59 days in Maryland Itinerary

59 days in Maryland Itinerary

Created using Inspirock Maryland itinerary builder

This plan was created by another user.  Make it your plan

Route & dates

59 days in Maryland Itinerary

Start: Washington DC
train:  45​min
1
Baltimore
— 8 nights
Drive:  1​h 45​min
2
St. Michaels
— 8 nights
Drive:  2​h
3
Ocean City
— 13 nights
Drive:  2​h 15​min
4
Solomons
— 7 nights
Drive:  5​h 15​min
5
Oakland
— 6 nights
Drive:  1​h 15​min
6
Cumberland
— 7 nights
Drive:  1​h 45​min
7
Sharpsburg
— 8 nights
Drive:  1​h 30​min
End: Washington DC

8
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.
Step off the beaten path and head to U.S. Naval Academy and Fell's Point. Explore the numerous day-trip ideas around Baltimore: Book Plate (in Chestertown), Annapolis (Maryland State House, Maryland World War II Memorial, & more) and Elk Neck State Park (in North East). Next up on the itinerary: admire the architecture and history at Fort McHenry National Monument, appreciate the extensive heritage of Federal Hill Park, meet the residents at National Aquarium, and explore the world behind art at Baltimore Museum of Art.

For reviews, traveler tips, photos, and other tourist information, read our Baltimore route planner.

Washington DC to Baltimore is an approximately 1-hour train ride. You can also drive; or take a bus. In August in Baltimore, expect temperatures between 86°F during the day and 71°F at night. Cap off your sightseeing on the 11th (Sat) early enough to go by car to St. Michaels.

Things to do in Baltimore

Parks Nature Historic Sites

Side Trips

Annapolis, Book Plate, Ripken Stadium, Elk Neck State Park, Havre de Grace Promenade
Highlights from your plan
The Walters Art Museum ©
The Walters Art Museum
Horseshoe Casino ©
Horseshoe Casino

8
nights
St. Michaels

St. Michaels ©
You'll explore the less-touristy side of things at Chesapeake Bay Maritime Museum and Blackwater Distilling. Change things up with these side-trips from St. Michaels: Cambridge (Choptank River Lighthouse, Harriet Tubman Museum and Educational Center, & more), Terrapin Beach Park (in Stevensville) and Harriet Tubman Underground Railroad National Historical Park (in Church Creek).

To see reviews, more things to do, traveler tips, and other tourist information, use the St. Michaels trip planner .

Traveling by car from Baltimore to St. Michaels takes 2 hours. Alternatively, you can do a combination of bus and taxi. In August, daytime highs in St. Michaels are 84°F, while nighttime lows are 67°F. Finish up your sightseeing early on the 19th (Sun) so you can go by car to Ocean City.

Things to do in St. Michaels

Parks Museums Wildlife

Side Trips

Cambridge, Easton, Stevensville, Phillips Wharf Environmental Center, Harriet Tubman Underground Railroad National Historical Park
Highlights from your plan
Chesapeake Bay Maritime Museum ©
Chesapeake Bay Maritime Museum
Blackwater National Wildlife Refuge ©
1879 Hooper Strait Lighthouse ©
1879 Hooper Strait Lighthouse

13
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.
Discover out-of-the-way places like Assateague Island National Seashore and Northside Park. Explore Ocean City's surroundings by going to Chesapeake Bay Farms (in Pocomoke City) and Salisbury (Coco's Funhouse, Salisbury Zoo, & more). There's lots more to do: admire the majestic nature at Assateague State Park, stroll through Ocean City Beach, get in on the family fun at Frontier Town, and see the interesting displays at Ripley's Believe it or Not!.

To see photos, reviews, ratings, and tourist information, read Ocean City visit planner .

Drive from St. Michaels to Ocean City in 2 hours. Alternatively, you can do a combination of taxi and shuttle; or do a combination of taxi and bus. August in Ocean City sees daily highs of 82°F and lows of 67°F at night. Wrap up your sightseeing on the 1st (Sat) to allow time to travel to Solomons.

