Artifacts found near Lake Sepasco, near NY 308's eastern terminus at Rock City, date to about 1685, when the Sepasco Native Americans built the Sepasco Trail from the Hudson River, eastward through modern-day Rhinebeck (then Sepasco or Sepascoot) to the lake, following roughly NY 308 and its side roads. The trail remained until 1802, when part of the Ulster and Delaware Turnpike—also known as the Salisbury Turnpike—was chartered over the trail and extended from Salisbury, Connecticut to the Susquehanna River at or near the Town of Jericho (now Bainbridge).