8 Best Hikes In Southern Vermont

The Long Trail — America’s oldest long-distance hiking trail, built between 1910 and 1930 — runs 272 miles along the spine of Vermont’s Green Mountains, from the Massachusetts state line in the south all the way to the Canadian border in the north. Day hikers can access well-marked sections of it and the more than 40 peaks connected by its network of side trails throughout the state. Southern Vermont, encompassing Windham and Bennington counties, offers some of the most rewarding stretches of the trail, along with waterfalls, wilderness areas, and summits with views stretching into four states on a clear day. Here are eight of the best hikes in the region.

Because the Long Trail and the Green Mountains themselves run north to south through the heart of the state, they’re never far from Vermont’s many towns and villages — making southern Vermont an excellent base for hikers and non-hikers alike. Not every trail here climbs to a summit. There are gentle waterfall walks, wilderness pond routes, and family-friendly ridge hikes woven throughout this corner of the state.

1. Stratton Mountain

At 3,940 feet, Stratton Mountain is the highest peak in southern Vermont and the highest point in Windham County. It holds a special place in American hiking history: it was here, on Stratton’s summit in 1909, that Benton MacKaye conceived the idea for a trail spanning the entire Appalachian Range — a vision that became the Appalachian Trail. In southern Vermont, the AT and the Long Trail are coincident, and both cross Stratton’s summit.

The standard route departs from the Long Trail/AT trailhead on Kelly Stand Road (also called Stratton-Arlington Road) and climbs 3.8 miles to the summit, gaining about 1,750 feet. The ascent is gradual for most of its length, with the upper section gaining more pitch. The wooded summit itself offers no views from the ground — but a 55-foot fire tower staffed by a seasonal Green Mountain Club caretaker provides sweeping 360-degree panoramas taking in Mt. Snow and Somerset Reservoir to the south, Glastenbury Mountain to the southwest, Mt. Equinox to the west, and Killington to the north. On a clear day, Mt. Monadnock in New Hampshire is visible to the east. The round trip is approximately 7.3 miles.

Trailhead: Kelly Stand Road (Stratton-Arlington Road), West Wardsboro/Arlington. Distance: ~7.3 miles RT. Elevation gain: ~1,750 ft. Difficulty: Moderate.

2. Bromley Mountain

Bromley Mountain, at 3,260 feet, is one of the most accessible summits in southern Vermont and one of the most rewarding for the effort involved. The Long Trail and Appalachian Trail coincide on the approach from Route 11/30 east of Manchester. From the parking area on the north side of Route 11/30, the trail follows Bromley Brook through northern hardwood forest, passes the Bromley Shelter at about 2.3 miles, and then opens onto a ski run for the final push to the summit.

The summit is broad and open — unusual on a New England peak — and shares space with Bromley Mountain Ski Resort’s infrastructure. The views are sweeping in all directions: Stratton Mountain to the south, Mt. Equinox to the west, and Magic Mountain, Glastenbury, and the Taconic Range spread across the horizon. The Green Mountain Club has installed a new observation tower at the summit, which significantly extends the already strong views. The round trip from Route 11/30 is approximately 5.8 miles with about 1,420 feet of elevation gain, making it a solid half-day hike for most people.

Trailhead: AT/LT parking on Route 11/30, approximately 5 miles east of Manchester Center. Distance: ~5.8 miles RT. Elevation gain: ~1,420 ft. Difficulty: Moderate.

3. Hamilton Falls (Jamaica State Park)

Hamilton Falls is the highest waterfall in Vermont, where Cobb Brook cascades 125 feet down a mountain slope through a pine-hemlock woodland and into a series of large potholes. The hike from Jamaica State Park follows the old West River Railroad bed — now the West River Trail — for two flat miles along the river before turning uphill on the Switch Road Trail for the final mile to the falls. The round trip is approximately 6 miles.

The falls are dramatic in spring and early summer when snowmelt and rain keep Cobb Brook running full. By mid-summer, the flow can slow considerably. The setting is stunning either way — the rock formations at the base are unusual, and there’s a short spur to the top of the falls. An important safety note: swimming at Hamilton Falls is not recommended and has resulted in multiple deaths. The currents above the falls are deceptively strong and the rocks are extremely slippery. Enjoy the falls from the designated viewing areas and wade in the calmer pools downstream if you want to cool off.

Jamaica State Park is in Jamaica (Windham County) and also offers camping, swimming at Salmon Hole, and mountain biking on the rail trail. A day use fee applies.

Trailhead: Jamaica State Park, Jamaica, VT. Distance: ~6 miles RT. Elevation gain: ~700 ft. Difficulty: Moderate.

4. Glastenbury Mountain

Glastenbury Mountain (3,748 feet) sits in the heart of the 23,000-acre Glastenbury Wilderness in the Green Mountain National Forest — one of the most remote and least-traveled stretches of the Long Trail anywhere in Vermont. The standard approach from Route 9 east of Bennington follows the AT/LT northward through dense boreal forest. The round trip to the summit and back is approximately 22 miles, making this route far better suited to an overnight stay at Goddard Shelter near the summit than a day hike.

The reward is considerable: a historic fire tower at the summit offers a full 360-degree panorama of southern Vermont’s wilderness — a view that feels genuinely remote in a way that the more-trafficked peaks do not. Glastenbury is also home to a layer of regional folklore; the surrounding area was the site of several unexplained disappearances between 1945 and 1950, and the mountain has a history of unusual reported occurrences going back further. Whether or not that adds to the appeal depends on the hiker. What is certain is that this is the most solitary and most authentically wild summit experience on this list.

