21 Meaningful and Blissful Things to do in St Marys County MD

WHY GO: There are bountiful things to do in St Mary’s County MD, a “can’t get there from here” section of Southern Maryland, bounded on three sides by water – the Potomac and Patuxent Rivers, and the Chesapeake Bay.

In the 1600’s, St. Mary’s drew early European settlers, most notably, a group of Catholics escaping persecution and execution in Protestant England, and you’ll never believe what archeologists found under fallow cornfields. And, as Jesuits and Plantation owners were the largest enslavers in Southern Maryland, that part of history is being told in a visceral way here as well.

Social Coffee Roasters Leonardtown MD

In the 1940’s, the population boomed after the Patuxent Naval Air Station (where NASA Test Pilots were trained) was established, and it still draws high-tech brainiacs to this quiet section of MD. Lately, the county’s only municipality – Leonardtown – has been going through a resurgence, with more and more young families moving in and attracting even more visitors.

View of oystermen off of Swanendel Inn property

But all is not just history here. You can visit wine, beer and spirits makers on a Beverage Maker Trail, “fly” an F-14 and B-1 Bomber, throw axes, be a Waterman for a few hours, peruse shops, and enjoy a suprisingly vibrant nightlife. Or – you can just escape from it all at one of two upscale boutique lodgings in bucolic settings far, far from civilization on this incredibly exciting Chesapeake area getaway.   

Things to Do in St. Mary’s County MD

Pulling crab pots, St. Mary's County MD

DO: Watermen’s Heritage Cruise

Captain Phil Langley’s ancestors “worked the tobacco fields and the water” way before the Naval Base arrived, back when the area was pure farmland. Seeing the potential in tourism, Langley transitioned to Charter Boat Captain, taking fishermen out on the Chesapeake through his Fish The Bay Charters – on his boat, the Lisa S.

Captain Phil Langley St Marys County MD

Five years ago, the State of Maryland, the Watermen’s Association, and Conservation groups formed a coalition to address the water’s dwindling natural resources – impelling watermen to get involved in tourism by offering Watermen’s Heritage Cruise. Believing that tourism was a budding local industry, Phil found a Coast-Guard inspected traditional wooden bay boat he could use for this purpose, allowing him to take a few dozen people out at a time.

Lisa S Watermen Heritage Tour MD

Phil’s tour begins after you’ve gotten lost a few times on dirt roads lined with cornfields, and a final few hundred yards on a rutted lawn drive. You’ll know you’re in the right place when you get to a delightful sandy-floored covered pavilion set with tables, a fire pit, a grill for cooking the “catch of the day” (for fishing charters), and other geegaws. Langley talks about the Chesapeake environment and conservation efforts, about crabs and oysters, and then invites you to step about his Crab Boat, the Lisa S.

Sponge crab on Watermens Heritage Tour on Lisa S

Though watermen can use “Trout Lines” in creeks and rivers, crab pots are only allowed to be set in the Bay, so out we go to pull some pots. You’ll learn the difference between young females (Sooks), mature females (Sallys) and males (Jimmys). Females have a “Capitol Building” design on their underside, while the males “apron” looks like the Washington Monument. If you’re lucky, there will be a “sponge crab” in the pot – a female with an exterior sponge-like eggsack underbelly that can contain up to 8 million eggs.

There’s plenty of opportunities to help pull up pots, though they are surprisingly heavy when heaved aboard. If the weather cooperates, you’ll head out to Point No Point Lighthouse, built in 1903 a few miles from the Potomac River in the Chesapeake on no point of land (hence the name). It’s in a romantically distressed state, without a resident keeper to take care of it, and though it was put up for auction eight years ago, the US Navy argued that it could not rest in private hands as its situated within target range. Contact Phil Langley to arrange a tour.

archeologists at work in the first Catholic Settlement in USA
Historic St. Marys City Archeologists at Work

TOUR: Historic Saint Mary’s City

One of the most important archeological digs in the United States, the 800 acre Historic Saint Mary’s City should be a pilgrimage site for every Catholic American. As Catholics were being slaughtered in England, 140 faithful arrived here in 1634, and stayed with the welcoming local tribe – the Yaocomico People – until the town and the first Catholic Church in Colonial America was built.  

St. Mary’s City grew for sixty years, then vanished into the cornfields and was lost for 200 years. By 1776, only plowed furrows marked the landscape. Now, archeologists are unearthing evidence of original structures, allowing historians to recreate buildings with complete accuracy.

