20 days in Maryland Itinerary

20 days in Maryland Itinerary

Created using Inspirock Maryland attractions planner

Plan created by another user. Make it yours

Route & dates

1
Cumberland
— 2 nights
2
Sharpsburg
— 4 nights
3
Ocean City
— 4 nights
4
St. Michaels
— 3 nights
5
Baltimore
— 6 nights

2
nights
Cumberland

Cumberland ©
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. Venture out of the city with trips to Swallow Falls State Park (in Oakland), Simon Pearce Factory Outlet and Glassblowing (in Mountain Lake Park) and FireFly Farms (in Accident). There's still lots to do: get lost in a book at Allegany County Library System - Washington Street Library, get great views at Dans Rock Scenic Overlook, do a tasting at Charis Winery, and grab your bike and head to Great Allegheny Passage.

To see maps, photos, more things to do, and tourist information, refer to the Cumberland trip itinerary builder tool.

Washington DC to Cumberland is an approximately 2.5-hour car ride. Expect little chillier evenings in Cumberland when traveling from Washington DC in February, with lows around °F. Finish up your sightseeing early on the 5th (Wed) so you can go by car to Sharpsburg.

Things to do in Cumberland

Parks Trails Outdoors

Side Trips

Swallow Falls State Park, Simon Pearce Factory Outlet and Glassblowing, FireFly Farms, Dans Rock Scenic Overlook, Allegany County Library System - Frostburg Library
Find places to stay Feb 3 — 5:
Highlights from your plan
Great Allegheny Passage ©
Great Allegheny Passage
Charis Winery ©
Charis Winery

4
nights
Sharpsburg

Sharpsburg ©
Sharpsburg is a town in Washington County, Maryland, United States, located approximately 13mi south of Hagerstown. Venture out of the city with trips to National Shrine Grotto of Lourdes (in Emmitsburg), Frederick (Carroll Creek Linear Park, Community Bridge Mural, &more) and Roddy Road Covered Bridge (in Thurmont). And it doesn't end there: take in the history at Antietam National Battlefield, stroll through Orchid Cellar Meadery and Winery, steep yourself in history at Tolson's Chapel, and take in the exciting artwork at JUST LOOKIN' GALLERY.

For more things to do, ratings, where to stay, and more tourist information, go to the Sharpsburg online trip itinerary planner.

You can drive from Cumberland to Sharpsburg in 1.5 hours. In February, daytime highs in Sharpsburg are °F, while nighttime lows are °F. Finish your sightseeing early on the 9th (Sun) to allow enough time to travel to Ocean City.

Things to do in Sharpsburg

Historic Sites Parks Nature

Side Trips

Frederick, Hagerstown, Chesapeake & Ohio Canal National Historical Park, Orchid Cellar Meadery and Winery, National Shrine Grotto of Lourdes
Find places to stay Feb 5 — 9:
Highlights from your plan
Antietam National Battlefield ©
Antietam National Battlefield
Clue IQ: An Escape Room Experience ©
Clue IQ: An Escape Room Experience
National Shrine Grotto of Lourdes ©
National Shrine Grotto of Lourdes

4
nights
Ocean City

Ocean City ©
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.
Change things up with these side-trips from Ocean City: Bishop's Stock Fine Art, Craft & Wine (in Snow Hill) and Salisbury (Pemberton Historical Park, Ward Museum of Wildfowl Art, &more). There's much more to do: take in the exciting artwork at Art League of Ocean City, enjoy the sand and surf at Ocean City Beach, look for gifts at A Little Bit Sheepish, and don't miss a visit to Main Street Berlin.

For reviews, maps, ratings, and more tourist information, use the Ocean City vacation planning app.

You can drive from Sharpsburg to Ocean City in 4 hours. In February, plan for daily highs up to °F, and evening lows to °F. Wrap up your sightseeing on the 13th (Thu) early enough to drive to St. Michaels.

Things to do in Ocean City

Parks Museums Historic Sites

Side Trips

Salisbury, Berlin, Bishop's Stock Fine Art, Craft & Wine
Find places to stay Feb 9 — 13:
Highlights from your plan
Ocean City Beach ©
Ocean City Beach
Art League of Ocean City ©
Art League of Ocean City
Ocean City Boardwalk ©
Ocean City Boardwalk

3
nights
St. Michaels

St. Michaels ©
You'll find plenty of places to visit near St. Michaels: Layton's Chance Vineyard and Winery (in Vienna), Harriet Tubman Underground Railroad National Historical Park (in Church Creek) and Cambridge (Choptank River Lighthouse & Blackwater National Wildlife Refuge).

To see more things to do, ratings, where to stay, and more tourist information, you can read our St. Michaels travel route planner.

You can drive from Ocean City to St. Michaels in 2 hours. Another option is to do a combination of bus and taxi. In February, daily temperatures in St. Michaels can reach °F, while at night they dip to °F. Wrap up your sightseeing on the 16th (Sun) to allow time to drive to Baltimore.

Things to do in St. Michaels

Museums Parks Spas

Side Trips

Cambridge, Tilghman Watermans Museum, The Oxford Museum, Layton's Chance Vineyard and Winery, Spas & Wellness
Find places to stay Feb 13 — 16:
Highlights from your plan
Chesapeake Bay Maritime Museum ©
Chesapeake Bay Maritime Museum
Lyon Rum Distillery & Tasting Room ©
Lyon Rum Distillery & Tasting Room
St. Michael's Museum ©
St. Michael's Museum

6
nights
Baltimore

Baltimore ©
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: Billy Goat Trail (in Potomac) and Annapolis (Annapolis Historic District & U.S. Naval Academy). There's much more to do: try your luck at Horseshoe Casino, see the interesting displays at American Visionary Art Museum, get a taste of the local shopping with Fell's Point, and explore the world behind art at The Walters Art Museum.

To plan Baltimore vacation without wasting time, ask Inspirock to design an itinerary.

Drive from St. Michaels to Baltimore in 2 hours. Alternatively, you can do a combination of taxi and bus. In February, daytime highs in Baltimore are °F, while nighttime lows are °F. Finish up your sightseeing early on the 22nd (Sat) so you can go by car back home.

Things to do in Baltimore

Parks Museums Historic Sites

Side Trips

Annapolis, Daniels Ghost Town, Billy Goat Trail, Divine's Gravesite, Prospect Hill Cemetary
Find places to stay Feb 16 — 22:
Highlights from your plan
Sagamore Spirit Distillery ©
Sagamore Spirit Distillery
Horseshoe Casino ©
Horseshoe Casino
National Aquarium ©
National Aquarium

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