50 days in Maryland Itinerary

50 days in Maryland Itinerary

Created using Inspirock Maryland trip itinerary planner

Plan created by another user.Make it yours

Route & dates

1
Oakland
— 5 nights
2
Cumberland
— 6 nights
3
Sharpsburg
— 6 nights
4
Chevy Chase
— 6 nights
5
Port Tobacco
— 6 nights
6
Cambridge
— 6 nights
7
Ocean City
— 6 nights
8
Baltimore
— 8 nights

5
nights
Oakland

Oakland ©
Oakland is a town in the west-central part of Garrett County, Maryland. Get in touch with nature at Swallow Falls State Park and Deep Creek Lake State Park. There's still lots to do: walk around Herrington Manor State Park, take a pleasant ride with a tour on horseback, see the interesting displays at Garrett County Historical Museum, and play a few rounds at Lodestone Golf Course.

To find photos, other places to visit, maps, and more tourist information, go to the Oakland day trip planning app.

Washington DC to Oakland is an approximately 3.5-hour car ride. Expect slightly colder temperatures when traveling from Washington DC in August; daily highs in Oakland reach °F and lows reach °F. Finish your sightseeing early on the 17th (Fri) so you can drive 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. Visit Gordon-Roberts House and Paw Paw Tunnel for their historical value. Take a break from the city and head to Great Allegheny Passage and Rocky Gap State Park. You'll find plenty of places to visit near Cumberland: Green Ridge State Forest (in Flintstone) and New Germany State Park (in Grantsville). There's much more to do: do a tasting at Charis Winery, browse the fresh offerings at Hill Top Fruit Market, see the interesting displays at Thrasher Carriage Museum, and admire the majestic nature at Casselman River Bridge State Park.

For ratings, traveler tips, where to stay, and tourist information, read Cumberland trip planner.

Getting from Oakland to Cumberland by car takes about 1.5 hours. While traveling from Oakland, expect somewhat warmer days and about the same nights in Cumberland, ranging from highs of °F to lows of °F. Cap off your sightseeing on the 23rd (Thu) early enough to go by car to Sharpsburg.

Things to do in Cumberland

Parks Nature Outdoors

Side Trips

Grantsville, Flintstone, Thrasher Carriage Museum
Highlights from your plan
Great Allegheny Passage ©
Great Allegheny Passage
Green Ridge State Forest ©
Green Ridge State Forest
New Germany State Park ©
New Germany State Park

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 Washington Monument State Park. Visit Historic Downtown Frederick and South Mountain State Battlefield for their historical value. Change things up with these side-trips from Sharpsburg: Worthington Manor Golf Club (in Urbana), Thurmont (Cunningham Falls State Park & Loy's Station Covered Bridge) 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, see where the action happens at Hagerstown Suns Municipal Stadium, bet on your favorite at Speedway, and relax in the rural setting at Jumbo's Pumpkin Patch.

To find where to stay, ratings, more things to do, and other tourist information, you can read our Sharpsburg online vacation planner.

You can drive from Cumberland to Sharpsburg in 1.5 hours. In August, plan for daily highs up to °F, and evening lows to °F. Cap off 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, Thurmont, Hagerstown, Worthington Manor Golf Club
Highlights from your plan
Antietam National Battlefield ©
Antietam National Battlefield
Historic Downtown Frederick ©
Historic Downtown Frederick
Worthington Manor Golf Club ©
Worthington Manor Golf Club

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. Escape the urban bustle at Audubon Naturalist Society Woodend Sanctuary and Sligo Creek Park. Venture out of the city with trips to McKee-Beshers Wildlife Management Area (in Poolesville), Harborfront Area (in National Harbor) and Montpelier Mansion (in Laurel). Pack the 31st (Fri) with family-friendly diversions at The Adventure Park at Sandy Spring. The adventure continues: admire the majestic nature at Seneca Creek State Park, walk around Glen Echo Park, get in on the family fun at Miniature Train and Carousel at Wheaton Regional Park, and admire the masterpieces at Ratner Museum.

For ratings, where to stay, maps, and other tourist information, go to the Chevy Chase online itinerary planner.

You can drive from Sharpsburg to Chevy Chase in 1.5 hours. August in Chevy Chase sees daily highs of °F and lows of °F at night. Wrap up your sightseeing on the 4th (Tue) early enough to travel to Port Tobacco.

