The Other Eastern Shore

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Compelling sites and stories of Shore culture and communities can be discovered off the beaten path

At the base of the eastbound Chesapeake Bay Bridge, a sign welcomes visitors to Queen Anne’s County, the gateway to the Eastern Shore. For many who brave the bridge, especially in summer, the Shore is synonymous with waterside restaurants, dock bars, marinas, crab feasts, and work boats tying up to drop off a day’s catch. Further down Route 50 in Talbot County, a weekend in the golden triangle of Easton, Oxford, and St. Michaels is the epitome of a Shore tour. 

But there's more to Maryland’s Eastern Shore. 

It’s a land of historic manor houses, grassroots airports, and museums that honor war heroes, founding families, local history, baseball heroes, and even mermaids. Take a detour off the highway, visit the other Eastern Shore, and discover much more about the Land of Pleasant Living. We take a tour, county-by-county, visiting sites within each. 

QUEEN ANNE’S COUNTY

Kennard African American Cultural Heritage Center

410 Little Kidwell Avenue, Centreville

When Lucretia Kennard became Queen Anne’s County Superintendent of Colored Schools in 1919, the Centreville Colored Industrial High School was the county’s only high school for African American students. Because Kennard saw the need for a high school with standards comparable to other county schools, she rallied local African American community members “who put their nickels and dimes together” to pay for the land, and later for the building’s lighting. In 1936, three years after her death, Kennard High School opened its doors. Thanks to a dedicated committee of alumni, teachers, and community supporters, the original Kennard High School is now the Kennard African American Cultural Heritage Center. It serves as a museum of African American life in Queen Anne’s County, with permanent displays of watermen, historic black communities, one-room schools, businesspeople, teachers, and veterans. It’s a gathering place for community events and the site of the annual Juneteenth celebration. While you’re there, be sure to visit one of the original classrooms, a space so small the math teacher taught from the room’s doorway. Look through 1950s-era yearbooks, graduation programs, and photos of original teachers, and former students. You’ll find images of school clubs, sports teams, and prom photos. Kennard is open for tours on the first Saturday of each month from 10 a.m. until 2 p.m. from May until October. Click here for more information on Kennard, its exhibits, and special programs. 

Kent Island Heritage Society

641 Dominion Road, #2703, Chester

Centuries before the Isle of Kent became a waterfront tourist destination, it was home to the Matapeake Indians. It became state’s first English settlement and was at one time a part of Virginia. From May through November, docents of the Kent Island Heritage Society don colonial attire and take visitors on a journey through the timeline of the island’s history. Join them at Cray House, a National Historic Trust site and one of the most unique structures on the Eastern Shore. Visit the historic Christ Church, among the oldest Episcopal churches in the nation. Tour Kirwan House, home of James Kirwan; schooner captain, businessman, and leader of a protest to Washington, D.C., demanding that the War Department keep a naval training base off Kent Island. The Old Stevensville Post Office and Train Depot round out the tour. The Kent Island Heritage Society shares this history with visitors on the first Saturday of every month from May through November, from 12 noon until 4 p.m. Click here for more information on Kent Island history, tours, and special events.

KENT COUNTY

Massey Air Museum

33451 Maryland Line Road, Massey

If you’re fascinated by flight and rural grassroots airports, take a detour off Route 213 to the Massey Aerodrome and Massey Air Museum. This cornfield-turned airport with a 3000’ grass runway was created by four general aviation pilots who wanted a place to land their planes. At Massey, take a walk through the community hangars. Go out on the grounds and sit inside the cockpits of a DC3 or AN3. Browse the library for aviation-related books and view the model display of the legendary Pan Am 314 clipper, one of the largest aircraft of its time. This display is personal; a past member of the Museum became a pilot in the early ’40s and flew the Clipper for Pan Am at the end of its era. And if you’re truly adventurous make a reservation with its owner to take flight in the open cockpit of a WWII biplane. For fun and flight, check out the Chili Fiesta Fly-in, an Antique Plane Fly-in, and the end-of-the-year Open Hangar Party. For pilots, Massey is a public airport; fly in on your own. Click here for information on tours, activities, and special events at Massey Aerodrome and Massey Air Museum.

