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By Dylan Roche
Photography by Jay Fleming
A picturesque region stretching between the Chesapeake Bay and the Atlantic Ocean, the Eastern Shore of Maryland offers a combination of natural beauty and historic charm. It’s a place where conservation reserves sit alongside quaint towns, where you’re as likely to see a blue heron as you are to see a traditional skipjack, and where there is no shortage of opportunities to explore, learn, or be entertained.
Because Maryland’s Eastern Shore was one of the first places settled by Europeans, it’s rich in history, with some buildings dating back to the Colonial Era. The region’s Dorchester County is also the birthplace of renowned abolitionist Harriet Tubman, who led enslaved people to freedom along the Underground Railroad. The region’s waterways, marshes, forests, and fields provide a haven for a wide variety of flora and fauna. Nature enthusiasts can spend hours birdwatching, hiking, sailing, or crabbing, possibly even seeing a bald eagle or a wild pony. When you leave the outdoors and return to society, you’ll find the many small towns of the Eastern Shore offer boutique shopping, waterfront dining, vibrant arts scenes, and all kinds of culture to take in!
Whether you’re making a weekend out of it or simply taking a day trip, the Eastern Shore boasts excursions that will leave lasting memories for people of all interests. Explore history, get lost in nature, and stop by a museum. Here are several places you won’t want to miss.
1. Eastern Neck National Wildlife Refuge
This 2,200-acre island off mainland Rock Hall serves as a refuge for migratory birds, with brackish marshes, ponds, forests, and grasslands you can explore. www.fws.gov/refuge/eastern-neck
2. Blackwater National Wildlife Refuge
This avian refuge boasts one-third of Maryland’s tidal wetlands, the highest concentration of nesting bald eagles on the Atlantic coast, and the largest population of the formerly endangered Delmarva Peninsula fox squirrels. www.fws.gov/refuge/blackwater
3. Wye Island
Tucked away in the tidal recesses of the Chesapeake Bay, this reserved area serves to stabilize 30 miles of shoreline threatened by erosion and offers a network of trails for hiking and nature viewing. www.visitmaryland.org/listing/attraction/wye-island-natural-resource-management-area
4. Terrapin State Park
This park combines a compact network of trails through forests, wetlands, and a stretch of sandy beach along the Chesapeake Bay—perfect for hikers who want to take a swim afterward. www.visitmaryland.org/listing/attraction/terrapin-nature-park-and-beach
5. Elk Neck State Park
Set on a peninsula formed by the Chesapeake Bay on one side and the Elk River on the other, this state park is a multi-use nature haven with an extensive campground, making it a great choice if you can’t do everything in one day. dnr.maryland.gov/publiclands/pages/central/elkneck.aspx
6. Assateague Island National Seashore
This renowned island encompasses 37 miles along the Atlantic Ocean, where wild horses roam the pristine beaches. www.visitmaryland.org/listing/attraction/assateague-island-national-seashore
7. Tuckahoe State Park
Perfect for boating and fishing, this park offers a 60-acre lake surrounded by wooded marshland. dnr.maryland.gov/publiclands/Pages/eastern/tuckahoe.aspx
8. Chesapeake Country Mural Trail
Tour Dorchester County by visiting these eight murals painted by nationally recognized artist Michael Rosato, each of which pays tribute to a noteworthy aspect of local culture or history. www.visitdorchester.org/chesapeake-country-mural-trail
9. Tilghman Watermen’s Museum
Explore the culture of the Chesapeake Bay’s watermen through exhibits showcasing their tools, traditions, and tales. This museum features not only artifacts but also artwork that pays tribute to the lifestyle of these skilled mariners, all on a picturesque waterfront campus. www.tilghmanmuseum.org
10. Academy Art Museum
Based in Easton, this museum houses exhibits that include more than 1,700 works dating from the 17th century to today. Take a tour or participate in an art class. www.academyartmuseum.org
11. Classic Motor Museum
