Between 1890 and 1930, the village was a busy port for passenger and then automobile ferry service across the Chesapeake Bay, with numerous stores and motels/resorts, including Maple Hall and the Bellfonte Hotel.

The role of Claiborne as a terminal for cross-Bay ferries was diminished in 1930 when the primary route shifted to Matapeake in Kent Island.

Its name can be traced back in honor of William Claiborne, a fur trader who founded an English settlement on nearby Kent Island in 1631.

Early land patents in Claiborne included "Rich Neck Manor," which was first granted 2,000 acres to Capt.

The area of town now known as "Old Claiborne," was located on Tilghman's Creek facing the Miles River.

A plat of it appears in an 1877 county atlas, showing eight main streets with the names: Rich Neck Road, Leeds, Ward, Progress, Monument, Tilghman, and Dom Pedro.

At its center was Henry Clay Square, a large area reserved for public buildings.

A second community, the "new" Claiborne, was started in 1886 when Gen. Joseph B. Seth and the Baltimore & Eastern Shore Railroad Company agreed to begin ferry and railroad service between Claiborne and Bay Ridge, on the western shore of the Chesapeake Bay.

Steamer service by the Baltimore, Chesapeake and Atlantic Railway continued until 1924 when BC&A had shifted its traffic to Love Point.

In 1927 the Baltimore, Chesapeake, & Atlantic Railway filed for bankruptcy and was sold at foreclosure on March 28, 1928.

In 1916, the recently amended Panama Canal Act precluded the operation for ferry lines by railroad companies, with exceptions permitted only via approval of the Interstate Commerce Commission.

A second ferry company, the Eastern Shore Development Steamship Company, began service in 1912 between Claiborne and Annapolis starting with the steamer "Atlantic" and then switching over in December 1912 to the steam yacht "Texas", formerly owned by Edward H. R. Green, the son of Wall Street investor Henrietta Green.

On Sunday evening it was not uncommon for traffic to be backed up several miles into Claiborne, waiting for the return ferry trip across the Chesapeake Bay.

Ferry service stopped running in December 1952, a few months after the Chesapeake Bay Bridge was built.

[3] As late as 1924 the Baltimore, Chesapeake and Atlantic Railway was operating daily except Sunday passenger trains east from Claiborne to various points on the DelMarVa peninsula: Easton, Hurlock, Salisbury's Union Station, Berlin and finally, Ocean City, Maryland.

and Eastern Shore Railroad in effect for 29 Sep 1890 "Denton Journal", 2 Dec 1893. article: "Claiborne now has a postoffice" "Denton Journal", 28 Aug 1915. article: "TO RESTORE COMPETITION" "Denton Journal", 17 Jan 1920. article: "The Governor has decide to have the Claiborne road built" PRR Corporate History[dead link‍] Guide to the Checklist of Maryland Post Offices "Talbot County: A History", Dickson Preston "Steamboats Out of Baltimore", Robert H. Burgess and H. Graham Wood "History of Talbot County Maryland 1661-1861", Oswald Tilghman Star Democrat, 7 Sep 1984 Annual Report of the Maryland Comptroller, 1915.