21 days in Maryland Itinerary

21 days in Maryland Itinerary

Created using Inspirock Maryland tour planner

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Route & dates

21 days in Maryland Itinerary

Start: Dubai
Fly + Drive:  20​h 30​min
1
Sharpsburg
— 4 nights
Drive:  1​h 30​min
2
Cumberland
— 3 nights
Drive:  4​h 45​min
3
Ocean City
— 4 nights
Drive:  1​h 30​min
4
Easton
— 4 nights
Drive:  1​h 30​min
5
Baltimore
— 4 nights
+3
train + subway + bus + Fly:  19​h
End: Dubai

4
nights
Sharpsburg

Sharpsburg ©
Sharpsburg is a town in Washington County, Maryland, United States, located approximately 13mi south of Hagerstown. Get out of town with these interesting Sharpsburg side-trips: C&O Canal Hike at Point of Rocks Boat Ramp (in Point of Rocks), Frederick (Clue IQ: An Escape Room Experience & Dragon Distillery, LLC) and Worthington Manor Golf Club (in Urbana). There's much more to do: witness the site of a historic battle at Antietam National Battlefield, stroll around Penn Mar Park, take in the views from Burnside's Bridge, and hike along Maryland Heights Trail.

To find where to stay, photos, more things to do, and other tourist information, you can read our Sharpsburg holiday planning website .

Dubai, United Arab Emirates to Sharpsburg is an approximately 20.5-hour combination of flight and car. The time zone difference when traveling from Dubai to Sharpsburg is minus 9 hours. Plan for much colder temperatures traveling from Dubai in November, with highs in Sharpsburg at 15°C and lows at 1°C. Wrap up your sightseeing on the 14th (Thu) to allow time to drive to Cumberland.

Things to do in Sharpsburg

Parks Outdoors Historic Sites

Side Trips

Frederick, Knoxville, Hagerstown, Surreybrooke Gardens, Worthington Manor Golf Club
Highlights from your plan
Clue IQ: An Escape Room Experience ©
Antietam National Battlefield ©
Antietam National Battlefield
Burnside's Bridge ©
Burnside's Bridge

3
nights
Cumberland

Cumberland ©
Cumberland, officially the City of Cumberland, is a western gateway city and seat of Allegany County, Maryland, United States and the primary city of the Cumberland, MD-WV Metropolitan Statistical Area. Get out of town with these interesting Cumberland side-trips: Swallow Falls State Park (in Oakland), Fun Unlimited (in McHenry) and Grantsville (House of Yoder & New Germany State Park). There's much more to do: grab your bike and head to Great Allegheny Passage, look for gifts at Schoolhouse Earth, browse the collection at Allegany County Library System - Washington Street Library, and contemplate the long history of Gordon-Roberts House.

To find maps, traveler tips, photos, and tourist information, refer to the Cumberland online trip planner .

Traveling by car from Sharpsburg to Cumberland takes 1.5 hours. In November, daytime highs in Cumberland are 14°C, while nighttime lows are 1°C. Cap off your sightseeing on the 17th (Sun) early enough to travel to Ocean City.

Things to do in Cumberland

Parks Nature Outdoors

Side Trips

Grantsville, Swallow Falls State Park, Fun Unlimited, Schoolhouse Earth, Allegany County Library System - Frostburg Library
Highlights from your plan
Swallow Falls State Park ©
Swallow Falls State Park
Charis Winery ©
Charis Winery

4
nights
Ocean City

Ocean City ©
One of the country's favorite vacation resorts, Ocean City draws nearly 8 million visitors annually with its oceanfront boardwalk, clean beaches, and amusement parks.
Explore Ocean City's surroundings by going to Chesapeake Bay Farms (in Pocomoke City), Crisfield Heritage Foundation (in Crisfield) and Salisbury (Ward Museum of Wildfowl Art, Ben's Red Swings Community Playground, & more). There's much more to do: enjoy the sand and surf at Ocean City Beach, play a few rounds at Rum Pointe Seaside Golf Links, get your game on at Marty's Playland, and view the masterpieces at Bishop's Stock Fine Art, Craft & Wine.

Plan a trip to Ocean City easily and quickly by telling Inspirock to suggest an itinerary.

Drive from Cumberland to Ocean City in 5 hours. Alternatively, you can do a combination of car and flight. November in Ocean City sees daily highs of 16°C and lows of 4°C at night. Wrap up your sightseeing on the 21st (Thu) early enough to drive to Easton.

Things to do in Ocean City

Parks Museums Outdoors

Side Trips

Salisbury, Snow Hill, Berlin, Chesapeake Bay Farms, Crisfield Heritage Foundation
Highlights from your plan
Ocean City Beach ©
Ocean City Beach
Ocean City Boardwalk ©
Ocean City Boardwalk
Rum Pointe Seaside Golf Links ©
Rum Pointe Seaside Golf Links

4
nights
Easton

Easton ©
Easton, Maryland is an incorporated town and the county seat of Talbot County, Maryland, United States. You'll find plenty of places to visit near Easton: Bruce Snake Gabrielson's Surf Art Gallery and Museum (in Chesapeake Beach), Lead Dog Charters (in Stevensville) and Phillips Wharf Environmental Center (in Tilghman). There's much more to do: soothe aching muscles at some of the top local wellness centers, see the interesting displays at Chesapeake Bay Maritime Museum, relax in the rural setting at P.A. Bowen Farmstead, and visit a coastal fixture at Choptank River Lighthouse.

To find maps, traveler tips, reviews, and more tourist information, read our Easton day trip app .

Getting from Ocean City to Easton by car takes about 1.5 hours. In November in Easton, expect temperatures between 17°C during the day and 5°C at night. Finish your sightseeing early on the 25th (Mon) so you can drive to Baltimore.

Things to do in Easton

Parks Museums Outdoors

Side Trips

Cambridge, St. Michaels, Chestertown, Wye Mills, Phillips Wharf Environmental Center
Highlights from your plan
Neild Museum and Herb Garden ©
Neild Museum and Herb Garden
Spas & Wellness
Lyon Distilling Company ©
Lyon Distilling Company

4
nights
Baltimore

Baltimore ©
A major center for tourism and travel, Baltimore is famous as the city where amateur poet Francis Scott Key wrote the lyrics for the United States' national anthem.
Venture out of the city with trips to Diehl's Produce Market (in Severna Park) and U.S. Naval Academy (in Annapolis). There's much more to do: try your luck at Horseshoe Casino, brush up on your knowledge of spirits at Sagamore Spirit Distillery, get your game on at Urban Axes Baltimore, and go for a stroll along the water at Inner Harbor.

For ratings, where to stay, other places to visit, and other tourist information, refer to the Baltimore trip itinerary builder app .

Traveling by car from Easton to Baltimore takes 1.5 hours. In November, daily temperatures in Baltimore can reach 16°C, while at night they dip to 7°C. Wrap up your sightseeing on the 29th (Fri) to allow time to travel back home.

Things to do in Baltimore

Parks Historic Sites Zoos & Aquariums

Side Trips

U.S. Naval Academy, Diehl's Produce Market
Highlights from your plan
Sagamore Spirit Distillery ©
Sagamore Spirit Distillery
Horseshoe Casino ©
Horseshoe Casino
Urban Axes Baltimore ©
Urban Axes Baltimore

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