Location: At the foot of the Spa Creek Bridge

Eastport's distinctive history, character and identity grew from
maritime roots. The marinas
that now serve pleasure boaters were
once filled with wooden workboats. So crowded was
the shoreline, it
was said that an enterprising cat could flit from boat to boat and skirt
the
entire peninsula without getting its feet wet.
Once a separate town, Eastport was annexed to Annapolis in 1951. Nevertheless, it retains a distinct local flavor and spirit.
Before the English arrived, the shores and waters surrounding you were traversed by Native Americans who had lived here for thousands of years, using dug-out canoes to harvest fish and oysters on these creeks. Algonquian tribes hunted and fished here, in this no-man’s land; an area that separated the warring Susquehannas to the north from the more peaceful Wicomicos and other nations to the south.
Wherever you wander on the Eastport Walking Tour, you’ll be treading on what was once the 300-acre parcel known as Horn Point. First patented in 1665 by Cecil Calvert, the Second Lord Baltimore, to Robert Clarkson, the grant extended from Todd’s Creek (what we now call Spa Creek) to Beasley’s Creek (now called Back Creek). It remained farmland for the next two hundred years.
Clarkson sailed to Maryland in 1657. He was a Quaker, as were most Anne Arundel County landowners at the time. He was once fined for refusing to bear arms. After Clarkson’s death in 1666, his widow re-married and the land passed to her new husband, Richard Hill, a planter, merchant, gentleman, and Quaker sympathizer. About the same time, 1665-66, a Quaker missionary named Elizabeth Harris was in Maryland converting colonists to Quakerism.
One of the more colorful characters in the Hill family was Henrietta Margaret Hill, who called herself “Henry Margaret.” She was born in 1751 and inherited all the land between here and the South River, three miles away. An early chart shows Back Creek as “Hill’s Back Creek.”
![]() Benjamin Ogle, Governor of Maryland from 1798 to 1801, found the pastures of Horn Point ideal for raising some of the state's first racehorses. |
With this large parcel of land as a dowry, Henry Margaret married Benjamin Ogle when she was nineteen years old.
Benjamin was the son of Samuel Ogle who served three terms as governor of Maryland. Benjamin himself was governor from 1798 to 1801. These men were instrumental in bringing thoroughbred horse racing to the colonies.
Benjamin died in 1809 and, according to legend, was buried somewhere near here in an unmarked grave. Nobody has found it yet.
When Henry Margaret died in 1815, the land was sold to settle the mortgage, held by Mr. Ogle’s mother. The Ogle’s 645 acres, including the original Horn Point tract, were sold to John Barber for $35 an acre. The Barbers sold off several parcels over the next 50 years, but the majority remained as Horn Point Farm. It’s hard to imagine an acre selling for $35 here, since any house on any lot in Eastport is generally considered a million-dollar property today.
After the Civil War, the Mutual Building Association of Annapolis bought a hundred acres of Horn Point to create 256 building lots. The first plat of 1868 laid out the numbered streets and Severn, Chesapeake and Chester avenues. The lots were small and inexpensive and suited a working community of people — black and white — who harvested the bounty of the Bay, worked in the boatyards, provided goods and services to their neighbors, or traveled across the creek to work in Annapolis homes or at the Naval Academy. The first bridge connecting Eastport to Annapolis was built in 1870.

This 1880s view of the Horn Point peninsula shows the distinctive mix of Eastport:
boatyards on the shore, buildings in the middle, and farmland beyond. During the
Revolutionary War, a fort on Horn Point helped defend Annapolis from invasion by
the British fleet. A historic plaque across the street from Site 1 tells of Lafayette's
encampment
in Annapolis.
By the 1920s, the town was flourishing and Eastport remained an independent village until 1951, when it was annexed into the City of Annapolis by popular vote. Old-time Eastporters claim that the election was rigged because all the men of voting age were off serving in the Korean War...
In the latter part of the 20th century, oyster and crab harvests waned and traditional wooden workboats gave way to modern fiberglas pleasure boats. Eastport's working past gave way to gentrification.
The boat yard you see beyond the information panel is now the annex to the Annapolis Yacht Club. After World War II, it was Arnie Gay’s yacht yard. Gay’s vision and leadership made Annapolis “America’s Sailing Capital.” He brought national and international racing to the area.
He arrived in Annapolis in 1945 aboard his schooner Delilah with less than $2 in his pocket. Mentored by John Alden in Bristol, Rhode Island, Arnie built a career in Annapolis as a boat broker, yachtsman, and sailing instructor to young people. Arnie owned two boat yards on Spa Creek: this one and another across the creek at the end of Shipwright Street near St. Mary’s Church. It was one of the first marinas tailored for pleasure boaters rather than workboats.
In 1978 Arnie won the Newport to Bermuda Race aboard Babe, an all-wooden Concordia sloop; it was the crowning achievement of his sailing career.

The popular yellow flags with the motto "We like it this way" flew first in 1998.To offset the potential loss to businesses from a temporary bridge closure, the community created the mock "Maritime Republic of Eastport" and declared independence from Annapolis.
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PO Box 3088 |
Annapolis, MD 21403
410 295-0104
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