55 days in Maryland Itinerary

55 days in Maryland Itinerary

Created using Inspirock Maryland trip itinerary builder

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Plan created by another user.Make it yours

Route & dates

Start: Washington DC
Drive:  45 min
1
Annapolis
— 6 nights
Drive:  2 h 30 min
2
Ocean City
— 8 nights
Drive:  1 h 45 min
3
Denton
— 7 nights
Drive:  2 h
4
Cockeysville
— 8 nights
Drive:  1 h 15 min
5
Germantown
— 8 nights
Drive:  1 h 15 min
6
Sharpsburg
— 8 nights
Drive:  1 h 45 min
7
Cumberland
— 9 nights
Drive:  2 h 45 min
End: Washington DC

6
nights
Annapolis

Annapolis ©
Capital of the United States for one year from 1783 to 1784, Annapolis has played a vital role in U.S.
Take a break from the city and head to Quiet Waters Park and Renditions Golf Club. Get a sense of the local culture at U.S. Naval Academy and Annapolis Historic District. Venture out of the city with trips to National Electronics Museum (in Linthicum Heights), Bowie (Allen Pond Park & Six Flags America) and Montpelier Mansion (in Laurel). There's still lots to do: see the interesting displays at Chase-Lloyd House, steep yourself in history at Thomas Stone National Historic Site, admire the natural beauty at William Paca Garden, and ponder the world of politics at Maryland State House.

For photos, where to stay, reviews, and tourist information, use the Annapolis trip builder app.

Washington DC to Annapolis is an approximately 1-hour car ride. You can also take a bus. In September, daily temperatures in Annapolis can reach 78°F, while at night they dip to 66°F. Finish your sightseeing early on the 13th (Thu) to allow enough time to drive to Ocean City.

Things to do in Annapolis

Parks Outdoors Historic Sites

Side Trips

Bowie, National Electronics Museum, Renditions Golf Club, Chesapeake Bay Environmental Center, Fort Smallwood Park
Highlights from your plan
U.S. Naval Academy ©
U.S. Naval Academy
Annapolis Historic District
Annapolis Historic District
National Electronics Museum ©
National Electronics Museum

8
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.
Get some cultural insight at Ocean City Life-Saving Station Museum and Flashback Old Time Photos. Escape the urban bustle at Ocean City Beach and Assateague Island National Seashore. Change things up with these side-trips from Ocean City: Salisbury (Salisbury Zoo, Coco's Funhouse, &more). There's still lots to do: take a leisurely stroll along Ocean City Boardwalk, learn about winemaking at Costa Ventosa Vineyard & Winery, tee off at Eagle's Landing Golf Course, and walk around Northside Park.

To find traveler tips, more things to do, ratings, and more tourist information, use the Ocean City trip website.

Drive from Annapolis to Ocean City in 2.5 hours. Alternatively, you can take a bus. In September in Ocean City, expect temperatures between 78°F during the day and 64°F at night. Finish your sightseeing early on the 21st (Fri) to allow enough time to travel to Denton.

Things to do in Ocean City

Parks Theme Parks Nature

Side Trips

Salisbury, Berlin, Costa Ventosa Vineyard & Winery, Assateague Island National Seashore
Highlights from your plan
Ocean City Boardwalk ©
Ocean City Boardwalk
Ocean City Beach ©
Ocean City Beach
Assateague Island National Seashore ©
Assateague Island National Seashore

7
nights
Denton

Denton ©
Denton is a town in Caroline County, Maryland. Get in touch with nature at Martinak State Park and Hog Neck Golf Course. You'll explore and learn at Chesapeake Bay Maritime Museum and The Oxford Museum. Venture out of the city with trips to Cambridge (Bay Country Shop, Blackwater National Wildlife Refuge, &more), Harriet Tubman Underground Railroad National Historical Park (in Church Creek) and Layton's Chance Vineyard and Winery (in Vienna). There's still lots to do: learn about winemaking at Crow Farm and Vineyard and Winery, view the masterpieces at Ouvert Gallery, look for gifts at The Preppy Redneck, and indulge in some culinary diversions at Eastern Shore Food Tours - Eating Easton.

For ratings, photos, where to stay, and other tourist information, use the Denton tour planner.

You can drive from Ocean City to Denton in 1.5 hours. In September, plan for daily highs up to 80°F, and evening lows to 62°F. Finish your sightseeing early on the 28th (Fri) so you can travel to Cockeysville.

Things to do in Denton

Parks Museums Nature

Side Trips

Cambridge, St. Michaels, Oxford, Easton, Adkins Arboretum
Highlights from your plan
Adkins Arboretum ©
Adkins Arboretum
Chesapeake Bay Maritime Museum ©
Chesapeake Bay Maritime Museum
Blackwater National Wildlife Refuge ©
Blackwater National Wildlife Refuge

8
nights
Cockeysville

Cockeysville ©
Cockeysville is a census-designated place (CDP) in Baltimore County, Maryland, United States. Get outdoors at Fort McHenry National Monument and Historic Shrine and Ma and Pa Trail. Appreciate the collections at American Visionary Art Museum and Baltimore Museum of Art. You'll find plenty of places to visit near Cockeysville: Liriodendron Mansion (in Bel Air), Rocks State Park (in Jarrettsville) and Baltimore (National Katyn Memorial, Federal Hill Park, &more). There's still lots to do: meet the residents at National Aquarium, enjoy the sea views from Seven Foot Knoll Lighthouse, stroll around Oregon Ridge Park, and learn about all things military at Historic Ships in Baltimore.

