Best Hikes Near Brattleboro, Vermont (and where to stay after)
Whether you're a hiker ⛰️🏃♀️ or more of a hiker 🧚 👣 🍄 the Brattleboro and West River Valley region of southern Vermont has perfect trails for you. If you're planning a trip and searching for the best Vermont hikes near a cozy place to stay, you're in the right spot.
The best time to hike in Vermont is any season where trails aren't covered in snow or mud — generally May through October. Early season hiking brings spring ephemerals; wildflowers that take advantage of sunlight to bloom before the leaves of trees close the canopy. It also means fewer crowds, abundant streams and waterfalls, and hillsides cloaked in creeping green.
photo Ethan Abitz
With temperatures rarely reaching above the 80°Fs, summer can also be a great time to hike in Vermont, especially to catch a sunrise or sunset. Lucky hikers may also spot wildlife like deer, turkey, hawks, and owls, and even the occasional porcupine (give them space). One of our favorite summer activities? Hiking to a hidden swimming hole to cool off on a hot day.
As the season shifts toward Vermont's famous fall foliage, hiking trails tend to swell with leaf peepers — and if you're looking for the best fall hikes in Vermont, this region is hard to beat. That's no reason to avoid them — there's room for everyone in the woods, and it's a popular time for good reason. If you'd rather take in the blazing view minus the possibility of a crowd, consider hiking midweek or early in the morning.
Pack your daypack (or your picnic basket) and get ready to explore Vermont's Green Mountains!
Here are our top 6 favorite trails close to Tanglebloom Cabin:
1. Putney Mountain — Brookline/Putney
GPS: 443 Putney Mountain Rd., Putney, VT
This is our favorite hike, and it's also super close to the cabin — the trailhead is just 3 miles away. Park in the lot on the left, and take the Ridgeline Trail to the summit. Take in the beautiful view — it's a great place to watch the sunrise or sunset (bring flashlights), or even have a picnic. From here you can either continue hiking north (straight) along the West Cliff Trail, or make it a 1.4-mile loop by following the West Cliff Trail south (left) back to the trailhead parking lot.
Across the road from the parking lot is another network of trails you can explore via the Hinton Trailhead. We recommend checking out the trail maps in advance if you'd like to plan a longer day hike on this beautiful southern Vermont ridgeline.
2. West River Trail — Rice Farm Road, Dummerston or Marina Trailhead, Brattleboro
GPS:
Rice Farm Road Access: 841 Rice Farm Road, Dummerston, VT
Marina Trailhead: 125 Spring Tree Road, Brattleboro, VT
An easy, flat trail great for walking, running, or biking, the West River Trail is one of the most accessible hikes near Brattleboro, Vermont. Be sure to take the interpretive loop into the RiverStone Preserve about 1 mile north of the Marina Trailhead.
Pro tip: The Marina restaurant is located at the Brattleboro trailhead and makes a great spot to have lunch or a drink while watching the sunset.
3. The Pinnacle — Brookline
GPS: 1200 Grassy Brook Rd., Brookline, VT
About 5 miles from the cabin is another epic hiking spot: The Pinnacle, via the Radford-Smith Trailhead. You'll see a small parking area and trail kiosk on your right. This is a good option if you want to spend 2–3 hours on the trail, as it leads to a viewpoint with a historic cabin worthy of spending some time. You can even catch a glimpse of Tanglebloom Cabin... well, if it weren't for all the trees!
Note: The Pinnacle cabin is available via reservation for camping. Please respect campers who may be present inside, as they've secured a paid reservation for use of the interior space.
4. Overlook Trail — Jamaica State Park
GPS: 48 Salmon Hole Lane, Jamaica, VT
Inside Jamaica State Park, just a 20-minute drive from Tanglebloom, you'll find a few great hiking options. One of our favorites is the Overlook Trail, which brings you to a lovely viewpoint. If you want something a little more mellow, stick to the West River Trail, which follows a historic railroad bed, making for a mostly flat and easy walk, run, or bike ride. Note there's a small day-use fee to enter the park.
Pro tip: The Salmon Hole is a good swimming hole just inside the park. Steps lead down to the water, and restrooms are available nearby.
5. Hamilton Falls — Jamaica State Park
GPS: 48 Salmon Hole Lane, Jamaica, VT
Access to this beautiful waterfall is possible via a 6.8-mile out-and-back hike (mostly flat and easy, with some uphill at the end). Swimming isn't recommended at the falls themselves, but there's a lovely swimming hole just inside Jamaica State Park (Salmon Hole). The falls are beautiful, but please respect posted rules and state park staff — deaths have occurred at the middle and upper portions of the falls. Never climb up or swim in the pools at the middle or top of the falls.
Bonus: Madame Sherri Forest — New Hampshire
GPS: Anne Stokes Loop, West Chesterfield, NH 03466
Just over the border in New Hampshire, explore the castle ruins just a short jaunt from the parking lot. If you have more time, hike to Indian Pond (2 miles round trip via the Anne Stokes Loop Trail) for a swim. Other hikes are also possible from here. A visit to Madame Sherri Forest pairs easily with an outing in downtown Brattleboro, Vermont.
Frequently Asked Questions
What are the best hikes near Brattleboro, Vermont? Putney Mountain, the West River Trail, and Jamaica State Park trails are three of the best and most accessible hikes near Brattleboro, all within a short drive of downtown.
What is the best time of year to hike in Vermont? May through October is ideal, once trails have cleared of snow and mud. Fall (September–October) is especially popular for foliage, while spring and summer offer quieter trails and swimming holes.
Is there a Vermont cabin near hiking trails? Yes — Tanglebloom Cabin sits within a few miles of Putney Mountain, The Pinnacle, and the West River Trail, making it an easy home base for exploring southern Vermont's best hikes.
→ Ready to get out and explore? Book a stay at Tanglebloom Cabinfor easy access to every trail on this list — and a wood-fired hot tub to soak in after your hike.
Tanglebloom Tiny Cabin is a glamping retreat and farm stay in Brookline, Vermont, nestled in the hills of Windham County. Located just 20 minutes from Brattleboro and within easy reach of Boston and New York City, it's Vermont's most wish-listed tiny cabin — and the perfect off-grid escape for couples, solo travelers, and anyone craving a slower pace.
