25 days in Maryland Itinerary

25 days in Maryland Itinerary

Created using Inspirock Maryland tour builder

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Route & dates

25 days in Maryland Itinerary

Start: Washington DC
Drive:  3 h 15 min
1
Oakland
— 2 nights
Drive:  2 h 15 min
2
Sharpsburg
— 4 nights
Drive:  1 h 30 min
3
Baltimore
— 6 nights
Drive:  1 h 45 min
4
St. Michaels
— 4 nights
Drive:  1 h 45 min
5
Ocean City
— 5 nights
Drive:  3 h 30 min
6
Solomons
— 3 nights
Drive:  1 h 30 min
End: Washington DC

2
nights
Oakland

Oakland ©
Oakland is a town in the west-central part of Garrett County, Maryland. Do some cultural sightseeing at Garrett County Historical Museum and The Discovery Center. Eschew the tourist crowds and head to Swallow Falls State Park and Great Allegheny Passage. Step out of Oakland with an excursion to Spruce Forest Artisan Village in Grantsville--about 42 minutes away. The adventure continues: contemplate the waterfront views at Deep Creek Lake State Park, see the interesting displays at The Oakland B&O Railroad Museum, look for gifts at FireFly Farms, and get some fabulous bargains at Simon Pearce Factory Outlet and Glassblowing.

To find ratings, reviews, where to stay, and tourist information, read our Oakland day trip website .

Washington DC to Oakland is an approximately 3.5-hour car ride. Plan for a bit cooler temperatures traveling from Washington DC in February, with highs in Oakland at 35°F and lows at 20°F. Cap off your sightseeing on the 10th (Mon) early enough to travel to Sharpsburg.

Things to do in Oakland

Parks Museums Trails

Side Trips

The Discovery Center, Great Allegheny Passage, Spruce Forest Artisan Village, Simon Pearce Factory Outlet and Glassblowing, FireFly Farms
Highlights from your plan
Swallow Falls State Park ©
Swallow Falls State Park
Deep Creek Lake State Park ©
Deep Creek Lake State Park

4
nights
Sharpsburg

Sharpsburg ©
Sharpsburg is a town in Washington County, Maryland, United States, located approximately 13mi south of Hagerstown. Get outdoors at Antietam National Battlefield and C&O Canal Hike at Point of Rocks Boat Ramp. Satisfy your inner culture vulture at Tolson's Chapel and Orchid Cellar Meadery and Winery. Next up on the itinerary: explore the different monuments and memorials at Antietam National Cemetery, do a tasting at Big Cork Vineyards, examine the collection at Brunswick Heritage Museum, and look for gifts at Turn the Page Bookstore.

To find other places to visit, ratings, maps, and other tourist information, you can read our Sharpsburg trip itinerary planner.

Traveling by car from Oakland to Sharpsburg takes 2.5 hours. Expect a bit warmer temperatures when traveling from Oakland in February; daily highs in Sharpsburg reach 45°F and lows reach 26°F. Wrap up your sightseeing on the 14th (Fri) to allow time to drive to Baltimore.

Things to do in Sharpsburg

Historic Sites Parks Museums

Side Trips

Boonsboro, Brunswick, Chesapeake & Ohio Canal National Historical Park, Big Cork Vineyards, Orchid Cellar Meadery and Winery
Highlights from your plan
Antietam National Battlefield ©
Antietam National Battlefield
Big Cork Vineyards ©
Big Cork Vineyards

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.
Discover out-of-the-way places like Fort McHenry National Monument and Historic Shrine and The Walters Art Museum. Satisfy your inner culture vulture at Fell's Point and Federal Hill Park. Explore Baltimore's surroundings by going to Annapolis (Maryland State House & U.S. Naval Academy), Glenview Mansion (in Rockville) and Frederick (Historic Downtown Frederick, Monocacy National Battlefield, &more). And it doesn't end there: see the interesting displays at Baltimore and Ohio Railroad Museum, take in the architecture and atmosphere at Saint Alphonsus Church, try to win big at Horseshoe Casino, and admire the masterpieces at Baltimore Museum of Art.

You can plan Baltimore trip in no time by asking Inspirock to help create your itinerary.

