Stockton, originally called Sandy Hill, grew up at the crossing of the post road from Snow Hill south to Virginia (whose track is generally followed by modern Maryland Route 12) with the road from Mattapony Landing on the Pocomoke River to the Chincoteague Bay (the eastern part of which is now Maryland Route 366), where small ocean-going vessels could drop anchor. The landing on Chincoteague Bay came to be known as George Island Landing. Settlement in the area began in the 1660s, when the area was still part of Somerset County. Worcester County was separated from Somerset in 1742, and by 1774 Sandy Hill had grown large enough to merit a chapel of ease within All Hallows' Parish, today called Holy Cross Chapel. Sandy Hill, unlike neighboring Girdletree, was never incorporated, but in 1870 the name of the town was officially changed, by act of the legislature, from Sandy Hill to Stockton, commemorating the Rev. Thomas H. Stockton, a prominent Methodist minister. In 1872 the Worcester County election district which took its name from Sandy Hill was renamed Stockton.