The Tupper House is notable for its Georgian-style design as well as its association with the Woodstock Stage Coach Company.

Built between 1838 and 1840, the Tupper House exemplifies the Georgian style. The two-story massing exhibits near-perfect symmetry, and the Neo-Classical trim, though simplistic, is painted a yellow color that strikingly contrasts with the black coating of the clapboard walls. Few changes have been made to the house's exterior over the years, though notably the original gable roof was replaced by a steeper jerkin one. The interior is similarly well preserved, with tin ceilings still standing in many rooms and two original fireplaces. The original carriage house and stables were also removed in 1902 by Willard L. Carr; however, their replacements were designed to follow the original plan as closely as possible.

Another important element of the Tupper House's heritage recognition is its location. Sitting on an elevated lot, the house overlooks Connell Road, which is one of Woodstock's busiest streets. Its surroundings include beautiful, fully-grown trees and several other elaborate houses, such as the James Carr House and the George Connell House.

The house is also recognized for its role as a Woodstock Stagecoach Company station. Shortly after its completion in 1840, the building was acquired by James R. Tupper. When Tupper became owner of the Woodstock Stage Coach Company the following year, he decided to convert the house into an inn. For the next twenty-five years, many travelers, particularly those going between Fredericton and Grand Falls, would come to the station to rest.