50 days in Maryland Itinerary

50 days in Maryland Itinerary

Created using Inspirock Maryland trip itinerary planner

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Route & dates

50 days in Maryland Itinerary

Start: Washington DC
Drive:  3​h 30​min
1
Oakland
— 5 nights
Drive:  1​h 15​min
2
Cumberland
— 6 nights
Drive:  1​h 45​min
3
Sharpsburg
— 6 nights
Drive:  1​h 30​min
4
Chevy Chase
— 6 nights
Drive:  1​h 15​min
5
Port Tobacco
— 6 nights
Drive:  1​h 45​min
6
Cambridge
— 6 nights
Drive:  1​h 45​min
7
Ocean City
— 6 nights
Drive:  3​h
8
Baltimore
— 8 nights
train:  45​min
End: Washington DC

5
nights
Oakland

Oakland ©
Oakland is a town in the west-central part of Garrett County, Maryland. Get outdoors at Swallow Falls State Park and Deep Creek Lake State Park. There's lots more to do: tee off at Lodestone Golf Course, get engrossed in the history at The Oakland B&O Railroad Museum, tour the water at your own pace with Deep Creek Marina and Boat Rentals, and stop by Schoolhouse Earth.

To find reviews, ratings, where to stay, and other tourist information, you can read our Oakland trip itinerary planner.

Washington DC to Oakland is an approximately 3.5-hour car ride. In August, Oakland is slightly colder than Washington DC - with highs of 72°F and lows of 57°F. Finish your sightseeing early on the 17th (Fri) to allow enough time to travel to Cumberland.

Things to do in Oakland

Outdoors Parks Tours

Side Trips

McHenry, FireFly Farms, Schoolhouse Earth
Highlights from your plan
Lodestone Golf Course ©
Lodestone Golf Course
Swallow Falls State Park ©
Swallow Falls State Park
Herrington Manor State Park ©
Herrington Manor State Park

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. Spruce Forest Artisan Village and Gordon-Roberts House will appeal to history buffs. Get outdoors at Great Allegheny Passage and Green Ridge State Forest. Go for a jaunt from Cumberland to Grantsville to see New Germany State Park about 30 minutes away. There's much more to do: stroll through Tri State Zoological Park, tee off at Rocky Gap Golf Course, examine the collection at Allegany Museum, and learn about winemaking at Charis Winery.

To see reviews, maps, other places to visit, and tourist information, go to the Cumberland travel route builder website .

You can drive from Oakland to Cumberland in 1.5 hours. While traveling from Oakland, expect somewhat warmer days and about the same nights in Cumberland, ranging from highs of 84°F to lows of 62°F. Finish up your sightseeing early on the 23rd (Thu) so you can travel to Sharpsburg.

Things to do in Cumberland

Parks Nature Outdoors

Side Trips

Grantsville, Flintstone, Thrasher Carriage Museum
Highlights from your plan
Green Ridge State Forest ©
Green Ridge State Forest
New Germany State Park ©
New Germany State Park
Spruce Forest Artisan Village ©
Spruce Forest Artisan Village

6
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 Cunningham Falls State Park. Explore the numerous day-trip ideas around Sharpsburg: Worthington Manor Golf Club (in Urbana), Loy's Station Covered Bridge (in Thurmont) and Frederick (Clue IQ: An Escape Room Experience, Dragon Distillery, LLC, & more). There's still lots to do: contemplate the waterfront views at Antietam Creek, admire the majestic nature at Greenbrier State Park, explore and take pictures at Jumbo's Pumpkin Patch, and make a trip to Gambrill State Park.

For maps, photos, where to stay, and tourist information, read our Sharpsburg trip itinerary planning website .

Traveling by car from Cumberland to Sharpsburg takes 1.5 hours. In August in Sharpsburg, expect temperatures between 84°F during the day and 62°F at night. Wrap up your sightseeing on the 29th (Wed) early enough to travel to Chevy Chase.

Things to do in Sharpsburg

Parks Nature Historic Sites

Side Trips

Frederick, Middletown, Hagerstown, Thurmont, Greenbrier State Park
Highlights from your plan
Antietam National Battlefield ©
Antietam National Battlefield
Worthington Manor Golf Club ©
Worthington Manor Golf Club
Historic Downtown Frederick ©
Historic Downtown Frederick

6
nights
Chevy Chase

Chevy Chase ©
Chevy Chase is the name of both a town and an unincorporated census-designated place (CDP) in Montgomery County, Maryland. Audubon Naturalist Society Woodend Sanctuary and Montpelier Mansion will appeal to history buffs. Take a break from the city and head to Seneca Creek State Park and Sligo Creek Park. Change things up with these side-trips from Chevy Chase: Bowie (Allen Pond Park & Six Flags America), McKee-Beshers Wildlife Management Area (in Poolesville) and Harborfront Area (in National Harbor). Pack the 31st (Fri) with family-friendly diversions at The Adventure Park at Sandy Spring. Next up on the itinerary: find something for the whole family at Miniature Train and Carousel at Wheaton Regional Park, shop like a local with Waverly Street Gallery, hunt for treasures at Takoma Park Farmers Market, and stroll through Glen Echo Park.

For where to stay, reviews, ratings, and tourist information, refer to the Chevy Chase journey maker site .

Getting from Sharpsburg to Chevy Chase by car takes about 1.5 hours. August in Chevy Chase sees daily highs of 84°F and lows of 65°F at night. Finish your sightseeing early on the 4th (Tue) so you can travel to Port Tobacco.