Things to do in Ocean City

Outdoors Parks Theme Parks

Side Trips

Salisbury, Berlin, Assateague Island National Seashore, Chesapeake Bay Farms
Highlights from your plan
Northside Park ©
Northside Park
Parasailing & Paragliding
Fishing Charters & Tours

7
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 Janes Island State Park and Spring Cove Marina. Explore Solomons' surroundings by going to Somers Cove Marina (in Crisfield), American Chestnut Land Trust (in Prince Frederick) and Point Lookout State Park (in Scotland). Next up on the itinerary: enjoy the sea views from Calvert Marine Museum and Drum Point Lighthouse, explore the galleries of Historic St. Mary's City, do a tasting at Slack Winery, and admire the majestic nature at Calvert Cliffs State Park.

To see other places to visit, traveler tips, and other tourist information, you can read our Solomons day trip planner.

Traveling by car from Ocean City to Solomons takes 3.5 hours. In September, daytime highs in Solomons are 79°F, while nighttime lows are 63°F. Finish your sightseeing early on the 8th (Sat) so you can travel to Oakland.

Things to do in Solomons

Parks Nature Museums

Side Trips

Crisfield, Lusby, Leonardtown, American Chestnut Land Trust, Piney Point Lighthouse Museum & Historic Park
Highlights from your plan
Janes Island State Park ©
Janes Island State Park
Spring Cove Marina ©
Spring Cove Marina
Point Lookout State Park ©
Point Lookout State Park

6
nights
Oakland

Oakland ©
Oakland is a town in the west-central part of Garrett County, Maryland. Eschew the tourist crowds and head to Swallow Falls State Park and Garrett County Historical Museum. There's lots more to do: contemplate the waterfront views at Deep Creek Lake State Park, relax in the rural setting at Firefly Farms, admire the majestic nature at Herrington Manor State Park, and have fun at Adventure Sports Center International.

To find out how to plan a trip to Oakland, use our trip itinerary maker.

Traveling by car from Solomons to Oakland takes 4.5 hours. Traveling from Solomons in September, expect Oakland to be little chillier, temps between 68°F and 52°F. Wrap up your sightseeing by early afternoon on the 15th (Sat) to allow time for travel to Cumberland.

Things to do in Oakland

Outdoors Parks Nature

Side Trips

McHenry, FireFly Farms, The Discovery Center, Schoolhouse Earth
Highlights from your plan
Swallow Falls State Park ©
Swallow Falls State Park
Deep Creek Lake State Park ©
Deep Creek Lake State Park
Herrington Manor State Park ©
Herrington Manor State Park

7
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. You'll explore the less-touristy side of things at New Germany State Park and Spruce Forest Artisan Village. Change things up with a short trip to Green Ridge State Forest in Flintstone (about 32 minutes away). There's lots more to do: learn about winemaking at Charis Winery, contemplate the long history of Gordon-Roberts House, admire the majestic nature at Casselman River Bridge State Park, and explore the landscape on two wheels at Great Allegheny Passage.

To find maps, other places to visit, and more tourist information, read Cumberland journey planner.

Traveling by car from Oakland to Cumberland takes 1.5 hours. While traveling from Oakland, expect a bit warmer days and about the same nights in Cumberland, ranging from highs of 80°F to lows of 56°F. Cap off your sightseeing on the 22nd (Sat) early enough to travel to Sharpsburg.

