28 days in Maryland Itinerary

Created using Inspirock Maryland sightseeing planner
Make it your trip
Fly to Washington Dulles International Airport, Drive to Hagerstown
1
Hagerstown
— 5 nights
Drive
2
Baltimore
— 9 nights
Drive
3
Easton
— 3 nights
Drive
4
Ocean City
— 4 nights
Drive
5
Oakland
— 5 nights
Drive to Washington Dulles International Airport, Fly to Chandigarh

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Hagerstown — 5 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, Our Lady of the Mountain, &more), Frederick (Historic Downtown Frederick, Mount Olivet Cemetery, &more) and Roddy Road Covered Bridge (in Thurmont). The adventure continues: admire the masterpieces at Washington County Museum of Fine Arts, indulge your thirst for a good beer at Cushwa Brewing Company, take in nature's colorful creations at Surreybrooke Gardens, and examine the collection at Train Room & Museum.

To find traveler tips, more things to do, reviews, and other tourist information, read our Hagerstown attractions planning tool.

Chandigarh, India to Hagerstown is an approximately 28-hour combination of flight and car. Traveling from Chandigarh to Hagerstown, you'll gain 10.5 hours due to the time zone difference. In December, Hagerstown is cooler than Chandigarh - with highs of 9°C and lows of 0°C. Finish your sightseeing early on the 24th (Sat) so you can drive to Baltimore.
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Historic Sites · Parks · Museums · Breweries & Distilleries
Side Trips
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Baltimore — 9 nights

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: MGM National Harbor (in Oxon Hill), National Harbor (The Awakening Sculpture & Harborfront Area) and Annapolis (William Paca House & Garden, Maryland State House, &more). There's lots more to do: try to win big at Horseshoe Casino, see the interesting displays at Geppi's Entertainment Museum, explore the world behind art at The Walters Art Museum, and stop by Hampden.

To see maps, reviews, ratings, and tourist information, refer to the Baltimore trip planner.

Traveling by car from Hagerstown to Baltimore takes 1.5 hours. Expect a daytime high around 11°C in December, and nighttime lows around 3°C. Finish your sightseeing early on the 2nd (Mon) so you can drive to Easton.
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Side Trips
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Easton — 3 nights

Easton, Maryland is an incorporated town and the county seat of Talbot County, Maryland, United States. Venture out of the city with trips to Hopkins Original Art (in St. Michaels) and Solomons (Spring Cove Marina & Calvert Marine Museum and Drum Point Lighthouse). There's still lots to do: relax and rejuvenate at some of the top local wellness centers, admire the masterpieces at Academy Art Museum, see the interesting displays at Chesapeake Bay Maritime Museum, and sample the fine beverages at Lyon Rum Distillery.

To find other places to visit, traveler tips, and more tourist information, use the Easton travel route builder tool.

Getting from Baltimore to Easton by car takes about 1.5 hours. In January, daily temperatures in Easton can reach 7°C, while at night they dip to -2°C. Wrap up your sightseeing on the 5th (Thu) to allow time to drive to Ocean City.
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Museums · Shopping · Parks · Historic Sites
Side Trips
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Ocean City — 4 nights

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.
Venture out of the city with trips to Salisbury (Ward Museum of Wildfowl Art, Eastern Shore Baseball Hall of Fame Museum, &more) and Snow Hill (Julia A. Purnell Museum & Bishop's Stock Fine Art, Craft & Wine). There's much more to do: stroll around Northside Park, tee off at GlenRiddle Golf Club, make a splash at Splash Mountain Water Park, and enjoy the sand and surf at Ocean City Beach.

To see ratings, maps, photos, and tourist information, go to the Ocean City holiday planning website.

You can drive from Easton to Ocean City in 1.5 hours. In January, daytime highs in Ocean City are 7°C, while nighttime lows are -3°C. Cap off your sightseeing on the 9th (Mon) early enough to go by car to Oakland.
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Museums · Parks · Outdoors · Golf
Side Trips
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Oakland — 5 nights

Oakland is a town in the west-central part of Garrett County, Maryland. Get out of town with these interesting Oakland side-trips: Toasted Goat Winery (in Frostburg) and Cumberland (Great Allegheny Passage & Charis Winery & Distillery). There's lots more to do: contemplate the waterfront views at Deep Creek Lake State Park, have fun and explore at The Discovery Center, play a few rounds at Lodestone Golf Course, and revel in the low prices at Simon Pearce Factory Outlet and Glassblowing.

For where to stay, other places to visit, photos, and more tourist information, use the Oakland trip itinerary builder.

Traveling by car from Ocean City to Oakland takes 5.5 hours. Plan for slightly colder temperatures traveling from Ocean City in January, with highs in Oakland at 0°C and lows at -9°C. Cap off your sightseeing on the 14th (Sat) early enough to travel back home.
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Parks · Museums · Outdoors · Wineries
Side Trips
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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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