The site of the Lakewood Inn in Madison was originally a Native American settlement along Lake Wesserunsett in Lakewood Grove that was transformed in 1895 into a small amusement park and then built upon by a spiritualist group. At the close of the 19th century, Herbert L. Swett took over management of Lakewood, acquiring and further developing the complex of buildings comprising a resort, restaurant, and theater from 1926 to 1945. The Lakewood Inn was constructed at a cost of $20,000. The original structure included a dining room, kitchen, and lobby. It was known for its high-quality dining services.

The caption reads, "Lakewood Inn at night, Skowhegan, Maine."

The Tichnor Brothers printing company published this type of postcard circa 1938.