Vermont in October: The Route 100 Road Trip You Need to Take This Fall

Vermont doesn't announce itself. It just appears. A covered bridge around a bend, a church steeple rising above the trees, a hillside so red it looks like it's on fire.

Route 100 is 216 miles of exactly that.

It runs north to south through the heart of Vermont, from Stamford to Newport, cutting through small towns, dairy farms, and mountain passes. No billboards. No chain restaurants. Just two lanes and the kind of scenery that makes you pull over every twenty minutes.

October is when Vermont shows off. Peak foliage hits between October 10 and 20, and if you're there for it, you'll understand why people come back year after year.

WHERE TO START

Fly into Burlington (BTV) for the northern section, or Boston (BOS) if you want to drive up from the south. Either way, you'll need a rental car. Route 100 is not a public transit situation.

TOWNS WORTH STOPPING IN

Stowe: ski town energy without the snow. Great food, great coffee, great base for a night or two.

Woodstock: covered bridges, a village green, and a general store that's been open since 1886. Classic Vermont.

Grafton: blink and you'll miss it, but don't. One of the best-preserved 19th-century villages in New England.

Warren: tiny, tucked in, perfect. The Warren Store is worth the detour alone.

WHAT TO EXPECT

Crisp air. Wood smoke. Roads lined with maples turning orange and red. The kind of quiet that feels rare.

Mornings are cold. Pack layers. Drive slow. Stop when something catches your eye. It usually will.

HOW TO BOOK

Flights into Burlington or Boston fill up fast in October. Same with rental cars. Fall foliage season is real, and availability drops quickly.

Book both early.

✈️ Flights: [Search flights here]

🚗 Rental car: [Compare rental cars here]

Peak foliage: October 10 to 20. The leaves won't wait.