8 days in Maryland Itinerary

8 days in Maryland Itinerary

Created using Inspirock Maryland trip planner
Make it your trip
Fly
1
St. Michaels
— 1 day
Drive
2
Ocean City
— 1 night
Drive
3
Baltimore
— 4 nights
Drive
4
Sharpsburg
— 1 night
Drive
5
Cumberland
— 1 night
Drive to Washington Dulles International Airport, Fly to Chicago

S M T W T F S
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31
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5

St. Michaels — 1 day

Kick off your visit on the 27th (Thu): view the masterpieces at Hopkins Original Art, then take an in-depth tour of 1879 Hooper Strait Lighthouse, then see the interesting displays at Chesapeake Bay Maritime Museum, and finally stop by Take Me Home.

For where to stay, other places to visit, traveler tips, and other tourist information, refer to the St. Michaels journey builder tool.

Chicago to St. Michaels is an approximately 3.5-hour flight. You can also drive; or do a combination of bus and taxi. The time zone difference when traveling from Chicago to St. Michaels is 1 hour. In October, plan for daily highs up to 70°F, and evening lows to 53°F. Wrap up your sightseeing on the 27th (Thu) early enough to drive to Ocean City.
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Museums · Historic Sites · Shopping

Ocean City — 1 night

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.
Kick off your visit on the 28th (Fri): identify plant and animal life at Ayers Creek Adventures, then play a few rounds at Eagle's Landing Golf Course, and then enjoy the sand and surf at Ocean City Beach.

To find traveler tips, maps, reviews, and other tourist information, use the Ocean City trip itinerary planner.

Traveling by car from St. Michaels to Ocean City takes 2 hours. Alternatively, you can do a combination of taxi and shuttle; or do a combination of taxi and bus. In October in Ocean City, expect temperatures between 69°F during the day and 53°F at night. Finish your sightseeing early on the 28th (Fri) so you can drive to Baltimore.
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Outdoors · Parks · Tours · Golf
Side Trip

Baltimore — 4 nights

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.
Museum-lovers will appreciate The Walters Art Museum and B&O Railroad Museum. Satisfy your inner culture vulture at Fort McHenry National Monument and Historic Shrine and Fell's Point. Explore the numerous day-trip ideas around Baltimore: Annapolis (Annapolis Historic District & U.S. Naval Academy). Next up on the itinerary: try your luck at Horseshoe Casino, get up close and personal with brilliant marine life at National Aquarium, brush up on your knowledge of spirits at Sagamore Spirit Distillery, and examine the collection at American Visionary Art Museum.

To see photos, more things to do, reviews, and more tourist information, go to the Baltimore vacation maker website.

Drive from Ocean City to Baltimore in 3 hours. Alternatively, you can take a bus. In October, daytime highs in Baltimore are 70°F, while nighttime lows are 55°F. Wrap up your sightseeing on the 1st (Tue) to allow time to drive to Sharpsburg.
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Historic Sites · Parks · Museums · Nature
Side Trip

Sharpsburg — 1 night

Sharpsburg is a town in Washington County, Maryland, United States, located approximately 13mi south of Hagerstown. Kick off your visit on the 2nd (Wed): take in the history at Antietam National Battlefield, steep yourself in history at Tolson's Chapel, and then examine the collection at Chesapeake & Ohio Canal National Historical Park.

To see maps, ratings, and more tourist information, read our Sharpsburg trip itinerary app.

Drive from Baltimore to Sharpsburg in 1.5 hours. Expect little chillier evenings in Sharpsburg when traveling from Baltimore in November, with lows around 34°F. Wrap up your sightseeing on the 2nd (Wed) early enough to drive to Cumberland.
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Historic Sites · Parks · Museums · Nature
Side Trip

Cumberland — 1 night

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. Kick off your visit on the 3rd (Thu): steep yourself in history at Paw Paw Tunnel, then examine the collection at Allegany Museum, and then stroll through Great Allegheny Passage.

To see photos, reviews, other places to visit, and more tourist information, refer to the Cumberland road trip planner.

You can drive from Sharpsburg to Cumberland in 1.5 hours. In November, plan for daily highs up to 54°F, and evening lows to 34°F. Wrap up your sightseeing on the 3rd (Thu) to allow time to drive back home.
more
Outdoors · Parks · Museums · Historic Sites

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.
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