21 days in Maryland Itinerary

21 days in Maryland Itinerary

Created using Inspirock Maryland itinerary planner

Plan created by another user. Make it yours
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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3
nights
Ocean City

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, sample the tasty concoctions at Burley Oak Brewing Company, tee off at Eagle's Landing Golf Course, and examine the collection at Ocean City Life-Saving Station Museum.

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 · Breweries & Distilleries

Side Trips

3
nights
Easton

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: Blackwater National Wildlife Refuge (in Cambridge) and P.A. Bowen Farmstead (in Brandywine). And it doesn't end there: indulge in some culinary diversions at Eastern Shore Food Tours - Eating Easton, don't miss a visit to Choptank River Lighthouse, steep yourself in history at The Third Haven Friends Meeting House, and soothe aching muscles at some of the top local wellness centers.

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

5
nights
Baltimore

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: U.S. Naval Academy (in Annapolis), Sharp's at Waterford Farm (in Brookeville) and Larriland Farm (in Woodbine). The adventure continues: try to win big at Horseshoe Casino, take in the architecture and atmosphere at Saint Alphonsus Church, brush up on your knowledge of spirits at Sagamore Spirit Distillery, and explore the world behind art at The Walters Art Museum.

For where to stay, traveler tips, photos, and other tourist information, go to the Baltimore online trip maker.

Traveling by car from Easton to Baltimore takes 1.5 hours. In November, plan for daily highs up to 57°F, and evening lows to 43°F. Wrap up your sightseeing on the 10th (Tue) to allow time to drive to Hagerstown.

Things to do in Baltimore

Parks · Historic Sites · Nature · Zoos & Aquariums

Side Trips

5
nights
Hagerstown

Hagerstown is a city in Washington County, Maryland, United States. Venture out of the city with trips to Sugarloaf Mountain (in Dickerson), Frederick (National Museum of Civil War Medicine, Monocacy National Battlefield, &more) and National Shrine Grotto of Lourdes (in Emmitsburg). On the 11th (Wed), spend a day delving into the history of Antietam National Battlefield. The adventure continues: explore the wealth of natural beauty at C&O Canal Trust, relax in the rural setting at Green Meadows Petting Farm, contemplate the long history of Tolson's Chapel, 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

Parks · Nature · Historic Sites · Museums

Side Trips

4
nights
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. Explore Cumberland's surroundings by going to New Germany State Park (in Grantsville), Oakland (Swallow Falls State Park & Deep Creek Lake State Park) and Schoolhouse Earth (in Friendsville). There's lots more to do: explore the landscape on two wheels at Great Allegheny Passage, contemplate the long history of Spruce Forest Artisan Village, do a tasting at Charis Winery, and immerse yourself in nature at Casselman River Bridge State Park.

You can plan Cumberland trip in no time by asking Inspirock to help create your itinerary.

Getting from Hagerstown to Cumberland by car takes about 1.5 hours. Expect a daytime high around 54°F in November, and nighttime lows around 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 · Outdoors

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.