TOP 30 Best Challenging hikes in Vermont

Dynamic Cycling Adventures is a premier cycling institution located at 236 Apple Tree Lane in Burke, Vermont, United States. We offer exhilarating cycling experiences for riders of all levels, from beginners to seasoned pros. Our expert guides will lead you on thrilling adventures through scenic landscapes, challenging terrain, and breathtaking views. Whether you're looking for a leisurely ride through the countryside or an intense mountain biking excursion, Dynamic Cycling Adventures has something for everyone. Join us for an unforgettable cycling journey and discover the beauty of Vermont on two wheels.

The Stowe Recreation Path is a picturesque park located in Stowe, Vermont, United States. This popular outdoor destination offers a scenic trail that winds through the stunning natural landscapes of Vermont, providing visitors with a peaceful and relaxing environment to enjoy walking, biking, and jogging. The path is surrounded by lush forests, mountain views, and charming streams, making it the perfect spot for nature lovers and outdoor enthusiasts. Whether you're looking for a leisurely stroll or a challenging bike ride, the Stowe Recreation Path is a must-visit destination for anyone seeking a tranquil escape in the heart of Vermont's beautiful countryside.

Sunset Trail is a scenic park located on Sunset Ridge Trail in the charming town of Underhill, Vermont. This beautiful outdoor space offers visitors the opportunity to explore nature, enjoy breathtaking views, and unwind in a peaceful setting. Whether you're looking for a leisurely stroll, a challenging hike, or a place to have a picnic with family and friends, Sunset Trail has something for everyone. Come and experience the beauty of Vermont at Sunset Trail.

The Clarendon Gorge Appalachian Trailhead is a picturesque park located at 2000 Vermont 103 in Shrewsbury, Vermont, United States. This institution serves as a starting point for hikers looking to explore the renowned Appalachian Trail. The park offers stunning views of the Clarendon Gorge, a natural wonder that attracts visitors from near and far. With its well-maintained trails and peaceful surroundings, the Clarendon Gorge Appalachian Trailhead is the perfect destination for outdoor enthusiasts seeking adventure and tranquility in equal measure.

Black Falls DGC is a disc golf course located at 2356 Black Falls Road in Montgomery, Vermont, United States. This scenic course offers a challenging and fun experience for disc golf enthusiasts of all skill levels. With beautiful surroundings and well-maintained fairways, players can enjoy a day of outdoor recreation in a peaceful setting. Whether you're a beginner looking to improve your skills or a seasoned pro seeking a new course to conquer, Black Falls DGC is the perfect destination for a day of disc golfing.

Weathersfield Trail is a picturesque park located at 368-2 Weathersfield Trail in Weathersfield, Vermont, United States. This beautiful natural area offers visitors a serene escape into the great outdoors, with winding trails that meander through lush forests and open meadows. Whether you're looking for a leisurely stroll, a challenging hike, or a peaceful spot to enjoy a picnic, Weathersfield Trail has something for everyone. Come explore this hidden gem and immerse yourself in the beauty of Vermont's landscape.

ArborTrek Canopy Adventures, located at 1239 Edwards Road in Cambridge, Vermont, offers a thrilling escape from the everyday rush as you soar through the wilds of the Green Mountains of Northern Vermont. Recognized as one of the top zipline courses in the USA, ArborTrek is a must-visit tourist attraction for adventure seekers. Experience the Zip Line Canopy Tour, fully-guided eco-adventures that combine high-speed ziplines with stunning views and commentary on the local ecology. Test your physical abilities on the Treetop Obstacle Course and Climbing Adventure, featuring over 90 elements for sliding, balancing, jumping, climbing, and more.

Sunset Ledge Trail Head is a park located in Lincoln, Vermont, United States. This 2.1-km out-and-back trail is considered moderately challenging, taking an average of 46 minutes to complete. It is a popular spot for hiking and walking, offering a chance to enjoy solitude during quieter times of the day. The best time to visit is between June and October, with dogs welcome on a leash. The trail offers a short but somewhat challenging hike up to a spectacular mountaintop viewpoint, with stunning views especially during the fall foliage season. The trail is rocky and muddy in some areas, but the beautiful scenery at Sunset Ledge makes it worth the trek. Visitors have reported a great experience on this trail, enjoying the views, the moderate difficulty level, and the opportunity to explore the natural beauty of Vermont.

