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Hikes
United States
New Hampshire

Cheshire County

Easy hikes and walks in Cheshire County

4.7

(68)

1,016

hikers

81

hikes

Easy hiking trails in Cheshire County, New Hampshire, offer diverse landscapes for outdoor exploration. The region is characterized by forested mountains, serene natural areas, and a network of trails suitable for various skill levels. Hikers can explore river valleys, woodlands, and numerous ponds and reservoirs. This area provides accessible paths for those seeking easy hiking trails amidst its natural beauty.

Best easy hiking trails in Cheshire County

  • The most popular easy hiking route is Anne Stokes Loop Trail, a…

Last updated: May 12, 2026

7

hikers

#1.

Anne Stokes Loop Trail

3.37km

01:03

120m

120m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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Easy

5

hikers

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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2

hikers

6.35km

01:55

20m

500m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

2

hikers

1.09km

00:22

60m

50m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

1

hikers

2.14km

00:45

180m

10m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

1

hikers

2.05km

00:32

10m

0m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

2.11km

00:38

70m

60m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

2.11km

00:40

0m

250m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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Popular around Cheshire County

Easy hikes in Monadnock State Park

Easy hikes in Pisgah State Park

Easy hikes around Jaffrey

Easy hikes around Troy

Easy hikes in Bear Mountain State Forest

Easy hikes around Keene

Easy hikes around Marlborough

Easy hikes around Hinsdale

Easy hikes in Annett State Forest

Easy hikes in Rhododendron State Park

Other adventures in Cheshire County

Monadnock-Sunapee Greenway Trail — Backpacking southern New Hampshire’s hidden gem

Hiking Collection by

Jamie S.

Tips from the Community

Jamie S.
April 9, 2025, Small chapel

​The Center Pond Chapel is a small, privately-owned chapel located near Center Pond along the Monadnock-Sunapee Greenway (MSG) in southwestern New Hampshire. There is sometimes fresh, bottled water at the chapel and a trash receptacle for hikers, but it shouldn't be relied upon as your only source of water.

0

0

Sam
February 14, 2025, Pitcher Mountain

short hike, part of the 52 with a view

0

0

Sam
February 14, 2025, Mount Monadnock Summit

any trail is a great trail at monadnock!

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0

Pitcher Mountain showcases incredible 360 degree panoramic views that reach across the many surrounding hillsides and pastures including the Green Mountains, Mount Monadnock, and on a very clear day, the White Mountains of Mount Washington and Mount Lafayette. Atop Pitcher Mountain there are blueberry pastures where you can PYO blueberries. This area has been named one of the best places for blueberry picking hikes in America! Don't forget to pop a donation in the box available.

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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.

1

0

At the peak of Gap Mountain, you get a good view of the White Mountains and of Gap Mountain Reservation.

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0

Philip
September 26, 2023, Mount Monadnock Summit

Challenging and exciting at the same time.

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0

Zachary
September 22, 2023, Madame Sherri House

The ruins of the Madam Sherri House. The ruins are truly special and well worth a visit. The main structure that remains is a spiraling triple-arched stone staircase fit for a storybook leading up to the stone bones of a mansion.

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Frequently Asked Questions

How many easy hiking trails are there in Cheshire County?

Cheshire County offers a wide selection of easy hiking trails, with over 29 routes specifically categorized as easy. In total, the region features more than 80 hiking routes across various difficulty levels, ensuring options for every preference.

What kind of terrain can I expect on easy hikes in Cheshire County?

Easy hikes in Cheshire County typically feature gentle elevation changes through forested terrain, along river valleys, and around serene ponds and reservoirs. Many trails, like the Anne Stokes Loop Trail, offer a peaceful experience through woodlands. You'll also find accessible rail trails providing flat, easy walking surfaces.

Are there any easy trails with scenic viewpoints in Cheshire County?

Yes, many easy trails offer rewarding views. While Mount Monadnock itself has more challenging ascents, some trails within its vicinity provide scenic perspectives. For example, the Pitcher Mountain Trail offers an easy walk with potential for views of the surrounding landscape. The region's forested mountains and river valleys inherently provide picturesque settings.

Can I find easy trails that are suitable for families with children?

Absolutely. Many easy trails in Cheshire County are perfect for families. Paths like the Appel Way Trail in Keene are paved and relatively flat, making them ideal for strollers or young children. Rail trails throughout the county also provide safe and accessible options for family outings.

Are there any easy hikes that feature waterfalls or gorges?

Yes, Cheshire County is home to natural features like Chesterfield Gorge. The Chesterfield Gorge Trail is an easy 0.6-mile path that allows you to explore the gorge with its falls and cascades. Another option is the Eliza Adams Gorge via Monadnock-Sunapee Greenway, offering a slightly longer easy hike through a similar natural setting.

What do other hikers say about the easy trails in Cheshire County?

The easy trails in Cheshire County are highly regarded by the komoot community, with an average rating of 4.7 stars from over 40 reviews. Hikers often praise the peaceful forested environments, well-maintained paths, and the accessibility of routes suitable for various abilities. Many appreciate the opportunity to explore natural beauty without strenuous climbs.

Are there any circular easy walks in Cheshire County?

Yes, you can find several circular easy walks. The Beech Hill Loop is a great example, offering a 2.1 km (1.3 miles) circular route that allows you to start and end at the same point, perfect for a relaxed outing.

What are some notable landmarks or attractions I can see near easy hiking trails?

Cheshire County offers several interesting landmarks and natural attractions. You can find trails near Lily Pond or Spofford Lake, providing beautiful waterside scenery. The region is also known for Mount Monadnock Summit, which, while a more challenging climb itself, has easier trails in its surrounding Monadnock State Park, such as the Pumpelly Trail.

Are there any short, easy walks for a quick outdoor escape?

For a quick outdoor escape, Cheshire County has several short and easy options. The Chesterfield Gorge Trail is only 0.6 miles (1.0 km) and takes just under 20 minutes to complete. Another short option is the Pitcher Mountain Trail, which is about 1.1 km (0.7 miles).

What is the best time of year to enjoy easy hikes in Cheshire County?

Cheshire County offers pleasant hiking experiences throughout much of the year. Spring brings lush greenery, while summer provides warm weather for exploring. Autumn is particularly popular for its vibrant fall foliage, making it a spectacular time for easy walks. Even in winter, some trails are accessible for snowshoeing or gentle walks, though conditions should always be checked.

Are there easy trails that are dog-friendly in Cheshire County?

Many trails in Cheshire County are dog-friendly, allowing you to enjoy the outdoors with your canine companion. It's always recommended to check specific trail regulations before heading out, but generally, the region's extensive network of rail trails and forested paths, such as the Cascade Link Trail, welcome leashed dogs.

Are there any easy trails that are part of longer regional routes?

Yes, some easy trails in Cheshire County connect to or are part of longer regional routes. For instance, the Monadnock Sunapee Greenway offers sections that are considered easy, allowing you to experience a portion of this extensive trail system. The Appalachian Trail also passes through the broader region, with accessible sections for day hikes.

Most popular routes in Cheshire County

Hiking in Cheshire County

Most popular attractions in Cheshire County

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Didn’t find what you were looking for?

Check out more Hikes throughout Cheshire County below and find the perfect route in your destination.

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

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