Discover why you’re always welcome in Maryland

Discover the Great Chesapeake Bay Loop

While some may think of Chesapeake Bay as a wedge that has split the state into its Eastern Shore on one side, and central and southern Maryland on the other, for centuries this major waterway was actually a highway that connected the small towns and cities along its coast. Today, the Great Chesapeake Bay Loop is a collection of communities and people who live along its shores and keep the area’s more than 300 years of history and culture — and ties to the water — alive.

You can experience it by heading out on the water with Chesapeake Bay Storytellers, a selection of tour companies and institutions trained to lead groups out on the bay and along its shores to learn about its history, nature, ecology and more. Among them are storyteller Capt. Dan Hamilton of Megalodon Adventure Charters, who takes guests on kayak trips, dolphin excursions, fishing charters or hunts for giant fossilized shark teeth and other ancient artifacts, and storyteller Jill Ferris of the Chesapeake Bay Maritime Museum, where well-worn stories about sailors are intermixed with shipbuilding demonstrations and sailing outings on vintage boats.

You can also discover the secrets of the bay with Watermen’s Heritage Tour, where local men and women who still make their living working the waters of Chesapeake Bay share their knowledge with visitors. At Solomons Island Heritage Tours, schoolteacher and commercial fisher Capt. Rachel Dean teaches you what it’s like to harvest blue crabs, finfish and oysters, while LochJaw Charters takes guests out on its 44-foot commercial crabbing boat, where, between setting and raising traps, you can learn about the local lighthouses or the role of the bay during the War of 1812.

Explore small towns and scenic byways

The Great Chesapeake Bay Loop is more than just tours offering insight into life on its waters, it also encompasses charming towns and cities, the traditions of locals who have lived along its shores for hundreds of years, small family run businesses, artists communities and an overall welcoming atmosphere.

The upper half of the Chesapeake Bay is home to quintessential towns like Rock Hall, where you can explore implements from the early days of oystering, crabbing, and fishing at the Waterman’s Museum. Chestertown, established in 1706, has brick sidewalks lined with quaint shops, restaurants and inns, and Kent Narrows, home to the Chesapeake Bay Environmental Center where you can go biking, birding, hiking and kayaking.

Along the lower loop of the bay, visitors will discover historic St. Mary’s City, a living museum that is home to a reconstructed Indigenous Woodland hamlet, a tall ship, and a mid-1600s style tobacco farm. The area is also home to Leonardtown, which is popular with artisans and is home to the state’s only arts and entertainment district, and Easton, considered the cultural capital of the Eastern Shore thanks to its annual art festival, the Academy Art Museum and Avalon Theatre.

There are wide selections of scenic byways and road trips through that state waiting for you to explore — and based on various interests. History bugs will love the Star-Spangled Banner route (the national anthem was penned in Maryland), which highlights sites associate with the War of 1812, when British troops passed through the state on their way to burn Washington. Or spend a day tracing the escape route actor John Wilkes Booth used to flee Washington after assassinating President Abraham Lincoln in 1865.

Food lovers will whet their appetites following all or a portion of the Maryland Crab & Oyster Trail, which highlights delicious stops in five geographic regions of the state, highlighting everything from local harvesters and oyster bars to wharf side crab houses and food festivals. There are also hook-and-cook charters where you can prepare and eat your catch at the end of an excursion. And wine lovers will appreciate the several trails that crisscross the various regions of Maryland highlighting local vintages — some from vineyards that are centuries old.

Learn more about the Underground Railroad

One important drive to explore is the Harriet Tubman Underground Railroad Scenic Byway, which takes you along the network of trails, waterways and safe houses used by enslaved people to flee to the north in the 1800s and escape slavery. The trail is named after Tubman, the famed abolitionist who helped rescue approximately 70 enslaved people and even lived for some time in St. Catharines, Ont.

The 200-kilometre trail from Cambridge to Goldsboro along the Eastern Shore includes nearly 20 stops and takes three to four hours to compete. It includes the Harriet Tubman Museum and Educational Center, which is home to historical displays, literature and videos about slavery, the Underground Railroad, and the pre- and post-Civil War eras, and at the Harriet Tubman Underground Railroad State Park and Visitor Center, home to Immersive exhibits depict Tubman’s childhood while enslaved, her flight to freedom and her rescue missions.

Maryland is considered one of the most powerful destinations in the world when it comes to Underground Railroad storytelling, with several other sites located around the state and Chesapeake Bay. Among the network of freedom sites and tours visitors can experience are the Frederick Douglass Freedom and Heritage Trail and Tour where you walk through the historic Fells Point neighbourhood in Baltimore to see Underground Railroad sites associated with the abolitionists, and the Josiah Henson Museum and Park in Rockville where the Reverend Josiah Henson, the inspiration for Harriet Beecher Stowe’s novel “Uncle Tom’s Cabin,” lived and worked as a slave from 1795 to 1830.

As well, this year marks the 60th anniversary of the passage of the Civil Rights Act, with Maryland declaring 2024 the Year of Civil Rights. Discover more about this recent era in history at Baltimore’s Lillie Carroll Jackson Civil Rights Museum, named for and located in the former home of the freedom fighter, or by following Storyways: A Journey of Faith and Freedom, a driving tour through Wicomico, Worcester and Somerset counties on the Eastern Shore that includes significant civil rights sites such as segregated hotels, beaches and schools.

Go to VisitMaryland.org for more travel inspiration and information to plan your next trip to the state.