Hillsboro is the oldest town in Caroline County. Evidence shows that as early as 1694 there was an Anglican chapel-of-ease located on the Eastern bank of the Tuckahoe.
Commercially Hillsboro was the site of a tobacco warehouse, one or more general stores, a shoe factory, and a tavern.
The first newspaper to be published in Caroline County was published in Hillsboro in 1831 by Lucas Brothers.
Hillsboro previously known as Tuckahoe Bridge was named in the honor of Lord Hillsboro of the Calvert Family.
In 1804 there was a fever epidemic in Hillsboro then again in 1816; both occurred in the same house the Seller residence.
Hillsboro was the site of the Tri-County fair and the meeting place of Congressional Conventions.
Every edition of the U.S. Geological Survey’s map of Hillsboro. Tap a year, or press play to watch the town change.
1905Denton sheet · 1:62,500
U.S. Geological Survey historical topographic maps (public domain), via Esri’s collection of the scans. The red ring marks the center of Hillsboro.
From the old history books
What they wrote about Hillsboro in 1920
Passages that mention Hillsboro, cut from the printed page as they were published.
History of Caroline County, Maryland, from its beginning1920Read the page →
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appears to have l)een the first rector of St. John's Parish, remained until 1753, Shortly before the Revolution the three settlements at Tuckahoe Bridge (Hillsboro), Choptauk Bridge (Greensboro) and Nino Bridges (Bridgetown) seem to have been quite thriving and apparenth^ contended for the honor and advantage of having the main church and vestry house in which the rector was to live. The Ves-
Text read by machine from the scan; it may contain errors.
History of Caroline County, Maryland, from its beginning1920Read the page →
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nincli rivalry existed between the villages of Hillsboro, Greensboro, and Bridgetown, each of which fought for the honor of having an P]piscopal church erected within its limits. Hillsboro won out, but soon after a chapel was erected at Bridgetown, bricks, shells, mortar, etc., for which were hauled from a wharf along the Choptank river.
Text read by machine from the scan; it may contain errors.
Scans and text from the Internet Archive. Books published in 1930 or earlier, which are in the public domain.
Founding dates: Wikidata, Wikipedia, the U.S. post office records of Blevins & Helbock (CC0) and the Census. Homes by year built: Census ACS 2020–24. National Register of Historic Places: National Park Service (list of May 22, 2026). Old photos, postcards and papers: Wikimedia Commons, the Library of Congress and other public archives, credited on each item’s page. Maps: U.S. Geological Survey historical topographic maps (via Esri) and Sanborn fire-insurance maps (Library of Congress). History text and census tables: Wikipedia (CC BY-SA 4.0). Places that used to be: USGS Geographic Names Information System (2021). How TownRatings grades history →
From Wikimedia Commons (1), the Library of Congress (1), the National Register of Historic Places (1), Wikipedia, U.S. Geological Survey historical maps, U.S. Census counts (via Wikipedia), the US Post Offices dataset (Blevins & Helbock), the USGS Geographic Names Information System and old county and town histories (Internet Archive). Archive images are copied here with their credits and licenses, shown on each photo’s page. Refreshed monthly.