The original Highland House was the Small family farmhouse, and the Smalls ran a farm on the property in the 1700s. By the 1800s they began taking in guests as Cape Cod tourism grew. The business thrived, and the Smalls added cottages. They removed the windmill and placed the Millstone House on that spot. The original farmhouse and Millstone House were later moved to other locations in Truro. The present Highland House Museum was built as a hotel in 1906, with a central dining room on the first floor and 15 rooms on the second floor. The farm provided much of the food for guests, rent was $8.00 per week for room and three meals per day, evening entertainment was provided in the main hall, and most guests stayed for the entire summer.