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Looking to take in the colors of the season? Head up to Vermont’s southwest region, commonly know as Bennington County, but recently dubbed the Shires. Here, visitors can enjoy hiking, car shows, antiquing, apple and pumpkin picking, crafts fairs, farm dinners, museums, gondola rides, covered bridges, and more.


At the end of a Vermont country road awaits a slice of heaven called the Windham Hill Inn, the sister property of Kennebunkport’s White Barn Inn. Although the region beckons visitors to explore it, once they’ve checked into the Windham Hill Inn, they won’t want to venture far from the property, with its 21 elegantly appointed rooms and charming innkeeper, Katya. A sprawling 160 acres of unspoiled land surround the exquisitely renovated farmhouse and barn, the perfect place for a romantic getaway. Here, you will want to linger over the Sunday paper, sit on your deck sipping hot cider and sampling homemade confections, and marvel at millions of colorful leaves as they dance in the breeze. 311 Lawrence Drive, West Townshend, 802-874-4080.


It’s easy to see why All Days and Onions is a popular spot. A blend of delicious aromas wafts through the place, making it difficult for patrons to pick just one item from the menu. Breakfast—the French toast, in particular—is a great way to dig in, but be sure to sample something decadent from the in-house bakery before you leave. 519 Main Street, Bennington, 802-447-0043.

Drive directly to darling Dorset Village and dine at Mio Bistro (reservations are helpful). Chef Leo Ledoux creates masterpieces from scratch every day using whole organic foods. Patrons’ favorites include the red snapper and the Tuscan veggie pizza, which you can grab on the go. 3239 Route 30, Dorset, 802-231-2530.

In Manchester Village, the Reluctant Panther offers sumptuous gourmet cuisine. There, small bites like roasted beets and homemade ricotta share space on the menu with hearty entrees like a fennel-crusted rack of lamb, all of which showcase the restaurant’s commitment to celebrating Continental cuisine with panache. Plus, mountain and creek views add to the dining experience. 39 West Road, Manchester Village, 802-362-2568.


Visit Hildene, the home of Robert Todd Lincoln, son of President Abraham Lincoln and Mary Todd Lincoln, in Manchester. The gracious Georgian revival mansion is set on 412 preserved acres of gorgeous Vermont landscape. Enjoy the gardens, trails, and woods as you learn about the Lincoln family legacy. 940 Hildene Road, Manchester, 802-362-1788.

Stop by Grafton Village, one of the most picturesque villages in Vermont, which is home to restored buildings, shops, galleries, and museums. Check out the Grafton Village Cheese Shop, where visitors can watch as cheddar cheese is made. Grab a wedge and a bottle of wine and enjoy a picnic by a covered bridge.

Discover the magic of Vermont’s Fall Sampler Tours. Leave the more well-known trails behind and enjoy instead an intimate narrated tour off the beaten path. Discover the area’s history and hidden treasures, like an abandoned marble quarry, a working alpaca farm, or local artisans’ studios. Tours meet at Adams Park, located at 5080 Main Street, every day from 1 p.m. until 4 p.m. 802-362-4997.