The Local's Complete Guide to Things to Do in Southern Maryland (2026)
"Okay, but what is there actually to do down there?"
If I had a dollar for every time someone asked me that about Southern Maryland, I could probably afford waterfront property in Solomons Island. The honest answer? Far more than most people expect — and it's better for it, because the crowds are still manageable, the prices are still reasonable, and the blue crabs are still the real thing.
This guide covers St. Mary’s County, Calvert County, and Charles County — the full tri-county stretch that makes up Southern Maryland — with specific callouts for Waldorf, La Plata, Leonardtown, Lexington Park, Prince Frederick, Solomons, California, and beyond. Whether you’re a foodie, an outdoor adventurer, a history nerd, a craft beverage enthusiast, or just a parent trying to find something to do on a Saturday, there’s a section here for you.
Whether you’re new to the area, thinking about moving here, or just figuring out what your weekends could look like, this guide pairs perfectly with my Living in Southern Maryland overview, which breaks down neighborhoods, housing, and lifestyle in more detail.
The Quick Answer: What Is Southern Maryland Like?
Southern Maryland is a region where working watermen still pull blue crabs from the Chesapeake Bay, where tobacco barns have been converted into tasting rooms, and where you can hike to ancient shark's teeth fossils in the morning and sip estate wine by the afternoon.
It spans three counties — Charles (the most suburban, anchored by Waldorf), Calvert (a long peninsula between the Bay and the Patuxent River), and St. Mary's (the most rural and historic, stretching to the tip of the state) — each with its own distinct personality and pace.
Outdoor Adventures & State Parks
Southern Maryland is one of the most underrated outdoor destinations on the East Coast, full stop.
Calvert Cliffs State Park (Lusby, Calvert County) is a must. A moderate hike through forested trails leads you to the Chesapeake Bay shoreline, where exposed cliffs reveal millions of years of fossil history — you can literally pick up Miocene-era shark's teeth off the beach. It's free, it's stunning, and it never gets old.
Point Lookout State Park (Scotland, St. Mary's County) sits at the very southern tip of Maryland where the Potomac River meets the Chesapeake Bay. It's one of the best spots in the state for fishing, crabbing, hiking, and Civil War history — the site of one of the largest Union prisoner-of-war camps during the war.
Other outdoor highlights worth knowing:
- Greenwell State Park (Hollywood, St. Mary's) — kayaking, equestrian trails, fishing, and family picnic areas along the Patuxent River
- Newtowne Neck State Park (Compton, St. Mary's) — paddleboarding paradise on Breton Bay, plus hiking and bird-watching
- Myrtle Point Park (California, St. Mary's) — serene waterfront park perfect for a quiet afternoon
- Mallows Bay Park (Nanjemoy, Charles County) — kayak among the "Ghost Fleet," the eerie remains of over 100 WWI-era wooden steamships now designated a National Marine Sanctuary
On the Water
Southern Maryland has been a waterman's territory for centuries, and that culture is very much alive. Whether you want to charter a fishing boat out of Solomons, rent a kayak at Greenwell, or hop on a Cruisin Tikis floating tiki bar cruise out of Solomons Island, the water is always on the agenda. St. Clement's Island — accessible by ferry from Colton's Point — marks the original landing site of Maryland's first colonists in 1634.
History & Heritage
If you love history, Southern Maryland is genuinely dangerous — you'll lose entire weekends to it.
Historic St. Mary's City is Maryland's first capital and one of the most significant archaeological sites in the country. It's an outdoor living history museum where you can explore reconstructed 17th-century colonial buildings, walk the grounds of the original settlement, and understand why Maryland was founded the way it was.
Sotterley Plantation (Hollywood) is a working 18th-century tidewater plantation that tells a complex, honest story about colonial Maryland, including its history of enslavement. It's one of the few surviving tidewater plantations in the country and worth several hours of your time.
Other history stops:
- Jefferson Patterson Park & Museum (St. Leonard, Calvert County) — archaeological site with 9,000 years of human history, walking trails, and rotating exhibits
- Piney Point Lighthouse Museum & Historic Park (Piney Point, St. Mary's) — climb the 1836 lighthouse for panoramic Potomac River views
- Historic Port Tobacco Village (La Plata, Charles County) — one of the oldest communities in Maryland, with a reconstructed courthouse and rich colonial-era context
- Patuxent River Naval Air Museum (California, St. Mary's) — free admission, incredible aircraft displays, and the only place in Maryland where you can stand next to a full-scale test aircraft from NAS Pax River
Solomons Island: A Town That Does Everything Right
Solomons Island in Calvert County deserves its own section because it's genuinely unlike anywhere else in the region. It's a small waterfront community at the southern tip of Calvert County where the Patuxent River meets the Chesapeake, and it punches well above its weight in terms of things to do.
