A road trip from Baltimore to Assateague Island is one of the best ways to experience Maryland’s incredible mix of history, waterfront towns, scenic backroads, and beautiful coastal landscapes.
Along the way, you’ll discover fascinating stories, unforgettable local food, peaceful waterfront views, and plenty of fun places that are easy to miss if you drive straight to the beach.
By the time you reach the coast, you’ll have explored some of the state’s most memorable attractions, learned about remarkable moments in American history, and found a few hidden surprises that make the journey just as rewarding as the destination.
If you’re looking for the perfect Maryland road trip packed with unique stops, helpful travel tips, and amazing scenery from start to finish, this itinerary has you covered.
1. Baltimore
We’re kicking off this road trip in Baltimore, famous for its historic harbor, blue crabs, and colorful waterfront neighborhoods packed with museums, ships, and great seafood restaurants.
Start at the Inner Harbor, where you can tour the USS Constellation, explore the National Aquarium with more than 20,000 animals, or climb Federal Hill Park for wide views across the water and city skyline.
Walk the cobblestone streets of Fell’s Point, browse the shops and cafés, then visit Fort McHenry, the 1814 battlefield that inspired Francis Scott Key to write “The Star-Spangled Banner” during the War of 1812.
Before heading off to our next stop, grab a classic Maryland crab cake, snap a photo with the colorful rowhouses, and enjoy one of the East Coast’s most historic waterfront cities.
2. Annapolis
From Baltimore, it’s about a 40-minute drive to Annapolis, a waterfront city on the Chesapeake Bay that is best known as the home of the United States Naval Academy and one of the country’s best preserved colonial towns.
Spend time strolling along Main Street, where you’ll find local boutiques, ice cream shops, and seafood restaurants before reaching City Dock, where sailboats fill the harbor and historic buildings line the waterfront.
Tour the Maryland State House, the oldest state capitol still in continuous legislative use, then explore the Naval Academy grounds, watch the Noon Formation if it’s scheduled, and visit the Naval Academy Museum.
Don’t forget to treat yourself to fresh oysters or a bowl of Maryland crab soup before you leave.
3. St. Michaels
As you cross onto Maryland’s Eastern Shore, make a stop in St. Michaels, a charming waterfront town on the Miles River that is famous for its maritime heritage, fresh seafood, and beautifully preserved historic streets.
The Chesapeake Bay Maritime Museum is the highlight here, with 18 acres of exhibits, floating boats, a working shipyard, and the 1879 Hooper Strait Lighthouse overlooking the water.
Take a walk along Talbot Street to browse locally owned shops, sample homemade ice cream, or settle into a dockside restaurant serving freshly caught crab, oysters, and rockfish while boats drift through the harbor.
St. Michaels was nicknamed “the town that fooled the British” after local legend says residents hung lanterns in trees during the War of 1812, causing British cannon fire to sail over the town instead of hitting its homes.
4. Cambridge
From St. Michaels, drive about 35 minutes to Cambridge, a historic city on the Choptank River that is one of Maryland’s oldest communities and is well known for its waterfront, Harriet Tubman’s legacy, and easy access to the region’s incredible wildlife areas.
Visit the Harriet Tubman Museum and Educational Center, then explore part of the 125-mile Harriet Tubman Underground Railroad Byway to learn about her life and the landscapes that shaped her remarkable journey to freedom.
Just outside town, Blackwater National Wildlife Refuge protects more than 30,000 acres of tidal marshes where you can drive the 3.6-mile Wildlife Drive, spot bald eagles, great blue herons, and migrating waterfowl, or paddle peaceful creeks by kayak.
Before getting back on the road, wander along Cambridge’s marina, enjoy fresh Chesapeake Bay seafood at a local restaurant, and soak in the relaxed waterfront setting.
5. Harriet Tubman Underground Railroad National Historical Park
A short drive from Cambridge brings you to Harriet Tubman Underground Railroad National Historical Park.
It’s a powerful place that tells the story of one of America’s greatest freedom fighters in the same landscapes where she was born and carried out many of her rescue missions.
Begin at the Harriet Tubman Underground Railroad Visitor Center, where interactive exhibits, short films, and personal stories explain her remarkable life, the Underground Railroad, and the dangerous journeys to freedom across Maryland’s Eastern Shore.
Step outside to explore peaceful walking paths, scenic views, and surrounding wetlands that look much like they did in Tubman’s time, giving you a deeper understanding of the environment she expertly navigated.
This stop adds an unforgettable layer of history to your road trip before you continue east toward Assateague Island.
6. Berlin
As you get closer to the coast, take a break in Berlin, a small historic town just over an hour away from Harriet Tubman Underground Railroad National Historical Park.
It’s known for its beautifully preserved Main Street, locally owned shops, and welcoming small-town charm.
Stroll past colorful Victorian buildings, browse independent bookstores, antique shops, art galleries, and cafés, then stop for a sweet treat at Island Creamery, a local favorite famous for its homemade ice cream.
Movie fans might recognize Berlin from films like *Runaway Bride* and *Tuck Everlasting*, while history lovers can admire more than 45 buildings listed on the National Register of Historic Places throughout the downtown district.
It’s an easy place to slow down for an hour or two, giving you one last chance to enjoy Maryland’s Eastern Shore before swapping brick sidewalks for sandy beaches and wild horses.
7. Ocean City
Before reaching Assateague Island, make one more stop in Ocean City, Maryland’s most popular beach destination.
Here you’ll find 10 miles of sandy shoreline, a lively boardwalk, and endless ocean views that create a fun change of pace from the quiet towns along the Eastern Shore.
Walk the nearly 3-mile Ocean City Boardwalk and enjoy rides at Trimper Rides, classic arcades, Thrasher’s French Fries, Fisher’s Popcorn, and plenty of spots to grab fresh seafood with an Atlantic Ocean view.
If you want to get out on the water, book a dolphin watching cruise, try paddleboarding in Isle of Wight Bay, or cast a line from the Oceanic Fishing Pier, which stretches into the inlet near the southern end of town.
After soaking up the beach atmosphere, it is only a short drive across the Verrazano Bridge to Assateague Island, where wild horses, quiet beaches, and protected coastal landscapes bring your road trip to an unforgettable finish.
8. Assateague Island National Seashore
Just across the bridge from Ocean City, Assateague Island National Seashore stretches for 37 miles along Maryland and Virginia, protecting sandy beaches, rolling dunes, salt marshes, maritime forests, and the famous wild horses that freely roam the island.
Spend your time relaxing on the beach, paddling through quiet bays, fishing, or hiking trails like the 0.5 mile Life of the Forest Trail, where signs explain how plants and animals survive in this constantly changing coastal environment.
Keep your camera ready because you might spot wild horses grazing beside the road, white-tailed deer wandering through the trees, sika deer in the marshes, or shorebirds searching for food along the shoreline.
Whether you stay for a few hours or camp beneath the stars, Assateague Island is the perfect ending to this Maryland road trip, combining incredible wildlife, peaceful scenery, and one of the East Coast’s most unforgettable coastal landscapes.
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