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Routes
Running Trails
United States
New Hampshire

Cheshire County

The best running trails in Cheshire County

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.

Best jogging routes in Cheshire County

  • The most popular jogging route is Cheshire Recreational Rail…

Last updated: April 24, 2026

4

runners

#1.

Dublin Trail

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…

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Hard

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…

Hard
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3

runners

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…

Hard

2

runners

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…

Hard

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…

Easy

1

runners

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…

Moderate

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…

Moderate

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…

Easy

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…

Easy

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.…

Hard
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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

Other adventures in Cheshire County

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Hiking Collection by

Jamie S.

Tips from the Community

Sam
February 14, 2025, Mount Monadnock Summit

any trail is a great trail at monadnock!

0

0

mtm05005
November 8, 2023, Kilburn Trailhead

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.

0

0

mtm05005
October 17, 2023, Gilson Pond

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.

1

0

mtm05005
October 17, 2023, Thoreau's Seat

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.

0

0

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.

1

0

Zachary
October 17, 2023, Kilburn Pond

The pond is great for swimming and the edge is lined with large stones that are perfect for scrambling, picnicking, and enjoying the water.

0

0

mtm05005
October 17, 2023, Kilburn Trailhead

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.

0

0

mtm05005
October 17, 2023, Cheshire Rail Trail

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.

1

0

Frequently Asked Questions

How many running routes are available in Cheshire County?

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.

Are there any easy or family-friendly running paths in Cheshire County?

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.

What kind of terrain can I expect on running trails in Cheshire County?

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.

Are there any circular running routes in the area?

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.

Can I bring my dog on the running trails in Cheshire County?

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.

What natural features or landmarks can I see while running in Cheshire County?

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.

Is public transport available to access running trailheads?

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.

Are there any permits required for jogging on trails in Cheshire County?

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.

What is the best time of year to go running in Cheshire County?

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.

Are there places to eat or stay near the running routes?

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.

How long are the running routes in Cheshire County?

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).

Most popular routes in Cheshire County

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Didn’t find what you were looking for?

Check out more Running Trails & Routes throughout Cheshire County below and find the perfect route in your destination.

Pisgah State ParkRhododendron State ParkMarlboroughTroyJaffreyHinsdaleKeeneWest SwanzeyWinchesterMonadnock State ParkBear Mountain State ForestAnnett State Forest

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