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A little history: Chester was originally known as Flamstead (after an old town in Hertfordshire). The grantees made no effort to settle it, and it was re-granted as New Flamstead in 1763. It was permanently settled in 1764 and renamed Chester in 1766, for George Augustus Frederick, the eldest son of King George III, among whose hereditary title was Earl of Chester. The early residents of Chester were a progressive bunch and adopted their own Declaration of Independence in 1774, some twenty months ahead of the Continental Congress. And now, Chester is the ‘picture-postcard’ town that comes to mind when you think of Vermont. It’s "Gingerbread Victorians" command you to stop and check out the village with its quaint shops and elegant buildings. Churches, restaurants, shops, galleries and lodging surround the village green and bring back the nostalgia of a bygone time. Buy a teddy bear, dine by candlelight, and observe historic architecture… 
Chester Depot
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When in town make sure to visit Chester Depot, a place seemingly untouched by time. Upon approaching the depot you’ll see railroad tracks and a Victorian train station. These tracks still carry freight and "The Green Mountain Flyer", an excursion train with turn-of-the-century cars, which operates regularly July thru Labor Day, and during peak visitation periods.See Chester’s Stone House Village. These pre-Civil War stone houses were built with locally quarried stone and have an interesting history. Some were part of the underground railroad. Chester and its outskirts offers something for everyone in all seasons. Activities: Hiking trails, Summer Theater, Antiquing, Shopping, Fishing, Swimming, Boating , Bicycling, Horseback Riding, Golf, Tennis, Alpine slide, Skiing, Snow-shoeing, Horse drawn sleigh rides and town events. Summer
Glory in the enjoyment of open farmlands separated by the old rock walls, the preservation of the unique "add-on" Vermont architecture, the quiet, scenic back roads. 
Shopping at the village green
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Fall
Witness the autumnal spectacle of the changing leaves, painted by natures brush as nowhere else in the world. Fall foliage varies between mid-September through late October. Winter
Plentiful cross-country and Alpine skiing within minutes, or simply enjoy sledding, snow-shoeing, hiking and the winter festivals. Then curl up with Teddy next to our crackling fireplace and sip hot cider. Spring
Quiet time in Vermont. Watch nature come alive in the fields and forests. Miss the crowds. Peruse in the Teddy Bear Shoppe.
Click a link below for more Lodging info:
Hugging Bear Inn and Shoppe
244 Main St.
Chester, Vermont 05143
(800) 325-0519
(802) 875-2412
(802) 875-2339 (fax-line available only upon request)
www.HuggingBear.com
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