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If you’re like me and crave a break from the hustle and bustle, Southeast Maryland offers some of the most secluded and charming towns I’ve ever explored. Nestled along the Chesapeake Bay and amid sprawling marshlands, these hidden gems provide a peaceful retreat filled with natural beauty and rich history.
From tiny fishing villages accessible only by boat to quiet coastal communities with storied pasts, each location offers a unique escape.
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Whether you’re seeking solitude, stunning waterfront views, or a tight-knit community spirit, these ten secluded towns have something special. Join me as I countdown my top picks for places where you can truly get away from it all in Southeast Maryland.
10. Wenona
With a population of just over 100 residents, Wenona is a tiny fishing village that captures the essence of seclusion. I find its quiet streets and close-knit community refreshing—a stark contrast to busy urban centers. Fishing is the lifeblood here, and you can often see watermen heading out on their boats at dawn.
Activities include crabbing, fishing, and simply soaking in the expansive views of Tangier Sound. There’s a simplicity to life in Wenona that I truly appreciate, and the sunsets over the water are absolutely breathtaking.
What makes Wenona particularly secluded is its location at the southern tip of Deal Island, accessible by a single road that feels like it’s leading you to the edge of the world.
Where is Wenona?
Wenona is situated at the very end of Deal Island Road in Somerset County, surrounded by the waters of the Chesapeake Bay. Its remote location means there’s minimal traffic and few visitors, enhancing its peaceful atmosphere.
The town is about 30 miles southwest of Salisbury, but the winding roads and coastal landscapes make it feel much farther from modern life. Reaching Wenona involves a scenic drive over Deal Island Bridge, and as you continue south, the world seems to slow down—a perfect setting for those seeking solitude.
9. Wingate
Wingate is a small community of around 70 people, tucked away in Dorchester County’s vast wetlands. I love how the town is enveloped by the Blackwater National Wildlife Refuge, making it a haven for nature enthusiasts like myself.
Birdwatching is exceptional here, with opportunities to see bald eagles, herons, and countless other species. The primary industries are fishing and crabbing, echoing the town’s deep connection to the Chesapeake Bay.
Wingate’s sparse population and expansive natural landscapes offer unparalleled privacy and a chance to reconnect with nature in its purest form.
Where is Wingate?
Located along the eastern shore of the Chesapeake Bay, Wingate is accessible via Maryland Route 335. Its remote position amidst miles of wetlands and waterways enhances its seclusion.
The town is approximately 20 miles southwest of Cambridge, but the journey through serene landscapes makes it feel much more isolated. Getting to Wingate involves traversing quiet country roads, and as you approach, the modern world fades away—ideal for a quiet retreat.
8. Piney Point
Piney Point is a quiet coastal town with a population of around 800 residents. I was enchanted by its historic lighthouse, one of the oldest on the Potomac River, which adds a nostalgic charm to the area. The town offers secluded beaches perfect for peaceful walks, fishing, and kayaking.
Maritime activities are central here, with many locals involved in fishing, boating, and oyster harvesting. What sets Piney Point apart is its serene waterfront and the absence of commercial overdevelopment, allowing me to enjoy the unspoiled beauty of the Chesapeake Bay’s tributaries.
Where is Piney Point?
Nestled in St. Mary’s County, Piney Point sits at the southernmost tip of Maryland’s Western Shore. Its location on the Potomac River, just before it meets the Chesapeake Bay, contributes to its secluded atmosphere.
The town is about 75 miles south of Washington, D.C., but feels worlds away due to the surrounding waterways and rural landscapes. Access is via Maryland Route 249, which winds through quiet, wooded areas—making the journey to Piney Point a tranquil experience in itself.
7. Fishing Creek
With a population hovering around 150, Fishing Creek offers a true escape into nature. I appreciate the expansive natural landscapes here, including vast marshlands and open water views. The town is part of Hoopers Island, known for its historic fishing villages and unobstructed sunsets over the Chesapeake Bay.
Fishing and crabbing dominate the local industry, and there’s a sense of timelessness as you watch the watermen at work. The sparse population and the surrounding environment provide unparalleled privacy, making it a perfect spot for those seeking solitude.
Where is Fishing Creek?
Fishing Creek is located on Middle Hoopers Island in Dorchester County, accessible via Maryland Route 335 and Hoopers Island Road. The town is about 25 miles south of Cambridge, but the series of bridges and causeways you cross to get there enhance its remote feel.
The drive itself is scenic, with water on both sides and wildlife all around. Fishing Creek’s position between the Honga River and the Chesapeake Bay contributes to its seclusion, making it a hidden gem along Maryland’s Eastern Shore.
6. Dameron
Dameron is a peaceful locale with a population of roughly 200 people, enveloped by forests and waterways. I find its tranquility unmatched, with plenty of opportunities for kayaking, hiking, and birdwatching. The town is near Point Lookout State Park, where you can explore Civil War history and enjoy pristine beaches.
Agriculture and fishing are prominent industries, reflecting the area’s rural roots. Dameron’s seclusion comes from its distant position from major roads and towns, offering a serene environment away from the bustle.
