42 days in Maryland Itinerary

Created using Klarna Trips Maryland route planner
Make it your trip
Drive
1
Oakland
— 3 nights
Drive
2
Cumberland
— 5 nights
Drive
3
Sharpsburg
— 4 nights
Drive
4
Baltimore
— 10 nights
Drive
5
Elkton
— 3 nights
Drive
6
Ocean City
— 7 nights
Unknown
7
Assateague Island
— 2 nights
Unknown
8
St. Michaels
— 5 nights
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9
Stevensville, Kent Island
— 2 nights
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Oakland — 3 nights

Oakland is a town in the west-central part of Garrett County, Maryland. Oakland is known for nature, adventure, and museums. Your trip includes some of its best attractions: admire the majestic nature at Swallow Falls State Park, walk around Herrington Manor State Park, play a few rounds at Lodestone Golf Course, and take an in-depth tour of The Oakland B&O Railroad Museum.

To find reviews, ratings, photos, and tourist information, you can read our Oakland trip itinerary builder app.

Washington to Oakland is an approximately 2.5-hour car ride. Traveling from Washington in August, things will get little chillier in Oakland: highs are around 72°F and lows about 57°F. Wrap up your sightseeing on the 8th (Mon) to allow time to drive to Cumberland.
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Find places to stay Aug 5 — 8:

Cumberland — 5 nights

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. Venture out of the city with trips to Hagerstown (C&O Canal Trust, Hagerstown City Park, &more), Green Ridge State Forest (in Flintstone) and New Germany State Park (in Grantsville). There's still lots to do: explore the landscape on two wheels at Great Allegheny Passage, don't miss a visit to Sideling Hill Welcome Center, immerse yourself in nature at Casselman River Bridge State Park, and browse the fresh offerings at Hill Top Fruit Market.

For traveler tips, photos, ratings, and more tourist information, refer to the Cumberland trip itinerary maker tool.

Traveling by car from Oakland to Cumberland takes 1.5 hours. When traveling from Oakland in August, plan for somewhat warmer days in Cumberland, with highs around 84°F, while nights are about the same with lows around 62°F. Finish your sightseeing early on the 13th (Sat) so you can drive to Sharpsburg.
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Find places to stay Aug 8 — 13:

Sharpsburg — 4 nights

Sharpsburg is a town in Washington County, Maryland, United States, located approximately 13mi south of Hagerstown. Venture out of the city with trips to C&O Canal Hike at Point of Rocks Boat Ramp (in Point of Rocks), Lockhouse 49 (in Clear Spring) and Western Maryland Rail Trail (in Big Pool). Next up on the itinerary: take in the history at Antietam National Battlefield, learn about winemaking at Orchid Cellar Meadery and Winery, take some stellar pictures from Annapolis Rock, and explore the activities along Antietam Creek.

For other places to visit, where to stay, ratings, and tourist information, go to the Sharpsburg online visit planner.

Getting from Cumberland to Sharpsburg by car takes about 1.5 hours. In August, plan for daily highs up to 84°F, and evening lows to 62°F. Finish up your sightseeing early on the 17th (Wed) so you can go by car to Baltimore.
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Find places to stay Aug 13 — 17:

Baltimore — 10 nights

City of Firsts

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.
Get out of town with these interesting Baltimore side-trips: Six Flags America (in Bowie), Emmitsburg (National Shrine Grotto of Lourdes & National Shrine of St. Elizabeth Ann Seton) and Harborfront Area (in National Harbor). And it doesn't end there: try your luck at Horseshoe Casino, contemplate the long history of Fort McHenry National Monument and Historic Shrine, learn about all things military at Historic Ships in Baltimore, and take a tour by water with Boat Tours & Water Sports.

To find traveler tips, other places to visit, and tourist information, refer to the Baltimore online driving holiday planner.

Traveling by car from Sharpsburg to Baltimore takes 1.5 hours. Expect a bit warmer evenings in Baltimore when traveling from Sharpsburg in August, with lows around 71°F. Wrap up your sightseeing on the 27th (Sat) to allow time to drive to Elkton.
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Find places to stay Aug 17 — 27:

Elkton — 3 nights

The town of Elkton is the county seat of Cecil County, Maryland, United States. Explore Elkton's surroundings by going to Betterton Beach (in Betterton), Havre de Grace (Bulle Rock Golf Club, Susquehanna State Park, &more) and Fisherman’s Park (in Darlington). There's more to do: awaken your taste buds at M/V Bay Breeze of Chesapeake City and admire the majestic nature at Elk Neck State Park.