Sumner Hall (Grand Army of the Republic #25) 

206 Queen Street, Chestertown

In 1886, Union veterans of the Civil War formed the Grand Army of the Republic, an organization founded on friendship, charity, and loyalty to the Constitution. Chestertown’s Charles Sumner Hall (GAR #25) is one of the two remaining African American halls in the United States. Named for Senator Charles Sumner, GAR#25 was chartered in 1880, constructed in 1908, and fully restored in 2014. Today Sumner Hall serves as an educational site, a social hall, a gallery, a museum, and a place to honor African American Civil War veterans and other members of the armed services. Visit this historic hidden gem when you’re in Chestertown. View the exhibits and artifacts, learn the history of African Americans in Kent County, and hear the stories of the United States Colored Troops veterans who founded Sumner Hall—your docent may be a descendant. While you’re there, ask about the Commodore Collection. In 2021, approximately 2,000 documents were discovered in the attic of a home set for demolition. Nearly 100 of the documents, dated from the 1600s to the 1800s, tell the story of free and enslaved African Americans in Kent and Queen Anne’s County. The Commodore Collection, named for the Commodore family’s role in rescuing the documents, is now owned by Sumner Hall and available for viewing online. Sumner Hall is open to the public each Saturday of the year from 10 a.m. until 1 p.m. Before your visit, visit sumnerhall.org for any schedule changes. To arrange a tour outside of regular hours, contact them at info@sumnerhall.org. Click here to view the Commodore Collection.

TALBOT COUNTY

The Oxford Museum

101 S. Morris Street, Oxford

This beautiful, historic town on the Tred Avon River is home to the Oxford-Bellevue Ferry, the oldest privately-owned ferry in use in the United States and the historic Robert Morris Inn, built in 1710 and named for founding father Robert Morris. At 101 Mill Street, The Water’s Edge Museum honors the history and lives of Maryland’s Black Founding Families and their descendants. At 101 S. Morris Street, the Oxford Museum’s window exhibit, born from Covid creativity, is a year-round invitation to learn about the past, present, and the people of the small town that was the country’s first colonial port. Inside the Museum, “From Colonial Past to Present, Oxford in Business” is its current exhibit. You’ll learn about the “glory days” of 68 businesses and 11 grocery stores to present-day establishments and Oxford’s existence as a town of 800 full-time and part-time residents. Old photos, ledgers, insurance maps, and pictures are part of the Museum’s look back in time. You’ll find out how early telephones became a marketing tool and why a grocery worker considers himself the first version of what we know today as Amazon delivery. Bring your children; the Museum offers kid-related activities connected to the current exhibit. If ice cream and history are a natural fit, visit the Scottish Highland Creamery next door, pick up a scoop, and enjoy it in the Museum’s gardens.  Click here for more information on the Oxford Museum’s exhibits and hours. Click here for information on the Waters Edge Museum’s exhibits and hours.

Town of Easton

In 1836, Frederick Douglass was jailed for a week near the Easton Courthouse as punishment for an attempted escape. In 1878, he returned to Easton as an abolitionist, author, newspaper editor, and statesman. In one day, Douglass spoke at Bethel AME Church, Asbury United Methodist Church, and the Easton Courthouse. Through the efforts of the Frederick Douglass Honor Society, a statue in his honor was placed on the Talbot County Courthouse lawn (pictured). Each September, the Honor Society pays tribute to Douglass in an all-day series of events (2024 exact date to be determined). The festivities begin with a parade and welcome ceremony at the Talbot County Court House. There’ll be a marketplace, live entertainment, and a lecture at the Talbot County Free Library by Derrick Spires, Professor of Literature in English at Cornell University. Bring your kids—the Children’s Village features hands-on activities, free coloring books, games, prizes, and photographs with Frederick Douglass. Click here to learn more about the Frederick Douglass Honor Society and its events. 

Frederick Douglass on the Hill

505 South Street, Easton

Any time is a good time to visit the mural commissioned by the Douglass family to honor his life and legacy. The mural depicts Douglass and his wife, Anna Murray Douglass, his journey from slavery to freedom, and the proud military service of Douglass’ descendants. It was painted by renowned muralist Micahel Rosato, creator of “Take My Hand,” the Harriett Tubman mural on display in Cambridge. Click here for information about Frederick Douglass on the Hill.

CAROLINE COUNTY

Museum of Rural Life Caroline County Historical Society

16 N 2nd Street, Denton

Caroline County may be the smallest of the Eastern Shore counties and the only one untouched by the waters of the Chesapeake or the Atlantic but packed in its 326 square miles is a rich history of agriculture, shipbuilding, military service, and a powerfully effective if less well-known, underground railroad network. The Museum is located in the Taylor-Brown House, owned in 1819 by merchant Solomon Brown and later by the African American Taylor family. Current exhibits honor veterans of WWI and II, for which the Museum produces its own movies starring local actors. Sea Stories features the county’s sailors, captains, and shipbuilders in the age of sail and steam. FDR on the Courthouse Green tells the story of Roosevelt’s 1938 Labor Day visit to Denton. Click here to find out more about the Museum of Rural Life and the Caroline County Historical Society.

