Directions from Wildwood Crest, 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.


Smyrna River

National And State Parks – Kenton, Delaware

The Smyrna River is a river, approximately 15 mi (24 km) long, in central Delaware in the United States. It rises in northwestern Kent County, approximately 3 mi (5 km) northwest of Kenton, and flows generally ENE, past Smyrna and ... More on AnglerWeb.com

“Partridge Hill” Built c. 1760

Landmarks – Elkton, Maryland

Inscription. Home of Henry Hollingsworth, merchant, legislator and colonel of Elk Battalion of Militia in Revolutionary Way as Commissary for the Eastern Shore. He obtained supplies for the Americans and French allies embarking near ... More on HMDB

Charles W. Baldwin Hall

Landmarks – Millersville, Maryland

Built in 1861 as a memorial to Charles W. Baldwin, a Methodist minister. Arched windows, lofty ceilings, hardwood floors; available ... More on Search.visitmaryland.org

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  • Inscription. Constructed 1861, Relocated 1895, Enlarged 1935, Relocated to this site, 2 June 1981, Rededicated, 21 May 1983, By the Severn, Cross Roads Foundation, , Location. 39° 3.575′... More on HMDB

Memorial To Edward Berge

Sightseeing – Baltimore, Maryland

Inscription. As a memorial to his friend Edward Berge, this enlargement of his "Sea Urchin" by Henry Berge was presented to the City of Baltimore by Frederick R. Huber 1959. Completed 1961. , Location. 39° 17.806′ N, 76° ... More on HMDB

5th Street Playground

Parks – Annapolis, Maryland

Separate play space for 2-5 year olds (tot lot). Grassy area, mulch, huge playweb, and many levels. More on KaBoom.org

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Port Hole

Bars – Baltimore, Maryland

Port Hole - Twenty dollar cover? Nope. Celebrities? None. Port Hole is nowhere near the pages of Us Weekly or TMZ, but hey, beer is beer, whiskey is whiskey. A friendly neighborhood bar ... More on clubzone

British 24 Pounder

Landmarks – Annapolis, Maryland

Inscription. Captured on the British flagship Confiance on Lake Champlain, September 11, 1814, by Commodore Thomas MacDonough. This gun has a dent on the muzzle from an American shot which caused the gun to recoil and kill the British ... More on HMDB

Rock Hall Landing Marina

Things To Do – Rock Hall, Maryland

Liquor warehouse with \"The coldest beer in town.\" They offer a large selection ... More on Yahoo! Travel

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  • Floating Docks, Electric, Cable TV, Pumpout, Pool, Bathouses, BBQ Area, Hi & Dry Service, Bike Rental, Lodging, Playground More on Search.visitmaryland.org

Maryland Golf & Country Club

Golf Courses – Bel Air, Maryland

Extremely well maintained, never crowded (as it is a private course), with an extremely challenging and beautiful layout that never gets dull. More on GolfReview

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  • One of the best country club courses I have ever played. Extremely well maintained, never crowded (as it is a private course), with an extremely challenging and beautiful layout that never gets dul... More on GolfReview

  • Maryland Golf & Country Club is an 18-hole regulation length golf course in Bel Air, Maryland. This championship layout has 3 sets of teeboxes for a fun, but challenging golfing experience. Online ... More on TheGolfCourses.net

Rose Hill

Landmarks – Earleville, Maryland

Inscription. Home of General Thomas Marsh Forman (1758–1845), Aide to General William Alexander, known as Lord Stirling, and a representative in the General Assembly, 1790 and 1800. He served with Major George Armistead, Fort ... More on HMDB

Another Chicken

Restaurants – Baltimore, Maryland

Holiday Restaurant

Restaurants – Brooklyn, Maryland

Papa John's Pizza

Restaurants – Towson, Maryland

This is pretty standard delivery pizza. More on Judysbook.com

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  • This is pretty standard delivery pizza. The crust, which you can get in thick or thin, is pretty tas... More on Judysbook.com

  • These bright white storefronts are accented with green and red details and photos of the chain's boyish founder. The simple menu focuses on ... More on CitySearch