience the serene beauty of ponds like Kilburn Pond on the Kilburn Loop. For panoramic vistas, consider trails leading towards Mount Monadnock Summit. You might also encounter lakes such as Lily Pond or Spofford Lake near some routes.
While some trailheads might be accessible via local public transport routes in larger towns like Keene, many of Cheshire County's more remote trails and state parks are best reached by car. It's advisable to check local bus schedules for specific towns if you plan to rely on public transport for access to trails like the Cheshire Rail Trail.
Generally, individual joggers do not require specific permits for most public trails, including the rail trails. However, state parks like Monadnock State Park may have entrance fees or parking fees, especially during peak seasons. It's always a good idea to check the specific park's website for the most current information on fees or regulations before your visit.
Cheshire County offers great running opportunities year-round. Spring and fall provide pleasant temperatures and beautiful scenery, with vibrant foliage in autumn. Summer is also popular, though it can be warm, making early morning or late afternoon runs ideal. Winter running is possible on many trails, especially the flatter rail trails, but requires appropriate gear for snow and ice.
Yes, many towns connected by the rail trails or located near state parks offer amenities. Keene, for instance, has various cafes, pubs, and accommodation options close to sections of the Cheshire Rail Trail and Ashuelot Rail Trail. Smaller towns like Fitzwilliam, Troy, and Walpole also provide local establishments where you can refuel or find lodging after your run.
The running routes in Cheshire County vary significantly in length. You can find shorter loops like the Gilson Pond Remote Campsites Loop at 2.0 miles (3.1 km), perfect for a quick run. For longer distances, the Cheshire Recreational Rail Trail offers extended sections, with one popular segment being 13.8 miles (22.2 km).


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