Directions from Chesapeake, Virginia to Oxford, Maryland





UpTake Roadtrip Beta

We've selected a few points along the way for you to stop. We are trying to surface things you may not find elsewhere, but if we make some poor choices, please understand. Your feedback is appreciated.


Hockley-in-the-Hole Patented August 25, 1664

Landmarks – Annapolis, Maryland

Inscription. To Edward, Joshua, and John Dorsey, sons of Edward Dorsey who settled in Maryland in 1650. The patent was signed by Charles Calvert, then Lieutenant General, and later Third Lord Baltimore. This plantation has been the ... More on HMDB

Battle Creek Cypress Swamp Sanctuary

Museums – Port Republic, Maryland

'Battle Creek Cypress Swamp' 250px The 'Battle Creek Cypress Swamp', Maryland, in spring Designation U.S. National Natural Landmark Location Calvert ... More on Wikipedia

Food Lion

Grocery Convenience Shopping – Fruitland, Maryland

“Canterbury Mannor” 1000 Acres

Landmarks – Easton, Maryland

Inscription. Laid out for Richard Tilghman Chirurgeon as “Mannor of Tilghmans Fortune” 20th July 1659. Sold by him to Richard Preston 3rd Sept. 1665, as the “Mannor of Canterbury” “together with all royaltys ... More on HMDB

Millennium Tours Inc.

Tours – Chesapeake Beach, Maryland

Malin Farms

Things To Do – Preston, Maryland

pumpkin patch- already gathered from the field, prepicked produce Crops are usually available in May, June, July, August. We have containers full of flowers and hanging baskets. Fresh produce is available all summer long-cantaloupes, ... More on pumpkinpatchesandmore.org

The Right Will Prevail Prince Georges County World War I Monument

Landmarks – Upper Marlboro, Maryland

Inscription. This monument perpetuates the memory of the sons and daughters of Prince Georges County who, true to the traditions of their county and the teachings of their forefathers, served their country in the Great War of 1917-1918. ... More on HMDB

Historic Annapolis

Landmarks – Arnold, Maryland

Inscription. Historic Annapolis. 5 miles. United States Naval Academy. , Erected by Maryland Historical Trust, Maryland State Highway Administration. , Location. 39° 3.288′ N, 76° 31.538′ W. Marker is in Arnold, ... More on HMDB

Anna Ella Carroll Unofficial Cabinet Member

Landmarks – Woolford, Maryland

Inscription. Anna Ella Carroll was born on Maryland's Eastern Shore in 1815. Often called an unofficial member of President Abraham Lincoln's cabinet, she was a Unionist author and newspaper reporter who had traveled extensively throughout ... More on HMDB

Calvert County Historical Society

Museums – Prince Frederick, Maryland

The Calvert County Historical Society oversees the preservation of county history out of its headquarters at Linden. From a newly established Headquarters Room on site at Linden, visitors can find ... More on Heritage

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  • �One of the two finest examples of mid-18th. century Georgian architecture in Calvert County is the Weems House. . . . It typifies the kind of dwelling erected by Maryland�s wealthiest tobacco plan... More on Calverthistory.org

Machipongo River

Things To Do – Machipongo, Virginia

Fish House

Restaurants – Onancock, Virginia