60 days in Maryland Itinerary

60 days in Maryland Itinerary

Created using Inspirock Maryland trip builder

Make it your trip
Drive
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

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.
Family-friendly places like Urban Axes Baltimore and The Adventure Park at Sandy Spring 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 Susquehanna State Park (in Havre de Grace). And it doesn't end there: observe the fascinating underwater world at National Aquarium, brush up on your military savvy at Historic Ships in Baltimore, examine the collection at American Visionary Art Museum, 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.

Things to do in Baltimore

Parks · Nature · Museums · Outdoors

Side Trips

Hagerstown

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

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.

Things to do in Hagerstown

Parks · Nature · Outdoors · Trails

Side Trips

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 Allegany County Library System - Washington Street Library. Change things up with these side-trips from Cumberland: Green Ridge State Forest (in Flintstone) and New Germany State Park (in Grantsville). There's much more to do: contemplate the long history of Gordon-Roberts House, 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.

Things to do in Cumberland

Parks · Nature · Trails · Outdoors

Side Trips

Oakland

— 3 nights
Oakland is a town in the west-central part of Garrett County, Maryland. Bring the kids along to Horseback Riding Tours and Wisp Resort. Next up on the itinerary: immerse yourself in nature at Swallow Falls State Park, see the interesting displays at Garrett County Historical Museum, explore the activities along Deep Creek Lake State Park, and have some family-friendly fun at Funland.

For where to stay, reviews, traveler tips, and tourist information, read our Oakland tour itinerary builder website.

Traveling by car from Cumberland to Oakland takes 1.5 hours. Traveling from Cumberland in July, things will get a bit cooler in Oakland: highs are around 73°F and lows about 59°F. Wrap up your sightseeing on the 30th (Thu) early enough to travel to Assateague Island.

Things to do in Oakland

Parks · Nature · Outdoors · Museums

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.

Things to do in Assateague Island

Nature · Parks · Wildlife
Highlights from your trip

Ocean City

— 9 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.
You'll visit kid-friendly attractions like Ocean City Beach and Ocean City Boardwalk. Change things up with these side-trips from Ocean City: Chesapeake Bay Farms (in Pocomoke City), Crisfield (Crisfield Heritage Foundation & Janes Island State Park) and Salisbury (Coco's Funhouse, Salisbury Zoo, &more). The adventure continues: stroll around Northside Park, take a tour by water with Boat Tours & Water Sports, have some family-friendly fun at Baja Amusements, and take in the waterfront at Oceanic Fishing Pier.

To see maps, reviews, and tourist information, go to the Ocean City trip itinerary maker app.

The Route module can help you plan travel from Assateague Island to Ocean City. In August, daily temperatures in Ocean City can reach 82°F, while at night they dip to 67°F. Wrap up your sightseeing on the 10th (Mon) to allow time to drive to St. Michaels.

Things to do in Ocean City

Parks · Fun & Games · Outdoors · Theme Parks

Side Trips

St. Michaels

— 4 nights
Kids will enjoy Eastern Neck National Wildlife Refuge and Ferry Park. Explore St. Michaels' surroundings by going to Matapeake Clubhouse and Beach (in Stevensville), Jug Bay Wetlands Sanctuary (in Lothian) and Merkle Wildlife Sanctuary (in Upper Marlboro).

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.

Things to do in St. Michaels

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 Battle Creek Cypress Swamp Sanctuary. Explore the numerous day-trip ideas around Solomons: Chesapeake Beach (Chesapeake Beach Railway Trail & Bruce Snake Gabrielson's Surf Art Gallery and Museum), Historic Port Tobacco Village (in Port Tobacco) and Edward T Hall Aquatic Center (in Prince Frederick). There's lots more to do: enjoy the sea views from Calvert Marine Museum and Drum Point Lighthouse, get engrossed in the history at Jefferson Patterson Park & Museum, admire the majestic nature at Calvert Cliffs State Park, and go for a stroll along the water at Spring Cove Marina.

For more things to do, photos, where to stay, and tourist information, use the Solomons road trip planning website.

Traveling by car from St. Michaels to Solomons takes 2.5 hours. In August, plan for daily highs up to 83°F, and evening lows to 67°F. Finish your sightseeing early on the 20th (Thu) to allow enough time to drive back home.

Things to do in Solomons

Parks · Museums · Outdoors · Nature

Side Trips

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.