58 days in Maryland Itinerary

58 days in Maryland Itinerary

Created using Inspirock Maryland travel planner

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

Route & dates

58 days in Maryland Itinerary

Start: Washington DC
Drive:  2​h 45​min
1
Cumberland
— 6 nights
Drive:  1​h 45​min
2
Sharpsburg
— 8 nights
Drive:  1​h 15​min
3
Rockville
— 8 nights
Drive:  1​h 15​min
4
Baltimore
— 9 nights
Drive:  1​h 15​min
5
Havre de Grace
— 8 nights
Drive:  1​h 45​min
6
St. Michaels
— 8 nights
Drive:  2​h
7
Ocean City
— 10 nights
Drive:  3​h
End: Washington DC

6
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. Change things up with these side-trips from Cumberland: Green Ridge State Forest (in Flintstone), Oakland (Deep Creek Lake State Park, Bill's Marine Service - Day Rentals, & more) and McHenry (Funland & Wisp Resort). Next up on the itinerary: explore the landscape on two wheels at Great Allegheny Passage, experience rural life at Firefly Farms, make a trip to National Road & Toll House, and contemplate the long history of Paw Paw Tunnel.

To see ratings, other places to visit, more things to do, and other tourist information, read our Cumberland trip builder tool .

Washington DC to Cumberland is an approximately 2.5-hour car ride. Expect slightly colder evenings in Cumberland when traveling from Washington DC in August, with lows around 62°F. Cap off your sightseeing on the 9th (Thu) early enough to travel to Sharpsburg.

Things to do in Cumberland

Parks Outdoors Nature

Side Trips

Oakland, Flintstone, McHenry, Grantsville, National Road & Toll House
Highlights from your plan
Swallow Falls State Park ©
Swallow Falls 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. Change things up with these side-trips from Sharpsburg: Speedway (in Hagerstown), Thurmont (Loy's Station Covered Bridge & Cunningham Falls State Park) and Frederick (National Museum of Civil War Medicine, C. Burr Artz Public Library, & more). On the 10th (Fri), spend a day delving into the history of Antietam National Battlefield. Spend the 16th (Thu) exploring nature at Chesapeake & Ohio Canal National Historical Park. Next up on the itinerary: explore the activities along Antietam Creek, brush up on your military savvy at Boonsborough Museum of History, look for gifts at Turn the Page Bookstore, and see the interesting displays at Hagerstown Roundhouse Museum.

To see photos, more things to do, and more tourist information, read our Sharpsburg trip planner .

You can drive from Cumberland to Sharpsburg in 1.5 hours. In August in Sharpsburg, expect temperatures between 84°F during the day and 62°F at night. Finish up your sightseeing early on the 17th (Fri) so you can travel to Rockville.

Things to do in Sharpsburg

Parks Nature Historic Sites

Side Trips

Frederick, Hagerstown, Boonsboro, Thurmont, Big Cork Vineyards
Highlights from your plan
Clue IQ: An Escape Room Experience ©
Clue IQ: An Escape Room Experience
Antietam National Battlefield ©
Antietam National Battlefield

8
nights
Rockville

Rockville ©
Rockville is a city located in the central region of Montgomery County, Maryland. Explore Rockville's surroundings by going to Bowie (Six Flags America & Allen Pond Park), Greenbelt National Park (in Greenbelt) and Montpelier Mansion (in Laurel). Pack the 18th (Sat) with family-friendly diversions at The Adventure Park at Sandy Spring. Next up on the itinerary: tee off at Worthington Manor Golf Club, look for all kinds of wild species at McKee-Beshers Wildlife Management Area, relax in the rural setting at Lewis Orchard, and explore the landscape on two wheels at Sligo Creek Park.

To see where to stay, reviews, more things to do, and other tourist information, use the Rockville road trip planning site .

Traveling by car from Sharpsburg to Rockville takes 1.5 hours. Expect a daytime high around 83°F in August, and nighttime lows around 63°F. Finish your sightseeing early on the 25th (Sat) to allow enough time to travel to Baltimore.

Things to do in Rockville

Parks Theme Parks Outdoors

Side Trips

Bowie, Port Tobacco, The Adventure Park at Sandy Spring, Harborfront Area, Glen Echo Park
Highlights from your plan
Seneca Creek State Park ©
Seneca Creek State Park
The Adventure Park at Sandy Spring ©
The Adventure Park at Sandy Spring
Allen Pond Park ©
Allen Pond Park

9
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.
Venture out of the city with trips to Annapolis (Maryland State House, Hammond-Harwood House, & more), Oregon Ridge Park (in Cockeysville) and Ladew Topiary Gardens (in Monkton). And it doesn't end there: try to win big at Horseshoe Casino, explore and take pictures at Oriole Park at Camden Yards, admire the masterpieces at The Walters Art Museum, and stroll through Kinder Farm Park.

