Woodbourne is bordered by the town of Neversink, the hamlet of Grahamsville, the hamlet of Loch Sheldrake, the hamlet of Old Falls, and the hamlet of Hasbrouck. The major thoroughfares of Woodbourne are New York State Routes 42 and 52. The center of the hamlet is where the two highways briefly overlap and cross the Neversink River. According to the Sullivan County Historical Society, the northern part of the Town of Fallsburg was settled by Europeans in the 1780s, many of whom migrated from Ulster County, NY in search of cheap, fertile land. In 1830, a man named Gabriel Ludlum (or Ludlam) relocated his law practice from the nearby hamlet of Hasbrouck, and named the area Woodbourne.