The best walks and hikes in Cheshire County
4.8
(66)
802
hikers
81
hikes
Hiking in Cheshire County, New Hampshire, offers a diverse landscape characterized by forested hills, prominent mountains like Mount Monadnock, and numerous state parks. The region features a mix of challenging ascents and gentler paths winding through natural areas and alongside water bodies. Trails often traverse varied terrain, including woodlands, open ridges, and areas around ponds and reservoirs. The county's landscape includes significant natural areas such as Pisgah State Park and the Connecticut River Valley.
Best hiking trails in Cheshire County
…Last updated: April 26, 2026
5.0
(1)
42
hikers
2.86km
01:24
510m
0m
The White Dot Trail offers a moderate yet rewarding hike up Mount Monadnock, covering 1.8 miles (2.9 km) with a significant elevation gain of 1684 feet (513 metres). You'll begin…
5.0
(1)
15
hikers
6.92km
02:35
450m
450m
Embark on the Mount Monadnock via White Dot and Lost Farm Trail Loop, a moderate hike covering 4.3 miles (6.9 km) with a significant elevation gain of 1466 feet (447…
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14
hikers
10.9km
03:43
560m
570m
Embark on the Bald Rock and Monadnock Mountain Loop, a moderate hiking route that challenges you with varied terrain and rewarding views. This 6.8-mile (10.9 km) loop involves steep climbs,…
13
hikers
10.6km
03:46
580m
580m
Embark on the Monadnock Mountain via Birchtoft to Hinkley Loop, a moderate hike spanning 6.6 miles (10.6 km) with a significant elevation gain of 1912 feet (583 metres). You can…
7
hikers
3.37km
01:03
120m
120m
Embark on the Anne Stokes Loop Trail for an easy hike through the serene Madame Sherri Forest. This route spans 2.1 miles (3.4 km) and involves a gentle elevation gain…
6
hikers
3.58km
01:32
490m
0m
Embark on the Dublin Trail, a moderate hike that quickly transitions from forested paths to a steep, rocky ascent. You'll navigate worn terrain and encounter sections requiring hands-on rock scrambling…
3.0
(1)
4
hikers
8.25km
02:19
190m
120m
Embark on a moderate hiking adventure up Hubbard Hill and Pitcher Mountain, covering 5.1 miles (8.2 km) with an elevation gain of 621 feet (189 metres). You can expect to…
5
hikers
1.04km
00:19
40m
40m
Step into the dramatic rock canyon of Chesterfield Gorge, where towering walls, some reaching 70 feet high, have been carved by Wilde Brook. This easy hiking route offers a quick…
5.0
(2)
4
hikers
7.63km
02:09
160m
160m
Embark on a moderate hike to Stoddard Rocks via Pioneer Lake, a 4.7-mile (7.6 km) route that takes about 2 hours and 9 minutes to complete. You'll gain 535 feet…
2
hikers
6.35km
01:55
20m
500m
Embark on the easy Pumpelly Trail, a pleasant hiking route spanning 3.9 miles (6.3 km) with a gentle elevation gain of 80 feet (24 metres). You can expect to complete…
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Other adventures in Cheshire County
Tips from the Community
This mountain never disappoints. Always a fun quick hike.
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From the cleared hilltop of Hubbard Hill, you are afforded wonderful views that span across the green landscape of Andorra Forest.
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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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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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Frequently Asked Questions
How many hiking trails are available in Cheshire County?
Cheshire County offers a wide variety of hiking experiences, with over 50 routes available. These range from easy strolls to more challenging ascents, catering to different skill levels.
What are the typical difficulty levels for hiking trails in Cheshire County?
The trails in Cheshire County offer a good mix of difficulties. You'll find approximately 16 easy routes, 34 moderate routes, and 3 more difficult trails, ensuring options for every hiker.
What kind of terrain can I expect on hikes in Cheshire County?
Hiking in Cheshire County primarily features forested hills, prominent mountains like Mount Monadnock, and numerous state parks. Trails often traverse varied terrain, including woodlands, open ridges, and paths alongside ponds and reservoirs.
Are there any family-friendly hiking trails in Cheshire County?
Yes, Cheshire County has several easy trails suitable for families. For example, the Daniels Mountain & Ann Stokes loop — Madame Sherri Forest is an easy option, as is the Kilburn Pond and John Summers Trail loop — Pisgah State Park.
Are there circular hiking routes in Cheshire County?
Many trails in Cheshire County are designed as loops, offering varied scenery without retracing your steps. Notable circular routes include the Mount Monadnock Loop – White Mountains and the Pisgah Ridge and Reservoir loop — Pisgah State Park.
What are some notable viewpoints or landmarks along the hiking trails?
Hikers can enjoy stunning views from the Mount Monadnock Summit. Another popular spot is Thoreau's Seat, accessible via the Thoreau's Seat via Lost Farm Trail loop, which offers scenic vistas.
Can I find hiking trails that go past lakes or ponds?
Yes, Cheshire County features several beautiful trails that incorporate water bodies. You can explore areas around Lily Pond and Goose Pond, with specific trails like the Kilburn Pond and John Summers Trail loop.
What is the best time of year to hike in Cheshire County?
While hiking is enjoyable year-round, many consider autumn the best time due to the vibrant fall foliage. Spring offers lush greenery, and summer is ideal for longer days, though some trails can be busy. Winter hiking is also possible for experienced hikers with proper gear.
Are dogs allowed on hiking 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 you go. Generally, dogs should be kept on a leash and owners are expected to clean up after their pets.
What do other hikers enjoy most about the trails in Cheshire County?
The trails in Cheshire County are highly rated by the komoot community, with an average score of 4.8 stars from over 40 reviews. Hikers frequently praise the diverse landscapes, well-maintained paths, and the rewarding views from summits like Mount Monadnock.
Are there any challenging hikes for experienced hikers?
Yes, for those seeking a challenge, Cheshire County offers routes like the Wantastiquet Mountain & Monadnock Trails Loop – Madame Sherri Forest, which is rated as difficult and provides a strenuous workout with significant elevation changes.
Is public transport available to reach trailheads in Cheshire County?
Public transport options to reach specific trailheads in Cheshire County are limited. It is generally recommended to travel by car to access most hiking starting points, as many are located in more remote natural areas.
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