28 days in Maryland Itinerary

28 days in Maryland Itinerary

Created using Inspirock Maryland vacation planner
Make it your trip
Fly to Washington Dulles International Airport, Drive to Cumberland
1
Cumberland
— 4 nights
Drive
2
Hagerstown
— 6 nights
Drive
3
St. Michaels
— 5 nights
Drive
4
Ocean City
— 4 nights
Drive
5
Baltimore
— 8 nights
Fly

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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. Get out of town with these interesting Cumberland side-trips: Oakland (Garrett County Historical Museum, Swallow Falls State Park, &more), Wisp Resort (in McHenry) and FireFly Farms Market (in Accident). There's lots more to do: grab your bike and head to Great Allegheny Passage, see the interesting displays at Allegany Museum, do a tasting at Charis Winery & Distillery, and don't miss a visit to Allegany Fairgrounds.

To find where to stay, photos, and tourist information, read Cumberland trip planner.

Toronto, Canada to Cumberland is an approximately 7.5-hour combination of flight and car. You can also drive. Traveling from Toronto in December, you will find days in Cumberland are somewhat warmer (9°C), and nights are about the same (0°C). Finish your sightseeing early on the 24th (Fri) so you can drive to Hagerstown.
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Parks · Museums · Nature · Outdoors
Side Trips

Hagerstown — 6 nights

Hagerstown is a city in Washington County, Maryland, United States. Venture out of the city with trips to Frederick (Weinberg Center for the Arts, Historic Downtown Frederick, &more), Emmitsburg (National Shrine of St. Elizabeth Ann Seton & National Shrine Grotto of Lourdes) and Surreybrooke Gardens (in Middletown). There's lots more to do: explore the world behind art at Washington County Museum of Fine Arts, make a trip to Lockhouse 49, witness the site of a historic battle at Antietam National Battlefield, and contemplate the long history of Tolson's Chapel.

To see reviews, photos, traveler tips, and tourist information, you can read our Hagerstown trip builder app.

Drive from Cumberland to Hagerstown in 1.5 hours. In December in Hagerstown, expect temperatures between 9°C during the day and 0°C at night. Finish your sightseeing early on the 30th (Thu) to allow enough time to travel to St. Michaels.
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Historic Sites · Museums · Parks · Nature
Side Trips

St. Michaels — 5 nights

Explore the numerous day-trip ideas around St. Michaels: Outstanding Dreams Farm (in Preston) and Cambridge (Long Wharf Park & Neild Museum and Herb Garden).

For traveler tips, maps, ratings, and other tourist information, refer to the St. Michaels trip site.

You can drive from Hagerstown to St. Michaels in 2.5 hours. December in St. Michaels sees daily highs of 11°C and lows of 2°C at night. Cap off your sightseeing on the 4th (Tue) early enough to go by car to Ocean City.
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Museums · Parks · Shopping · Historic Sites
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.
Venture out of the city with trips to Salisbury (Eastern Shore Baseball Hall of Fame Museum & Pemberton Historical Park), Julia A. Purnell Museum (in Snow Hill) and Crisfield Heritage Foundation (in Crisfield). And it doesn't end there: walk around Northside Park, indulge in some personalized pampering at OC Massage, examine the collection at Ocean City Life-Saving Station Museum, and make a splash at Oceancity Watersports.

To find photos, other places to visit, traveler tips, and more tourist information, refer to the Ocean City visit planner.

Getting from St. Michaels to Ocean City by car takes about 2 hours. Other options: do a combination of taxi and shuttle; or do a combination of taxi and bus. January in Ocean City sees daily highs of 7°C and lows of -3°C at night. Wrap up your sightseeing on the 8th (Sat) to allow time to drive to Baltimore.
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Museums · Parks · Outdoors · Beaches
Side Trips

Baltimore — 8 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.
Change things up with these side-trips from Baltimore: Calvert Marine Museum and Drum Point Lighthouse (in Solomons), Annapolis (U.S. Naval Academy, Hammond-Harwood House, &more) and Chesapeake Heritage & Visitors Center (in Chester). There's lots more to do: try to win big at Horseshoe Casino, admire the natural beauty at Howard Peters Rawlings Conservatory and Botanic Gardens of Baltimore, get up close and personal with brilliant marine life at National Aquarium, and see the interesting displays at American Visionary Art Museum.

To see maps, more things to do, where to stay, and more tourist information, read our Baltimore online road trip planner.

Getting from Ocean City to Baltimore by car takes about 3 hours. Other options: take a bus. In January, daily temperatures in Baltimore can reach 6°C, while at night they dip to -1°C. Wrap up your sightseeing on the 16th (Sun) early enough to fly back home.
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Museums · Historic Sites · Parks · Neighborhoods
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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