21 days in Maryland Itinerary

21 days in Maryland Itinerary

Created using Inspirock Maryland itinerary planner

Make it your trip
Drive
1
Ocean City
— 3 nights
Drive
2
Easton
— 3 nights
Drive
3
Baltimore
— 5 nights
Drive
4
Hagerstown
— 5 nights
Drive
5
Cumberland
— 4 nights
Drive

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Ocean City

— 3 nights

The White Marlin Capital of the World

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 the numerous day-trip ideas around Ocean City: Crisfield Heritage Foundation (in Crisfield), Salisbury (Eastern Shore Baseball Hall of Fame Museum & Pemberton Historical Park) and Chesapeake Ghost Walks (in Marion Station). There's much more to do: stroll through Ocean City Beach, see the interesting displays at Ocean City Life-Saving Station Museum, tee off at Eagle's Landing Golf Course, and indulge your thirst for a good beer at Burley Oak Brewing Company.

For maps, traveler tips, more things to do, and tourist information, refer to the Ocean City trip planner.

Washington DC to Ocean City is an approximately 3-hour car ride. You can also take a bus; or do a combination of train and bus. October in Ocean City sees daily highs of 69°F and lows of 53°F at night. Wrap up your sightseeing on the 2nd (Mon) to allow time to drive to Easton.

Things to do in Ocean City

Parks · Museums · Outdoors · Nature

Side Trips

Easton

— 3 nights
Easton, Maryland is an incorporated town and the county seat of Talbot County, Maryland, United States. Get out of town with these interesting Easton side-trips: P.A. Bowen Farmstead (in Brandywine) and Blackwater National Wildlife Refuge (in Cambridge). And it doesn't end there: indulge in some culinary diversions at Eastern Shore Food Tours - Eating Easton, explore the galleries of 1879 Hooper Strait Lighthouse, relax and rejuvenate at some of the top local wellness centers, and contemplate the long history of The Third Haven Friends Meeting House.

To find ratings, reviews, traveler tips, and other tourist information, read Easton trip planner.

Traveling by car from Ocean City to Easton takes 1.5 hours. Expect a daytime high around 58°F in November, and nighttime lows around 40°F. Finish your sightseeing early on the 5th (Thu) to allow enough time to drive to Baltimore.

Things to do in Easton

Museums · Tours · Historic Sites · Parks

Side Trips

Baltimore

— 5 nights

City of Firsts

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.
Get out of town with these interesting Baltimore side-trips: Sharp's at Waterford Farm (in Brookeville), Larriland Farm (in Woodbine) and U.S. Naval Academy (in Annapolis). There's much more to do: try to win big at Horseshoe Casino, take in the waterfront activity at Inner Harbor, observe the fascinating underwater world at National Aquarium, and take in the architecture and atmosphere at Saint Alphonsus Church.

To see ratings, photos, other places to visit, and more tourist information, read Baltimore sightseeing planning website.

Drive from Easton to Baltimore in 1.5 hours. Expect a daytime high around 57°F in November, and nighttime lows around 43°F. Finish your sightseeing early on the 10th (Tue) so you can drive to Hagerstown.

Things to do in Baltimore

Parks · Historic Sites · Nature · Zoos & Aquariums

Side Trips

Hagerstown

— 5 nights
Hagerstown is a city in Washington County, Maryland, United States. Venture out of the city with trips to Frederick (National Museum of Civil War Medicine, Monocacy National Battlefield, &more), National Shrine Grotto of Lourdes (in Emmitsburg) and Green Meadows Petting Farm (in Ijamsville). The adventure continues: explore the wealth of natural beauty at C&O Canal Trust, contemplate the long history of Tolson's Chapel, relax in the rural setting at Frog Eye Farm, and snap pictures at Burnside's Bridge.

To see other places to visit, where to stay, maps, and tourist information, read our Hagerstown online route planner.

You can drive from Baltimore to Hagerstown in 1.5 hours. Expect slightly colder evenings in Hagerstown when traveling from Baltimore in November, with lows around 37°F. Finish up your sightseeing early on the 15th (Sun) so you can go by car to Cumberland.

Things to do in Hagerstown

Nature · Parks · Historic Sites · Museums

Side Trips

Cumberland

— 4 nights
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. Explore Cumberland's surroundings by going to Schoolhouse Earth (in Friendsville), New Germany State Park (in Grantsville) and Oakland (Swallow Falls State Park & Deep Creek Lake State Park). The adventure continues: grab your bike and head to Great Allegheny Passage, contemplate the long history of Spruce Forest Artisan Village, admire the majestic nature at Rocky Gap State Park, and sample the fine beverages at Charis Winery & Distillery.

To find traveler tips and other tourist information, read Cumberland day trip planning website.

You can drive from Hagerstown to Cumberland in 1.5 hours. In November, daytime highs in Cumberland are 54°F, while nighttime lows are 34°F. Wrap up your sightseeing on the 19th (Thu) early enough to travel back home.

Things to do in Cumberland

Parks · Nature · Historic Sites · Trails

Side Trips

Maryland travel guide

4.1
Casinos · Specialty Museums · Aquariums
The Old Line State
Perhaps best known as the birthplace of religious and political freedom in the United States, Maryland retains the spirit of colonial America, with stately 18th-century villages and historical landmarks. Although it's one of the nation's smallest states, there is no shortage of things to do here and you may find your itinerary fills up quickly. Make time in your vacation to tour Maryland's diverse landscape, which includes mountain peaks, picturesque Atlantic coastline, and the bustling city of Baltimore. Military buffs will enjoy touring the state's four Civil War Trails, where you can follow the footsteps of U.S. soldiers, or visiting the port city of Annapolis, home to the United States Naval Academy.