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Places Welcoming You

A map of Maryland showing a route through Baltimore.

The rare vacation destination that truly offers something for everyone, Maryland is home to historic cities, quiet coastal outposts and a breezy, easy-going attitude that ranks it high among the East Coast’s most pleasant stopovers. Whether you’re wandering white-sand beaches or charming cobblestone streets, a visit here feels like stepping back to a simpler time. It doesn’t hurt that some of the nations’ most unique and impressive historic sites dot the route. From Lexington Park to Greensboro, make the most of the mid-Atlantic on this epic trip around Chesapeake Bay.

1) Lexington Park

Starting Point

One of the most southern points of the Bay’s western shore, Lexington Park is the perfect jumping off point for exploring the Chesapeake region. First-timers should start at the famed Patuxent River Naval Air Museum to learn more about the area’s longtime dedication to aviation research and development. More than 25 unique aircraft are on display at the museum. From there, Point Lookout State Park, which juts out on a peninsula between the bay and the Potomac River, serves up nature and history galore. Marsh walks, an environmental center and a Civil War museum highlight the best of the sprawling park, while walks like the Periwinkle Point Trail give visitors the chance to explore at their own pace. Paddling, waterfowl hunting and fishing are also popular pastimes.

A single-masted sailboat glides past a church with New England-style spire.


2) Annapolis

Drive 66 miles • 1 hour, 32 minutes

Sixty-five miles up the coast, the state capital of Annapolis on the Chesapeake Bay welcomes visitors with an eye for sailboats and sandy beaches. One of the nation’s most historic cities, it’s easily walkable and many tourists are content to explore the charming colonial architecture and cobblestone streets of the downtown district, but for those seeking a different perspective, there’s no place better than Sandy Point State Park just east of town. First opened in 1952, the park offers boat rentals, sailing, a nature center and more. Head to the rock jetties off South and East beaches for some of the best fishing and birdwatching in the park. No trip to Annapolis would be complete with a visit to the city’s most famous landmark, the Naval Academy. The singular experience includes a film and guided tour that puts you in the shoes of the country’s newest midshipmen. Learn how the training at this world-famous academy shapes naval leadership for years to come.

3) Woodbine

Drive 53 miles • 55 minutes

About an hour inland, the rural town of Woodbine is home to one of Maryland’s most unexpected attractions, the Days End Horse Farm. Home to nearly 150 animals on a rotating basis, the farm is renowned for rescuing neglected and injured horses and nursing them back to health for adoption. Visitors can tour the facilities and learn more about equine neglect and rehabilitation, as well as volunteer with the one-of-a-kind animals and their caretakers. After a day on the farm, relax at the award-winning Black Ankle Vineyards in nearby Mt. Airy. Built on a foundation of family-first sustainability, the vineyard has been listed as one of the 100 best in America and offers regular tastings of their latest vintage.

Recommended Stopovers

Ramblin’ Pines Family Campground & RV Park • Woodbine, MD – (410) 795-5161

4) Baltimore

Drive 33 miles • 39 minutes

One of the great port cities of the Industrial Age, Baltimore has reinvented itself as a entrepreneurial and neighborly destination, with top-notch attractions, welcoming boutiques, and a low-key charm you won’t find anywhere else. From Camden Yards to the National Aquarium, there’s plenty to keep you busy, but visitors who want a new perspective on the historic locale should join a kayak tour of the iconic Inner Harbor. Family-friendly museums, scenic islands and impressive naval vessels are easily accessible as you paddle the popular shoreline route. History buffs should extend their trip with a visit to Fort McHenry in the Locust Point neighborhood. A victory flag flying over the fort during the War of 1812 inspired Francis Scott Key to pen “The Defence of Fort M’Henry,” a poem that was later put to music and renamed the “Star Spangled Banner,” America’s national anthem.

5) Elkton

Drive 61 miles • 1 hour, 5 minutes

Sixty miles north along U.S. Route 40, a stretch of colonial highway that passes rolling hills and scenic shoreline, the quaint town of Elkton sits at the headwaters of the Chesapeake Bay. Home to antique shops, galleries and cafes, the town’s Main Street has old-school allure, but it’s the picturesque countryside that’s the biggest draw. Fair Hill Stables offers the chance to explore the tranquil surrounds on horseback as you navigate trails that range from beginner to experienced. For a dose of local history, try the Sheriff John F. DeWitt Museum, which is run by the county historic society and features military memorabilia from the Revolutionary War to today.

Two anglers sit in a powerboat in a river with tall reeds growing on the bank.


6) Greensboro

Drive 50 miles • 1 hour, 7 minutes

Nestled on the banks of the Choptank River, the small town of Greensboro is a paradise for anglers in search of serene water and plenty of good fishing. Boat launches are abundant on the 71-mile tributary, as are fishable piers, shore spots and charter companies that can guide you to the best eddies and pools. From bass to bluefish, perch and catfish, the river draws locals from across the state hoping to cash in on the trophy-size yields. If even bigger game is on your radar, nothing beats a day downriver, where the boating, watersports, and, of course, fishing are among the best in the country. Aim for striped bass, flounder and rockfish as you explore the waters leading to the Chesapeake. For something quieter, nature lovers can head upriver to the Pelot Bird Sanctuary to see great blue herons.

Recommended Stopovers

Holiday Park Campground • Greensboro, MD – (410) 482-6797