Things to do in Cumberland

Parks Nature Trails

Side Trips

Grantsville, Flintstone, Thrasher Carriage Museum
Highlights from your plan
Rocky Gap State Park ©
Rocky Gap State Park
Paw Paw Tunnel ©
Paw Paw Tunnel
Gordon-Roberts House ©
Gordon-Roberts House

8
nights
Sharpsburg

Sharpsburg ©
Sharpsburg is a town in Washington County, Maryland, United States, located approximately 13mi south of Hagerstown. Step off the beaten path and head to Antietam National Battlefield and Antietam Creek. Change things up with these side-trips from Sharpsburg: Thurmont (Cunningham Falls State Park, Loy's Station Covered Bridge, & more), National Shrine Grotto of Lourdes (in Emmitsburg) and Frederick (National Museum of Civil War Medicine, Baker Park, & more). Spend the 26th (Wed) exploring nature at Chesapeake & Ohio Canal National Historical Park. There's still lots to do: stroll the grounds of Rose Hill Cemetery, take in the views from Burnside's Bridge, look for gifts at Turn the Page Bookstore, and admire the masterpieces at Washington County Museum of Fine Arts.

To find maps, traveler tips, other places to visit, and tourist information, use the Sharpsburg driving holiday planner .

You can drive from Cumberland to Sharpsburg in 1.5 hours. Expect a daytime high around 79°F in September, and nighttime lows around 56°F. On the 30th (Sun), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Sharpsburg

Parks Nature Historic Sites

Side Trips

Frederick, Hagerstown, Thurmont, Turn the Page Bookstore, National Shrine Grotto of Lourdes
Highlights from your plan
Antietam National Battlefield ©
Antietam National Battlefield
Historic Downtown Frederick ©
Historic Downtown Frederick
Burnside's Bridge ©
Burnside's Bridge

Similar Plans

60 days in Maryland BY A USER FROM TURKEY May, outdoors, relaxing, shopping, wildlife, popular & hidden gems PREFERENCES: May, outdoors, relaxing, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 5 days in Maryland BY A USER FROM UNITED STATES May, outdoors, relaxing, beaches, museums, shopping, wildlife, popular sights PREFERENCES: May, outdoors, relaxing, beaches, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 7 days in Maryland BY A USER FROM UNITED KINGDOM April, teens, outdoors, relaxing, beaches, shopping, wildlife, popular sights PREFERENCES: April, teens, outdoors, relaxing, beaches, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 5 days in Maryland BY A USER FROM UNITED STATES May, outdoors, relaxing, beaches, museums, shopping, wildlife, popular sights PREFERENCES: May, outdoors, relaxing, beaches, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 15 days in Maryland BY A USER FROM UNITED KINGDOM July, kids, culture, outdoors, beaches, historic sites, popular sights PREFERENCES: July, kids, culture, outdoors, beaches, historic sites ATTRACTION STYLE: Popular sights PACE: Medium 6 days in Maryland BY A USER FROM ISRAEL June, culture, outdoors, romantic, wildlife, hidden gems PREFERENCES: June, culture, outdoors, romantic, wildlife ATTRACTION STYLE: Hidden gems PACE: Medium 2 days in Maryland BY A USER FROM UNITED STATES March, outdoors, relaxing, museums, wildlife, popular sights PREFERENCES: March, outdoors, relaxing, museums, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 3 days in Maryland BY A USER FROM UNITED STATES April, culture, relaxing, romantic, hidden gems PREFERENCES: April, culture, relaxing, romantic ATTRACTION STYLE: Hidden gems PACE: Medium 1 day in Maryland BY A USER FROM UNITED STATES May, beaches, historic sites, museums, popular sights PREFERENCES: May, beaches, historic sites, museums ATTRACTION STYLE: Popular sights PACE: Medium 31 days in Chicago, Minnesota & Maryland BY A USER FROM SWITZERLAND May, outdoors, beaches, wildlife, fast-paced, hidden gems PREFERENCES: May, outdoors, beaches, wildlife ATTRACTION STYLE: Hidden gems PACE: Fast-paced 31 days in Chicago, Minnesota & Maryland BY A USER FROM SWITZERLAND May, outdoors, beaches, wildlife, fast-paced, hidden gems PREFERENCES: May, outdoors, beaches, wildlife ATTRACTION STYLE: Hidden gems PACE: Fast-paced 7 days in Maryland BY A USER FROM UNITED STATES August, teens, popular sights PREFERENCES: August, teens ATTRACTION STYLE: Popular sights PACE: Medium
View more plans