The story of the Inn began in the 1820's when the original Colonial home was built across from the village green in Chester, Vermont. During the Victorian era changes included adding a tower, bow windows and a big wrap around porch which transformed the place into a Queen Anne style Victorian. When the last of the founding family was gone in the 1950's the place was used briefly by the town as overflow for the neighboring schoolhouse.
The Carriage House is 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 the early 1980's, renovations for the Inn were completed, including adding a bathroom for every room. Not long after that the Hugging Bear Shoppe was established in our attached barn. Teddy Bears, you ask? Yes, the theme of the Hugging Bear Inn revolved around teddy bears, family, fun, and enjoying the lovely countryside of Vermont. The Inn closed in February 2021.