The Calvert Marine Museum is world-class for a regional museum. You can see live river otters (OtterMania! is a seasonal event the kids go absolutely wild for), climb the Drum Point Lighthouse tower, and learn about the region's fossil record and maritime heritage.
For food and drink in Solomons, the options include:
- Angler's Seafood Bar & Grill — waterfront dining with daily seafood specials and a full breakfast menu
- Boomerangs Original Ribs & Seafood — a local institution since 1990, known for from-scratch sides and baby back ribs
- Tiki Bar & Grill — signature cocktails, live music, and a full menu with that unmistakable waterfront tiki energy
- Trifecta — three women, one vision, Southern Maryland favorites with a Polynesian twist; open Wednesday through Monday
- Ruddy Duck Brewery (Dowell, adjacent to Solomons) — craft beer with a waterfront view, exactly as it should be
Leonardtown: The Heart of St. Mary's County
Leonardtown is one of those small towns that consistently surprises people. The historic town square, a waterfront park with a public pier, and a genuinely eclectic local business scene make it a destination, not just a pass-through.
Shepherd's Old Field Market (SOF) is the anchor of it all — a renovated warehouse behind the Leonardtown Fire House that houses more than 50 vendors, a Botanic Deli Café, the Brudergarten Beer Garden, the Salted Scoop ice cream shop, and an axe throwing venue. It's open Tuesday through Sunday and is exactly the kind of place that makes you wonder why you ever doubted Southern Maryland.
Other Leonardtown must-visits:
- Port of Leonardtown Winery — award-winning wines from multiple local vineyards; open 7 days a week with live music on many weekends
- Jubilee Farm Fermentations — an artisanal farm winery on a historic saltwater farm along Blake Creek; open Thursdays and weekends for an unhurried, off-the-beaten-path tasting experience
- St. Mary's County Arts Council — local art, jewelry, paintings, and sculpture in the arts and entertainment district
- Fenwick Street Used Books & Music — vinyl, books, tarot cards, and author events; the kind of shop that becomes a habit
- Leonardtown Wharf Park — the perfect spot for a sunset over the bay, no agenda required
- The Butterfly Trail — an outdoor walking trail through town featuring local sculptures, landmarks, and public art
The annual End of Summer Beach Party Blowout drops 40 tons of sand right in the center of Leonardtown Square — yes, literally. If that's not a thing you need to see, I don't know what to tell you.
La Plata & Charles County: Suburban with Soul
Waldorf gets the traffic and the big-box stores, but La Plata — the county seat of Charles County — has the character.
Small-town shopping in La Plata includes:
- Bird City Records — where vinyl never died
- Kanto Games & Collectibles — trading card games, Warhammer, board games
- Dream BIG Boutique and Business Center — women's fashion and local business support
- Centerpiece Boutique and Design — trend-forward local boutique
- Market at The Charles — gourmet grocery with local and international selections
For dining in Charles County, Captain Billy's Crab House and Captain John's Crab House (established 1963) are both Southern Maryland institutions you need to experience at least once. Bollywood Masala brings authentic Indian cuisine, and Chobas African Kitchen and Bakery — the first African kitchen and bakery in Southern Maryland — is a genuinely exciting addition to the local food scene.
The Mattawoman Creek Art Center in Waldorf offers rotating exhibitions and community arts programs, and serves as a quiet cultural hub for the county.
Wineries, Breweries & the Craft Beverage Scene
Southern Maryland's agricultural roots — particularly in tobacco farming — have transitioned beautifully into a thriving craft beverage scene. Old barns are tasting rooms now, and the wines coming out of this region are winning real awards.
Wineries to Know
- Port of Leonardtown Winery (Leonardtown) — open daily; collaborates with multiple local vineyards; live music on many weekends
- Running Hare Vineyard (Prince Frederick, Calvert County) — one of Southern Maryland's most scenic estate vineyards, often described as “a little bit of Tuscany right here in Southern Maryland”; hosts tastings, live music, and private events
- Perigeaux Vineyards and Winery (St. Leonard, Calvert County) — scenic peninsula setting between Saint Leonard Creek and the Patuxent River; acres of estate vineyards
- Xella Winery and Vineyard (Mechanicsville, St. Mary's) — family-run, biodynamic-leaning farming, bold wines; open Saturdays
- Corteau Vineyards (Mechanicsville) — weekday evening hours plus weekend tastings; a local favorite for a low-key wine afternoon
- Fridays Creek Winery — a boutique winery contributing to the region's growing reputation for quality estate wines
The Patuxent Wine Trail
St. Mary's County's Patuxent Wine Trail connects multiple local wineries and is ideal for a weekend itinerary — especially in fall when the vineyards are at their most photogenic.
