Directions from Annapolis, Maryland to Crisfield, 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.


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

Talbot Country Club

Golf Courses – Easton, Maryland

Talbot Country Club is an 18-hole regulation length golf course in Easton, Maryland. This medium-length layout features 4 sets of teeboxes for the enjoyment of golfers of all skill levels. Online t... More on TheGolfCourses.net

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  • This course features water hazards coming into play on ten holes. The small greens are well bunkered, and the fairways are relatively flat. This course ... More on Golf.com

Trinity P.E. Church

Landmarks – Woolford, Maryland

Inscription. This church was built prior to 1690. In the graveyard are buried Governor Thomas King Carroll, many revolutionary heroes and other distinguished Marylanders. , Erected by Dorset Chapter, N. S. D. A. R. , Location. 38° ... More on HMDB

Drum Bay

Things To Do – Saxis, Virginia

Easton - Third Haven Friends Meeting House

Things To Do – Easton, Maryland

Believed to be the oldest frame building in ... More on TripAdvisor

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  • Inscription. Meeting House, of the, Society of Friends, 1682-1684 One of the oldest frame houses of worship in the United States. In continuous use since it was built. , Erected by Maryland Histor... More on HMDB

Bloxom Vineyard and Winery

Wineries And Vineyards – Bloxom, Virginia

35 acre old Victorian farm with 6 acres of Chardonnay, Merlot and Cabernet, just minutes south of Chincoteague Island on Virginia?s Eastern Shore. Hours: May-October, Wed.-Sun. 1-5 pm Free wine tasting. Food: chocolate confections. ... More on Virginia.org

Point Lookout Marina

Parks – Ridge, Maryland

Full-service marina, easy access to bay. 160 slips, yachts to 200 ft., fuel/repair service, pool, picnic area, playground. ... More on Search.visitmaryland.org

Mason-Dixon Marker

Parks – Mardela Springs, Maryland

Southern end of north-south line of the Mason-Dixon boundary, installed to settle boundary disputes between Penn/Calvert families, ... More on Search.visitmaryland.org

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  • Southern end of north-south line of the Mason-Dixon boundary, installed to settle boundary disputes between Penn/Calvert ... More on Search.visitmaryland.org

Elks Golf Club

Golf Courses – Salisbury, Maryland

Elks Golf Club is a 9-hole regulation length golf course in Salisbury, Maryland. This short layout will reward good shots and provide a fun golf outing for everyone. Online tee times may be availab... More on TheGolfCourses.net

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  • The 9-hole "Elks" course at the Elks Golf Club facility in Salisbury, Maryland features 6,200 yards of golf from the longest tees for a par of 72 . The course rating is 68.2 and it has a slope rati... More on golflink.com

Teackle Mansion

Landmarks – Princess Anne, Maryland

The 200-year old Teackle Mansion was residence to the influential Littleton Dennis Teackle of the early 19th century. A symbol of early Americans’ determination to build a new nation, a new e... More on Heritage

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  • Inscription. Built 1801 Built by Littleton Dennis Teackle Home of Somerset County Historical Society Setting of George Alfred Townsend's novel "The Entailed Hat", , Location. 38° 12.212′... More on HMDB

Transpeninsular Line

Landmarks – Delmar, Maryland

Inscription. Transpeninsular line between Maryland and three lower counties of Pennsylvania (now Delaware), Middle Point 8 miles, ← First run 1751, agreed upon 1760 and finally ratified 1769 by King George III. Thus ending almost ... More on HMDB

Home Run Baker Park

Parks – Trappe, Maryland

Inscription. This Park is Dedicated to Hall of Fame Inductee, John Franklin "Home Run" Baker (1886-1963): Baseball's First Home Run Hero and "As fine a citizen as any town could have.": Of all the ... More on HMDB

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  • Park Fact Sheet Park Home Run Baker Park Talbot County, Maryland Website Address 4200 Main Street Trappe, ... More on Usssa1.com

Latitude 38 Bistro & Spirits

Restaurants – Oxford, Maryland

One of our favorite appetizers is the Latitude 38 Oysters (in season).. the freshest Bay oysters baked in a... More on TripAdvisor

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  • If you are entertaining friends for dinner you will look like a star for picking a fine restraunt. More on Yahoo! Travel

  • The owners at Latitude 38 will pick you up at Mears Marina if you travel to Oxford by boat (no charge) make... More on Yahoo! Travel

Shucking House Cafe

Restaurants – Chincoteague, Virginia

Super Soda Center

Restaurants – Easton, Maryland