Historic St Mary's City Elizabethian Style buildings

Separation of Church and State

St. Mary’s City was modeled on an Italian Baroque spoke and wheel design, with the town in the center, the Church on one extreme side and Statehouse on the other: the visceral separation of Church and State. During this time, brick was expensive, so most structures, with the exception of foundations and cellars, were made of wood – explaining the town’s disappearance. 

You’ll be surprised to find Elizabethan- style buildings here – indicating that first buildings in the new world reflected those back in England, and not the “Colonial-style” that evolved later. But what most people see first here are the “Ghost Frames” that outline the places where homes and buildings once stood.

First Coffee Shop in the New World

Part of the joy in exploring Historic St. Mary’s City is in the details about life here in the 1600’s, and comparing it to life today. Like most entrepreneurs, Garret Van Swearingen opened up a private high-end tavern and inn at a time when “Ordinary” establishments were required to provide just the ordinary basics. Swearingen’s place is but one of the fully reconstructed buildings on site – with his original cobblestone floor and brick cellar. (Many Swearingen decendents visit here to see the very first Coffee Shop in the New World).

Professional archeologists thrill to be on the threshold of new findings here, and students from all over the country work summers for college-credit during the site’s ten-week Archeological Field School. They recently unearthed the ruins of the 1636 home of Leonard Calvert – son of George Calvert who established Maryland. The last mention of this house was in 1685, so that particular find was a bonanza for historians who hope to discover other clues of Calvert’s life buried in the earth. 

Jesuit Church at Historic St Marys City rebuilt on original footprint

Jesuit Chapel Rebuilt on Original Footprint

Perhaps the most dramatic recreation on its original foundation is of the large brick Jesuit Chapel, built in 1667. There were only two historic references to this place – one that called it a “Great Brick Chapel” and another that noted “hooligans threw stones through the windows.” Historians researched Jesuit Churches in Europe at the time to get a better picture of how this one might have appeared, and based on all of this information, rebuilt the Church on its original Maryland site. It was the first place in Colonial America where Catholics could pray without fear of execution.

In later 1600’s, the practice of Catholicism in this region was banned (except in the privacy of one’s own home). So, the Jesuits took this church apart brick by brick and moved it a less conspicuous place. The St. Mary’s Sheriff (St. Mary’s was the first Sheriff’s office in the colonies, still in operation; twitter handle is @firstsheriff) locked the front door in 1695. And when reopened in 2009, the current St. Mary’s Sheriff unlocked the “same” door.

In 1990, three 17th century lead coffins were unearthed here. They were sent to the Smithsonian, and via DNA research the remains were determined to be Philip Calvert, governor and chancellor of Maryland, his wife Anne Wolsley Calvert, and their infant son. The coffins were returned to Historic St Mary’s – and the remains of the Calverts, along with 63 other souls buried in the same plot (including at least one of African decent), will also be returned from DC via horse-drawn carriages and a police escort on a date TBD.

The Dove, Historic St Mary's City MD

The Dove

Don’t leave Historic St. Mary’s City before heading down to the river to the replica of the Maryland Dove. This type of ship was the “delivery truck” of the 1600’s. Compared to the 40-ton Mayflower, which shuttled 102 passengers and supplies to the New World, the four ton two mast square rigged Dove would have had a crew of seven – no passengers.

The story of the Dove and its companion 400-ton ship, The Ark, (140 passengers, 40 crew), is a tale wonderfully told by costumed docents, like the lively Joe Greeley, Interpretive Supervisor for Waterfront. On November 22, 1633, the Ark and Dove set off from England, facing a treacherous storm two days later.

The crew of the Ark believed that they witnessed the Dove going down, but chose to continue on to the New World. A mere three months later – on February 24, both ships arrived and sailed together up the Potomac. A month later (in March 1634), they landed first on St. Clements’s Island, which was deemed too small, and then on this site. The 1978 recreation of the Dove gives visitors a good idea of the close quarters and harsh environment seafarers would have endured. Check website for dates and times open.

St Johns Museum, Historic St Marys City MD

VISIT: St. John’s Museum

Managed by Historic St. Mary’s City, but located about a mile away on the St. Mary College Campus, this museum, built on the footprint of the 1638 home of landed gentry, evokes the 17th century (though not historically accurate on the exterior). Inside this refreshing climate controlled museum, you’ll find the complete archeological remains of a stone-lined cellar, a partial room with original hearth, and mounds of dirt left to illustrate what an archeological site looks like if left alone.