You can drive from Sharpsburg to Baltimore in 1.5 hours. Traveling from Sharpsburg in February, you can expect nighttime temperatures to be somewhat warmer in Baltimore, with lows of 32°F. Cap off your sightseeing on the 20th (Thu) early enough to go by car to St. Michaels.

Things to do in Baltimore

Historic Sites Museums Parks

Side Trips

Frederick, Annapolis, Glenview Mansion
Highlights from your plan
U.S. Naval Academy ©
U.S. Naval Academy
Fell's Point ©
Fell's Point

4
nights
St. Michaels

St. Michaels ©
Shop till you drop at Queenstown Premium Outlets and The Amish Market. Discover out-of-the-way places like Boat Tours & Water Sports and Saint Michaels Winery. Venture out of the city with trips to Harriet Tubman Museum and Educational Center (in Cambridge), Layton's Chance Vineyard and Winery (in Vienna) and Harriet Tubman Underground Railroad National Historical Park (in Church Creek).

To find traveler tips, other places to visit, maps, and other tourist information, you can read our St. Michaels vacation planner.

Traveling by car from Baltimore to St. Michaels takes 2 hours. Alternatively, you can take a bus; or do a combination of bus and taxi. Expect a daytime high around 46°F in February, and nighttime lows around 30°F. Finish your sightseeing early on the 24th (Mon) to allow enough time to drive to Ocean City.

Things to do in St. Michaels

Museums Shopping Wineries

Side Trips

Stevensville, Harriet Tubman Museum and Educational Center, Old Wye Church, Harriet Tubman Underground Railroad National Historical Park, The Oxford Museum
Highlights from your plan

5
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.
Take a break from the city and head to Assateague State Park and Rum Pointe Seaside Golf Links. Step off the beaten path and head to Northside Park and Main Street Berlin. Get out of town with these interesting Ocean City side-trips: Salisbury (Pemberton Historical Park, Ward Museum of Wildfowl Art, &more), Chesapeake Bay Farms (in Pocomoke City) and Bishop's Stock Fine Art, Craft & Wine (in Snow Hill). The adventure continues: see the interesting displays at Ocean City Life-Saving Station Museum, shop like a local with Flashback Old Time Photos, take a leisurely stroll along Ocean City Boardwalk, and indulge your thirst for a good beer at Burley Oak Brewing Company.

For photos, other places to visit, traveler tips, and tourist information, go to the Ocean City journey planner.

You can drive from St. Michaels to Ocean City in 2 hours. Another option is to take a bus. In February in Ocean City, expect temperatures between 45°F during the day and 30°F at night. Finish up your sightseeing early on the 29th (Sat) so you can travel to Solomons.

Things to do in Ocean City

Parks Outdoors Historic Sites

Side Trips

Berlin, Salisbury, Bishop's Stock Fine Art, Craft & Wine, Chesapeake Bay Farms, Janes Island State Park
Highlights from your plan
Northside Park ©
Northside Park
Assateague State Park ©
Assateague State Park
Ocean City Life-Saving Station Museum ©

3
nights
Solomons

Solomons ©
Solomons, also known as Solomons Island, is an unincorporated community and census-designated place (CDP) in Calvert County, Maryland, United States. Explore hidden gems such as Calvert Marine Museum and Drum Point Lighthouse and Flag Ponds Nature Park. Do some cultural sightseeing at Annmarie Garden and Historic St. Mary's City. Get out of town with these interesting Solomons side-trips: Cambridge (Harriet Tubman Birthplace Marker & Blackwater National Wildlife Refuge) and Slack Winery (in Ridge). There's still lots to do: brush up on your military savvy at Patuxent River Naval Air Museum and deepen your knowledge of military history at "On Watch" Monument.

To see reviews, other places to visit, where to stay, and tourist information, go to the Solomons trip itinerary maker site .

Traveling by car from Ocean City to Solomons takes 3.5 hours. In February, plan for daily highs up to 46°F, and evening lows to 31°F. Wrap up your sightseeing on the 3rd (Tue) early enough to drive back home.

Things to do in Solomons

Museums Parks Wineries

Side Trips

Cambridge, Slack Winery, Patuxent River Naval Air Museum, "On Watch" Monument, Historic St. Mary's City
Highlights from your plan
Blackwater National Wildlife Refuge ©
Flag Ponds Nature Park ©
Flag Ponds Nature Park

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