Southern Vermont Foliage Hotspots: 7 Places to Peep Leaves in Brattleboro, VT

Southern Vermont foliage is some of the finest around—every autumn, world class colors flank our hills and add a festive flair to our outdoor adventures. Photogenic views of rivers and ponds, mountainsides, sunsets, and more make Brattleboro a true Vermont foliage hotspot. These seven leaf-peeping locations are all within minutes of Brattleboro, and a number of them are within easy walking distance of our downtown Brattleboro hotel.

southern Vermont foliage along the Connecticut River


Brews with Views: Whetstone Station & The Marina

Brattleboro is home to two waterfront eateries with amazing foliage views, and they’re different enough to warrant visiting both.

Whetstone Station extends out over the Connecticut River so far that part of the building is technically in New Hampshire. This hoppin’ brew pub consistently ranks among the best outdoor dining spots in Vermont, thanks to Mt. Wantastiquet’s stunning backdrop and a creative selection of hard-to-find Vermont craft beer. Their grilled sirloin tips are out of this world, too. Take note: Whetstone doesn’t do reservations, so dining tables can be scarce during prime dinner hours on weekends in the fall. Hit it for a late lunch or appetizers in the 3-5 p.m. window and you should be golden.

The Marina, situated at the north end of town, has a large deck looking out across the West River at the foothills of the Green Mountains. This west-facing gem just might be Brattleboro’s best sunset spot. Get the Mudslide cocktail—a delicious take on the white Russian—for dessert, and watch daylight fade through the maples’ red-and-yellow filters. You can also walk or bike the West River Trail starting at the Marina parking lot (see below).

Mt. Wantastiquet: A Brattleboro Classic

latchis-marquee-wantastiquetYou can’t visit Brattleboro without noticing this mountain towering over downtown on the opposite shore of the Connecticut River. Walk across the Route 119 bridge—scenic in its own right—then turn left onto the dirt Mountain Road, which ends at the trailhead. For a gentler, longer hike, you can follow a wide trail as it makes switchbacks up to the top. Shorter, steeper shortcuts exist as well. On a clear day, you can see all the way to the ski slopes of Mount Snow to the east-northeast, with neighboring Haystack to its south. Hiking Mt. Wantastiquet is especially rewarding for its bird’s-eye view of our town—you can even see the Latchis Theater marquee shining from 900 feet above.

Brattleboro Retreat Trails

The Retreat Trails include a variety of hiking and walking options, mostly on the easier side. The woods themselves are full of pretty colors, with a few hilltop vantage points to look out at surrounding scenery. Walking from downtown, find the nearest trailhead at the end of Oak Street, then take the short, steep climb up Tower Road for views of downtown with the Connecticut and Mt. Wantastiquet in the background (you may have to wander a bit past the tower itself for an unobstructed view). From there, walk down to the Cedar Street trailhead and continue across the road to the Ice Pond Trail. Brilliant southern Vermont foliage rims the pond, making stunning reflections in the water.

Harris Hill Ski Jump

Adjacent to the Retreat Trails, Harris Hill Ski Jump makes a great stop on your way up or down the Ice Pond Trail. You can also climb the stairs that run next to the ramp. This Brattleboro landmark dates to 1922 and still hosts internationally sanctioned competitions each winter. In the fall, it’s great for southern Vermont foliage, facing blazing mountainsides to the east.

Living Memorial Park

Living Memorial Park, in West Brattleboro, offers yet another unique set of Vermont foliage views. It’s an ideal spot for a picnic, and you can even drive to the top of the hill. The park is also right next door to the Brattleboro Farmers’ Market and Creamery Covered Bridge.

Southern Vermont Foliage on the West River Trail

Pick up the West River Trail from the Marina parking lot and log as many miles as you wish alongside this scenic waterway northwest of where it joins the Connecticut. The trail is paved and mostly flat, perfect for a family bike ride or a leisurely stroll.

Paddling Around Brattleboro

Shove off into the Retreat Meadows, the West River, or the Connecticut itself for a serene flatwater paddle with prime southern Vermont foliage all around. You can rent a canoe or kayak in town.


Of course, your room at the Latchis Hotel can offer stunning Vermont foliage views of its own. Ask about our Mountain View rooms when booking your stay—you’ll see a number of the above attractions right from your window.