Trailhead: AT/LT trailhead on Route 9, approximately 5 miles east of Bennington. Distance: ~22 miles RT (best as overnight). Elevation gain: ~3,000 ft. Difficulty: Strenuous.

5. Haystack Mountain (Wilmington)

Not to be confused with the Haystack ski area, Haystack Mountain near Wilmington (Windham County) is a compact and satisfying day hike offering one of the best open summit views in southwestern Vermont. The trail is approximately 3.2 miles round trip with around 1,100 feet of elevation gain — moderately steep but well within reach for most hikers in reasonable condition. The wooded approach gives way to open ledges at the top with views stretching across the Deerfield River valley, Mt. Snow, Stratton Mountain, and on clear days as far as Mt. Greylock in Massachusetts.

The trailhead is accessed from Haystack Road off Route 100 near Wilmington. Haystack Mountain is a good choice for an afternoon hike or when conditions are marginal on higher peaks — it’s lower in elevation than Stratton or Bromley, so cloud ceilings that obscure those summits will often leave Haystack in the clear.

Trailhead: Haystack Road off Route 100, Wilmington. Distance: ~3.2 miles RT. Elevation gain: ~1,100 ft. Difficulty: Moderate.

6. Lye Brook Falls

Lye Brook Falls, at 125 feet, is a multi-tiered cascade of horsetails and slides within the 15,680-acre Lye Brook Wilderness — the largest wilderness area in the Green Mountain National Forest. The trailhead is accessed from Manchester, making this one of the most convenient wilderness hikes in Bennington County. The trail is approximately 4.6 miles round trip with modest elevation gain, passing through the forest before arriving at the base of the falls.

The wilderness setting makes this hike feel more remote than its distance suggests. Swimming at the falls is not recommended as the pools are quite shallow; it’s primarily a scenery destination. The broader Lye Brook Wilderness also contains Bourn Pond and a network of backcountry routes — for hikers wanting a longer outing, it’s possible to continue beyond the falls into the wilderness interior. Stratton Pond, the largest body of water on the Long Trail, can be accessed via connecting trails from the Lye Brook area for a more ambitious overnight trip.

Trailhead: East Manchester Road, Manchester. Distance: ~4.6 miles RT. Elevation gain: ~1,000 ft. Difficulty: Moderate.

7. Bald Mountain (Woodford)

Near Woodford Hollow about four miles east of Bennington, Bald Mountain offers a manageable half-day hike with good views of the Green Mountains and the neighboring Taconic Range to the west. The summit reaches around 2,160 feet, making this a lower-elevation option that’s accessible earlier in the season than the higher peaks and suitable when higher terrain is icy or snowbound. The views from the summit take in the Bennington Monument and Mt. Greylock in Massachusetts — a particularly good combination for hikers based in Bennington who want a quick outing without driving far.

The round trip is approximately 7.2 miles with about 1,500 feet of elevation gain, putting it at the lower end of the moderate category. The trail sits on the edge of the Glastenbury Wilderness, so the forest character is similar — dense and quiet — without requiring the full commitment of a Glastenbury summit attempt.

Trailhead: Route 9, approximately 4 miles east of Bennington. Distance: ~7.2 miles RT. Elevation gain: ~1,500 ft. Difficulty: Moderate.

8. Putney Mountain

Putney Mountain, in Windham County, is the easiest hike on this list and one of the best family-friendly options in southern Vermont. The main loop is just 1.2 miles with under 200 feet of elevation gain — essentially a flat walk through hardwood forest to a ridge-top viewpoint. What makes Putney Mountain worth knowing about is its reputation as one of the premier hawk-watching sites in the Northeast. During spring and fall migration, hundreds — and on peak days, thousands — of raptors ride the thermals along the ridge. Broad-winged hawks, sharp-shinned hawks, Cooper’s hawks, American kestrels, ospreys, bald eagles, and peregrine falcons all pass through in season. Birders and naturalists gather here every autumn, particularly during the broad-winged hawk peak in mid-September.

Parking is on Old Athens Road in Putney. The trail is maintained by the Putney Mountain Association and is well-marked. Dogs are welcome on leash. For families with young children, this is a genuinely excellent introduction to Vermont hiking — the distance is manageable, the path is clear, and the hawk show, when it happens, is memorable for any age.

Trailhead: Old Athens Road, Putney. Distance: ~1.2 miles (loop). Elevation gain: ~200 ft. Difficulty: Easy.

Planning Your Southern Vermont Hiking Trip

Southern Vermont’s main hiking bases are Manchester and Bennington in the west, and Brattleboro in the east. Manchester is the most convenient for Stratton, Bromley, and Lye Brook Falls; Bennington is the natural base for Glastenbury and Bald Mountain; Jamaica and Wilmington are easy access points for Hamilton Falls and Haystack Mountain respectively. Most trails are best hiked between late May and mid-October. The Long Trail in particular can be extremely muddy in May and early June during mud season — the Green Mountain Club requests that hikers avoid the most fragile sections during this period to prevent erosion.

If you’re combining hiking with a broader Vermont road trip, our guide to fun places to visit in Vermont in winter covers what the region offers in the off-season. For what to bring, our road trip packing list has the trail essentials covered. And if the rain rolls in, our guide to keeping your shoes dry while hiking in the rain is worth a read before you head out — Vermont weather being what it is.