The Canty Trail is a picturesque park and popular tourist attraction located on Old Turnpike Road in Mendon, Vermont, United States. This beautiful outdoor space offers visitors a peaceful and serene environment to enjoy nature and take in the stunning scenery of the surrounding area. Whether you're looking for a leisurely stroll, a challenging hike, or simply a place to relax and unwind, The Canty Trail has something for everyone. With its well-maintained pathways, lush greenery, and abundant wildlife, this park is the perfect destination for nature lovers and outdoor enthusiasts alike. So come and explore The Canty Trail and experience the natural beauty of Vermont at its finest.

Duxbury Window Trail is an 8.0-km out-and-back trail located at 3188 Duxbury Road, Bolton, Vermont, United States. This challenging trail takes an average of 3 h 24 min to complete and is popular for backpacking, camping, and hiking. Enjoy some solitude during quieter times of day on this year-round trail that is beautiful to visit anytime. Dogs are welcome but must be on a leash. The trail features steep rocky areas, two great overlooks, and some muddy spots further up. The trail is well-maintained with minimal bugs and offers beautiful views. However, some parts of the trail may be poorly marked, so be prepared to rely on GPS. Overall, Duxbury Window Trail offers a variety of terrain, waterfalls, and beautiful foliage, making it a great hike for all levels of hikers.

Snake Mountain Trail is a picturesque park located at 2601 Mountain Road in Addison, Vermont. This scenic trail offers stunning views of the surrounding landscapes and is a popular destination for hiking and nature enthusiasts. The trail is well-maintained and offers a moderate level of difficulty, making it suitable for hikers of all skill levels. Visitors can expect to encounter a variety of wildlife and plant species along the way, adding to the overall experience of exploring this beautiful natural area. Whether you're looking for a challenging hike or a peaceful stroll through nature, Snake Mountain Trail is the perfect destination for outdoor adventure.

Silver Lake Trail is a picturesque hiking trail located in Salisbury, Vermont, United States. This popular tourist attraction offers visitors the opportunity to immerse themselves in the natural beauty of the area while enjoying a leisurely stroll or a challenging hike. The trail meanders through lush forests, past bubbling streams, and eventually leads to the stunning Silver Lake. Whether you're a seasoned hiker or just looking for a peaceful escape from the hustle and bustle of everyday life, Silver Lake Trail is the perfect destination for outdoor enthusiasts of all levels. Come and explore this hidden gem in the heart of Vermont's countryside.

Battell Trailhead is a picturesque park and popular tourist attraction located at 1922-1940 Elder Hill Road in Lincoln, Vermont, United States. This scenic trailhead offers visitors the opportunity to explore the beautiful natural surroundings, including hiking trails and stunning views. Whether you're looking for a leisurely stroll or a challenging hike, Battell Trailhead has something for everyone to enjoy. Come and experience the beauty of Vermont's outdoors at Battell Trailhead.

Red Gate Trail is a picturesque park located at 228-306 West Union Street in Manchester, Vermont. This beautiful natural setting offers visitors a chance to explore lush greenery, winding trails, and peaceful surroundings. Whether you're looking for a leisurely stroll or a challenging hike, Red Gate Trail has something for everyone. Take in the fresh air, listen to the sounds of nature, and enjoy a relaxing day outdoors at this hidden gem in the heart of Vermont.

Wrightsville Beach DGC is a disc golf course located in the picturesque town of Middlesex, Vermont, United States. Surrounded by lush greenery and stunning mountain views, this course offers a challenging yet enjoyable experience for players of all skill levels. With well-maintained fairways and strategically placed obstacles, Wrightsville Beach DGC provides a perfect setting for a day of outdoor recreation and friendly competition. Whether you're a seasoned disc golfer or just looking to try something new, this course is a must-visit destination for anyone seeking a fun and engaging outdoor activity in the heart of Vermont.

