Directions from Norfolk, Virginia to Saint Michaels, 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.


Battle of Caulks Field War of 1812

Landmarks – Chestertown, Maryland

Inscription. Kent County Militia under Lt. Col. Philip A. Reed marched from Belle Air (Fairlee) to meet British Forces here on August 31, 1814. The British with 15 killed, were repulsed and their commander, Sir Peter Parker, mortally ... More on HMDB

Port Republic - American Chestnut Land Trust

Things To Do – Prince Frederick, Maryland

Fifteen miles of hiking trails, including an interpretive trail, open year-round. Guided canoe trips and nature hikes. ... More on Search.visitmaryland.org

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  • Fifteen miles of serene public hiking trails in two locations. Annual seasonal events for families include: Earth Day Celebration in the spring; Family Day ... More on Discover America

SegZone Tour of Annapolis

Tours – Annapolis, Maryland

Annapolis is a beautiful city and the trolley tour is the way to see it. More on TripAdvisor

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  • Our guide was very knowledgable and informative and an excellent driver, a lot of the streets are very, v... More on TripAdvisor

  • We took the 60 minute trolley tour in the afternoon. Annapolis is a beautiful city and the trolley tour is ... More on TripAdvisor

Wye Grist Mill and Museum

Museums – Wye Mills, Maryland

Inscription. Out of hundreds of mills on the East Coast in colonial times, only a few survive, and fewer still operate. As the oldest working mill in Maryland (1682), the flour producing “grist” mill in front of you has ... More on HMDB

Debtors Prison

Landmarks – Accomac, Virginia

Inscription. Built in 1783 in one corner of the jailyard to serve as a residence for the jailer, the building served in this capacity for 41 years. Iron bard, oak batten doors and locks were added in 1842 when it was converted into ... More on HMDB

Cape Charles Historical Society

Museums – Cape Charles, Virginia

?Hear? the locomotive whistle of the founding railroad and ?smell? the salt air on elegant steamers like the Elisha Lee, thanks to a rich archival photo collection that brings this 1886 bayside rai... More on Virginia.org

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  • This museum of a coastal town is filled with character and excitment, striving to preserve and protect the history of Cape Charles and surrounding its areas. Visitors are invited to explore the var... More on Heritage

Anne Arundel County Fairground

Things To Do – Crownsville, Maryland

Anne Arundel County Fairground - Let’s face it. Going out in the city can get waaaaaay too expensive. Dinner, drinks, post-drinks, and then if you throw on bottle service, fughetaboutit. Which is why delis like Anne Arundel County ... More on clubzone

Mikes Tavern

Things To Do – East New Market, Maryland

Mikes Tavern - You might see a celeb here. But he/she will probably be on one of the many flat screen TVs lining the walls. Mikes Tavern is the place you’d likely go to to ... More on clubzone

Hooper Strait

Landmarks – Saint Michaels, Maryland

Hooper Strait is a passage, just over a mile in width, which connects Chesapeake Bay with Tangier Sound. The eastern Maryland mainland forms the northern boundary of the strait, and Bloodsworth Island, once renowned as a haven for ... More on LighthouseFriends.com

Birthplace Marker of Harriet Tubman

Landmarks – Cambridge, Maryland

Tubman was called "The Moses of Her People" because of her courageous work on the Underground Railroad. She helped more ... More on Search.visitmaryland.org

East Moon Asian Bistro

Restaurants – Bowie, Maryland

Tiramisu was just right! More on Yahoo! Travel

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  • But the the service is quick and the food is great. More on Yahoo! Travel

  • I LOVE East moon!! The waitresses are not very friendly. But the the service is quick and the food is great. I have eaten there many times and everytime ... More on Yahoo! Travel

Pope's Tavern at the Oxford Inn

Restaurants – Oxford, Maryland

It remains a good value --all rooms have been updated, and many have window seats and /or... More on Frommers

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  • Go to MASONS in Easton, the food and service is ALWAYS fantastic . More on TripAdvisor

  • New owners have put a lot of TLC into this well-established inn, located beside Town Creek and close to eve... More on Frommers

Chester River Yacht & Country Club

Golf Courses – Chestertown, Maryland

Chester River Yacht & Country Club is an 18-hole regulation length golf course in Chestertown, Maryland. This short layout has 3 sets of teeboxes for a fun, but challenging golfing experience. Onli... More on TheGolfCourses.net

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  • Even though this course is short, it plays more difficult than it looks. The small greens demand good approach shots for birdie opportunities. Water hazards come into play on several holes. Guests ... More on Golf.com