Directions from Annapolis, Maryland to Princess Anne, 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.


Asbury United Methodist Church

Landmarks – Allen, Maryland

Inscription. The original sanctuary was built in 1829 on 1/2 acre of land purchased on September 12 for $50 from Sarah Stewart and Andrew Anderson. That building, constructed from lumber from trees cut from the lot, was moved to another ... More on HMDB

Bennetts Point Farm

Landmarks – Queenstown, Maryland

Inscription. Originally called “Morgans Neck.” Surveyed in 1658 for Henry Morgan of the “Isle of Kent” as two tracts of 150 acres each. Henry Morgan was given the land for transporting two indentured servants ... More on HMDB

Choptank Riverboat Company - Home of the Dorothy Megan and the Choptank River Queen Paddle Boats

Things To Do – Hurlock, Maryland

Authentic paddle wheel boat cruises Choptank River for lunch, dinner, sightseeing or charter. Waterfront atmosphere ... More on Search.visitmaryland.org

Richardson Maritime Museum

Museums – Cambridge, Maryland

Topics: maritime, wooden, boats, history, general, 17th, century, 18th, 19th, 20th, civil, war, living history, local ... More on MuseumStuff.com

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  • Chesapeake Bay ship models and waterman artifacts honor the craftsmen and culture of Eastern Shore boatbuilding. Watch ... More on Search.visitmaryland.org

Pocomoke Sound

Things To Do – Mears, Virginia

St. Josephs Church

Landmarks – Queen Anne, Maryland

Inscription. Originally a mission of Old Bohemia founded March 18, 1765, by Father Joseph Mosley, S. J. Oldest section built 1782, additions made 1848 and 1903. Father Mosley is one of three priests interred under Chapel. Since 1868, ... More on HMDB

The Amish Market

I love to come here every time I am in the area if for no other reasn than just the smell of it! More on TripAdvisor

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  • Wir dachten an einen Farmers Market im üblichen Sinn und wurden leider sehr von der Sache enttäuscht. Berei... More on TripAdvisor

  • While you are visiting the Eastern Shore, don't forget to drop in and visit our wonderful ... More on TripAdvisor

Assateague Island National Seashore

Beaches – Berlin, Maryland

We were luck as our tent was free of any leaks and was unaffectted by the wind. More on TripAdvisor

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  • The beach is very clean and not too crowded. More on igougo

  • The wild ponies of Assateague and Chincoteague Islands are a remnant of the early days of our country's his... More on igougo

Frederick Douglass Marker

Things To Do – Easton, Maryland

Frederick Douglass was born in 1818 on a farm that is now Trappers Corner in Talbot County. There ... More on Search.visitmaryland.org

97 9 FM Bay Country

Things To Do – Pocomoke City, Maryland

H & G Restaurant

Restaurants – Easton, Maryland

Not Just Salads

Restaurants – Chincoteague, Virginia

Terrible service...slow and unfriendly. I have eaten there 3 times over the past 2 years and each time the service has gotten ... More on Yahoo! Travel