Directions from Cape May, New Jersey to Chestertown, 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.


Skybox Bar & Grill LLC

Bars – Baltimore, Maryland

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Horse and Carriage Rides

Things To Do – Baltimore, Maryland

Well-behaved dogs are allowed on the carriage rides. More on DogFriendly.com

Elks Lodge of Millville

Things To Do – Millville, New Jersey

Lobby Bar (The)

Bars – Baltimore, Maryland

Enter in style at the Lobby Bar as the plush interiors catch your eye even with all ... More on Yahoo! Travel

Bohemia Anchorage

Things To Do – Earleville, Maryland

Inscription. Home of the Lusbys in the early 1700s. Ruth Lusby and Commodore Jacob Jones married in 1821. Made the Anchorage their home and enlarged it in 1835. Jones served on the “Philadelphia” when it ran aground at ... More on HMDB

Charm City Inn

Bars – Baltimore, Maryland

Charm City Inn, located at 500 S Lehigh St, is your garden variety pub. It’s not going to win any raves of "Hottest. Bar. Ever.," but it’s a serviceable place to relax and unwind. Just keep your expectations grounded.... More on clubzone

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Charles Carroll House

Museums – Annapolis, Maryland

If you can appreciate that a wealthy family would risk their land, fortune, and very lives for the sake of ... More on Yahoo! Travel

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  • When the United States of America was but a few colonies of the British Empire. The Carroll family risked ... More on Yahoo! Travel

  • During the Revolution there were at least four Charles Carrolls who were active on the side of the patriots... More on Ci.annapolis.md.us

Memorial Circle & Market House Plaza

Landmarks – Annapolis, Maryland

Inscription. Established 1977 by, the City of Annapolis, Maryland Department of Natural Resources, Program Open Space, Maryland Commission on The Capital City, The Federated Garden Glubs of Maryland, John Apostol, Mayor, , Erected ... More on HMDB

Chesapeake Bay Fly Fishing

Things To Do – Saint Michaels, Maryland

From the headwaters to the Virginia line the Chesapeake offers some of the finest fly and light tackle fishing anywhere. This is the home to the striped bass. During the spawning run in the early spring to its exodus down the bay ... More on AnglerWeb.com

Felton Crest Vineyards

Wineries And Vineyards – Felton, Delaware

Ercole Incorporated

Restaurants – Perryville, Maryland

Don't leave without trying the cheesecake! More on Yahoo! Travel

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  • The subs there are great I like the tuna melt sub myself. More on Yahoo! Travel

  • the best pizza place in the USA.VERY GOOD PEOPLE I love everthing on menu.a truly ITALIAN food .thank you . More on Yahoo! Travel

Panache Cuisine LLC

Restaurants – Glen Burnie, Maryland

Honor ¢ Valor ¢ WWI ¢ WWII ¢ Korea ¢ Vietnam

Landmarks – Centreville, Maryland

Inscription. To honor the veterans of Queen Annes County who served their country in time of war and especially those who made the supreme sacrifice so that we and future generations may enjoy freedom. , Location. 39° 2.7′ ... More on HMDB