Loading...

🎉 Enjoy a Free 7-Day Supporter Trial and Unlock Exclusive Perks — No Credit Card Required. Learn more.

Explore hiking trails

Find tips, photos and maps for 160 miles (258 km) of hiking trails from the MyHikes community.

52 trails found near: "Winchester, NH"

Within:
30 miles
Difficulty:
Any
Features:
  
Trail Type:
Any
Default image for Mt. Wantastiquet & Madame Sherri's Castle, a 3.9-mile trail in Chesterfield, NH (US)
3.9 Miles
6.3 km
Moderate Out-and-Back
Default image for Red Diamond Trail, a 1.7-mile trail in Keene, NH (US)
1.7 Miles
2.7 km
Moderate Loop
Default image for Tully Mountain, a 1.1-mile trail in Orange, MA (US)
1.1 Miles
1.8 km
Moderate Out-and-Back
Default image for Jacobs Hill & Spirit Falls Hike, a 1.8-mile trail in Royalston, MA (US)
1.8 Miles
2.9 km
Moderate Loop
Default image for Cheshire Rail Trail, a 5.6-mile trail in Keene, NH (US)
5.6 Miles
9 km
Easy Out-and-Back
Default image for Gap Mountain Trail, a 2.8-mile trail in Troy, NH (US)
2.8 Miles
4.5 km
Moderate Out-and-Back
Default image for Hermit's Castle , a 4.5-mile trail in Erving, MA (US)
4.5 Miles
7.2 km
Hard Out-and-Back
Default image for Tully Trail to Spirit Falls Hike, a 3.4-mile trail in Royalston, MA (US)
3.4 Miles
5.5 km
Moderate Out-and-Back
Default image for Farley Ledges, a 2.0-mile trail in Erving, MA (US)
2 Miles
3.2 km
Hard Loop
Default image for Doane's Falls, a 0.2-mile trail in Royalston, MA (US)
0.2 Miles
0.3 km
Easy Out-and-Back
Default image for White Arrow Trail to Mt Monadnock Summit, a 5.0-mile trail in Jaffrey, NH (US)
5 Miles
8 km
Hard Out-and-Back
Default image for Pocumtuck Ridge Trail, a 0.8-mile trail in Greenfield, MA (US)
0.8 Miles
1.3 km
Easy One-Way
Loading...
Showing 1 to 12 of 52 Hiking Trails

Trails by Category

You May Also Like

Pennsylvania's Grand Canyon - Explore Pennsylvania's Grand Canyon, officially named Pine Creek Gorge, including hiking trails, vistas, overlooks, waterfalls, backcountry campsites, backpacking trails.

Pennsylvania's Grand Canyon

Explore Pennsylvania's Grand Canyon, officially named Pine Creek Gorge, including hiking trails, vistas, overlooks, waterfalls, backcountry campsites, backpacking trails.

Read
Colorado's Million Dollar Highway - Plan a day's drive adventure along the iconic Million Dollar Highway in Colorado. Explore the best short trails, roadside stops, waterfalls, vistas, ghost towns, and hot springs within a ~6 hour road trip.

Colorado's Million Dollar Highway

Plan a day's drive adventure along the iconic Million Dollar Highway in Colorado. Explore the best short trails, roadside stops, waterfalls, vistas, ghost towns, and hot springs within a ~6 hour road trip.

Read
Glacier's Going-to-the-Sun Road - Discover the breathtaking beauty of Glacier National Park along the iconic Going-to-the-Sun Road. From stunning roadside stops to picturesque waterfalls and vistas, this engineering marvel offers endless opportunities for exploration.

Glacier's Going-to-the-Sun Road

Discover the breathtaking beauty of Glacier National Park along the iconic Going-to-the-Sun Road. From stunning roadside stops to picturesque waterfalls and vistas, this engineering marvel offers endless opportunities for exploration.

Read
New York's Best Waterfalls - Whether you're planning a day hike, roadside stop, or a leisurely short walk, this guide provides hikers, travelers, and locals alike with 63 different locations to over 100 scenic waterfalls to help plan your next adventure!

New York's Best Waterfalls

Whether you're planning a day hike, roadside stop, or a leisurely short walk, this guide provides hikers, travelers, and locals alike with 63 different locations to over 100 scenic waterfalls to help plan your next adventure!

Read