The museum does an excellent and compelling job conveying day-to-day life in St. Mary’s – including sordid tales of murder, abuse, and a tight-fisted land-owner forced by the English Court to pay his maid. Plan at least an hour here if you love Historical Fiction, because, at least in 1600’s Maryland, truth was stranger than fiction. Check website for hours.

former slave plantation in Maryland open for tours
Historic Sotterley Visitors Center, St. Marys County MD

TOUR: Historic Sotterely

A tidewater plantation with Manor House and restored original outbuildings, Historic Sotterley tells the complete 300-year history of working the land here from 1699-1961, including 160 years of slavery and Reconstruction through the Civil Rights era. Set right on the Patuxent River, the original plantation encompassed 2,000 acres. Sotterley Org now administers the original structures on just 94 acres.

The first owner of the plantation, James Bowles, was an agent of Royal African Co. – a British slave trading enterprise. Slave ships arrived to a wharf on his land, and because of that, Sotterley is recognized in the Middle Passage Port Marker Project – an organization that provides a means for individuals and communities to formally honor and remember the millions of Africans who died and those who survived the transatlantic voyage known as the Middle Passage.

It’s also included in the 10 Million Names Project, and is a UNESCO Site of Memory for the Routes of Enslaved Peoples Project.

Interior of Manor house of a Maryland Farm plantation
Historic Sotterley Manor Home with Asian Staircase and Furnishings MD

The Manor House the Bowles built in 1703, with extensions added later on, showcases some of the magnificent work of skilled enslaved people. Its distinct Chinese Chippendale staircase, with rectangular design, could very well be in a contemporary home, as could the blood red painted walls favored by Mabel Satterlee Ingalls, Sotterley’s last owner.

Slave dwelling at  Sotterly Plantation in Maryland
Slave Dwelling Interior Historic Sotterley, St. Marys County MD

Docents talk honestly about the horrors of slavery. Unlike Plantations farther south, Sotterly does not romanticize the life of humans who were considered property here. Exhibits include chains and yokes, and down a steep hill, the 1830 slave dwelling has been left as it was when whole families lived in it.

John Hanson Briscoe – a descendant of a slave owner, and Agnes Kane Callum – a PhD Genealogist and descendent of an enslaved person owned by the Hanson family, served on Sotterley’s Board of Directors together – spearheading a new generation of possibilities for cooperation and dialog.

Although Briscoe and Callum recently passed away, their legacy continues in the hundreds of decendents who are members of Sotterley Org. When the museum is not open, the public is invited to bring dogs to walk on six miles of bucolic trails. Check website for entry fees and times and dates open.

First Navy Aircraft model by Curtiss
PAX River Naval Air Museum MD

GO: Patuxent River Naval Air Museum

On November 14, 1910, Eugene Ely flew a newly built Curtiss “Pusher.” Ely took off from Hampton Roads VA, thus sparking interest from the US Navy. A model of the airplane stands near the entrance to the great Patuxent River Naval Air Museum which showcases the timeline of Naval Aviation from the 18th century on.

Vintage F-14 cockpit simulator at PAX River Naval Air Museum
Flight Simulator PAX River Naval Air Museum MD

Though it’s cool to see many prototypes and experimental flying ships, some that made it, some that didn’t – it’s even cooler to sit in the cockpit of a vintage F-14 Trainer that was once used as a simulator. For an extra fee, you can choose from a dozen or so types of military aircraft, and “fly” and land them without fear of hurting yourself. I “flew” an F-14 and B1 Bomber, and let’s just say, I’m glad they were merely simulations.

Navy Rescue Helicopter in Naval Air Museum
Rescue Copter PAX RIver Naval Air Museum MD

Inside and out, you’ll see the best and weirdest experimental aircraft through time. The nearby Pax River Naval Air Test Center was established to train aviators adept in Testing and Evaluating the latest aircraft. There’s a Sikorsky UH-3A Sea King, used by the US Marines and Navy for cargo transport, rescue and anti-sub warfare. There’s a Lockheed Martin X-35 Joint Strike Fighter (X stands for “experimental) designed to replace several other planes.

Outside there are fighter jets with names you’d recognize: Hornet, Phantom, Tomcat, along with a stealth Boeing X-32B Demonstrator from 2000-2002, and the strangest looking craft of all – the Grumman E-2B Hawkeye “Eye in the Sky.” Looking like a conventional prop plane capped with a flying saucer, it was used in airborne early warning in the ‘60’s.

