Fall will be here before we know it! Autumn is the best time to explore the hiking trails in Brattleboro. While many admire the fall colors in Vermont from the road, those who hit the trails are rewarded with unforgettable views and crisp, refreshing air. From fiery reds to bright yellows, the landscape bursts with color, making it the perfect season to experience some of the best hikes in Vermont. Whether planning a day trip or a weekend escape, fall in Vermont is all about embracing the outdoors.
Brattleboro in the fall is a vibrant mix of natural beauty and small-town charm, offering an authentic taste of fall in Vermont. As brilliant shades of red, orange, and yellow blanket the surrounding hills, the town is alive with seasonal markets, local art, and cozy cafés perfect for warming up after a hike. The hiking trails in Brattleboro provide easy access to some of the most stunning views of Vermont fall foliage, winding through colorful forests and leading to scenic overlooks. Known for its creative spirit and welcoming vibe, Brattleboro is a great home base for exploring the best hikes in Vermont.
Staying at the Inn on Putney Road offers the perfect blend of comfort and location for your fall getaway in Vermont. We are located just a short drive from downtown Brattleboro. From our property, you will have access to the Retreat Trails, some of the best hiking trails in Brattleboro. Our Inn provides a peaceful retreat after a day of exploring the vibrant Vermont fall foliage. Guests enjoy elegant rooms, a gourmet breakfast each morning, and direct access to scenic riverside paths and wooded trails—ideal for experiencing the beauty of hiking in Vermont. Whether you’re here for a weekend or a longer stay, the Inn on Putney Road is your home base for discovering the best hikes in Vermont. Reserve your room now.
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Exploring the hiking trails in Brattleboro and beyond is one of the best ways to experience fall color in Vermont. The views from the various hiking trails are breathtaking. Though there are nearly endless options when it comes to hiking trails in the Brattleboro area, here are some great options to explore this fall:
- Mount Monadnock has been designated a National Natural Landmark and is an incredible place to spend a fall afternoon. Though it’s a challenging hike, you’ll find an amazing bare rock summit offering 100-mile views of six New England States. Mount Monadnock is considered one of the most hiked mountains in the world, and there is no better time than fall to enjoy the spectacular views from the top.
- Just 9 miles southwest of Brattleboro, Sweet Pond State Park offers a peaceful escape into nature. The 1.3-mile loop trail around the pond is perfect for a leisurely walk, especially on a crisp afternoon surrounded by vibrant fall color in Vermont.
- Though it’s technically located in Hinsdale, New Hampshire, Mount Wantastiquet is just a short distance from downtown Brattleboro. From the top of Mount Wantastiquet, you’ll enjoy panoramic views of Brattleboro and the river valley. During the fall months, the views are even more spectacular.
- Molly Stark State Park, located on the scenic byway of the same name, has a variety of trails worthy of exploration during fall in Vermont. Hiking up to the fire lookout tower on Mt. Olga is one of the most popular activities in the park.
- The lesser-known Chesterfield Gorge Natural Area is a hidden gem offering stunning views, especially during the peak of fall in Vermont. Just under a mile, the rugged trail loops around the gorge, making it an easy and rewarding hike for those looking to enjoy brilliant foliage and peaceful surroundings just over the border in New Hampshire.
- Pisgah State Park spans over 13,000 acres, making it the largest property in New Hampshire’s State Park system. Just a short drive from Brattleboro, it offers miles of hiking trails through dense forests, perfect for soaking in the season’s vibrant colors. With trails for all skill levels, it’s an excellent spot for a full day of exploring during the height of autumn.
- Explore the scenic trails of Madame Sherri Forest, just across the river in Chesterfield, NH. Hike through vibrant woodlands, enjoying the fall color, and discover the unique ruins of Madame Sherri’s stone staircase, an intriguing piece of local history surrounded by natural beauty.
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The Retreat Trails in Brattleboro offer a convenient and scenic way to experience hiking in Vermont. Over nine miles of interconnected paths wind through forested hills and open meadows. Accessible from our property, these trails are perfect for catching sweeping views of Vermont fall foliage without getting in a car.
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