The Vermont Cheese Trail isn’t a “trail” in any real sense—it’s a network of dairies clustered, roughly, in three sections of the state: southern, central, and northern. Spend your first night in the south at the Old Tavern at Grafton (from $150), just steps from the award-winning Grafton Village Cheese Company. The inn’s a rural-Colonial classic: You can wake up under period-style linens, sip coffee in the lobby beside an oil painting of George Washington, and eat local, free-range eggs for breakfast.
The central part of the state is home to nearly twenty dairies and the charming Woodstock Inn & Resort (from $255), located on the village green in Woodstock. A new chef has greatly improved the dining quality, and guests get passes to Billings Farm, a working farm and museum where you can check out traditional New England agricultural techniques.
Fast-forward 200 years at the fully modernized Topnotch Resort & Spa (from $325) in Stowe, within a few hours’ drive from another dozen cheesemakers in the north. The hotel’s fresh off a big face-lift and its restaurant, Norma’s, has one of the largest local-cheese lists in the state.