56 days in Maryland Itinerary

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

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Cumberland — 5 nights

Change things up with these side-trips from Cumberland: Accident (FireFly Farms Market & Deep Creek Lavender Farm), Oakland (Deep Creek Lake State Park, Swallow Falls State Park, &more) and New Germany State Park (in Grantsville).

To find maps, where to stay, reviews, and tourist information, use the Cumberland online trip itinerary builder.

Exeter, UK to Cumberland is an approximately 16.5-hour combination of flight and car. The time zone changes from Greenwich Mean Time to Eastern Standard Time, which is usually a -5 hour difference. Expect a daytime high around 31°C in September, and nighttime lows around 15°C. Finish up your sightseeing early on the 10th (Sat) so you can go by car to Baltimore.
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Parks · Nature · Outdoors · Museums
Side Trips
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Baltimore — 24 nights

City of Firsts

Explore the numerous day-trip ideas around Baltimore: Larriland Farm (in Woodbine), Leister Park (in Hampstead) and Days End Farm Horse Rescue (in Lisbon). Spend the 17th (Sat) exploring nature at Fort McHenry National Monument and Historic Shrine. And it doesn't end there: try to win big at Horseshoe Casino, step aboard USS Constellation, take in the waterfront activity at Inner Harbor, and see the interesting displays at American Visionary Art Museum.

To see more things to do, photos, other places to visit, and more tourist information, go to the Baltimore day trip planning site.

Getting from Cumberland to Baltimore by car takes about 2.5 hours. Traveling from Cumberland in September, expect a bit warmer with lows of 22°C in Baltimore. Finish your sightseeing early on the 4th (Tue) so you can drive to St. Michaels.
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Parks · Historic Sites · Museums · Outdoors
Side Trips
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St. Michaels — 5 nights

Venture out of the city with trips to Cambridge (Choptank River Lighthouse, Long Wharf Park, &more), Outstanding Dreams Farm (in Preston) and Harriet Tubman Underground Railroad National Historical Park (in Church Creek).

To find traveler tips, maps, more things to do, and more tourist information, you can read our St. Michaels trip planner.

Drive from Baltimore to St. Michaels in 2 hours. Alternatively, you can drive; or do a combination of bus and taxi. Expect a daytime high around 24°C in October, and nighttime lows around 13°C. Cap off your sightseeing on the 9th (Sun) early enough to go by car to Ocean City.
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Museums · Parks · Wildlife · Breweries & Distilleries
Side Trips
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Ocean City — 7 nights

The White Marlin Capital of the World

Change things up with these side-trips from Ocean City: Salisbury (Ward Museum of Wildfowl Art, Salisbury Zoo, &more) and Bishop's Stock Fine Art, Craft & Wine (in Snow Hill). There's much more to do: take a leisurely stroll along Ocean City Boardwalk, see the interesting displays at Ocean City Life-Saving Station Museum, kick back and relax at Ocean City Beach, and shop like a local with Art League of Ocean City.

For reviews, maps, traveler tips, and other tourist information, read our Ocean City trip itinerary planning website.

Traveling by car from St. Michaels to Ocean City takes 2 hours. Alternatively, you can drive; or do a combination of taxi and shuttle; or do a combination of taxi and bus. In October, daily temperatures in Ocean City can reach 24°C, while at night they dip to 13°C. Finish up your sightseeing early on the 16th (Sun) so you can go by car to Solomons.
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Museums · Outdoors · Parks · Shopping
Side Trips
Find places to stay Oct 9 — 16:
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Solomons — 6 nights

Change things up with these side-trips from Solomons: Mechanicsville (Maryland International Raceway & Forrest Hall Farm & Orchard), Port Tobacco (Historic Port Tobacco Village & Saint Ignatius Church) and Stevensville (Lead Dog Charters & Casey Michelle Charters).

To find photos, maps, and other tourist information, use the Solomons online day trip planner.

Traveling by car from Ocean City to Solomons takes 3.5 hours. Expect a daytime high around 24°C in October, and nighttime lows around 13°C. Finish your sightseeing early on the 22nd (Sat) so you can drive to Hagerstown.
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Historic Sites · Museums · Parks · Outdoors
Side Trips
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Hagerstown — 8 nights

Change things up with these side-trips from Hagerstown: Fort Frederick State Park (in Big Pool), Emmitsburg (National Fallen Firefighters Memorial, National Shrine of St. Elizabeth Ann Seton, &more) and Frederick (Baker Park, Community Bridge Mural, &more).

To see maps, other places to visit, more things to do, and more tourist information, you can read our Hagerstown online journey builder.

Getting from Solomons to Hagerstown by car takes about 2.5 hours. Expect a daytime high around 23°C in October, and nighttime lows around 11°C. Wrap up your sightseeing on the 30th (Sun) early enough to travel back home.
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Parks · Nature · Historic Sites · Museums
Side Trips
Find places to stay Oct 22 — 30:
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Maryland travel guide

4.2
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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