NASA Space Suits for Toddlers on Sale
Gift Shop PAX River Naval Air Museum MD

Don’t miss the great gift shop where proud parents can purchase a NASA Flight suit for their baby or toddler. Check website for hours, dates, and admission fees.

Attraction information signage in Leonardtown MD

Things to do in Leonardtown MD

In the dead center of St. Mary’s County, Leonardtown, the County’s only municipality, was deemed “A most Convenient Place” for county officials to meet. It served as the Capitol of Maryland early in its history. The town still wears this slogan proudly, and has become Southern Maryland’s only “Arts District.” 

Attempting to draw more residents and tourists here, local government has been working on a multi-phase plan to create a centrally located multi-purpose park and food hall, along with building an amphitheater, boardwalks, and a greenway along the waterfront.  The town has already zhuzhed up main street to make it oh so appealing.

Leonardtown MD park seating downtown

Now, young families are moving in, adding to a great creative energy. Tap into some of that energy by patronizing the attractions, shops, restaurants, and bars in Leonardtown’s picturesque downtown. There’s a vibrant nightlife, and weekends bustle, thanks to locals making a difference. We’ve got our favorites – so stop in and choose your own.

Watermen's Mural at L Town Alley Leonardtown MD

L Town Alley

To brighten up downtown, artists were asked to paint colorful murals in formerly dim alleyways. The result? Pizzazz’y depictions of life in St. Mary’s County and Leonardtown in particular. Wander around and find them – they make great backdrops for Instagram pics.

Moll Dyer's Rock Leonardtown MD

Moll Dyer Rock Outside of Tudor Hall

New Jersey has its Devil, said to wander the Jersey Pine Barrens, still. Leonardtown has its own folktale, the crux of which concerns one Moll Dyer, who lived alone in Leonardtown in the 1600’s and was accused of witchcraft. One bone-chilling winter’s night, ill informed, enraged townspeople ran the poor old woman out of her home, and she froze to death against a rock. That rock, now displayed outside of Tudor Hall, was said to have borne the imprint of her frozen hand from that night. The story of Moll Dyer, once told to scare people, is now a cautionary tale about how misunderstandings can have lethal consequences.

North End Gallery Leonardtown MD
North End Gallery Leonardtown MD

For nearly 40 years, 25-30 artisans have been exhibiting and selling juried, high-end and unique pieces of jewelry, sculpture, ceramics, furniture, paintings, photography, and more at great prices.

Discover lots of talent with great back-stories. Diana Manchak creates sculptural ceramic bowls and jars with a “surprise” (e.g., lobster top with “pats of butter” inside). And Mickey Kunkle, still turns out funky beaded light plastic jewelry “for women who love to be seen.”

St Marys MD Arts Council Gallery Leonardtown

If you’re looking for something hand-made and not too expensive, in the know locals come to the Arts Council Gallery for one of a kind arts and crafts.

Marie and Nash gift shop interior Leonardtown MD

Marie & Nash

This eclectic – and rather cavernous  – Marie & Nash gift shop sounds and smells like a luxury spa. That’s because, scattered among the richly textured clothing, jewelry, art, and other “Small Batch, Artist Made, and Sustainable” goods, there are scented candles and calming lotions, and other smell-good stuff – all displayed with thought and creativity. This store would go over big in New York City, and is so downright awesome, its worth a trip.

Sweets

Pop into Flour Donuts and Bakery or the Kneaded Baking Co. for something fresh from the oven – or if you prefer your treats frozen, cross room at Kneaded Baking to their Salted Scoop Ice Cream.

The REX Bar Leonardtown MD

Rex Theater

Up to 300 people can ball out in the restored REX Theater that now serves as both a bar and event venue. Check the calendar for bands, comedians, burlesque, boxing, and more. Owners Kiera and Joe Kurley bend over backwards to see that guests have a good time. They’ve even hired DJ’s for weddings here.

Front of SOF Market Leonardtown MD

Shepherd’s Old Field (SOF Market)

Helmed by the vivacious and engaging Gerrie Lheureux, the enclosed SOF Market is a “retail incubator” in a “town within a town.” Over 90 vendors now sell their unique wares inside the former Old Leonardtown Hardware Store, which Lheureux renovated to look like a main street complete with a concrete floor stamped to look like brick.

There’s a Brew House (the stylish Brudergarten) with an outdoor patio and upstairs room dedicated to vets, police, firefighters, nurses – First Responders, all. You’ll find vendors that include a coffee shop and eatery, in-house barbershop, yoga and fitness studio, charcuterie to go, a burger carryout, tattoo shop, reflexology studio, and so much more! This wonderful community is worth checking out.

