18 days in Maryland Itinerary

18 days in Maryland Itinerary

Created using Inspirock Maryland itinerary planner

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Make it your trip
Fly to Washington Dulles International Airport, Drive to Hagerstown
1
Hagerstown
— 4 nights
Drive
2
Cumberland
— 4 nights
Drive
3
Ocean City
— 5 nights
Drive
4
St. Michaels
— 4 nights
Fly

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Hagerstown

— 4 nights
Hagerstown is a city in Washington County, Maryland, United States. Discover out-of-the-way places like Shenandoah Valley Discovery Museum and C&O Canal Trust. Kids will appreciate attractions like Explore More Discovery Museum and Rocking S Ranch. Venture out of the city with trips to Stonewall Jackson's Headquarters (in Winchester) and Harrisonburg (James Madison University & A Dream Come True Playground). There's lots more to do: explore the world behind art at Washington County Museum of Fine Arts, stroll around Hagerstown City Park, go for a walk through The Hagerstown Cultural Trail, and hunt for treasures at Pennsylvania Dutch Market.

To see more things to do, ratings, maps, and more tourist information, use the Hagerstown online tour itinerary planner.

Orlando to Hagerstown is an approximately 9-hour combination of flight and car. You can also drive. In July, Hagerstown is a bit cooler than Orlando - with highs of 86°F and lows of 68°F. Wrap up your sightseeing on the 5th (Sun) to allow time to drive to Cumberland.

Things to do in Hagerstown

Parks · Museums · Nature · Childrens Museums

Side Trips

Cumberland

— 4 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 appreciate attractions like Great Allegheny Passage and Blackwater Outdoor Adventures. Eschew the tourist crowds and head to Swallow Falls State Park and Spruce Forest Artisan Village. You'll find plenty of places to visit near Cumberland: Mountain Trail Rides Horseback Riding & More (in Davis), The Discovery Center (in Swanton) and New Germany State Park (in Grantsville). Next up on the itinerary: admire the majestic nature at Rocky Gap State Park, sample the fine beverages at Charis Winery & Distillery, admire nature's wide array of creatures at Tri State Zoological Park, and examine the collection at Allegany Museum.

For photos, more things to do, and more tourist information, go to the Cumberland trip builder.

Traveling by car from Hagerstown to Cumberland takes 1.5 hours. Expect a daytime high around 86°F in July, and nighttime lows around 65°F. Finish up your sightseeing early on the 9th (Thu) so you can travel to Ocean City.

Things to do in Cumberland

Parks · Outdoors · Nature · Trails

Side Trips

Ocean City

— 5 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.
Explore hidden gems such as Jolly Roger Amusement Park and Trimper's Rides and Amusement Park. Attractions like Ocean City Boardwalk and Frontier Town make great kid-friendly stops. Explore the numerous day-trip ideas around Ocean City: Fenwick Island State Park (in Fenwick Island) and Ocean City Boardwalk (in Ocean City). There's much more to do: stroll around Northside Park, play a few rounds at Lost Treasure Golf, examine the collection at Ripley's Believe it or Not! Ocean City, and let the kids burn off some steam at Planet Maze/Lasertron/Lost Galaxy Golf.

For where to stay, traveler tips, other places to visit, and other tourist information, refer to the Ocean City route app.

Getting from Cumberland to Ocean City by car takes about 4.5 hours. Other options: do a combination of car and flight. In July, daytime highs in Ocean City are 84°F, while nighttime lows are 70°F. Finish your sightseeing early on the 14th (Tue) to allow enough time to drive to St. Michaels.

Things to do in Ocean City

Outdoors · Theme Parks · Parks · Museums

Side Trips

St. Michaels

— 4 nights
Eschew the tourist crowds and head to Boat Tours & Water Sports and Spas. Bring the kids along to Matapeake Clubhouse and Beach and Ferry Park. Explore St. Michaels' surroundings by going to Adkins Arboretum (in Ridgely) and Tuckahoe State Park (in Queen Anne).

To find maps, photos, reviews, and tourist information, use the St. Michaels trip planner.

You can drive from Ocean City to St. Michaels in 2 hours. Other options are to do a combination of shuttle and taxi; or do a combination of bus and taxi. July in St. Michaels sees daily highs of 87°F and lows of 71°F at night. Finish up your sightseeing early on the 18th (Sat) so you can catch the flight back home.

Things to do in St. Michaels

Parks · Outdoors · Museums · Wildlife

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.