🍁  Vermont’s Route 100 — From the Triangle to the Trees

After wandering through the mysteries of the Bennington Triangle, it turns out the perfect next stop is… Bennington itself. Because that’s where Vermont Route 100 begins — the most scenic drive in the entire state, and honestly one of the best in New England.

Route 100 is Vermont showing off. This winding two‑lane highway runs the full length of the state, more than 200 miles from bottom to top, hugging the eastern side of the Green Mountains the whole way. In October, it becomes a rolling ribbon of color — hills blazing in red and gold, quiet lakes reflecting the sky, rivers slipping through the trees, and covered bridges popping up like they were placed there just for your camera.

It’s the kind of road where every bend feels like a postcard.

You pass through tiny villages with white steeples, old farms tucked into the hills, waterfalls you can hear before you see, and long stretches where the forest arches overhead like a tunnel of color. We stayed on Route 100 almost the entire way, with just one detour planned: Smugglers’ Notch up north — because honestly, how do you resist a name like that?

If the Bennington Triangle gave us Vermont’s eerie side, Route 100 is the soft, golden, leaf‑peeping side — the part that makes you roll the windows down, breathe in the cold air, and remember why fall feels like magic.