Things To Do
Whetstone Beer Co.
Fun local brewery with an AMAZING rooftop deck overlooking the Connecticut River!
Main Street
Lots of fun store-fronts to peruse along Main Street in downtown Brattleboro!
Little Black Mountain Trailhead
Beautiful, quick 1.2 mile out-and-back trail to the top of Black Mountain! Great views for very minimal effort (hint: head off trail to the right when you get to the top to find our favorite spot on a group of open rocks overlooking the valley)
Wantastiquet Mountain Trail
Just across the bridge from town, this 3.7 mile out-and-back is a gentle climb up switchbacks for a beautiful summit view of downtown Brattleboro and the surrounding area. End your hike and head over to Whetstone for a post-hike beer!
West River Trail
Flat 3.5 mile end-to-end trail along the beautiful West River! Perfect for running, walking, or biking!
Dummerston Covered Bridge
If weather permits, this is a wonderful swimming hole under an old, covered bridge with fantastic mountain views!
Green River Covered Bridge
Another amazing swimming hole at the dam on the Green River!
Yalla Vermont
Unbelievable falafel - line can be long but so worth it!
Haystack Mountain
For those wanting a slightly more rigorous hike, Haystack Mountain Trail is a 4.1 mile out-and-back with a beautiful summit view of southern Vermont. About a 45 minute drive from Guilford/Brattleboro.