Things to do in Chevy Chase

Parks Theme Parks Wildlife

Side Trips

Bethesda, Bowie, McKee-Beshers Wildlife Management Area, Sligo Creek Park, Harborfront Area
Highlights from your plan
Audubon Naturalist Society Woodend Sanctuary ©
Sligo Creek Park ©
Sligo Creek Park
Seneca Creek State Park ©
Seneca Creek State Park

6
nights
Port Tobacco

Port Tobacco ©
Port Tobacco, officially Port Tobacco Village, is a town in Charles County, in southern Maryland, United States. Popular historic sites such as Thomas Stone National Historic Site and Surratt House Museum are in your itinerary. Step out of the city life by going to American Chestnut Land Trust and Indian Head Rail Trail. Change things up with these side-trips from Port Tobacco: Cedarville State Forest (in Brandywine), Prince Frederick (Second Looks Books & Battle Creek Cypress Swamp Sanctuary) and Sotterley Historic Plantation (in Hollywood). There's still lots to do: visit Saint Ignatius Church, browse the exhibits of St. Clement's Island State Park, don't miss a visit to Moll Dyer Rock, and admire the majestic nature at Purse State Park.

To see reviews, more things to do, where to stay, and more tourist information, you can read our Port Tobacco visit planning tool.

Traveling by car from Chevy Chase to Port Tobacco takes 1.5 hours. September in Port Tobacco sees daily highs of °F and lows of °F at night. Cap off your sightseeing on the 10th (Mon) early enough to travel to Cambridge.

Things to do in Port Tobacco

Parks Outdoors Nature

Side Trips

Prince Frederick, Coltons Point, Cedarville State Forest, Indian Head Rail Trail, Capital Clubhouse
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. You'll enjoy a bit of beach vacationing at Breezy Point Beach and Elms Beach Park. Take a break from the city and head to Blackwater National Wildlife Refuge and Adkins Arboretum. You'll find plenty of places to visit near Cambridge: Martinak State Park (in Denton), Chesapeake Bay Environmental Center (in Grasonville) and St. Michaels (The Preppy Redneck, Chesapeake Bay Maritime Museum, &more). The adventure continues: make a trip to Choptank River Lighthouse, examine the collection at The Oxford Museum, stop by Choptank Charlie's Emporium, and let your taste buds guide you at Eastern Shore Food Tours - Eating Easton.

For where to stay, traveler tips, and more tourist information, read our Cambridge online travel planner.

Traveling by car from Port Tobacco to Cambridge takes 2.5 hours. In September in Cambridge, expect temperatures between °F during the day and °F at night. Finish your sightseeing early on the 16th (Sun) to allow enough time to drive to Ocean City.

Things to do in Cambridge

Parks Outdoors Museums

Side Trips

St. Michaels, Jefferson Patterson Park & Museum, Elms Beach Park, Adkins Arboretum, Martinak State Park
Highlights from your plan
Adkins Arboretum ©
Adkins Arboretum
Jefferson Patterson Park & Museum ©
Jefferson Patterson Park & Museum
Blackwater National Wildlife Refuge ©
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 in touch with nature at Ocean City Beach and Assateague Island National Seashore. Get out of town with these interesting Ocean City side-trips: Salisbury (Salisbury Zoo, Coco's Funhouse, &more). There's still lots to do: get active on the water at 48th St. Watersports, play a few rounds at Eagle's Landing Golf Course, admire the majestic nature at Assateague State Park, and get your game on at Ocean City Screams Haunted House.

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

You can drive from Cambridge to Ocean City in 1.5 hours. Expect a daytime high around °F in September, and nighttime lows around °F. Finish your sightseeing early on the 22nd (Sat) so you can drive to Baltimore.

Things to do in Ocean City

Parks Nature Outdoors

Side Trips

Salisbury, Assateague Island National Seashore, Assateague State Park
Highlights from your plan
Ocean City Beach ©
Ocean City Beach
48th St. Watersports ©
48th St. Watersports
Assateague Island National Seashore ©
Assateague Island National Seashore

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.
Your inner history buff will appreciate Fort McHenry National Monument and Historic Shrine and Ladew Topiary Gardens. Explore the numerous day-trip ideas around Baltimore: Gunpowder Falls State Park (in Bradshaw), Liriodendron Mansion (in Bel Air) and Annapolis (Maryland State House, William Paca Garden, &more). There's still lots to do: try your luck at Horseshoe Casino, admire nature's wide array of creatures at National Aquarium, explore the world behind art at The Walters Art Museum, and shop like a local with Fell's Point.

Plan a trip to Baltimore easily and quickly by telling Inspirock to suggest an itinerary.

You can drive from Ocean City to Baltimore in 3 hours. Another option is to take a bus. In September, daytime highs in Baltimore are °F, while nighttime lows are °F. Cap off your sightseeing on the 30th (Sun) early enough to go by car back home.

Things to do in Baltimore

Historic Sites Parks Fun & Games

Side Trips

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

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