About Us

Welcome Everyone! We are a place where those who came as children are now bringing their children - whether to experience the magic of the Hugging Bear or to have the rite of passage of picking out their first teddy bear (or second or third!). Established in an era when many Victorian inns were too formal to accommodate children, the Hugging Bear has embraced visiting families of all kinds - often bears and their human chaperones. We are a great base to allow you to explore all this region has to offer. We look forward to seeing you soon.

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The Bed

The Inn is situated on a Village Green of shops and restaurants. We are adjacent to a historical schoolhouse, now the home of the Chester Historical Society; a cemetery dating back to the town’s founding in 1761; and city owned open space. 


We have six rooms of various configurations to accommodate couples, singles, and families. Common space includes a dining room, living room, and den with games, library, wireless internet access, cable television, and a cheerful fireplace. A wrap around porch is a great place to people watch and the second story balcony has wonderful views of nearby historic town lands and buildings.


The Breakfast

Wake up to a hearty country breakfast where seconds are encouraged and there is plenty of Vermont maple syrup for your pancakes. We are glad to accommodate food allergies. We use local ingredients when available.

The Bears

The Hugging Bear has always been home to teddy bears - from the whimsical to the cuddly, the artistic to the endearing. Children, grandparents and bear collectors have been adopting their bears from our Shoppe for almost 40 years. We have a large selection of Steiff collectibles, artist bears and Muffy Vanderbear. You will find puppets (Folkmanis and others), Webkinz, Gund, Boyd's, Bearington, Princess, Douglas, jewelry, cards, cups, shirts, hats, books and other bearaphernalia.




​In wintertime, Chester town parks have sledding and an ice rink  - within walking distance. Skiing is nearby with Okemo Resort (14 miles) and Magic Mountain (12 miles). Cross country skiers can find one of Vermont's best groomed trail systems just south of us at Grafton's Trails Center.

In warmer seasons, the town parks have tennis courts, skateboard park, and swimming pool. There are plenty of country roads and historic sites to explore by bike, on foot, or car. We are glad to help you find trail heads, swimming holes, and more.