The Hugging Bear Inn & Shoppe (Chester, Vermont)
Carriage House
The Hugging Bear Carriage House is one of the finest examples of carriage barns in New England. It was constructed circa 1905 and shares the Colonial Revival style - notably the gambrel form of roof - with several contemporary Chester Village buildings. The projecting loft gable and the pyramidal capped cupola distinguish the finely constructed barn.
Questions? Want to make a reservation? Call us at (800) 325-0519
About Chester, Vermont

A Little History of Chester, VT

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.

Now, Chester is the "picture-postcard" town that comes to mind when you think of Vermont. Its "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.

Area Attractions

Bonnie's Bundles Dolls Bonnie's Bundles Dolls. For forty years, original handmade cloth dolls that are one-of-a-kind, made in Vermont from the finest cottons and yarns, and designed, cut, assembled, stuffed and wigged from start to finish by Vermont doll artist Bonnie Watters. She has made and sold over 13,000 dolls and welcomes visitors to her studio, a few minutes away from the Inn. [ ]
Chester Depot Chester Depot. 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.

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.

Area Activities

The Hugging Bear Inn, the lovely town of Chester and the surrounding Vermont countryside are perfect for couples looking for a romantic get-away, families looking for fun for both children and adults, and singles and groups looking for their favorite activities and recreation. We are happy to help plan your trip and ensure that yo visit is enjoyable and memorable.


Chester boasts two wonderful hiking trails: the popular Lost Mine Trail and a new two-mile loop in the nearby forests. This six-foot-wide trail begins in a cathedral-like forest area, follows streams and mildly ascends to the top of a hill where the sun breaks through in patches. Deer tracks are visible and birds chirp in the dense woods. It's a great way to spend the day after one of our homemade breakfasts.

On the Lost Mine Hiking Trail, which runs two miles, visitors encounter a mossy stream that runs through a steep-sided ravine, pine and hemlock groves, forest management areas, mature hardwood forest, a high ridgeline and a historic mine. The mine, which was started in 1894 and was last operated in the 1930s, is one of only three known sources of Chesterite - a silicate mineral with a unique crystal structure - which was first discovered here back in 1977.

Other Activities

Summer theater, antiquing, shopping, fishing, swimming, boating , bicycling, horseback riding, golf, tennis, alpine slide, skiing, snow-shoeing, horse drawn sleigh rides and town events. In the 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. In Fall, witness the autumnal spectacle of the changing leaves, painted by nature's brush as nowhere else in the world. Fall foliage varies between mid-September through late October. For winter, there is 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 is quiet time in Vermont, but you can watch nature come alive in the fields and forests, miss the crowds and peruse in the Teddy Bear Shoppe.

The Hugging Bear is a Green Hotel in the Green Mountain State
Proud Member | Okemo Valley Chamber of Commerce Chester, Vermont | The Vermont For All Seasons