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Routes
Hikes
United States
New Hampshire
Cheshire County

Jaffrey

Easy hikes and walks around Jaffrey

5.0

(19)

277

hikers

31

hikes

Easy hiking trails around Jaffrey, New Hampshire, are characterized by the prominent Mount Monadnock and its surrounding protected highlands. The region features diverse forest types, picturesque lakes, and ponds, offering varied natural environments for outdoor activities. The landscape includes hills under 200m and provides a network of trails suitable for different abilities.

Best easy hiking trails around Jaffrey

  • The most popular easy hiking route is Pumpelly Trail, a 3.9 miles (6.3 km) trail that takes 1 hour 54 minutes…

Last updated: May 2, 2026

2

hikers

#1.

Pumpelly Trail

6.35km

01:55

20m

500m

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

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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
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2.11km

00:40

0m

250m

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

Easy

9

hikers

4.21km

01:24

190m

190m

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

Easy

3.14km

00:50

30m

30m

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

Easy
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Tips from the Community

Sam
February 14, 2025, Mount Monadnock Summit

any trail is a great trail at monadnock!

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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

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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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mtm05005
July 21, 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.

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

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Mount Monadnock is known as America's Favorite Mountain with approximately 35 miles of maintained hiking trails. The mountain is nearly 1,000 ft higher than any other mountain peak within 30 miles and the summit rises 2,000 ft above the surrounding landscape.

2

0

Great view at the top. It's a little tough but worth the view.

Translated by Google

2

1

Frequently Asked Questions

How many easy hiking trails are available around Jaffrey?

Jaffrey offers a good selection of easy hiking trails, with 9 routes specifically categorized as easy. In total, there are over 30 hiking routes in the area, catering to various skill levels.

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

Easy hikes in Jaffrey typically feature varied woodlands, gentle ascents, and paths around picturesque lakes and ponds. While the region is dominated by Mount Monadnock, the easy trails generally avoid significant elevation gains, focusing on accessible paths through diverse forest types and protected highlands.

Are there any short, easy loop trails in Jaffrey?

Yes, for a short and easy loop, consider the Gilson Pond Loop. This 2.0-mile (3.1 km) trail leads through woodlands around Gilson Pond and can often be completed in under an hour, making it perfect for a quick outing.

Which easy trails are suitable for families with children?

Many easy trails in Jaffrey are family-friendly due to their manageable distances and gentle terrain. The Gilson Pond Loop is a great option for families. Additionally, the rail trails in the area, such as the multi-use trail extending from downtown Jaffrey, offer flat, accessible paths suitable for all ages.

Are dogs allowed on the easy hiking trails in Jaffrey?

Generally, dogs are welcome on trails in the Jaffrey area, including those within Monadnock State Park, provided they are kept on a leash. It's always a good idea to check specific trail regulations before you go, especially for protected areas, but most easy woodland paths are dog-friendly.

What are some scenic viewpoints accessible from easy trails?

While many easy trails focus on woodland scenery, you can still find beautiful views. The Jaffrey Center Historic District offers stunning views of Mount Monadnock, and some rail trails pass by scenic ponds and wetlands. For specific viewpoints, consider exploring areas like Thoreau's Seat or Stony Top, which might be accessible via slightly longer but still manageable routes.

When is the best time of year to go hiking in Jaffrey?

Jaffrey offers hiking opportunities year-round. Spring brings lush greenery, while summer is ideal for enjoying the lakes. Fall is particularly popular for its spectacular foliage, with vibrant colors across the diverse forest types. Even winter offers chances for snowshoeing on some trails, making it a versatile destination.

Are there any easy trails that offer fall foliage views?

Absolutely. The diverse forest types around Jaffrey make it a prime location for fall foliage. Trails like the Gap Mountain North Trail, while offering some elevation, provide excellent opportunities to experience the vibrant autumn colors. Many woodland paths and rail trails will also be beautiful during this season.

What attractions can I find near the easy hiking trails?

Beyond the trails themselves, the area around Jaffrey is rich with natural attractions. You can visit the Monadnock Visitor Center for information, or explore highlights like Thoreau's Seat and Monte Rosa. The region's picturesque lakes and ponds also offer serene spots to relax after a hike.

What do other hikers enjoy most about the easy trails in Jaffrey?

The easy trails in Jaffrey are highly rated by the komoot community, with an average score of 4.8 stars. Reviewers often praise the quiet woodlands, well-maintained paths, and the opportunity to experience the natural beauty of the Monadnock region without strenuous effort. The variety of routes, from lakeside strolls to gentle forest paths, is also frequently highlighted.

Are there less crowded easy hiking options in Jaffrey?

While Mount Monadnock itself can be popular, many of the easier, shorter trails tend to be less crowded, especially on weekdays or outside peak season. Consider exploring trails like the Cascade Link Trail or the Royce Trail for a more tranquil experience away from the main mountain routes.

Is parking available at the trailheads for easy hikes?

Yes, parking is generally available at trailheads, particularly within Monadnock State Park. However, for popular areas like Monadnock State Park, day-use reservations are highly recommended, especially on weekends, due to parking limitations. Always check specific parking instructions for your chosen trailhead.

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