Top Attractions and Activities
Near Your Second Home
in Southern Maryland

A second home in Southern Maryland is your base and gateway to endless adventures. When you buy a home in Southern Maryland, you gain access to a raft of activities and adventures. Here are some of the top attractions and activities that make Southern Maryland an exceptional place to own a property.

Outdoor Activities

From breathtaking cliffs to serene riverside trails, the region offers countless ways to enjoy the outdoors.

Calvert Cliffs State Park, located along the Chesapeake Bay, is for hikers, fossil hunters, and outdoor enthusiasts. Its towering cliffs, formed 10 to 20 million years ago, hold fossils of ancient sharks, whales, rays, and giant seabirds. The park features a sandy beach accessible via the 1.8-mile Red Trail, a freshwater fishing pond, and 13 miles of hiking trails. While the beach is perfect for exploration, access beneath the cliffs is restricted due to erosion, and fishing requires a Maryland non-tidal license for visitors 16 and older.

Myrtle Point Park is a 192-acre oasis along the Patuxent River that offers nature trails, picnic spots, and breathtaking views. Just a short drive from downtown Leonardtown, this peaceful park ranks high on the list because of its pristine shoreline, lush tidal wetlands, and archaeological sites dating back over 9,000 years. The park offers over seven miles of scenic trails through its forests and wetlands, plus two miles of waterfront for sunbathing, swimming, or kayaking.

Also located along the picturesque Patuxent River, the 500-acre Jefferson Patterson Park & Museum (JPPM) is a must-visit destination in Southern Maryland. JPPM is home to over 70 archaeological sites that tell stories dating back 10,000 years, from prehistoric times to the Colonial era.

Mallows Bay Park offers history, wildlife, and outdoor recreation, all in one place. Designated as Maryland’s first National Marine Sanctuary in 2019, Mallows Bay Park is famous for the “Ghost Fleet,” which consists of nearly 200 historic shipwrecks, including over 100 World War I-era steamships. Visitors can explore the park through kayaking tours around the Ghost Fleet, hiking trails with interpretive signs, or relaxing wildlife watching along the shore. The calm waters are perfect for fishing, and a small boat ramp makes it easy for paddlers to enjoy the sanctuary.

As an area rich in history and culture, Southern Maryland is a destination for exploring stories, landmarks, and traditions. Here are some of the historical and cultural attractions in Southern Maryland:

Historic St. Mary’s City is Maryland’s first colonial capital and one of the most significant historical landmarks in the United States. The state itself manages the living history venue, which features interactive exhibits, archaeological discoveries, and insights into early colonial life. 

Explore the Chesapeake Bay’s prehistoric past, natural history, and maritime heritage at the Calvert Marine Museum. Located in Solomons, this family-friendly destination features interactive exhibits, live river otters, and the largest collection of Miocene fossils outside the Smithsonian. Visitors can also climb the Drum Point Lighthouse for stunning views, watch paleontologists uncover fossils, and explore the iconic Chesapeake workboats.

A must-visit for history buffs interested in the Civil War era, the Dr. Samuel A. Mudd House & Museum gives visitors a look into the Victorian-era home where Dr. Mudd treated John Wilkes Booth after President Lincoln’s assassination. Guided tours reveal the Mudd family’s story, Booth’s escape, and the events of that night. 

Dining

When it comes to shopping and dining, Southern Maryland has everything you need, from fresh seafood to cozy wineries and bustling retail centers. 

Since 1963, Captain John’s Crab House has been a beloved destination for fresh, Southern Maryland-style seafood. From all-you-can-eat shrimp to expertly seasoned king crab legs, every meal here is a treat.

A favorite among residents and visitors, Sweetbay Restaurant is a neighborhood gem that makes you feel right at home. Whether you’re there for a casual brunch or dinner, their well-crafted menu is sure to please. Some of the restaurant’s bestsellers are their seafood linguine, poke nachos, and crab-topped oysters.

La Vela Italian Restaurant brings the vibrant flavors of Southern Italy to the heart of Southern Maryland. Try starting with the fresh, pillowy bread rolls, then move on to the standout dishes like its swordfish special and fettuccine bolognese. The restaurant’s cream of crab soup is a local favorite.

Nightlife and Entertainment

Southern Maryland’s nightlife and entertainment scene offers a mix of excitement and relaxation, perfect for a day out or to enjoy the night. From live baseball games to thrilling drag races and cozy neighborhood bars, there’s something for everyone to enjoy here.

Catch a Southern Maryland Blue Crabs baseball game for an evening of family-friendly entertainment. As part of the Atlantic League of Professional Baseball, the Blue Crabs deliver high-energy games with over 70 home games per season.

For adrenaline-pumping action, head to Maryland International Raceway, the region’s premier drag racing venue. Located in Mechanicsville, this top-notch track hosts over 100 events annually and has some of the most exciting drag racing in the country. 

If you’re looking for a slice of paradise in Solomons, MD, the Tiki Bar & Grill is the spot. This seasonal gem, open from April through October, combines waterfront views, vibrant tiki vibes, and a stellar drinks menu. Kick back with live music, savor bites like fried pickles and mozzarella sticks, and don’t miss out on their signature Mai Tais. The mahi tacos, beach-themed cocktails, friendly service, and fun atmosphere will keep you coming back for more.

Annual Events and Festivals

Southern Maryland has a calendar of events that celebrate the region’s rich history, culture, and community spirit. Here are some must-visit events:

• Southern Maryland Heritage Festival: Hosted at Historic Sotterley, the Southern Maryland Heritage Festival is a two-day celebration of the region’s rich history, culture, and cuisine. Live music across multiple stages, artisanal vendors, and historical exhibits are just some of the highlights that attendees can look forward to.
• St. Mary’s County Fair: Every September, St. Mary’s County Fairgrounds comes alive with thrilling rides, fun games, delicious fair food, and live music. This four-day event also features a special Open Horse Show.
• ArtsFest at Annmarie Sculpture Garden: Held annually at the Annmarie Sculpture Garden in Solomons, ArtsFest brings together over 170 accomplished artists, along with 4 stages hosting over 30 musical performances.

Find Your Escape in Southern Maryland

Southern Maryland is more than just a destination—it’s a lifestyle filled with attractions and activities that make every visit unforgettable. When you’re ready to find your perfect second home in Southern Maryland, McNelis & Associates of Berkshire Hathaway HomeServices PenFed Realty is the real estate team to call.

With over 30 years of experience and a deep understanding of the Chesapeake Bay lifestyle, Chris McNelis and her expert team are the best real estate agents to help you navigate the Southern Maryland market. Whether you’re looking for a peaceful retreat or a smart investment, the team has the guidance and expertise you need to buy Southern Maryland real estate. Call 240-561-3149 today or send an email to schedule a consultation.