Inn History

In 1850, a unique Italian Colonnade home was built and situated across form the village green in Chester, Vermont. It saw many years, many seasons and went through many changes. It had different owners, was a schoolhouse for a period and went through the Victorian era, which changed this home into a beautiful Queen Anne style Victorian home by adding a tower, bow windows and a big wrap around porch. Circa 1905, a Carriage House was constructed on the property. One of the finest examples of carriage barns in New England, it 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 executed barn.

In 1982, this Victorian home went through another transformation when it was renovated to accommodate guests with a private bathroom in every bedroom. The Hugging Bear Inn was born and continued to welcome families, children, and everyone from all over the world that love Vermont, enjoy a Bed and Breakfast Inn and, most of all, have a passion for Teddy Bears. Teddy Bears, you ask? Yes, the theme of the Hugging Bear Inn revolves around teddy bears, family, fun, collecting and enjoying the lovely countryside of Vermont.

Not long after the Inn was established, the Hugging Bear Shoppe began. It's a gift shop that quickly grew from one to four extensive rooms of the finest selection of teddy bears in the Northeast, with over 10,000 teddy bears and similar products available for purchase.