Where is Dameron?
Situated in St. Mary’s County at the southern end of Maryland’s Western Shore, Dameron is reached via Maryland Route 235. The town is approximately 80 miles south of Baltimore, but the drive through rolling farmlands and forests makes it feel like a different world.
Its proximity to the Chesapeake Bay and lack of commercial development enhance its secluded vibe. Getting there involves navigating quiet country roads, making the journey as calming as the destination itself.
5. Neavitt
Neavitt is a picturesque waterfront community with a population of around 120 residents. I was charmed by its winding roads and classic Maryland farmhouses set amid vast open spaces. Boating, fishing, and cycling are popular activities, thanks to the town’s location along the shoreline of the Choptank River.
The main industries are maritime in nature, including boatbuilding and oyster farming. Neavitt’s seclusion is due to its position at the end of a peninsula, surrounded by water on three sides and accessed by a single road.
Where is Neavitt?
Located in Talbot County, Neavitt lies about 14 miles southwest of Easton and is accessible via Route 579. The town sits on the tip of a peninsula between Broad Creek and the Choptank River.
Its remote location, combined with the surrounding waterways, makes it feel isolated from the rest of the Eastern Shore. The drive to Neavitt takes you through scenic farmlands and forested areas, enhancing the sense of escape. It’s a destination where the journey is just as enjoyable as the arrival.
4. Elliott Island
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Unwind in Elliott Island, is a hidden gem with a population of fewer than 100 people. I find its rustic charm and natural beauty incredibly soothing. Surrounded by wildlife refuges like Fishing Bay, the area is perfect for kayaking, birdwatching, and photography.
The community is tight-knit, with fishing and crabbing forming the backbone of local industry. Elliott Island’s seclusion comes from its location amid vast marshlands, accessible by a single, winding road that often feels like it’s leading you away from civilization.
Where is Elliott Island?
Elliott Island is nestled in Dorchester County, at the end of Elliott Island Road off Maryland Route 335. The town is about 30 miles south of Cambridge, but the remote wetlands and lack of nearby towns make it feel much further away.
The drive includes stretches of road flanked by marshes and waterways, contributing to the area’s isolated feel. Reaching Elliott Island involves immersing yourself in nature, making it an ideal spot for those looking to truly disconnect.
3. Hoopers Island
Experience the quiet allure of Hoopers Island, a chain of three islands with a combined population of around 400 residents. I was captivated by the historic fishing villages and the unobstructed views of Chesapeake Bay sunsets.
Fishing, crabbing, and oystering are the main industries, continuing traditions that span generations. Activities include visiting local crab houses, exploring small museums, and enjoying the abundant wildlife. The islands’ remoteness, connected to the mainland by bridges, adds to their secluded charm.
Where is Hoopers Island?
Hoopers Island is located in Dorchester County, south of Cambridge, and is accessible via Hoopers Island Road off Maryland Route 335. The islands stretch southward into the Chesapeake Bay, enhancing their isolation.
The drive includes crossing historic bridges with panoramic water views, reinforcing the feeling of leaving the mainland behind. Hoopers Island’s unique geography and limited accessibility make it a perfect getaway for those seeking peace and a connection to Maryland’s maritime heritage.
2. Taylors Island
Discover the serene landscapes of Taylors Island, home to about 170 residents. I appreciate the sprawling acres of untouched land meeting peaceful waterfront views. Outdoor activities abound, including hiking in the Taylors Island Wildlife Management Area, kayaking, and fishing.
The community has a rich history, with several sites listed on the National Register of Historic Places. Taylors Island’s seclusion is a result of its geographic isolation, with the island only accessible by a single bridge, ensuring a tranquil environment.
Where is Taylors Island?
Taylors Island is part of Dorchester County and is located west of Cambridge, across the Little Choptank River. Accessible via Maryland Route 16 and the James Causeway Bridge, the island is about 15 miles from the mainland.
The surrounding waterways and the absence of major roads contribute to its secluded feel. The journey to Taylors Island takes you through scenic countryside and calm waters, making it a peaceful escape from everyday life.
1. Smith Island
Smith Island tops my list with its remote charm and unique way of life. Home to around 250 residents, this secluded community is accessible only by boat, which to me adds to its appeal.
Surrounded by the Chesapeake Bay’s tranquil waters and rich marshlands, the island is known for its traditional watermen culture and the famous Smith Island Cake.
Activities include exploring the small villages of Ewell, Rhodes Point, and Tylerton, kayaking through marshes, and birdwatching. The main industries are crabbing and oystering, and the lack of cars and roads gives the island a peaceful, timeless quality.
Where is Smith Island?
Located about 12 miles west of Crisfield in Somerset County, Smith Island sits in the middle of the Chesapeake Bay. Its isolation is amplified by the fact that it’s only reachable by ferry or private boat, with daily ferries departing from Crisfield.
The island’s seclusion is due to its remote location and the surrounding expanse of water, which creates a barrier from the mainland. Getting there involves a scenic boat ride, offering stunning views of the bay and a sense that you’re leaving the rest of the world behind—making Smith Island a truly unique and secluded destination.
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