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

Getting from Baltimore to Elkton by car takes about 1.5 hours. Traveling from Baltimore in August, expect little chillier with lows of 66°F in Elkton. Wrap up your sightseeing on the 30th (Tue) to allow time to drive to Ocean City.
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Parks · Outdoors · Nature · Wineries
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Find places to stay Aug 27 — 30:

Ocean City — 7 nights

The White Marlin Capital of the World

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.
Venture out of the city with trips to Salisbury (Ben's Red Swings Community Playground & Salisbury Zoo). There's lots more to do: take a leisurely stroll along Ocean City Boardwalk, kick back and relax at Ocean City Beach, find something for the whole family at Trimper Rides and Amusement Park, and cool off at Splash Mountain Water Park.

To find reviews, traveler tips, photos, and other tourist information, you can read our Ocean City itinerary planner.

You can drive from Elkton to Ocean City in 2.5 hours. Expect a daytime high around 82°F in August, and nighttime lows around 67°F. Wrap up your sightseeing on the 6th (Tue) to allow time to travel to Assateague Island.
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Find places to stay Aug 30 — Sep 6:

Assateague Island — 2 nights

Kick off your visit on the 7th (Wed): look for all kinds of wild species at Assateague Island National Seashore. On the 8th (Thu), you'll have a packed day of sightseeing: capture your vacation like a pro with Assateague Island Tours.

Discover how to plan a Assateague Island trip in just a few steps with Klarna Trips's itinerary builder.

Use the Route module to find suitable travel options from Ocean City to Assateague Island. Expect a daytime high around 78°F in September, and nighttime lows around 64°F. Wrap up your sightseeing by early afternoon on the 8th (Thu) to allow enough time to travel to St. Michaels.
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Find places to stay Sep 6 — 8:
Highlights from your trip

St. Michaels — 5 nights

Change things up with these side-trips from St. Michaels: Robin Hill Farm and Vineyards (in Brandywine), Harriet Tubman Underground Railroad National Historical Park (in Church Creek) and Jug Bay Wetlands Sanctuary (in Lothian).

To find ratings, where to stay, reviews, and other tourist information, go to the St. Michaels trip itinerary site.

Explore your travel options from Assateague Island to St. Michaels with the Route module. In September in St. Michaels, expect temperatures between 80°F during the day and 62°F at night. Finish your sightseeing early on the 13th (Tue) so you can drive to Stevensville.
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Find places to stay Sep 8 — 13:

Stevensville, Kent Island — 2 nights

Stevensville is a census-designated place (CDP) in Queen Anne's County, Maryland, and is the county's most populous place among both CDPs and municipalities. On the 14th (Wed), hike along Terrapin Nature Park, get outside with Casey Michelle Charters, then see what you can catch with Lead Dog Charters, and finally brush up on your knowledge of spirits at Blackwater Distilling & Tavern. Get ready for a full day of sightseeing on the 15th (Thu): admire the masterpieces at Bruce Snake Gabrielson's Surf Art Gallery and Museum, head outdoors with American Chestnut Land Trust, and then make a splash at Edward T Hall Aquatic Center.

For more things to do, ratings, where to stay, and tourist information, read Stevensville road trip planning site.

You can drive from St. Michaels to Stevensville in an hour. In September, daytime highs in Stevensville are 78°F, while nighttime lows are 64°F. Finish up your sightseeing early on the 15th (Thu) so you can go by car back home.
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Find places to stay Sep 13 — 15:

Maryland travel guide

4.2
Casinos · Specialty Museums · Aquariums
The Old Line State
Perhaps best known as the birthplace of religious and political freedom in the United States, Maryland retains the spirit of colonial America, with stately 18th-century villages and historical landmarks. Although it's one of the nation's smallest states, there is no shortage of things to do here and you may find your itinerary fills up quickly. Make time in your vacation to tour Maryland's diverse landscape, which includes mountain peaks, picturesque Atlantic coastline, and the bustling city of Baltimore. Military buffs will enjoy touring the state's four Civil War Trails, where you can follow the footsteps of U.S. soldiers, or visiting the port city of Annapolis, home to the United States Naval Academy.
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