To find where to stay, other places to visit, more things to do, and other tourist information, read Cockeysville driving holiday planner.

You can drive from Denton to Cockeysville in 2 hours. In September, plan for daily highs up to 81°F, and evening lows to 66°F. Finish up your sightseeing early on the 6th (Sat) so you can travel to Germantown.

Things to do in Cockeysville

Parks Historic Sites Museums

Side Trips

Baltimore, Bel Air, Gunpowder Falls State Park, Ladew Topiary Gardens, Rocks State Park
Highlights from your plan
National Aquarium ©
National Aquarium
Horseshoe Casino ©
Horseshoe Casino

8
nights
Germantown

Germantown ©
Germantown is an urbanized census-designated place in Montgomery County, Maryland. Step out of the city life by going to Audubon Naturalist Society Woodend Sanctuary and Indian Head Rail Trail. Get out of town with these interesting Germantown side-trips: Glen Echo Park (in Glen Echo), National Capital Trolley Museum (in Colesville) and Miniature Train and Carousel at Wheaton Regional Park (in Wheaton). Pack the 10th (Wed) with family-friendly diversions at The Adventure Park at Sandy Spring. And it doesn't end there: tee off at Worthington Manor Golf Club, see where the action happens at Xfinity Center, indulge your thirst for a good beer at The Brookeville Beer Farm, and immerse yourself in nature at Seneca Creek State Park.

For traveler tips, other places to visit, maps, and tourist information, go to the Germantown road trip planning app.

Getting from Cockeysville to Germantown by car takes about 1.5 hours. Traveling from Cockeysville in October, you can expect nighttime temperatures to be slightly colder in Germantown, with lows of 47°F. Wrap up your sightseeing on the 14th (Sun) to allow time to travel to Sharpsburg.

Things to do in Germantown

Outdoors Parks Theme Parks

Side Trips

McKee-Beshers Wildlife Management Area, National Capital Trolley Museum, Takoma Park Farmers Market, Sligo Creek Park, Capital Crescent Trail
Highlights from your plan
Worthington Manor Golf Club ©
Worthington Manor Golf Club
National Capital Trolley Museum ©
National Capital Trolley Museum

8
nights
Sharpsburg

Sharpsburg ©
Sharpsburg is a town in Washington County, Maryland, United States, located approximately 13mi south of Hagerstown. Get in touch with nature at Antietam National Battlefield and Greenbrier State Park. Museum-lovers will appreciate National Museum of Civil War Medicine and Pry House Field Hospital Museum. Get out of town with these interesting Sharpsburg side-trips: Frederick (Gambrill State Park, Historic Downtown Frederick, &more), Emmitsburg Antique Mall (in Emmitsburg) and Thurmont (Cunningham Falls State Park & Loy's Station Covered Bridge). The adventure continues: examine the collection at Chesapeake & Ohio Canal National Historical Park, stop by Turn the Page Bookstore, get great views at High Rock Overlook, and stroll the grounds of Rose Hill Cemetery.

Planning Sharpsburg trip won't be overwheling when you use's Insprock itinerary maker.

You can drive from Germantown to Sharpsburg in an hour. In October, plan for daily highs up to 68°F, and evening lows to 46°F. Cap off your sightseeing on the 22nd (Mon) early enough to go by car to Cumberland.

Things to do in Sharpsburg

Parks Nature Historic Sites

Side Trips

Frederick, Hagerstown, Middletown, Thurmont, Boonsboro
Highlights from your plan
Antietam National Battlefield ©
Antietam National Battlefield
Historic Downtown Frederick ©
Historic Downtown Frederick

9
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. Get in touch with nature at Great Allegheny Passage and Swallow Falls State Park. Satisfy your inner culture vulture at Gordon-Roberts House and The Oakland B&O Railroad Museum. You'll find plenty of places to visit near Cumberland: FireFly Farms (in Accident), McHenry (Deep Creek Marina and Boat Rentals, Adventure Sports Center International, &more) and Green Ridge State Forest (in Flintstone). There's much more to do: admire the majestic nature at Rocky Gap State Park, explore the activities along Deep Creek Lake State Park, tee off at Lodestone Golf Course, and examine the collection at Garrett County Museum of Transportation.

Inspirock's itinerary builder makes planning a Cumberland trip simple and quick.

You can drive from Sharpsburg to Cumberland in 1.5 hours. In October, plan for daily highs up to 68°F, and evening lows to 47°F. Wrap up your sightseeing on the 31st (Wed) to allow time to travel back home.

Things to do in Cumberland

Parks Outdoors Nature

Side Trips

Oakland, McHenry, Grantsville, Flintstone, FireFly Farms
Highlights from your plan
Great Allegheny Passage ©
Great Allegheny Passage
Swallow Falls State Park ©
Swallow Falls State Park
The Discovery Center ©
The Discovery Center

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