Craft Beer & Spirits
- Ruddy Duck Brewery & Grill (Dowell/Solomons area) — waterfront craft beer with rotating taps and live music; open daily
- Mully's Brewery (Prince Frederick, Calvert County) — a family-owned operation started in 2012 by Cindy and Jason Mullikin; a genuine community taproom with a rotating lineup of ales and lagers
- Scorpion Brewing Company — another regional craft brewery earning a loyal following across Southern Maryland
- Patuxent Brewing Company (Waldorf, Charles County) — bringing craft beer culture to the Charles County side of the region
- Tobacco Barn Distillery, Rosie Cheeks Distillery, Pathfinder Farm Distillery, and Wandering Wolf Distillery — all part of the craft spirits scene showcased each January at the Spirits of Maryland: Southern Maryland tasting event, hosted at the PAX River Naval Air Museum
Annual Festivals & Events Worth Calendaring
Southern Maryland runs a full calendar of community events throughout the year that reflect the culture and character of the region.
Some of the most popular annual events include:
- Southern Maryland Sunflower Festival at Serenity Farm in Benedict (Charles County) — held Labor Day Weekend (for 2026, September 5–6). Expect six acres of sunflowers, hayrides, a petting farm, live music, and local food vendors, with discounted advance tickets and free parking.
- Lavender Days Festival at Dixon Family Farm in St. Mary's County — held June 13–14, 2026. Maryland's only waterfront lavender farm event, featuring thousands of lavender plants in bloom, U-Cut bouquets, lavender distillation demos, and craft beverages. It sells out, so plan ahead.
- St. Mary's County Oyster Festival in Leonardtown — held each October, celebrating local oysters with food, live entertainment, and competitions.
- Spirits of Maryland: Southern Maryland — a January tasting event at the PAX River Naval Air Museum highlighting regional distilleries and craft spirits.
- OtterMania! at the Calvert Marine Museum in Solomons — a seasonal spring event centered around the museum’s beloved river otters, with family-friendly activities.
- Spring Fling in Solomons — a spring celebration on Solomons Island with vendors, music, and waterfront fun.
- Calvert County Community Resource Fair — a spring event connecting residents with local resources, organizations, and services.
The sunflower and lavender festivals alone are worth building a weekend around if you love flowers, photos, and a laid-back farm atmosphere.
Arts, Culture & Live Entertainment
The arts scene in Southern Maryland is more vibrant than the region's rural reputation suggests.
Annmarie Sculpture Garden & Arts Center in Solomons is a genuine gem — a walkable outdoor sculpture garden nested in the woods along the Patuxent River, with rotating gallery exhibitions and workshops for all ages and skill levels. It's one of those places that locals take for granted until a friend from out of town loses their mind over it.
Maryland International Raceway (Budds Creek, St. Mary's County) hosts NHRA national events and is a major regional draw for motorsports fans. If you've never watched drag racing up close, this is a solid introduction.
Above Par Golf near Leonardtown offers a different kind of afternoon for those who prefer their competition on a green.
For Families with Kids
Southern Maryland is genuinely kid-friendly, especially outdoors.
- Calvert Marine Museum (Solomons) — river otters, lighthouse climbs, hands-on fossil exhibits
- Calvert Cliffs State Park — fossil hunting on the beach is one of those childhood memories that sticks
- Junior Historian Program at Piney Point Lighthouse Museum — a four-day program for ages 8–12 with history and environmental lessons (limited spots; register early)
- Sunflower Festival at Serenity Farm — hayrides, face painting, petting farm, and free parking
- Shepherd's Old Field Market in Leonardtown — the Salted Scoop ice cream shop alone will make you the best parent in the county
For the Food Lover
Southern Maryland's food culture centers on one thing above all others: blue crabs. This is not a tourist attraction — it's a way of life. Captain John's Crab House in Charles County has been at it since 1963. T&J's Cove, The Lighthouse Restaurant and Dock Bar, and Captain Billy's Crab House are also consistently named local favorites.