Trail 87 is a vibrant and eclectic institution located at 271 Vermont Route 100 in Dover, Vermont. This dynamic space combines a bar, cafe, food establishment, night club, restaurant, and store all under one roof. Whether you're looking for a delicious meal, a fun night out, or some unique shopping finds, Trail 87 has it all. With a laid-back atmosphere and friendly staff, this institution is the perfect place to relax, socialize, and enjoy a variety of entertainment options. Visit Trail 87 for a truly memorable and diverse experience in the heart of Vermont.

Healdville Trail is a picturesque park and popular tourist attraction located at 625 Station Road in Mount Holly, Vermont, United States. This scenic trail offers visitors the opportunity to explore the beautiful natural surroundings of Vermont, with lush forests, rolling hills, and stunning mountain views. Whether you're looking for a leisurely stroll or a more challenging hike, Healdville Trail has something for everyone. Come and experience the beauty of the Vermont countryside at Healdville Trail.

Sucker Brook Hollow Trail is a picturesque park and tourist attraction located on Saint George Road in Williston, Vermont, United States. This beautiful trail offers visitors the opportunity to immerse themselves in nature and enjoy a peaceful escape from the hustle and bustle of everyday life. With its serene atmosphere, lush greenery, and scenic views, Sucker Brook Hollow Trail is the perfect place for hiking, birdwatching, and picnicking. Whether you're looking for a relaxing day out or a challenging outdoor adventure, this trail has something for everyone to enjoy. Come explore the natural beauty of Vermont at Sucker Brook Hollow Trail!

Mount Haystack Trail is a picturesque park located at 184 Upper Dam Road in Wilmington, Vermont, United States. This institution offers visitors a beautiful and serene setting to explore nature and enjoy outdoor activities. The trail winds through lush forests, past babbling brooks, and up to the stunning Mount Haystack summit. Whether you're looking for a challenging hike or a peaceful stroll, Mount Haystack Trail has something for everyone. Come and experience the beauty of Vermont's landscape at this lovely park.

Townshend State Forest is a beautiful park located in Townshend, Vermont, United States. This expansive forest offers a peaceful retreat for nature lovers, hikers, and outdoor enthusiasts. With miles of hiking trails, scenic overlooks, and picnic areas, visitors can enjoy the stunning natural beauty of Vermont. The forest is home to a variety of wildlife and plant species, making it a perfect spot for birdwatching and nature photography. Whether you're looking for a leisurely stroll through the woods or a challenging hike to a mountain summit, Townshend State Forest has something for everyone to enjoy. Come experience the tranquility and beauty of this hidden gem in southern Vermont.

Five Tree Hill - Parking Area is a popular tourist attraction located at 690 Sunset Hill Road in Williston, Vermont, United States. This park offers a variety of hiking trails, with the Overlook via Sucker Brook Hollow Trail being the top choice among users on AllTrails.com. This 3.9 km trail has a 4.5-star rating from 702 reviews and offers an elevation gain of 162 m. The longest trail in the park is the Sucker Brook Hollow and Five Tree Hill Trail, which is 6.8 km long. With a total of 3 trails, Five Tree Hill Country Park has received an average 4.5-star rating from 1,339 AllTrails community reviews. If you're looking for a challenge, the Sucker Brook Hollow and Five Tree Hill Trail offers the most elevation gain at 234 m. The park's second-highest elevation gain can be found on the Overlook via Sucker Brook Hollow Trail at 162 m.

Jay Peak Resort, State Side Base is a premier ski and snowboard destination located at 219 Jay Peak Road in Jay, Vermont, United States. Nestled in the picturesque Green Mountains, this resort offers top-notch amenities and facilities for winter sports enthusiasts of all levels. From challenging slopes to scenic trails, visitors can enjoy a variety of outdoor activities in a stunning natural setting. With cozy accommodations, delicious dining options, and a welcoming atmosphere, Jay Peak Resort, State Side Base is the perfect place to experience the beauty and excitement of Vermont's winter wonderland.

