16 days in Maryland Itinerary

Created using Klarna Trips Maryland trip planner
Make it your trip
Fly to Washington Dulles International Airport, Drive to Sharpsburg
— 2 nights
— 2 nights
Ocean City
— 4 nights
St. Michaels
— 2 nights
— 4 nights


Sharpsburg — 2 nights

Sharpsburg is a town in Washington County, Maryland, United States, located approximately 13mi south of Hagerstown. Venture out of the city with trips to Fort Frederick State Park (in Big Pool) and Lockhouse 49 (in Clear Spring). There's lots more to do: witness the site of a historic battle at Antietam National Battlefield, contemplate the long history of Tolson's Chapel, take in the views from Burnside's Bridge, and relax in the rural setting at Frog Eye Farm.

For reviews, other places to visit, and more tourist information, you can read our Sharpsburg route planner.

New Delhi, India to Sharpsburg is an approximately 22.5-hour combination of flight and car. The time zone difference moving from India Standard Time to Eastern Standard Time is minus 10.5 hours. Traveling from New Delhi in September, expect nights in Sharpsburg to be colder, around 15°C, while days are little chillier, around 30°C. Finish up your sightseeing early on the 7th (Thu) so you can go by car to Cumberland.
Nature · Parks · Historic Sites
Side Trips
Find places to stay Sep 5 — 7:
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Cumberland — 2 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. On the 8th (Fri), explore the landscape on two wheels at Green Ridge State Forest and then admire the majestic nature at Rocky Gap State Park. Here are some ideas for day two: contemplate the waterfront views at Deep Creek Lake State Park, sample the fine beverages at Charis Winery & Distillery, and then grab your bike and head to Great Allegheny Passage.

To see maps, other places to visit, where to stay, and tourist information, read our Cumberland trip planner.

Getting from Sharpsburg to Cumberland by car takes about 1.5 hours. In September, daily temperatures in Cumberland can reach 31°C, while at night they dip to 15°C. Finish up your sightseeing early on the 9th (Sat) so you can go by car to Ocean City.
Parks · Nature · Trails · Outdoors
Side Trips
Find places to stay Sep 7 — 9:
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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.
Explore Ocean City's surroundings by going to Salisbury (Ward Museum of Wildfowl Art & Salisbury Zoo). There's lots more to do: take a leisurely stroll along Ocean City Boardwalk, make a splash at Splash Mountain Water Park, sample the fine beverages at Seacrets Distilling Company, and enjoy the sand and surf at Ocean City Beach.

For other places to visit, ratings, maps, and tourist information, read Ocean City trip maker app.

You can drive from Cumberland to Ocean City in 4.5 hours. Traveling from Cumberland in September, expect a bit warmer with lows of 20°C in Ocean City. Wrap up your sightseeing on the 13th (Wed) to allow time to drive to St. Michaels.
Parks · Outdoors · Tours · Breweries & Distilleries
Side Trips
Find places to stay Sep 9 — 13:
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St. Michaels — 2 nights

On the 14th (Thu), see the interesting displays at Chesapeake Bay Maritime Museum, then get a new perspective on things with Boat Tours & Water Sports, and then look for gifts at Olivins. Get ready for a full day of sightseeing on the next day: look for all kinds of wild species at Blackwater National Wildlife Refuge, take an in-depth tour of Harriet Tubman Museum and Educational Center, examine the collection at The Oxford Museum, then sample the fine beverages at Lyon Rum Distillery, and finally take in the exciting artwork at Hopkins Original Art.

For traveler tips, reviews, ratings, and tourist information, use the St. Michaels online travel planner.

Drive from Ocean City to St. Michaels in 2 hours. Alternatively, you can do a combination of shuttle and taxi; or do a combination of bus and taxi. In September, plan for daily highs up to 31°C, and evening lows to 19°C. Cap off your sightseeing on the 15th (Fri) early enough to go by car to Baltimore.
Museums · Shopping · Outdoors · Wildlife
Side Trips
Find places to stay Sep 13 — 15:
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Baltimore — 4 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.
You'll find plenty of places to visit near Baltimore: Annapolis (Annapolis Historic District & U.S. Naval Academy). There's still lots to do: try to win big at Horseshoe Casino, explore the wealth of natural beauty at Fort McHenry National Monument and Historic Shrine, get up close and personal with brilliant marine life at National Aquarium, and wander the streets of Fell's Point.

To find other places to visit, where to stay, traveler tips, and other tourist information, refer to the Baltimore tour itinerary builder tool.

You can drive from St. Michaels to Baltimore in 2 hours. Another option is to do a combination of taxi and bus. In September, plan for daily highs up to 32°C, and evening lows to 22°C. Finish your sightseeing early on the 19th (Tue) to allow enough time to fly back home.
Parks · Historic Sites · Nature · Neighborhoods
Side Trip
Find places to stay Sep 15 — 19:
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Maryland travel guide

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.