Patina + Stone Studio

Come in to ogle exceptional silver jewelry by Cynthia Rosenblatt at Patina+Stone Studio. A small shop, you’ll probably find Cynthia working at her desk the moment you walk in.

New View Fiber Works

Misti Dayton declares that though she “owns” New View Fiber Works, it’s really a 16 women strong cooperative of local artisans and farmers. New View supports a large community of yarn spinners, and in fact the shop is a dealer for a specific brand of spinning wheels. Though not a “yarn shop” (you’ll find mostly finished textiles, lace, and supplies), you can take knitting, crochet, felting, weaving, tatting, and, yes, spinning classes here

Leonardtown Wharf MD
Leonardtown Wharf

Leonardtown Wharf

For a few moments of serenity on the Potomac River, head to Leonardtown Wharf and esplanade – a short walk from downtown.

Axe Throwing at Action Lounge and Billiards Leonardtown MD

DO: Viking Axe Throwing at Action Lounge and Billiards

What’s more romantic than taking an ax and throwing it at a target? OK, so that doesn’t first spring to mind when talking romance, but for certain couples – like Viking Axe Throwing owners Kraig and Cori Erikson – it’s a scintillating way to engage with your heart’s desire. They’ve even seen marriage proposals here. The Eriksons teach you to throw these sharp implements – and set you up in one of the six bays inside or two outside – to go at it. Throwing axes, I mean. I can attest – it’s really fun.

Xella Winery and Vineyards tasting room

VISIT/TASTE: St. Mary’s Liquid Assets Trail

The collaborative spirit is strong in St. Mary’s County – especially as it pertains to independently owned enterprises. So celebrate this joint effort by indulging in the 13 craft beverage makers that form the St Mary’s Liquid Assets Trail. You can visit and taste the beer, spirits, cider, wine, coffee, and juice these businesses produce. Among them in no particular order:

Xella Vineyard, Mechanicsville

Xella Vineyard offers wine tastings in an adorably renovated old car shed, left on this former family farm. Math professor (Phoenix U), Erin Melanson, and her retired Naval officer husband, Les, bought the land in 2016 and turned it into a flourishing winery. Among traditional wines with unconventional names (Cougar Bait Chardonay, Uncle Charlie’s Mur-low, Dry Humor Rose), Xella prides itself on its very locally sourced Pear Wine – made with fruit grown on right on site.

Corteau Vineyards

Legend has it that soldiers stomped on this land, now nurturing Barbara, Bordeaux and other grapes, while heading to defend the Patuxent River during the War of 1812. Founding members of Port of Leonardtown Winery, Lyrel and Peter Byrne, opened their own winery, Corteau Vineyards, in 2022, and in addition to the award-winning reds referenced above, they are growing several varietals that have not yet reached full maturity, including Cabernet Sauvignon, Cabernet Franc, Gamay (also known as Beaujolais), Pinotage, Pinot Gris, Chardonnay, and Touriga Nacional (in a port-style).

Tobacco Barn Distillery Burboun, Creme, Coffee products

Tobacco Barn Distillery

The Tobacco Barn Distillery in Hollywood MD was recognized as the #1 Farm Distillery in the USA in 2023 by the American Craft Spirits Association. Founded by partners, Scott Sanders, Dan Dawson, and Sean Coogan in 2014, Tobacco Barn Distillery is a “ground to glass” operation, as it grows its own corn, and distills and bottles its Straight Bourbon Whiskey on site. Sweet tooths will want to try the Tobacco Barn Maryland Bourbon Cream that puts the Baileys version to shame. Oh so decadent. 

Port of Leonardtown Winery

Port of Leonardtown Winery is as local as it gets, and uses “no juice from other countries” in its wines. A collective of 12 farmers and one winemaker, Port of Leonardtown turns out Chardonnays, , the sweet white and red Breton Bay Breeze, and the best-selling Vidalacato, a Moscato-type wine described as a “fruit cocktail in a glass.” Slightly effervescent and refreshing, it’s the vineland version of 7-Up. 

Free State Cider

Although Free State Cider has no tasting room, you can find bottles at local farmers markets.  Owners Nicole and Jarred – and brother Joseph Dyson – sources their apples from North MD, for their both hard, sweet, and even bubbly ciders.  

