For group travelers bitten by the history bug, Maryland makes for a trip of endless diversions. After all, this 10,460-square-mile state has been dubbed “America in Miniature” for the crucial role it has played in many of the country’s most pivotal events, from its founding onward.
Whether it’s the ratification of the treaty that ended the Revolutionary War, the epic moments that gave birth to our nation’s anthem or the legendary heroism of the woman who led so many out of slavery, Maryland’s people and places have fascinating tales to tell. String them together thoughtfully and visitors are gifted with not only an unforgettable group trip but also the story of our nation’s four-century history.
Baltimore
Maryland’s largest city was founded in 1729 as a seaport for shipping tobacco and grain, and 300 years later the Inner Harbor is still the place to be. Marquee must-sees include the 82,000-square-foot Reginald F. Lewis Museum of Maryland African American History and Culture, which offers groups tours of its 11,000-object permanent collection.
“Before the one in D.C. opened, it was the largest African American museum on the East Coast,” said Eric Masterton, Visit Baltimore’s senior director of tourism. “It was really created to inspire, so they have all these great stories about notable African American figures from Maryland, like Supreme Court Justice Thurgood Marshall and Frederick Douglass.”
Also located on the Inner Harbor, Watermark whisks group visitors away on a 45-minute cruise with narration detailing Baltimore history. Leaders can opt to book a private charter to nearby Fort McHenry, zeroing in on the War of 1812, or even arrange for a Frances Scott Key reenactor to meet their group. The valiant defense of the fort against British bombardment inspired Key to pen “The Star-Spangled Banner.” Now a national monument, the site features ranger-led flag programs and other events.
Speaking of iconic writers, Edgar Allan Poe once walked Baltimore’s streets. Groups can pay homage to him at the Edgar Allan Poe House and Museum, as well as Westminster Burying Ground and Catacombs, his final resting place. Finally, groups will want to squeeze in a visit the B&O Railroad Museum, which Masterton called “the most comprehensive collection of American railroad artifacts in the entire world.” Group opportunities include specialized tours, train rides on the first mile of track laid in the U.S. and a behind-the-scenes look at the museum’s train restoration shop.
Anne Arundel County
Annapolis, which sits on the shores of the Chesapeake Bay in Anne Arundel County, isn’t just Maryland’s state capitol. Following the ratification of the Treaty of Paris on January 14, 1784, the city served as the country’s first peacetime capital. Nowadays, it boasts more 18th-century buildings than anywhere else in the country, including the William Paca House and Garden and the Charles Carroll House. Both beautifully restored sites were home to signers of the Declaration of Independence and offer private group tours. So does the three-floor Museum of Historic Annapolis, which can build custom experiences for groups that include stops at partner attractions like the Banneker-Douglass-Tubman Museum.
Maryland’s officially recognized museum of African American history and culture, the institution is housed in the former Mount Moriah African Methodist Episcopal Church, which is on the National Register of Historic Places.
“We’re just like a time capsule here in Annapolis,” said Jana Carter, assistant director of sales for Visit Annapolis and Anne Arundel County. “You can envision the founding fathers of this nation walking the streets. It’s still the same, especially the downtown area. We really are a museum without walls.”
Of course, Anne Arundel County has more to see outside of awe-inspiring Annapolis. Carter recommends groups pay a visit to Historic London Town and Gardens, which is in Edgewater, on the South River. Founded in 1683 as the county seat, it still contains the William Brown House, built in 1760, as well as two reconstructed Colonial buildings and 10 acres of gardens and woodland.
“They welcome buses, and you can get a private group tour there,” said Carter. “It’s fantastic just sitting on the grounds and taking in the waterfront views.”
Montgomery County
Conveniently located adjacent to the nation’s capital, Montgomery is Maryland’s most populous county, but it’s much more than a well-heeled bedroom community.
“We have a lot of historic sites, both for specifically African American history and American history in general,” said Montgomery County communications coordinator Aynae Simmons. “A fun fact: The town of Brookville was once the U.S capital for a day, so we have a lot of American history that people just don’t know about.”