Beyond crabs:
- Abell's Diner (Clements, St. Mary's) — classic American diner, no-frills, completely worth it
- Trifecta (Solomons) — Southern Maryland comfort food with a Polynesian twist
- Thai 99 (Solomons) — a family-run Thai restaurant that earns loyal regulars
- Chobas African Kitchen and Bakery (Waldorf area) — African cuisine and baked goods; genuinely exciting and unique
- Bobbi Rucci's Famous Italian Deli & Doughboys (La Plata) — a Charles County classic
Common Mistakes First-Timers Make
1. Treating Waldorf as the destination. Waldorf is a suburb with great highway access and big retail — but if you never leave Route 301, you've missed the actual Southern Maryland entirely. Get off the main road.
2. Underestimating drive times between counties. It can easily be 45–60 minutes from Waldorf to Leonardtown or Solomons. Plan accordingly when building a day-trip itinerary.
3. Missing shoulder season. Spring (April–June) and fall (September–October) are arguably the best times to be in Southern Maryland. Summer is beautiful but hot, and some waterfront spots get crowded.
4. Skipping the state parks. People drive past Calvert Cliffs and Point Lookout on the way to Ocean City without stopping. That is a mistake.
5. Assuming there's "nothing to do" in St. Mary's County. St. Mary's is the most rural of the three counties, and it is also the most distinctly Southern Maryland. The history, the water, the wine trails, and the pace of life there are exactly what people are increasingly moving here for.
People Also Ask: Southern Maryland FAQ
What is there to do in Solomons Island, Maryland?
Solomons Island offers the Calvert Marine Museum, waterfront dining (Angler's, Tiki Bar, Trifecta), Cruisin Tikis boat tours, Annmarie Sculpture Garden, Ruddy Duck Brewery, and kayaking on the Patuxent River. It's compact, walkable, and genuinely charming — plan at least half a day.
What outdoor activities are in Southern Maryland?
Hiking, kayaking, fishing, fossil hunting, paddleboarding, crabbing, and wildlife watching are all easily accessible. Calvert Cliffs State Park, Point Lookout, Greenwell State Park, and Mallows Bay Park are the top outdoor destinations.
Are there wineries in Southern Maryland?
Yes — Southern Maryland has a growing wine trail with several estate wineries including Port of Leonardtown Winery, Running Hare Vineyard, Perigeaux Vineyards, Xella Winery, and Corteau Vineyards. The Patuxent Wine Trail in St. Mary's County connects multiple stops and is especially popular in fall.
What annual festivals happen in Southern Maryland?
Major annual events include the Southern Maryland Sunflower Festival (Labor Day Weekend), the Lavender Days Festival in June, the St. Mary's County Oyster Festival in October, and Spirits of Maryland each January. The Calvert Marine Museum also runs seasonal events like OtterMania! each spring.
Is Leonardtown worth visiting?
Absolutely. Leonardtown's town square, Shepherd's Old Field Market, Port of Leonardtown Winery, Leonardtown Wharf Park, local boutiques, and a year-round event calendar make it one of the most walkable and enjoyable small towns in Maryland.
What is there to do in Charles County, Maryland?
Beyond Waldorf's retail and dining options, Charles County offers Historic Port Tobacco Village, Mallows Bay Ghost Fleet, Captain John's Crab House, La Plata's boutique shopping, Bird City Records, and Maryland International Raceway.
What is the best time of year to visit Southern Maryland?
Late spring through early fall is ideal, with peak outdoor season running from May through October. The Lavender Days Festival in June and Sunflower Festival in September are both seasonal highlights worth planning a trip around.
Ready to Make Southern Maryland Your Backyard?
If you've been reading this thinking, "Wait, this sounds like somewhere I'd actually want to live" — that's not an accident. I've been selling homes across Southern Maryland for years, and the number one thing I hear from buyers after they move here is that they had no idea how much was going on.
Whether you're exploring St. Mary's County for the rural lifestyle and water access, Calvert County for the peninsular charm and proximity to Pax River, or Charles County for the commuter-friendly location and growing amenities — each of these communities has a distinct quality of life that deserves a real conversation, not a generic search result.
I work with buyers and sellers across Southern Maryland, the broader Maryland market, and into Virginia — and my job isn't to push you anywhere. It's to make sure you understand your options clearly before you decide.
If you're curious about what life in Southern Maryland actually looks like day-to-day — or if you're ready to start the search — reach out. I'm happy to talk through the trade-offs honestly and help you figure out whether this is the right fit for your lifestyle, your budget, and your commute.
