20 days in Maryland Itinerary

20 days in Maryland Itinerary

Created using Inspirock Maryland route planner
Make it your trip
Drive
1
Cumberland
— 3 nights
Drive
2
Hagerstown
— 4 nights
Drive
3
Baltimore
— 5 nights
Drive
4
Ocean City
— 4 nights
Drive
5
St. Michaels
— 3 nights
Drive

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Cumberland — 3 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. Get out of town with these interesting Cumberland side-trips: Oakland (Garrett County Museum of Transportation, Swallow Falls State Park, &more) and Schoolhouse Earth (in Friendsville). Next up on the itinerary: grab your bike and head to Great Allegheny Passage, immerse yourself in nature at Rocky Gap State Park, brush up on your knowledge of spirits at Charis Winery & Distillery, and contemplate the long history of Gordon-Roberts House.

To see where to stay, more things to do, and other tourist information, refer to the Cumberland trip itinerary maker website.

Washington DC to Cumberland is an approximately 2.5-hour car ride. Traveling from Washington DC in May, expect slightly colder with lows of 52°F in Cumberland. Wrap up your sightseeing on the 15th (Sun) early enough to drive to Hagerstown.
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Parks · Nature · Historic Sites · Outdoors
Side Trips

Hagerstown — 4 nights

Hagerstown is a city in Washington County, Maryland, United States. You'll find plenty of places to visit near Hagerstown: Emmitsburg (National Shrine of St. Elizabeth Ann Seton & National Shrine Grotto of Lourdes) and Frederick (Historic Downtown Frederick, Weinberg Center for the Arts, &more). There's much more to do: explore the different monuments and memorials at Rose Hill Cemetery, steep yourself in history at Tolson's Chapel, and get to know the fascinating history of Antietam National Battlefield.

For other places to visit, reviews, photos, and other tourist information, refer to the Hagerstown vacation tool.

Traveling by car from Cumberland to Hagerstown takes 1.5 hours. Expect a daytime high around 74°F in May, and nighttime lows around 55°F. Wrap up your sightseeing on the 19th (Thu) to allow time to drive to Baltimore.
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Historic Sites · Museums · Parks · Nature
Side Trips

Baltimore — 5 nights

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 Annapolis (U.S. Naval Academy & Annapolis Historic District) and Fishpaws Marketplace (in Arnold). Spend the 21st (Sat) exploring nature at Fort McHenry National Monument and Historic Shrine. There's much more to do: try your luck at Horseshoe Casino, see the interesting displays at USS Torsk, learn about all things military at Historic Ships in Baltimore, and get up close and personal with brilliant marine life at Inner Harbor.

To see traveler tips, maps, ratings, and other tourist information, refer to the Baltimore online travel planner.

You can drive from Hagerstown to Baltimore in 1.5 hours. In May, plan for daily highs up to 75°F, and evening lows to 59°F. Finish your sightseeing early on the 24th (Tue) to allow enough time to drive to Ocean City.
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Parks · Museums · Historic Sites · Nature
Side Trips

Ocean City — 4 nights

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.
Ocean City is known for sightseeing, beaches, and theme parks. Your trip includes some of its best attractions: kick back and relax at Ocean City Beach, tee off at Rum Pointe Seaside Golf Links, indulge your thirst for a good beer at Burley Oak Brewing Company, and stroll around Northside Park.

Plan trip to Ocean City with our itinerary maker to find out where to go and what to do.

You can drive from Baltimore to Ocean City in 3 hours. Alternatively, you can take a bus. Traveling from Baltimore in May, you will find days in Ocean City are little chillier (69°F), and nights are about the same (55°F). Finish your sightseeing early on the 28th (Sat) to allow enough time to drive to St. Michaels.
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Outdoors · Parks · Wildlife · Tours
Side Trip

St. Michaels — 3 nights

Change things up with these side-trips from St. Michaels: Harriet Tubman Underground Railroad National Historical Park (in Church Creek) and Blackwater National Wildlife Refuge (in Cambridge).

To see traveler tips, other places to visit, reviews, and other tourist information, refer to the St. Michaels tour builder site.

Traveling by car from Ocean City to St. Michaels takes 2 hours. Alternatively, you can do a combination of shuttle and taxi; or do a combination of bus and taxi. Traveling from Ocean City in May, you will find days in St. Michaels are somewhat warmer (75°F), and nights are about the same (57°F). Finish up your sightseeing early on the 31st (Tue) so you can go by car back home.
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Museums · Breweries & Distilleries · Shopping · Wildlife
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.
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