DORCHESTER COUNTY

Handsell House

4837 Indiantown Road, Vienna

One mile off Route 50 in Vienna is Handsell House, a structure built on the Native American Chicone Village site known as Indiantown. The “old brick house at Chicone,” purchased by the Nanticoke Historic Preservation Alliance is used to interpret the life of all who lived at Handsell: Native Americans, the English, the enslaved, and later, free African Americans. On summer Saturdays Handsell House is open for tours. Docents in colonial attire demonstrate hearth cooking in the basement, basket weaving, woodworking, and other colonial crafts. The Chicone Village longhouse, the only authentically-built replica on the Eastern Shore, is open seven days a week. For one of the best, and largest, living history festivals in the region, come to Handsell House on October 14th. Immerse yourself in a full day of living history through the eyes of Native, African American, and European settlers. There’s another way to enjoy Handsell House: on travel days when you need a break before that last hour’s drive to the beach, take Exit 331 to Handsell. Get out, walk your dog, and let your kids run around the grounds. Take a smartphone tour—dial the phone number on the wayside sign and on your walk around the grounds, listen to the story of Handsell House. Click here for information on Handsell House. Click here for information on the Nanticoke River Jamboree.

CECIL COUNTY

Mt. Harmon Tidewater Plantation and Nature Preserve

600 Mt. Harmon Road, Earleville

Mt. Harmon at World’s End—it’s not the setting of a binge-worthy PBS series, but a 200-acre tidewater plantation and nature preserve. Imagine a transatlantic crossing from England to the northernmost part of the Chesapeake Bay, with nowhere else to go. The land, which seemed to exist at the end of the known world, was named World’s End by early American map makers. At the end of a two-mile tunnel of Osage trees, you’ll find 400 years of colonial history on the land occupied by Native Americans long before the arrival of Europeans. For history and nature lovers, a day pass is the best way to experience all of Mt. Harmon—the manor house, the outbuildings, the smokehouse, and the dwellings of the indentured and enslaved people who created the wealth that plantation owners enjoyed. The pass gives you all the time you’ll need to explore the grounds, gardens, and trails. Launch your kayak or canoe for a solo paddle. If a group tour is more to your liking, make plans to connect with Chestertown’s Sultana Foundation for a combined guided paddle and manor house tour. Bring a picnic and stay as long as you like. According to Paige Howard, Executive Director of the Friends of Mt. Harmon, “It’s like having your own estate without the mowing.” Summer is the high season for visitors, but Mt. Harmon’s historic, equestrian, and holiday seasonal activities take place almost all year round. Take part in the pop-up history tavern nights, the Mt. Harmon Paper Chase, the Revolutionary War and Colonial Festival, fall hayrides, and Mt. Harmon’s Bull and Oyster Roast Fundraiser. Complete the year with the Colonial Williamsburg-inspired Yuletide Festival and Holiday Marketplace. And before you know it, spring will return to Mt. Harmon. Come for a day at the races for the annual Point to Point Race—tailgate, wear a fancy hat, watch the antique carriage and hound parade, and, of course, the horses. Click here for information on Mt. Harmon, its tours, and special events.

WORCESTER COUNTY

The Mermaid Museum

4 Jefferson Street, Berlin

Nine miles from the Atlantic in downtown Berlin, the world’s first Mermaid Museums explores the international images, legends, and supposed sightings of these mythical creatures. It’s been described as a beautiful space. The best description of the magic inside the Mermaid Museum is through the words of its founder, photographer Alyssa Maloof: “The Mermaid Museum moves gently between legend, myth, fact, and fiction and provides a serene environment (it even has a calming mermaid fountain ) to meditate on this siren of the deep. The mermaid as a figure has long captivated multiple audiences from every culture around the world. Come see why at this small quirky museum. The museum features historical facts, legends, moving images, photo-ops, and even, if you squint your eyes, the famous discovered Cheeto that looks like, yes, a mermaid.” Click here for information on the Mermaid Museum’s hours and exhibits.

Ocean City Life-Saving Museum

813 South Atlantic Avenue, Ocean City 

Take some time away from the beach to visit The Ocean City Life-Saving Museum. The museum houses one of the best collections of Life-Saving equipment in the country. Learn the history of Life-Saving, the surfmen who rescued ships in distress, and the Ocean City surfer who built his own board. Look back at the history of Ocean City and Worcester County, discover the boardwalk of yesterday and the role of women in OC history. Make sure to visit the Aquarium Room’s sea creatures. On Saturdays through August, there are programs for the whole family—learn to tie a knot, brush up on beach safety, and feed sea creatures. Bring your kids to the Museum’s Little Learner program, co-sponsored by the Museum and the Ocean City Library. They’ll love the story time, hands-on activities, and live animal experiences. Museum curator Christine Okerblom encourages guests to visit year-round: “Here at the Museum, we have something to offer the entire family, from our summer programs to book signings with local authors to touring our historic Life-Saving Station. Each season brings forth different programs and events to enjoy.” Click here for information on the history, exhibits, and programs at the Ocean City Life-Saving Museum.