14 days in Maryland Itinerary

14 days in Maryland Itinerary

Created using Inspirock Maryland itinerary maker

Make it your trip
Fly to Washington Dulles International Airport, Drive to Boonsboro
1
Boonsboro
— 1 day
Drive
2
Frederick
— 1 night
Drive
3
Baltimore
— 6 nights
Drive
4
St. Michaels
— 2 nights
Drive
5
Ocean City
— 3 nights
Unknown
6
Assateague Island
— 1 night
Unknown

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Boonsboro

— 1 day
Boonsboro is a town in Washington County, Maryland, United States, located at the foot of South Mountain. Start off your visit on the 1st (Fri): stop by Turn the Page Bookstore, take in the history at South Mountain State Battlefield, and then take an in-depth tour of Washington County Rural Heritage Museum.

To find reviews, maps, traveler tips, and tourist information, use the Boonsboro trip planner.

Asheville to Boonsboro is an approximately 5-hour combination of flight and car. You can also drive. While traveling from Asheville, expect slightly colder days and about the same nights in Boonsboro, ranging from highs of 63°F to lows of 49°F. Finish your sightseeing early on the 1st (Fri) to allow enough time to drive to Frederick.

Things to do in Boonsboro

Shopping · Historic Sites · Museums

Side Trip

Frederick

— 1 night
Frederick is a city and the county seat of Frederick County in the U.S. state of Maryland. Your day by day itinerary now includes National Museum of Civil War Medicine, Monocacy National Battlefield and Frederick Visitor Center.

For photos, ratings, more things to do, and tourist information, read Frederick trip builder.

Frederick is very close to Boonsboro. Traveling from Boonsboro in October, expect nights in Frederick to be about the same, around 47°F, while days are somewhat warmer, around 70°F. Cap off your sightseeing on the 2nd (Sat) early enough to go by car to Baltimore.

Things to do in Frederick

Museums · Historic Sites · Shopping

Baltimore

— 6 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.
Your list of things to see and do now includes Baltimore Museum of Art, National Cryptologic Museum, Star-Spangled Banner Flag House, and other attractions. Your cultural itinerary includes sights like The Walters Art Museum and Riversdale House Museum.

To find reviews, other places to visit, traveler tips, and tourist information, you can read our Baltimore online trip maker.

Traveling by car from Frederick to Baltimore takes an hour. Alternatively, you can take a bus. Traveling from Frederick in October, you can expect nighttime temperatures to be somewhat warmer in Baltimore, with lows of 55°F. Wrap up your sightseeing on the 8th (Fri) to allow time to drive to St. Michaels.

Things to do in Baltimore

Museums · Historic Sites · Shopping · Neighborhoods

Side Trip

St. Michaels

— 2 nights
Your list of things to see and do now includes Ouvert Gallery, The Candleberry Shoppe, Olivins, and other attractions. Start off your visit on the 9th (Sat): visit a coastal fixture at 1879 Hooper Strait Lighthouse, examine the collection at Chesapeake Bay Maritime Museum, then enjoy the sea views from Choptank River Lighthouse, and finally look for gifts at The Candleberry Shoppe. On your second day here, see the interesting displays at St. Michael's Museum, take in the exciting artwork at Hopkins Original Art, then look for gifts at Olivins, and finally take in the exciting artwork at Ouvert Gallery.

For photos, maps, other places to visit, and tourist information, refer to the St. Michaels online trip itinerary planner.

Traveling by car from Baltimore to St. Michaels takes 2 hours. Alternatively, you can do a combination of bus and taxi. In October, daily temperatures in St. Michaels can reach 70°F, while at night they dip to 53°F. Finish your sightseeing early on the 10th (Sun) to allow enough time to drive to Ocean City.

Things to do in St. Michaels

Museums · Shopping · Historic Sites

Side Trip

Ocean City

— 3 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.
You've added Ripley's Believe it or Not! Ocean City, The Kite Loft, Oceanic Fishing Pier, and other attractions to your itinerary. Snapdragon and Ocean City Life-Saving Station Museum will appeal to museum buffs. There's much more to do: kick back and relax at Ocean City Beach, steep yourself in history at Main Street Berlin, and take a leisurely stroll along Ocean City Boardwalk.

To see where to stay, photos, other places to visit, and more tourist information, you can read our Ocean City road trip app.

You can drive from St. Michaels to Ocean City in 2 hours. Alternatively, you can do a combination of taxi and shuttle; or do a combination of taxi and bus. Expect a daytime high around 69°F in October, and nighttime lows around 53°F. Finish your sightseeing early on the 13th (Wed) so you can travel to Assateague Island.

Things to do in Ocean City

Museums · Shopping · Historic Sites · Parks

Side Trip

Assateague Island

— 1 night
To see reviews, traveler tips, maps, and tourist information, refer to the Assateague Island online driving holiday planner.

The Route module can help you plan travel from Ocean City to Assateague Island. In October, plan for daily highs up to 69°F, and evening lows to 53°F. Wrap up your sightseeing by early afternoon on the 14th (Thu) to allow enough time to travel back home.

Things to do in Assateague Island

Parks · Nature · Wildlife
Highlights from your trip

Maryland travel guide

4.1
Casinos · Aquariums · Specialty Museums
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.