19 days in Maryland Itinerary

19 days in Maryland Itinerary

Created using Inspirock Maryland tour itinerary builder

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Route & dates

19 days in Maryland Itinerary

Start: New York City
train:  2​h 45​min
1
Baltimore
— 4 nights
Drive:  1​h 30​min
2
Hagerstown
— 4 nights
Drive:  1​h 15​min
3
Cumberland
— 3 nights
Drive:  1​h 15​min
4
Oakland
— 2 nights
Drive:  6​h 15​min
5
Ocean City
— 4 nights
Drive:  4​h 30​min
End: New York City

4
nights
Baltimore

Baltimore ©
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.
Explore the numerous day-trip ideas around Baltimore: Annapolis (U.S. Naval Academy, Susan Campbell Park, & more). Next up on the itinerary: try your luck at Horseshoe Casino, admire the masterpieces at The Walters Art Museum, join in the after-dark buzz at Mustang Alleys, and wander the streets of Inner Harbor.

To find where to stay, reviews, and more tourist information, read Baltimore tour planning app .

New York City to Baltimore is an approximately 3-hour train ride. You can also drive; or fly. In July in Baltimore, expect temperatures between 89°F during the day and 74°F at night. Cap off your sightseeing on the 1st (Thu) early enough to go by car to Hagerstown.

Things to do in Baltimore

Neighborhoods Fun & Games Museums

Side Trip

Annapolis
Highlights from your plan
National Aquarium ©
National Aquarium
Urban Axes Baltimore ©
Urban Axes Baltimore
Fort McHenry National Monument ©
Fort McHenry National Monument

4
nights
Hagerstown

Hagerstown ©
Hagerstown is a city in Washington County, Maryland, United States. Kids will enjoy Harry Grove Stadium and Cunningham Falls State Park. Get out of town with these interesting Hagerstown side-trips: Frederick (Clue IQ: An Escape Room Experience & Dragon Distillery, LLC). Spend the 4th (Sun) exploring nature at Chesapeake & Ohio Canal National Historical Park. Next up on the itinerary: take in the history at Antietam National Battlefield, get your game on at Heavy Metal Playground, take in the pleasant sights at The Hagerstown Cultural Trail, and admire the majestic nature at Catoctin Mountain Park.

To find traveler tips, more things to do, maps, and other tourist information, use the Hagerstown trip itinerary app .

You can drive from Baltimore to Hagerstown in 1.5 hours. Traveling from Baltimore in August, you can expect nighttime temperatures to be little chillier in Hagerstown, with lows of 65°F. Finish your sightseeing early on the 5th (Mon) to allow enough time to drive to Cumberland.

Things to do in Hagerstown

Nature Parks Historic Sites

Side Trips

Frederick, Thurmont, Heavy Metal Playground, Antietam National Battlefield
Highlights from your plan
Clue IQ: An Escape Room Experience ©
Antietam National Battlefield ©
Antietam National Battlefield
Catoctin Mountain Park ©
Catoctin Mountain Park

3
nights
Cumberland

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. Family-friendly places like Adventure Sports Center International and Wisp Resort will thrill your kids. Step out of Cumberland to go to Grantsville and see New Germany State Park, which is approximately 30 minutes away. And it doesn't end there: explore the landscape on two wheels at Great Allegheny Passage, learn about winemaking at Charis Winery, admire the majestic nature at Rocky Gap State Park, and try to win big at Rocky Gap Casino Resort.

For photos, where to stay, maps, and other tourist information, read Cumberland holiday planning app .

Traveling by car from Hagerstown to Cumberland takes 1.5 hours. In August, plan for daily highs up to 84°F, and evening lows to 62°F. Finish your sightseeing early on the 8th (Thu) to allow enough time to drive to Oakland.

Things to do in Cumberland

Parks Outdoors Nature

Side Trips

McHenry, Grantsville, Rocky Gap Casino Resort
Highlights from your plan
Great Allegheny Passage ©
Great Allegheny Passage
Adventure Sports Center International ©
New Germany State Park ©
New Germany State Park

2
nights
Oakland

Oakland ©
Oakland is a town in the west-central part of Garrett County, Maryland. Start off your visit on the 9th (Fri): revel in the low prices at Simon Pearce Factory Outlet and Glassblowing, then have fun and explore at The Discovery Center, then explore the activities along Deep Creek Lake State Park, and finally walk around Herrington Manor State Park. Here are some ideas for day two: get engrossed in the history at The Oakland B&O Railroad Museum, then immerse yourself in nature at Swallow Falls State Park, and then play a few rounds at Lodestone Golf Course.

For other places to visit, reviews, photos, and tourist information, read Oakland day trip planning site .

You can drive from Cumberland to Oakland in 1.5 hours. In August, Oakland is slightly colder than Cumberland - with highs of 72°F and lows of 57°F. Finish up your sightseeing early on the 10th (Sat) so you can travel to Ocean City.

Things to do in Oakland

Nature Parks Outdoors

Side Trips

Simon Pearce Factory Outlet and Glassblowing, The Discovery Center
Highlights from your plan
Swallow Falls State Park ©
Swallow Falls State Park
Herrington Manor State Park ©
Herrington Manor State Park
The Discovery Center ©
The Discovery Center

4
nights
Ocean City

Ocean City ©
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.
You'll visit kid-friendly attractions like Ocean City Beach and Ocean City Boardwalk. There's lots more to do: find your balance on the water with some of the best stand-up paddleboarding in the area, get in on the family fun at Frontier Town, stroll around Northside Park, and race across the water with a speed boat tour.

Plan my day in Ocean City using traveler tips and tourist information provided by Inspirock.

Traveling by car from Oakland to Ocean City takes 5.5 hours. Alternatively, you can fly. Traveling from Oakland in August, expect Ocean City to be a bit warmer, temps between 82°F and 67°F. Cap off your sightseeing on the 15th (Thu) early enough to go by car back home.

Things to do in Ocean City

Outdoors Theme Parks Tours

Side Trip

Assateague State Park
Highlights from your plan
Ocean City Beach ©
Ocean City Beach
Ocean City Boardwalk ©
Ocean City Boardwalk
Parasailing & Paragliding

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