For where to stay, photos, other places to visit, and more tourist information, go to the Baltimore road trip app .

Drive from Rockville to Baltimore in an hour. Plan for somewhat warmer nights when traveling from Rockville in August since evenings lows in Baltimore dip to 71°F. Finish your sightseeing early on the 3rd (Mon) so you can travel to Havre de Grace.

Things to do in Baltimore

Parks Historic Sites Neighborhoods

Side Trips

Annapolis, Oregon Ridge Park, Ladew Topiary Gardens, Kinder Farm Park
Highlights from your plan
Sagamore Spirit Distillery ©
Sagamore Spirit Distillery
Horseshoe Casino ©
Horseshoe Casino
Oriole Park at Camden Yards ©
Oriole Park at Camden Yards

8
nights
Havre de Grace

Havre de Grace ©
Havre de Grace, abbreviated HdG, is a city in Harford County, Maryland, situated at the mouth of the Susquehanna River and the head of Chesapeake Bay. You'll find plenty of places to visit near Havre de Grace: Rocks State Park (in Jarrettsville), Elkton (West Meadow Park, Patriots Glen National Golf Club, & more) and Bel Air (Harford Mall & Liriodendron Mansion). Next up on the itinerary: admire all the interesting features of Ripken Stadium, admire nature's wide array of creatures at Plumpton Park Zoo, head outdoors with Schooner Sultana, and examine the collection at Upper Bay Museum.

For maps, where to stay, ratings, and other tourist information, use the Havre de Grace trip planner.

Traveling by car from Baltimore to Havre de Grace takes an hour. Traveling from Baltimore in September, you can expect nighttime temperatures to be a bit cooler in Havre de Grace, with lows of 60°F. Finish your sightseeing early on the 11th (Tue) to allow enough time to travel to St. Michaels.

Things to do in Havre de Grace

Parks Outdoors Museums

Side Trips

Chestertown, Elkton, Rising Sun, Aberdeen, Bel Air
Highlights from your plan
Susquehanna State Park ©
Susquehanna State Park
Millard Tydings Memorial Park ©
Millard Tydings Memorial Park
Steppingstone Museum ©
Steppingstone Museum

8
nights
St. Michaels

St. Michaels ©
Explore St. Michaels' surroundings by going to Cambridge (Emily’s Produce, Blackwater National Wildlife Refuge, & more), Adkins Arboretum (in Ridgely) and Prince Frederick (American Chestnut Land Trust & Second Looks Books).

Discover how to plan a St. Michaels trip in just a few steps with Inspirock's itinerary builder.

Traveling by car from Havre de Grace to St. Michaels takes 2 hours. In September, plan for daily highs up to 80°F, and evening lows to 62°F. Cap off your sightseeing on the 19th (Wed) early enough to go by car to Ocean City.

Things to do in St. Michaels

Outdoors Parks Shopping

Side Trips

Cambridge, Oxford, Prince Frederick, Chesapeake Beach, Bowles Farm Corn Maze
Highlights from your plan
American Chestnut Land Trust ©
American Chestnut Land Trust
Chesapeake Bay Maritime Museum ©
Chesapeake Bay Maritime Museum
Hopkins Original Art ©
Hopkins Original Art

10
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.
You'll find plenty of places to visit near Ocean City: Salisbury (Arthur W. Perdue Stadium (Delmarva Shorebirds), Poplar Hill Mansion, & more). Spend the 22nd (Sat) exploring nature at Assateague Island National Seashore. There's much more to do: get a new perspective on things with 48th St. Watersports, find something for the whole family at Jolly Roger Amusement Park, get your game on at Ocean City Screams Haunted House, and play a few rounds at Eagle's Landing Golf Course.

Find out how to plan Ocean City trip without stress by asking Inspirock to help create an itinerary.

You can drive from St. Michaels to Ocean City in 2 hours. Other options are to do a combination of taxi and shuttle; or do a combination of taxi and bus. Expect a daytime high around 78°F in September, and nighttime lows around 64°F. Finish up your sightseeing early on the 29th (Sat) so you can go by car back home.

Things to do in Ocean City

Parks Theme Parks Outdoors

Side Trips

Salisbury, Berlin, Assateague Island National Seashore
Highlights from your plan
Ocean City Beach ©
Ocean City Beach
Ocean City Boardwalk ©
Ocean City Boardwalk
Northside Park ©
Northside Park

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 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 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 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 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 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 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 5 days in Maryland BY A USER FROM UNITED STATES May, slow & easy, hidden gems PREFERENCES: May ATTRACTION STYLE: Hidden gems PACE: Slow & easy
View more plans