Things to do in Chevy Chase

Parks Theme Parks Wildlife

Side Trips

Bowie, Bethesda, Seneca Creek State Park, Miniature Train and Carousel at Wheaton Regional Park, Sligo Creek Park
Highlights from your plan
Seneca Creek State Park ©
Seneca Creek State Park
Sligo Creek Park ©
Sligo Creek Park

6
nights
Port Tobacco

Port Tobacco ©
Port Tobacco, officially Port Tobacco Village, is a town in Charles County, in southern Maryland, United States. Escape the urban bustle at American Chestnut Land Trust and Bowles Farm Corn Maze. Deepen your sense of the past at sights like Thomas Stone National Historic Site and Saint Ignatius Church. Get out of town with these interesting Port Tobacco side-trips: Surratt House Museum (in Clinton), Cedarville State Forest (in Brandywine) and Sotterley Historic Plantation (in Hollywood). There's lots more to do: immerse yourself in nature at Purse State Park, explore the galleries of St. Clement's Island, stop by Second Looks Books, and examine the collection at St. Clement's Island Museum.

To see photos, more things to do, where to stay, and more tourist information, use the Port Tobacco vacation maker site .

You can drive from Chevy Chase to Port Tobacco in 1.5 hours. In September in Port Tobacco, expect temperatures between 80°F during the day and 64°F at night. Finish your sightseeing early on the 10th (Mon) to allow enough time to travel to Cambridge.

Things to do in Port Tobacco

Parks Outdoors Nature

Side Trips

Prince Frederick, Coltons Point, Capital Clubhouse, Indian Head Rail Trail, Sotterley Historic Plantation
Highlights from your plan
Purse State Park ©
Purse State Park
Sotterley Historic Plantation ©
Sotterley Historic Plantation
Surratt House Museum ©
Surratt House Museum

6
nights
Cambridge

Cambridge ©
Cambridge is a city in Dorchester County, Maryland, United States. Get outdoors at Emily’s Produce and Breezy Point Beach. You'll find plenty of places to visit near Cambridge: Elms Beach Park (in Lexington Park), Adkins Arboretum (in Ridgely) and St. Michaels (The Preppy Redneck, Chesapeake Bay Maritime Museum, & more). There's lots more to do: head outdoors with Chesapeake Bay Environmental Center, go for a stroll along the water at Solomons Boat Ramp and Fishing Pier, identify plant and animal life at Blackwater National Wildlife Refuge, and immerse yourself in nature at Jefferson Patterson Park & Museum.

To find other places to visit, traveler tips, reviews, and more tourist information, read our Cambridge trip builder .

Traveling by car from Port Tobacco to Cambridge takes 2.5 hours. September in Cambridge sees daily highs of 79°F and lows of 60°F at night. Finish your sightseeing early on the 16th (Sun) so you can travel to Ocean City.

Things to do in Cambridge

Parks Outdoors Beaches

Side Trips

St. Michaels, Chesapeake Bay Environmental Center, Solomons Boat Ramp and Fishing Pier, Martinak State Park, Breezy Point Beach
Highlights from your plan
Adkins Arboretum ©
Adkins Arboretum
Jefferson Patterson Park & Museum ©
Jefferson Patterson Park & Museum
Blackwater National Wildlife Refuge ©

6
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 outdoors at 48th St. Watersports 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: kick back and relax at Ocean City Beach, examine the collection at Ocean City Life-Saving Station Museum, tee off at Eagle's Landing Golf Course, and get in on the family fun at Jolly Roger Amusement Park.

To see traveler tips, maps, other places to visit, and more tourist information, read our Ocean City vacation maker .

You can drive from Cambridge to Ocean City in 1.5 hours. In September, plan for daily highs up to 78°F, and evening lows to 64°F. Wrap up your sightseeing on the 22nd (Sat) early enough to drive to Baltimore.

Things to do in Ocean City

Parks Nature Outdoors

Side Trips

Salisbury, Assateague State Park, Assateague Island National Seashore
Highlights from your plan
Ocean City Beach ©
Ocean City Beach
Assateague Island National Seashore ©
Assateague State Park ©
Assateague State Park

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.
Visiting Fort McHenry National Monument and Inner Harbor will get you outdoors. Your inner history buff will appreciate Hammond-Harwood House and Ladew Topiary Gardens. Change things up with these side-trips from Baltimore: Liriodendron Mansion (in Bel Air) and Annapolis (Maryland State House, William Paca Garden, & more). The adventure continues: try to win big at Horseshoe Casino, tour the pleasant surroundings at Kinder Farm Park, visit a coastal fixture at Seven Foot Knoll Lighthouse, and wander the streets of Fell's Point.

To see maps, traveler tips, other places to visit, and other tourist information, use the Baltimore tour planner.

You can drive from Ocean City to Baltimore in 3 hours. Alternatively, you can take a bus; or take a shuttle. September in Baltimore sees daily highs of 81°F and lows of 66°F at night. Wrap up your sightseeing on the 30th (Sun) to allow time to take a train back home.

Things to do in Baltimore

Historic Sites Parks Fun & Games

Side Trips

Annapolis, Honeygo Wine and Spirits, Liriodendron Mansion, Ladew Topiary Gardens, Kinder Farm Park
Highlights from your plan
Gunpowder Falls State Park ©
Gunpowder Falls State Park
Hammond-Harwood House ©
Hammond-Harwood House

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