Like many towns in the West Country, Okehampton grew on the Medieval wool trade. Notable buildings in the town include the 15th century chapel of St. James, and Okehampton Castle. The town is also home to the Museum of Dartmoor Life.

Okehampton is also characterized by the large number of smaller villages and towns that surround it. Notable examples are the villages of Folly Gate, a small picturesque village which lies in close proximity to the village of Inwardleigh and Abbeyford woods, Belstone, known for its location on the very outskirts of Dartmoor, and Sticklepath.