55 days in Maryland Itinerary

55 days in Maryland Itinerary

Created using Inspirock Maryland tour planner

Make it your trip
Fly to Washington Dulles International Airport, Drive to Cumberland
1
Cumberland
— 5 nights
Drive
2
Hagerstown
— 8 nights
Drive
3
Baltimore
— 26 nights
Drive
4
St. Michaels
— 6 nights
Unknown
5
Assateague Island
— 1 night
Unknown
6
Ocean City
— 8 nights
Bus to Shore Transit Bus Terminal, Fly to Berlin

S M T W T F S
28
29
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29

Cumberland

— 5 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. Get out of town with these interesting Cumberland side-trips: Oakland (Garrett County Museum of Transportation & Garrett County Historical Museum), Green Ridge State Forest (in Flintstone) and New Germany State Park (in Grantsville). There's still lots to do: trek along Great Allegheny Passage, learn about winemaking at Charis Winery & Distillery, contemplate the long history of Paw Paw Tunnel, and examine the collection at Allegany Museum.

To find more things to do, ratings, maps, and other tourist information, go to the Cumberland visit planner.

Berlin, Germany to Cumberland is an approximately 16-hour combination of flight and car. Due to the time zone difference, you'll gain 6 hours traveling from Berlin to Cumberland. In December in Cumberland, expect temperatures between 9°C during the day and 0°C at night. Wrap up your sightseeing on the 6th (Mon) early enough to drive to Hagerstown.

Things to do in Cumberland

Museums · Parks · Historic Sites · Outdoors

Side Trips

Hagerstown

— 8 nights
Hagerstown is a city in Washington County, Maryland, United States. Explore Hagerstown's surroundings by going to Sugarloaf Mountain (in Dickerson), Frederick (Monocacy National Battlefield, Historic Downtown Frederick, &more) and Lancaster County Dutch Market (in Germantown). There's still lots to do: contemplate the waterfront views at C&O Canal Trust, steep yourself in history at Tolson's Chapel, appreciate the history behind National Shrine Grotto of Lourdes, and stroll through Catoctin Mountain Park.

For ratings, more things to do, traveler tips, and other tourist information, read our Hagerstown trip itinerary app.

You can drive from Cumberland to Hagerstown in 1.5 hours. Expect a daytime high around 9°C in December, and nighttime lows around 0°C. Finish your sightseeing early on the 14th (Tue) so you can drive to Baltimore.

Things to do in Hagerstown

Historic Sites · Parks · Museums · Nature

Side Trips

Baltimore

— 26 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.
Explore the numerous day-trip ideas around Baltimore: Sandy Spring (Underground Railroad Experience Trail Hikes & The Adventure Park at Sandy Spring), Annapolis (Banneker-Douglass Museum, U.S. Naval Academy, &more) and Fishpaws Marketplace (in Arnold). Spend the 17th (Fri) exploring nature at Fort McHenry National Monument and Historic Shrine. There's still lots to do: try your luck at Horseshoe Casino, sample the fine beverages at Sagamore Spirit Distillery, take an in-depth tour of B&O Railroad Museum, and see the interesting displays at American Visionary Art Museum.

For maps, photos, and more tourist information, use the Baltimore trip itinerary planning website.

Drive from Hagerstown to Baltimore in 1.5 hours. In December in Baltimore, expect temperatures between 11°C during the day and 3°C at night. Finish up your sightseeing early on the 9th (Sun) so you can go by car to St. Michaels.

Things to do in Baltimore

Museums · Parks · Historic Sites · Nature

Side Trips

St. Michaels

— 6 nights
You'll find plenty of places to visit near St. Michaels: Cambridge (Blackwater National Wildlife Refuge & Harriet Tubman Museum and Educational Center), Outstanding Dreams Farm (in Preston) and Harriet Tubman Underground Railroad National Historical Park (in Church Creek).

To find reviews, where to stay, photos, and tourist information, refer to the St. Michaels road trip tool.

Getting from Baltimore to St. Michaels by car takes about 2 hours. Other options: do a combination of bus and taxi. Expect a daytime high around 7°C in January, and nighttime lows around -2°C. Wrap up your sightseeing on the 15th (Sat) early enough to travel to Assateague Island.

Things to do in St. Michaels

Museums · Historic Sites · Breweries & Distilleries · Spas

Side Trips

Assateague Island

— 1 night
On the 16th (Sun), explore the wealth of natural beauty at Assateague Island National Seashore.

Plan trip to Assateague Island with our itinerary maker to find out where to go and what to do.

Explore your travel options from St. Michaels to Assateague Island with the Route module. In January, daily temperatures in Assateague Island can reach 7°C, while at night they dip to -3°C. Finish up your sightseeing early on the 16th (Sun) so you can travel to Ocean City.

Things to do in Assateague Island

Wildlife · Parks · Nature
Highlights from your trip

Ocean City

— 8 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 the numerous day-trip ideas around Ocean City: Salisbury (Eastern Shore Baseball Hall of Fame Museum & Ward Museum of Wildfowl Art). The adventure continues: stroll around Northside Park, get a dose of the wild on Ayers Creek Adventures, relax and rejuvenate at OC Massage, and examine the collection at Ocean City Life-Saving Station Museum.

For more things to do, photos, other places to visit, and tourist information, use the Ocean City trip site.

Explore your travel options from Assateague Island to Ocean City with the Route module. In January, daytime highs in Ocean City are 7°C, while nighttime lows are -3°C. Finish up your sightseeing early on the 24th (Mon) so you can travel back home.

Things to do in Ocean City

Outdoors · Parks · Museums · Tours

Side Trips

Maryland travel guide

4.1
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.