The best family-friendly hikes and walks in Rutland County
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651
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13
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Family friendly hiking trails in Rutland County traverse a diverse landscape within Vermont's Green Mountains, including sections of the Green Mountain National Forest. The region is characterized by forested mountain slopes, prominent peaks, and natural bodies of water. Hikers can explore areas with old-growth forests, waterfalls, and unique geological features, offering varied terrain for outdoor activities.
Best family friendly hiking trails in Rutland County
- The most popular family friendly hiking route is Deer Leap Rock via Appalachian Trail and Deer Leap Trail, a 2.2 miles (3.5 km) trail that takes 1 hour 16 minutes to complete. This moderate route offers rewarding vistas over the surrounding landscapes.
- Another top favourite among local hikers is Pesky Cairn Trail, an easy 4.3 miles (6.9 km) path. This trail features gentle elevation changes, making it suitable for a relaxed family outing.
- Local hikers also love the Pine Hill Park loop, a 5.8 miles (9.4 km) trail leading through varied terrain within a 325-acre city park, often completed in about 2 hours 36 minutes.
- Hiking in Rutland County is defined by forested mountains, scenic overlooks, and accessible park trails, with options ranging from easy family walks to more challenging ascents. The network offers routes for different ability levels, ensuring enjoyable experiences for all.
- The routes in Rutland County are highly rated by the komoot community with an average score of 4.8 stars from over 30 reviews. More than 600 hikers have used komoot to explore Rutland County's varied terrain.
Last updated: October 10, 2026
2
hikers
6.91km
01:54
130m
110m
Embark on the Pesky Cairn Trail, an easy hike covering 4.3 miles (6.9 km) with a gentle ascent of 418 feet (127 metres). You can expect to complete this route in about 1 hour and 54 minutes. The trail winds through a dense northern hardwood forest, offering a classic Green Mountain experience. As you hike, you will pass mossy boulder fields and steadily climb towards a tranquil clearing. The path's high point is marked by the large, weathered "pesky cairn" itself, a peaceful spot where you might glimpse Kent Pond through the trees.
To begin your hike, parking is readily available at Gifford Woods State Park. While the Pesky Cairn Trail is rated easy, be aware that sections can be rocky and slippery, especially after rain. You will encounter frequent roots and some short, steep pitches along the way. Wearing appropriate footwear is advisable, and paying attention to your footing will ensure a more enjoyable experience on these parts of the route.
This trail offers a quintessential Vermont hiking experience, immersing you in the natural beauty of the Green Mountains. The dense northern hardwood forest provides a rich canopy and a serene atmosphere throughout your journey. The presence of the distinctive "pesky cairn" at the trail's high point adds a unique landmark to your adventure, making it a memorable destination within the region.
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hikers
3.53km
01:16
300m
40m
Embark on a moderate hike to Deer Leap Rock, a rewarding journey that covers 2.2 miles (3.5 km) with an elevation gain of 995 feet (303 metres). You can expect to complete this route in about 1 hour and 15 minutes. The trail leads you through varied forest landscapes, transitioning from bright birch groves to deeper evergreen sections as you climb. Your efforts are well-rewarded at the summit, where Deer Leap Rock offers expansive views. From this vantage point, you can take in the Coolidge Range, Pico Peak, and the Green Mountains of Vermont. On exceptionally clear days, you might even glimpse the distant Adirondacks of New York.
Accessing the Deer Leap Rock trail is straightforward, with convenient parking located right off US Route 4. This makes it an easy destination to reach for a day trip. If you plan to bring your dog, know that the route is dog-friendly; just remember to keep your canine companion on a leash. Consider starting your hike earlier in the day to enjoy the views without crowds, especially during peak seasons.
This route is nestled within Gifford Woods State Park, offering a classic Vermont hiking experience. The trail itself is a segment of the historic Appalachian Trail, adding a layer of significance to your journey. It's a popular choice for those seeking a relatively short but impactful outing with significant scenic payoff. The diverse forest types you encounter reflect the rich natural environment of the region.
515km
168:28
21,190m
21,240m
Hike the difficult 320.2-mile Long Trail through Vermont's Green Mountain National Forest, gaining 69530 feet in elevation.
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9.37km
02:36
170m
170m
Hike the moderate 5.8-mile Pine Hill Park loop in Rutland, VT, featuring forests, vistas, and Rocky Pond, with 562 feet of gain.
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4
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2.14km
00:37
60m
60m
Hike the easy 1.3-mile Kent Brook Trail loop in Gifford Woods State Park, traversing a dense hardwood forest along Kent Brook.
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Tips from the Community
This is a great family-friendly spot, and only one mile from the parking lot via trail. A knob of smooth Vermont bedrock rises over Route 4, granting panoramic views south to Mount Killington and the surrounding peaks. Great spot for a picnic!
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Stratton Mountain is one of the most iconic peaks on the Long Trail, but not for its height, but rather for its historical significance. It was here in 1909 that James P. Taylor first imagined a “footpath in the wilderness,” which eventually became the Long Trail. The summit is forested, but a restored fire tower (that you can climb!) offers expansive 360-degree views of southern Vermont and the surrounding peaks. Today, Stratton is also home to a major ski resort, but the Long Trail bypasses the commercial slopes, staying on a quieter, wooded path. A nearby shelter, Stratton Pond Shelter, provides a peaceful overnight spot, just a short hike from the summit. This is a pretty built-up shelter (especially in comparison to the more common, simple three-sided lean-tos) so it's worth checking out even if you're not spending the night.