Learn about our nation’s heritage of automotive innovation by seeing one of the ever-evolving exhibits of these mint-condition classic cars, including pre- and post-WWII automobiles, mid-century muscle cars, vintage trucks, and much more. www.classicmotormuseum.org
12. Harriet Tubman Underground Railroad Visitor Center
Learn about the life of renowned abolitionist Harriet Tubman through an immersive experience that includes interactive exhibits and educational programs detailing her work leading enslaved people to freedom along the Underground Railroad. www.harriettubmanbyway.org/harriet-tubman/#visitorcenter
13. Stanley Institute
Visit this historic one-room schoolhouse where Black children learned throughout the late 19th and early 20th centuries. Gain an appreciation of what education was like for these students through preserved artifacts and interactive displays. www.visitdorchester.org/stanley-institute
14. Spocott Windmill
See a fully operational 19th-century windmill surrounded by a small historical village, including a colonial-era cottage and a one-room schoolhouse, which offers a glimpse into Maryland’s agricultural and social history. www.spocottwindmill.org
15. Oxford Museum
At this museum dedicated to one of Maryland’s oldest towns, learn about our state’s maritime heritage and colonial roots by viewing exhibits showcasing artifacts, photographs, documents, and other displays. www.oxfordmuseummd.org
16. Historic Cambridge
Officially incorporated in 1793, this quaint and charming city preserves much of its original architecture throughout a historic district spanning 40 blocks, including a bustling Main Street with options for shopping and dining. www.choosecambridge.com/221/Historic-Preservation-District
17. Historic St. Michaels
A picturesque waterfront community known for its rich maritime heritage, St. Michaels holds the distinction of being designated one of USA Today’s Top 10 Best Small Coastal Towns. Enjoy a leisurely stroll to see its historic homes, or explore by water on a boat tour. www.stmichaelsmd.com/st.-michaels-history
18. Chesapeake Maritime Museum
Whether you’re viewing an exhibit or exploring the working boatyard—where you can participate in hands-on exhibits—this museum offers an opportunity to fully immerse yourself in the history, culture, and ecology of the Chesapeake Bay region. www.cbmm.org
19. Oxford-Bellevue Ferry
Take a trip across the Tred Avon River aboard one of the oldest privately-operated ferries in the country. You’ll see picturesque views of nature as well as charming historic towns. www.visitmaryland.org/listing/attraction/oxford-bellevue-ferry-oxford
20. Accohannock Water Trail
Kayak or canoe along the tranquil waters of East Creek off Bending Water Park, where you can take in the region’s pristine landscape and see diverse wildlife in its natural habitat. www.somersettrailmix.com/kayaking-trails/accohannock-water-trail-marion
21. Sultana Sails
Enjoy a scenic view of the Chester River while learning about 18th-century maritime life aboard the Sultana, a meticulously crafted replica of a 1768 schooner where passengers can have a hands-on experience. www.sultanaeducation.org/public-sails
22. Patriot Cruises
Get out on the Miles River to see St. Michaels and the diverse wildlife of surrounding natural areas aboard one of these narrated cruises. www.patriotcruises.com
23. Bordeleau Winery
This serene vineyard sits along the Wicomico River and offers a natural ambiance and a breathtaking view as you enjoy tastings of its award-winning wines. www.bordeleauwine.com
24. Downtown Berlin
This historic city offers a little bit of everything when it comes to shopping and dining. A huge draw is its thriving arts scene, with its many galleries and live music venue. www.berlinmainstreet.com
25. Blue Elk Vineyard
This vineyard occupies 14 rolling acres along the Elk River, producing distinct grapes as unique as its barnyard-to-beach atmosphere. Enjoy the view of the water while you sample wine or cider in a tasting room converted from a 1930s horse barn. www.blueelkvineyard.com
Explore more places
www.wicomicotourism.org/things-to-do/attractions | www.visitmarylandscoast.org | www.downtownsnowhill.org www.visitdelaware.com/beaches/lewes/things-to-do | www.tourtalbot.org/things-to-do
© Annapolis Home Magazine
Vol. 15, No. 4 2024