4.7
(160)
1,382
hikers
30
hikes
Family friendly hiking trails in Windsor County, Vermont, are characterized by diverse landscapes shaped by the Ottauquechee and Connecticut River Valleys. The region features managed forests, historic carriage roads, and prominent natural features like Quechee Gorge. Hikers can explore a variety of environments, from riverine paths to woodland trails and hills offering panoramic views.
Last updated: July 8, 2026
1
hikers
4.46km
01:11
50m
50m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
2
hikers
9.59km
02:43
230m
200m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

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1
hikers
1.51km
00:25
10m
50m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
1
hikers
4.14km
01:11
100m
100m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
4.97km
01:16
20m
20m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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A very idyllic small town post office. Very cute.
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There really is EVERYTHING to walk here. Very pretty little town in Vermont, a postcard idyll.
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Very pretty small town in Vermont, postcard idyll.
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Lake Runnemede is a great place for a break during a long ride. The large body of water is home to many species of birds and fish. The water is visible from the road, so if you don't have time to stop, you can still get a great view as you ride by.
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This is a lovely run around the shores of Lake Runnemede along a relatively flat and grassy footpath that's right up on the water's edge, creating lovely scenes as you make your way around.
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Known as Vermont's Grand Canyon, you get a splendid view of the gorge from the road bridge. You can also park up your bike and take the hiking path to explore it further and go for a swim in the summer.
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Woodstock Middle Covered Bridge has spanned the Ottauquechee River since 1969 and was supposedly constructed without the use of any nails.
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Windsor County offers a fantastic selection of family-friendly hiking experiences. You'll find over 30 routes specifically curated for families, ranging from easy strolls to slightly more challenging paths suitable for older children.
Absolutely! Windsor County is home to many easy trails perfect for little legs and beginner hikers. For example, the Paradise Park Loop in Windsor offers a gentle 2.8-mile walk around Lake Runnemede, ideal for a relaxed family outing.
Many family-friendly trails in Windsor County boast beautiful scenery and interesting landmarks. You can enjoy panoramic views of the Ottauquechee River Valley from trails like Mount Peg Foot and Bridle Trails. The The Pogue and Mount Tom Trail offers views over Woodstock from Mount Tom's summit and passes by the picturesque The Pogue. Don't miss the iconic Quechee Gorge Bridge when exploring the Quechee Gorge Trail.
Yes, you can find trails that lead to beautiful water features. The Paradise Park Loop circles Lake Runnemede, perfect for a lakeside stroll. While not directly on a listed family trail, the Mill Ponds Waterfall Viewing Spot is a nearby highlight worth exploring.
Windsor County offers unique beauty in every season. Spring brings lush greenery, while summer is ideal for longer days and warmer weather. Fall is spectacular for vibrant foliage, and winter transforms the landscape into a snowy wonderland, though some trails may require snowshoes. Be mindful of 'mud season' in early spring when some trails can be very wet.
Many trails in Windsor County are dog-friendly, but policies can vary by specific park or land management. For instance, Paradise Park in Windsor generally welcomes dogs on leash. It's always best to check the specific regulations for Mount Ascutney State Park or Marsh-Billings-Rockefeller National Historical Park before heading out with your furry friend.
Yes, several family-friendly routes are designed as loops, making for a convenient and enjoyable outing. The Paradise Park Loop and The Pogue and Mount Tom Trail are excellent examples of circular routes that bring you back to your starting point.
Parking is generally available at or near the trailheads for most family-friendly routes in Windsor County. Popular spots like Quechee Gorge, Marsh-Billings-Rockefeller National Historical Park (for Mount Tom and The Pogue), and Paradise Park typically have designated parking areas. Some may have small fees or require permits, so it's good to check ahead.
Windsor County's diverse habitats, including managed forests and wildlife management areas, offer opportunities for wildlife spotting. You might see various bird species, especially in areas like the Windsor Grasslands Wildlife Management Area, as well as deer, squirrels, and other small mammals. Keep an eye out for tracks and listen for bird calls!
The family-friendly trails in Windsor County are highly rated by the komoot community, with an average score of 4.7 stars. Reviewers often praise the well-maintained paths, the beautiful natural scenery, and the accessibility for all ages. Many highlight the peaceful atmosphere and the variety of landscapes, from riverside walks to gentle climbs with rewarding views.
While many trails are natural surfaces, some paths in Windsor County are wide and relatively flat, making them more accessible for strollers. The Toonerville Trail is a good option, offering a mostly flat and even surface suitable for strollers, following an old rail bed.


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