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The Long Trail, the oldest long-distance hiking trail in the United States, begins at the Massachusetts–Vermont border near Williamstown, MA. This southern terminus is marked by a large wooden sign and lies at the junction where the Appalachian Trail (AT) continues and the Long Trail (LT) begins. The first 105 miles of the LT coincide with the AT before the two trails split at Maine Junction near Killington, VT. There are two primary approaches to reach the southern terminus: Via the Appalachian Trail from North Adams, MA: This route is approximately 3.8 miles and begins at Route 2 in North Adams, or via the Pine Cobble Trail from Williamstown, MA: This 3.3-mile trail starts at Pine Cobble Road in Williamstown and offers a scenic ascent to the LT's starting point. Both approaches take hikers to the VT/MA border, where the Long Trail officially begins its 272-mile journey northward through Vermont's Green Mountains to the Canadian border.
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The Kent Brook Trail is a straightforward loop trail that takes you through a beautiful part of Gifford Woods State Park. The Appalachian Trail cuts through the middle of the loop.
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Gifford Woods State Park is a popular destination for outdoor enthusiasts and Appalachian Trail through-hikers. The park has a wooded picnic area, two camping loops with water and restrooms, and one of Vermont's few remaining old-growth hardwood tree stands. The stand is home to grand-sized trees like sugar maple, beech, yellow birch, white ash, and hemlock, and the park's understory is rich with beautiful native wildflowers.
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Gifford Woods State Park is a popular destination for outdoor enthusiasts and Appalachian Trail through-hikers. The park has a wooded picnic area, two camping loops with water and restrooms, and one of Vermont's few remaining old-growth hardwood tree stands. The stand is home to grand-sized trees like sugar maple, beech, yellow birch, white ash, and hemlock, and the park's understory is rich with beautiful native wildflowers.
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Spanning 325 acres, this haven boasts 17 miles (ca. 27 km) of top-notch single-track trails. Ideal for mountain biking, and other outdoor sports in central Vermont. Explore old logging roads amid stunning forests and scenic vistas.
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Traverse Giorgetti to the park boundary near Rocky Pond on a singletrack, to avoid the eroded old pond road. You will be inspired to explore the great views, especially at Stegosaurus entrance overlooking the pond.
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Frequently Asked Questions
How many family-friendly hiking trails are available in Rutland County?
Rutland County offers a great selection of family-friendly hiking options. This guide features 13 carefully selected routes, with 4 easy and 7 moderate trails, ensuring there's something for every family's comfort level.
What is the best time of year for family hiking in Rutland County?
The prime hiking season in Rutland County runs from late spring to fall. Summer offers lush green forests, while autumn provides spectacular fall foliage, typically peaking in early to mid-October. Winter hiking is also possible with appropriate gear, offering a unique experience.
Are there any easy, circular routes suitable for families in Rutland County?
Yes, for families looking for an easy loop, the Pine Hill Park loop is a fantastic option. This 9.4 km moderate trail offers varied terrain within a 325-acre city park, making it a local favorite for hiking and trail running.
What do other hikers say about the family-friendly trails in Rutland County?
The family-friendly trails in Rutland County are highly rated by the komoot community, with an average score of 4.8 stars from 38 ratings. Hikers often praise the diverse landscapes, well-maintained paths, and the rewarding views found on many of the routes.
Are there any family-friendly trails with waterfalls in Rutland County?
While not directly on the routes in this guide, Rutland County is known for accessible waterfalls like Thundering Brook Falls. These are often short, boardwalk-accessible walks, perfect for a family outing to see a natural wonder.
Which family-friendly trails offer the best views in Rutland County?
For rewarding vistas, consider the Deer Leap Rock via Appalachian Trail and Deer Leap Trail. This moderate route leads to the Deer Leap Overlook, offering fantastic panoramic views without an extreme climb. The Bald Mountain Trail in Aitken State Forest also provides panoramic views of the Green Mountain range and surrounding valleys.
Are there any interesting natural landmarks or points of interest along these family-friendly routes?
Absolutely! Many trails offer access to beautiful natural features. For instance, the Deer Leap Rock via Appalachian Trail and Deer Leap Trail leads to the stunning Deer Leap Overlook. You can also find serene spots like Little Rock Pond, a beautiful lake that can be reached via easy paths.
Are the family-friendly trails in Rutland County suitable for strollers?
While many trails in Rutland County are natural paths, some areas offer more accessible options. Stone Meadow Park, for example, provides accessible walking trails through a meadow. For specific stroller suitability, it's always best to check individual route descriptions for surface type and elevation changes.
Are dogs allowed on family-friendly hiking trails in Rutland County?
Generally, dogs are welcome on trails in Rutland County, especially within the Green Mountain National Forest, provided they are kept on a leash and you practice Leave No Trace principles. Always check specific park or trail regulations before heading out, as some areas may have restrictions.
Are there any family-friendly trails that are particularly good for beginners or young children?
For beginners or families with young children, the Pesky Cairn Trail is an excellent choice. It's an easy 6.9 km route with minimal elevation gain, making it very manageable. Another easy option is the Kent Brook Trail, which is shorter at 2.1 km and also features gentle slopes.
Where can we find parking for these family-friendly trails?
Most trailheads in Rutland County, especially those leading into the Green Mountain National Forest or state parks, offer designated parking areas. For example, Pine Hill Park has its own parking facilities. For specific routes, details on parking availability are usually provided in the route descriptions.
Are there any family-friendly trails that are part of the famous Long Trail or Appalachian Trail?
Yes, both the Long Trail and the Appalachian Trail traverse Rutland County, offering extensive opportunities for day hikes. The Deer Leap Rock via Appalachian Trail and Deer Leap Trail is a moderate route that utilizes a section of the Appalachian Trail, providing a taste of these iconic paths.
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