Montgomery is known as Vermont's Covered Bridge Town. Its unique geography required many bridges, and as recently as the 1940s there were thirteen covered bridges within the town's limits. Today there are six covered bridges within town limits, and one which straddles the town line with Enosburg, the most of any town in the country.

Montgomery's heritage was firmly rooted in farming and the timber industry. Today it is a diverse community with several farms, many small businesses, artists, craftspeople, and a lively citizenry comprised of a mix of full-time and vacation residents. It is also an all season recreation destination.