Groups that would like to stretch their legs should start off at the C&O Canal National Historical Park, which pays tribute to the 184-mile waterway that was used for a century to transport goods like coal and lumber. It was also utilized by freedom seekers escaping enslavement. The area boasts beautiful cascades, the Great Falls Visitor Center and replica canal boat cruises. To experience a different kind of transportation, groups should head to the National Capital Trolley Museum in Colesville. It not only highlights vintage streetcars from around the world but also gives guests the chance to ride one.
Other delights abound in Montgomery County, including Glen Echo Park. Founded in 1891 to promote cultural enrichment and education, it was home for a time to American Red Cross founder Clara Barton and later the site of Civil Rights demonstrations. Groups can attend a dance in the historic Spanish Ballroom, take in an art exhibition or ride the century-old Dentzel Carousel. Make sure to leave time for a stop at the beautifully realized Josiah Henson Museum and Park in Rockville. A formerly enslaved man who became an Underground Railroad conductor, Reverend Henson was the inspiration behind the seminal book “Uncle Tom’s Cabin.”
The Eastern Shore
Comprising nine counties that line the east side of the Chesapeake Bay, Maryland’s Eastern Shore is filled with historical treasures that offer a peek into our country’s pastoral past. Nowhere is that more true than at the Burgess Rural Living Center, which debuted in 2022 in the Somerset County Visitor Center. Free to enter, the center contains a spectacular array of early Americana ephemera collected and maintained over decades by a local farmer. Exhibits include a general store, farmhouse kitchen and a blacksmith shop.
An even more recent addition to the line-up of area attractions, the Museum of Eastern Shore Culture specializes in presenting and preserving the traditional arts of the Delmarva Peninsula, such as the famed Ward Brothers waterfowl decoys.
“It just opened in November in downtown Salisbury,” said Maryland Office of Tourism communications specialist Connie Spindler. “They look at folk art as a jumping-off point for history and heritage, and what they’re putting forward is true and authentic and inclusive of local communities. So, that’s something groups should really enjoy.”
Little else has shaped the lives of the people of the Eastern Shore the way water has, and travelers can explore its impact at St. Michaels’ Chesapeake Bay Maritime Museum. Along with 12 exhibition buildings, a lighthouse and some 100 boats, it offers groups cruises aboard historic vessels and the chance to get hands-on in the museum’s shipyard. An hour south, the Harriet Tubman Underground Railroad Visitor Center in Cross Creek honors change-making of a different kind. It focuses on lesser-known tales of the abolitionist’s early life on the Eastern Shore and is sure to “knock people’s socks off,” according to Spindler.
St. Mary’s County
Dubbed “Maryland’s original destination,” St. Mary’s County sits on a peninsula surrounded by the Chesapeake Bay and the Potomac and Patuxent rivers. Maryland’s first colonists sailed these waters, arriving at St. Clement’s Island in 1634. They soon founded St. Mary’s City, the fourth permanent settlement in British North America.
But the county’s historical offerings don’t end there.
“One of the other themes we follow is the National Park Service’s Network to Freedom sites — we have four,” said Visit St. Mary’s executive director Liz Mildenstein. “So, group travelers are going to get a lot of historical bang for their buck here.”
One of those sites is the Old Jail in Leonardtown, where Underground Railroad freedom seekers were incarcerated. Built in in 1876, it’s now home to a group-friendly museum. Meanwhile, St. Clement’s Island Museum memorializes the landing of a contingent of mainly Catholic colonists who journeyed across the ocean in search of religious tolerance. Although the museum will close later this year for renovations, a water taxi will remain available to ferry groups to the island, which additionally features a replica of the Blackistone Lighthouse. It’s one of four in the county; light lovers will also want to visit Piney Point Lighthouse, the Potomac’s oldest.
But the county’s biggest attraction probably remains Historic St. Mary’s City, a living history museum and the location of Maryland’s first capital. In addition to showstoppers like the replica of the Dove, one of the settlers’ ships, there are archaeological sites.
“They’re still digging for more,” Mildenstein said. “So, you can do tours to those sites and talk to archaeologists, which I think groups will find really interesting.”