The Inn began life as a nineteenth-century sail loft, part of a working boatyard. Occasional town meetings were held there, as well as the village's first Masonic gatherings. In the 1920s, it was converted to an inn—the Wan-e-set—where tourists from Boston, arriving by steamer, spent long summer stays.
The Inn was sold to a succession of local residents in the mid-1950s, but was not fully reopened as a functioning inn until the early 1970's. In 1974, Tim Watts, a native of Tenants Harbor, purchased the now abandoned building, restored it and started the Inn again, under the name "East Wind Inn." Several years later he purchased an adjacent nineteenth-century sea captain's mansion that had been converted into a boarding house and added it to the inn, calling it the "Meeting House Annex."
Tim Watts passed away in 2012 and the inn was sold to Randy Deutsch, a long-time summer resident of Tenants Harbor who retired from law practice in San Francisco and who currently runs this historic New England bed and breakfast.