Why It’s an Amazing Fall Destination: You know a town takes their fall foliage seriously when they offer an online fall foliage color tracker. Plus, you’ll feel like a Gilmore Girl while you stroll through Brattleboro’s historic downtown which is packed with shops, galleries and restaurants along the edge of the Connecticut River.
Where to Spot the Best Fall Colors: You literally have to go over the river (the Connecticut River, that is) and through the woods to get to the Wantastiquet Natural Area Summit Trail, a 3.7-mile hike that includes waterfalls and river views. If you want to stay in the car, there are several nearby scenic byways including The Connecticut River Byway (watch out for moose!).
What to Eat and Drink: Mocha Joe’s is famous for their maple latte. For something stronger, grab a seat near the fireplace at Whetstone Station Restaurant and Brewery and sip on one of their seasonal drinks, like The Autumn Equinox. It’s a blend of vodka, triple sec and beet-apple-ginger puree.
And While You’re There…: Get lost in the dizzying array of vintage clothes, jewelry and home goods at Twice Upon a Time. Or escape falling temperatures by catching a movie at the gorgeous Latchis Theatre. The art deco building — which is also home to the Latchis Hotel — was built in 1938 and the inside walls are covered with hand-painted mythological murals. The annual Brattleboro Film Festival takes place in early November.