In 1760, James Philbrick of Hampstead, New Hampshire purchased the land that now comprises most of the Woodbound Inn property. He built a farm on the site of the Cathedral of the Pines (about 1 mile through the woods from the inn’s current location) where he and his wife raised their 18 children. Philbrick built another farmhouse in 1820 which is the cornerstone of the Main Inn.

Several owners followed and buildings were added and expanded through the years. In 1892, the building was first utilized as an inn called the “Lakeside Hotel”. In 1909, Albert Annett purchased the property and later renamed it the “Contoocook Inn”. During the early 1930s Ed Brummer & Jack Bean of Jaffrey, roommates at Dartmouth College, managed the inn. Jack left to go into the lumber business. Ed bought the Inn; all mortgage and no down payment. He renamed it the “Woodbound Inn”.

The Brummer family owned and operated the Woodbound Inn for 55 years. Improvements included Jed Brummer’s addition of the Edgewood banquet hall where weddings and other joyous occasions are celebrated. During the Brummer years the atmosphere of the inn was that of a continuous house party, where guests chose from a host of activities. In fact, so many guests returned at the same time each year that they expected and did find friends they knew from prior seasons.

​In 1989 the Woodbound Inn was sold to an investment group with plans for development. These plans did not come to fruition and the Inn again became a family owned establishment when the Kohlmorgen's purchased the property in 1994. In 2008, a group of investors purchased the inn and undertook an extensive renovation to the Main Inn, remodeling the rooms, the lobby, restaurant and bar.

In 2013, the Woodbound once again became family owned and operated. Rudy Rosalez and Laura Chapin desire to bring back the warm, family atmosphere that the Woodbound Inn has provided to past generations of guests while modernizing the inn and restaurant for the next generation.