The town is home to Jamaica State Park, noted for scenic camping spots and various swimming holes, including Hamilton Falls.

Earliest settlement of the town was along the West River near the Wardsboro Bridge, now called East Jamaica, where the first school was established in 1791; however, the building of new roads and bridges towards Manchester advanced settlement westward, so that by 1800 the town center was shifting to Jamaica Village.

Within the entire forty-two square-mile township developed as many as ten separate hamlets, each surrounded by outlying farms and linked to Jamaica Village by a network of roads.

In the first quarter of the nineteenth century, Jamaica Village also assumed increasing importance as a manufacturing center, largely for topographical reasons.

[4] Like many Vermont communities, the town's economy prospered with the introduction of Merino sheep in the early nineteenth century.

The sheep flourished on rocky hillsides, and as their numbers increased, bare land replaced forests, but this prosperity did not last.

Windham County contributed heavily to manning the 4th Vermont Infantry and nearly all of Jamaica's men joined Company I of that regiment.

This regiment saw heavy combat throughout the war but the Battle of the Wilderness took the greatest toll on those from the village of Jamaica.

[5] One of Jamaica's soldiers, Sergeant Henry W. Downs of Company I, 8th Vermont Infantry, won the Medal of Honor for bravery under fire.

Because of its setting near the river and the region's heavy snows, Jamaica has suffered through many damaging floods in the more than two hundred years since its founding.

In 1877, financing provided by the valley towns moved the languishing project forward with the first segment from Brattleboro to Londonderry.

Although it was never extended farther, the railroad provided valuable public transportation for the lower West River Valley until the 1930s, by which time automobile ownership had become almost universal.