60 days in Maryland Itinerary

60 days in Maryland Itinerary

Created using Inspirock Maryland trip builder
Make it your trip
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1
Baltimore
— 23 nights
Drive
2
Hagerstown
— 6 nights
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3
Cumberland
— 6 nights
Drive
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Oakland
— 3 nights
Unknown
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Assateague Island
— 1 night
Unknown
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Ocean City
— 9 nights
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7
St. Michaels
— 4 nights
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Solomons
— 6 nights
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Baltimore — 23 nights

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.
Family-friendly places like Urban Axes Baltimore and The Walters Art Museum will thrill your kids. You'll find plenty of places to visit near Baltimore: The Brookeville Beer Farm (in Brookeville), Annapolis (Annapolis Historic District, Ego Alley, &more) and Sandy Spring (The Adventure Park at Sandy Spring & Underground Railroad Experience Trail Hikes). And it doesn't end there: observe the fascinating underwater world at National Aquarium, take a tour by water with Boat Tours & Water Sports, get curious at Maryland Science Center, and admire nature's wide array of creatures at Inner Harbor.

For maps, ratings, other places to visit, and other tourist information, read our Baltimore holiday builder app.

Washington DC to Baltimore is an approximately 1.5-hour car ride. You can also take a train; or take a bus. In June, plan for daily highs up to 85°F, and evening lows to 69°F. Wrap up your sightseeing on the 15th (Wed) to allow time to drive to Hagerstown.
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Parks · Nature · Museums · Outdoors
Side Trips

Hagerstown — 6 nights

Hagerstown is a city in Washington County, Maryland, United States. Family-friendly places like Clue IQ: An Escape Room Experience and Washington Monument State Park will thrill your kids. Explore Hagerstown's surroundings by going to Frederick (C. Burr Artz Public Library, Historic Downtown Frederick, &more), Fort Frederick State Park (in Big Pool) and C&O Canal Hike at Point of Rocks Boat Ramp (in Point of Rocks). And it doesn't end there: take in the history at Antietam National Battlefield, get your game on at Heavy Metal Playground, hike along Western Maryland Rail Trail, and tour the pleasant surroundings at Maryland Heights Trail.

To find more things to do, where to stay, and tourist information, use the Hagerstown trip tool.

Traveling by car from Baltimore to Hagerstown takes 1.5 hours. Traveling from Baltimore in July, plan for slightly colder nights in Hagerstown, with lows around 68°F. Wrap up your sightseeing on the 21st (Tue) early enough to drive to Cumberland.
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Parks · Nature · Outdoors · Trails
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Cumberland — 6 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. Kids will enjoy Great Allegheny Passage and Gordon-Roberts House. Change things up with these side-trips from Cumberland: New Germany State Park (in Grantsville) and Green Ridge State Forest (in Flintstone). There's much more to do: browse the collection at Allegany County Library System - Washington Street Library, make a trip to Allegany Fairgrounds, see the interesting displays at Allegany Museum, and admire the majestic nature at Rocky Gap State Park.

For ratings, photos, reviews, and tourist information, you can read our Cumberland sightseeing planner.

Getting from Hagerstown to Cumberland by car takes about 1.5 hours. In July, daytime highs in Cumberland are 86°F, while nighttime lows are 65°F. Wrap up your sightseeing on the 27th (Mon) early enough to drive to Oakland.
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Oakland — 3 nights

Oakland is a town in the west-central part of Garrett County, Maryland. Bring the kids along to Swallow Falls State Park and Horseback Riding Tours. Next up on the itinerary: explore the activities along Deep Creek Lake State Park, explore the engaging exhibits at The Discovery Center, immerse yourself in nature at Herrington Manor State Park, and fly down the slopes at Wisp Resort.

To find traveler tips, where to stay, ratings, and other tourist information, read our Oakland attractions planning website.

Traveling by car from Cumberland to Oakland takes 1.5 hours. Traveling from Cumberland in July, expect Oakland to be little chillier, temps between 73°F and 59°F. Wrap up your sightseeing on the 30th (Thu) to allow time to travel to Assateague Island.
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Side Trips

Assateague Island — 1 night

Here are some ideas for day two: explore the wealth of natural beauty at Assateague Island National Seashore.

Start your trip to Assateague Island by creating a personalized itinerary on Inspirock.

Explore your travel options from Oakland to Assateague Island with the Route module. Traveling from Oakland in July, things will get a bit warmer in Assateague Island: highs are around 84°F and lows about 70°F. Finish up your sightseeing early on the 1st (Sat) so you can travel to Ocean City.
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Highlights from your trip

Ocean City — 9 nights

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.
Attractions like Ocean City Beach and Ocean City Boardwalk make great kid-friendly stops. Change things up with these side-trips from Ocean City: Salisbury (Coco's Funhouse, Salisbury Zoo, &more), Crisfield (Crisfield Heritage Foundation & Janes Island State Park) and Chesapeake Bay Farms (in Pocomoke City). There's much more to do: walk around Northside Park, take a leisurely stroll along Oceanic Fishing Pier, get your game on at Ocean City Screams Haunted House, and glide through the air with a parasailing or paragliding tour.

To find reviews, more things to do, traveler tips, and tourist information, you can read our Ocean City road trip planner.

Use the Route module to find suitable travel options from Assateague Island to Ocean City. August in Ocean City sees daily highs of 82°F and lows of 67°F at night. Wrap up your sightseeing on the 10th (Mon) early enough to drive to St. Michaels.
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Parks · Fun & Games · Outdoors · Theme Parks
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St. Michaels — 4 nights

Kids will enjoy Eastern Neck National Wildlife Refuge and Matapeake Clubhouse and Beach. Explore St. Michaels' surroundings by going to Merkle Wildlife Sanctuary (in Upper Marlboro), Jug Bay Wetlands Sanctuary (in Lothian) and Choptank River Lighthouse (in Cambridge).

For traveler tips, more things to do, and other tourist information, read St. Michaels trip planner.

Getting from Ocean City to St. Michaels by car takes about 2 hours. Other options: do a combination of shuttle and taxi; or do a combination of bus and taxi. In August in St. Michaels, expect temperatures between 84°F during the day and 67°F at night. Wrap up your sightseeing on the 14th (Fri) to allow time to drive to Solomons.
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Parks · Wildlife · Outdoors · Beaches
Side Trips

Solomons — 6 nights

Solomons, also known as Solomons Island, is an unincorporated community and census-designated place (CDP) in Calvert County, Maryland, United States. Kids will enjoy American Chestnut Land Trust and Bruce Snake Gabrielson's Surf Art Gallery and Museum. Explore the numerous day-trip ideas around Solomons: Chesapeake Beach Railway Trail (in Chesapeake Beach), Edward T Hall Aquatic Center (in Prince Frederick) and Historic Port Tobacco Village (in Port Tobacco). There's much more to do: visit a coastal fixture at Calvert Marine Museum and Drum Point Lighthouse, take an in-depth tour of Jefferson Patterson Park & Museum, take in the waterfront activity at Spring Cove Marina, and immerse yourself in nature at Greenwell State Park.

For reviews, maps, ratings, and tourist information, use the Solomons attractions planner.

You can drive from St. Michaels to Solomons in 2.5 hours. In August, daytime highs in Solomons are 83°F, while nighttime lows are 67°F. Cap off your sightseeing on the 20th (Thu) early enough to go by car back home.
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Parks · Museums · Outdoors · Nature
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Maryland travel guide

4.1
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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