The Robert Frost Trailhead is a picturesque park located on Recreation Lane in Shaftsbury, Vermont, United States. This tranquil and scenic trailhead serves as the starting point for the Robert Frost Trail, a popular hiking and walking path that winds through the beautiful Vermont countryside. Visitors can enjoy the natural beauty of the area, as well as the opportunity to explore the trail and immerse themselves in the poetry and legacy of the renowned American poet, Robert Frost. Whether you're looking for a leisurely stroll or a more challenging hike, the Robert Frost Trailhead is the perfect place to connect with nature and experience the beauty of Vermont.

The Killington Adventure Center is a thrilling amusement park and popular tourist attraction located at 3861 Killington Road in Killington, Vermont, United States. With a wide range of exciting activities and attractions, visitors can enjoy a day filled with adventure and fun. From zip lining and mountain biking to scenic chairlift rides and challenging ropes courses, there is something for everyone at the Killington Adventure Center. Whether you're seeking an adrenaline rush or simply looking to enjoy the beautiful surroundings, this institution offers a memorable experience for all ages.

Located in Fairlee, Vermont, the Glen Falls/Echo Mountain Trail is a picturesque park offering visitors a scenic hiking experience. The trail winds through lush forests, past babbling brooks, and up to Echo Mountain, providing breathtaking views of the surrounding landscape. Whether you're an experienced hiker looking for a challenge or a casual walker seeking a peaceful escape, this trail offers something for everyone. Don't forget to bring your camera to capture the beauty of nature at Glen Falls/Echo Mountain Trail.

Rocky Ridge Golf Club is a premier golfing destination located at 7470 Route 116 in Saint George, Vermont, United States. Nestled in the picturesque countryside, this club offers a challenging 18-hole course with stunning views of the surrounding landscape. The well-maintained greens and fairways provide an enjoyable experience for golfers of all skill levels. In addition to the course, Rocky Ridge Golf Club also features a pro shop, practice facilities, and a clubhouse with a restaurant and bar. Whether you are a seasoned golfer or just starting out, Rocky Ridge Golf Club is the perfect place to enjoy a day on the links.

Norwich Nature Area Trails is a picturesque park and tourist attraction located at 50 Church Street in Norwich, Vermont, United States. This beautiful natural area offers a network of scenic trails that wind through forests, meadows, and wetlands, providing visitors with the opportunity to immerse themselves in the tranquility of nature. Whether you're looking for a leisurely stroll, a challenging hike, or a peaceful spot to relax and enjoy the outdoors, Norwich Nature Area Trails has something for everyone. So come and explore this hidden gem in Vermont and discover the beauty of the great outdoors.

Clear River Disc Golf Course is a premier disc golf destination located in the picturesque town of Pittsfield, Vermont. Nestled along Vermont Route 100, this course offers players of all skill levels the opportunity to enjoy a challenging round of disc golf in a beautiful natural setting. With well-maintained fairways, scenic views, and a variety of obstacles to navigate, Clear River Disc Golf Course is a must-visit for disc golf enthusiasts. Whether you're a beginner looking to improve your skills or a seasoned pro seeking a new challenge, this course has something for everyone. Come experience the thrill of disc golf at Clear River Disc Golf Course today!

Chester Disc Golf is a premier disc golf course located at 65 Lovers Lane Road in the picturesque town of Chester, Vermont, United States. Surrounded by stunning natural beauty, this institution offers a challenging and enjoyable disc golf experience for players of all skill levels. With well-maintained fairways and scenic views, Chester Disc Golf is the perfect destination for disc golf enthusiasts looking to test their skills and have a great time outdoors. Whether you're a beginner or a seasoned pro, come and enjoy a round of disc golf at Chester Disc Golf today!

Hemlock Pete's Canoes and Kayaks is a premier outdoor store located at 149 Richardson Road in Orange, Vermont, United States. Specializing in high-quality canoes and kayaks, this institution offers a wide range of products for all levels of paddlers. Whether you're a beginner looking to explore local rivers or an experienced adventurer seeking new challenges, Hemlock Pete's has everything you need to enjoy the great outdoors. With expert staff and top-notch customer service, this store is your go-to destination for all things paddling.