Jamaica was a Stage Coach stop between Brattleboro and Manchester. The Livery Stable held about 60 horses and was across Mechanic Street where the Rainbow Garage was, behind the old Muzzy’s hardware shop.

According to “Hometown Jamaica: A Pictorial History of a Vermont Village” by Mark Worthen, after the house was built, it was popular to have “…singing get-togethers and dances on the magical flexible dance floor, a great place for reels and jigs. One of the most popular events was the “box social,” an occasion when the girl packed a lunch for two and ate with the boy who drew her name from a hat.”

In the 1920s and 1930s, if you couldn’t afford a place to live, you could cut firewood and stack it and be rewarded with a night’s lodging and a meal at the Jamaica House, however if your wood stack wasn’t satisfactory, you had to pay fifty cents to stay at someone’s house and eat a meal there.

(There are rumors that the hotel served as a brothel, but I couldn’t confirm that in my research).

The Jamaicahaus is a 2 ½ story white clapboard hotel with partially exposed sub-story, verandah with jigsaw cut balustrade. 2 story and 1 story side wings to right of main block. Built in 1814 by Nathaniel Cheney as a hotel. It has served as a hotel and restaurant ever since. The third floor was a ballroom with a floating dance floor, but now serves as an apartment.

The back of this building burned in the early 1900’s. It also caught fire in 1926 with a chimney fire that caught the roof on fire one June afternoon. The Fire Department came out and extinguished the fire. By 6:30 that evening it was again blazing in the rafters and the shingles under the slate roof. It was brought under control again.

The Jamaica House was one of the first buildings to have centralized heating.