Vermont’s Prettiest Town in Fall Isn’t Stowe – Insiders Know to Book This Village Instead.

The inns in the Stowe area begin to receive calls by late September, and the majority of them conclude with a courteous apology, full booking, and “try us in November.” By now, the rhythm is familiar. Stowe’s reputation as Vermont’s fall capital has been built over decades, and as a result, the town has a kind of seasonal traffic issue that the locals put up with with weary humor. The leaves remain magnificent. A clean lager is still poured from the von Trapp Bierhall. However, the town ceased to feel like a discovery at some point.

Longtime New Englanders have a more subdued option, which they usually only bring up after a second glass of wine and when they are confident you won’t share it on the internet. Richmond, Vermont, is located in the area where the Champlain Valley starts to climb into the Green Mountains, roughly twenty minutes east of Burlington. If you weren’t paying attention, you could drive through it in three minutes because it’s so tiny. Most people aren’t.

The Old Round Church, a sixteen-sided wooden structure from 1813 that resembles something a carpenter imagined after one too many ciders, is the focal point of the town. The maples behind it take on an almost staged orange hue in October. Nearly. A hawk circling somewhere above the Winooski River, the way the light strikes the steeple sideways in the late afternoon, and the silence that descends after the day-trippers have left for Burlington for dinner are just a few of the small details you will notice if you spend some time standing on the lawn.

I believe Richmond’s success stems from the fact that it hasn’t been refined into a brand. There isn’t a main street with carefully chosen shops selling reclaimed barnwood signs that read “Gather.” There are a few farms selling pumpkins on the honor system, a general store, and a reputable bakery where residents wait in line on Saturday mornings. The location still feels unique because of its modest infrastructure. There are moments when Stowe seems like Vermont performing Vermont. It feels like Vermont in Richmond.

I might be treating Stowe unfairly. The gondola ride up Mount Mansfield is a popular activity, and it’s arguable that the town attracts tourists. However, it feels like you’re walking around in early October with thousands of other people who have all read the same listicle. The leaves don’t give a damn. You could.

The journey through central Vermont is a slow pleasure in and of itself, and the drive from Boston takes just over three hours, slightly less than the trip to Stowe. If you have the patience for nostalgia at scale, stop by the Vermont Country Store along the way. The maple syrup is authentic, and the penny candy bins are genuinely entertaining. From there, the route meanders northward past roadside cider stands, dairy farms, and the occasional hand-painted sign promoting eggs.

The strategy is to do less once you get there. Take a stroll around the Round Church. As you travel a few miles up Cochran Road, you’ll notice how the hills blend together, each with a slightly different rust color. Have dinner at one of the town’s small eateries, where the server may be the owner’s daughter. After that, take a ten-minute drive to the trailheads in Bolton or Huntington, where the abundance of foliage is almost obscene.

The best moments in Vermont seem to occur outside of the well-known towns rather than inside them. One of those places is Richmond. Another question is whether it remains that way. For the time being, the church continues to stand silently at the bend in the road, waiting for someone to slow down. The rooms are still generally available.