St Francis Xavier Church St Mary's County

VISIT: New Towne Neck State Park, Newtown

Maryland’s newest State Park, New Towne Neck was the site of the second Jesuit Mission and encompasses the still-operating St. Francis Xavier’s Church – the second Church on the site (first built in 1662, this one in 1731). On hundreds of acres, most leased farmland, you can kayak from here, ride horses and hike.

Piney Point Lighthouse

VISIT: Piney Point Lighthouse, Museum, and Historic Park

Begin at the Piney Point Lighthouse Visitor’s Center which has a small gallery and exhibits, to learn about the U-1105 “Black Panther,” the first “stealth” German WWII submarine that ended up – though a confluence of events – in the waters a mile off Piney Point, and is now a popular dive spot. Then mosey over to the larger Museum building to be immersed in the life of ubiquitous Chesapeake watermen. Finally, stroll out to the white saltshaker Lighthouse – framed by industrial towers and pipes of the LNG pipeline directly behind it.

Built in 1836 on the Potomac, the lighthouse was here when Civil War gunboat patrols, organized by the Union Government, intercepted (or failed to intercept) Confederate blockade-runners. Apparently, locals were southern sympathizers who, in the dark of night, would help rebels cross through the blockades.

Private Beach Gazebo Piney Point St Marys County MD

On your way to the Piney Point lighthouse, note the modest beach homes and their respective fanciful private gazebos built across the street right on the beach.

VISIT: Point Lookout State Park, Scotland MD

You’ll find beautiful beaches, great kayaking and the most haunted lighthouse in the USA, according to many, at Point Lookout State Park. The lighthouse, built in 1830, was part of a Civil War prison complex housing 52,000 Confederate soldiers, 4,000 of whom died due to disease-bearing mosquitoes, heat and lack of food.

Best Restaurants in St. Mary’s County MD

Sweetbay Restaurant interior Leonardtown MD

EAT: Sweetbay Restaurant

This newly renovated and coolly nautical Sweetbay Restaurant hits the sweet spot in Leonardtown’s revival. Restauranteur, Peter Lupo, owner of Scarlet Oak Restaurant and Magnolia Kitchen + Bar in DC, was drawn to the town’s ongoing revitalization that of course had to include a trend-forward eatery. Patrons rave about the friendly staff, inventive cocktails, Crab Cakes, Wagyu Beef Burgers, and Truffle Fries – but every menu item seems to have its fans.

EAT: POV at Pier 450, Ridge

POV means “Point of View,” and yes, that view of the waterfront, from nearly every seat in the house, bedazzles, especially during sunset. But, so do the dishes that emerge from Chef Carlos’s kitchen. He and his team present an American Cuisine with international flare, and patrons have been known to drive hours to eat there.

Social Coffeehouse and cocktail Bar exterior Leonardtown MD

EAT/DRINK: Social Coffeehouse and Cocktail Bar

The uber popular Social Coffeehouse and Cocktail Bar is highly social, as its name would indicate. Formerly Duke’s Restaurant and Bar, it was constructed in the 1920’s as the first reinforced concrete structure in Southern Maryland. Over the years the building housed a duck pin bowling alley, grocery store, a Greyhound Bus office and more.

Historic bar at Social Coffeehouse and Cocktail Bar Leonardtown MD

Now, thanks to visionary owner of Social Coffeehouse, Sean Coogan – who reimagined the vast space as both a peppy cocktail bar and restaurant that specializes in boozy brunch and elevated pub grub, (plus his Social Coffee Roasters business) – this downtown corner of Leonardtown thrums with activity once again.  

Front Porch Restaurant Leonardtown MD

EAT: Front Porch, Leonardtown

Set inside the stately Sterling House, the Front Porch Restaurant had gone through three iterations before this one found success. Built in the 1850’s and purchased in 1911 by Lynwood and Ruth Sterling (who raised their 17 children here), the home was repurposed as a restaurant, but retains its period charm.

Old photos, artifacts and shadowboxes throughout bedrooms that now serve as intimate dining rooms illustrate the lively Sterling family – some who are still around and return to talk about life within these walls. Food, like popular salads and burgers, is good and fresh, with meat and produce from “down the street” and the Amish Produce Auction.

The Slice House Washington ST Leonardtown
The Slice House Leonardtown MD

EAT: The Slice House, Washington St, Leonardtown

The Slice House offers up wood-fired “NY Pizza” by the slice – and a great bar. What’s not to like? Plus – you can score a six-pack of your favorite craft beer on tap. The Slice House has its own instant canning machine.

Fresh caught flounder dish at Courtney's Restaurant Ridge MD

EAT: Courtney’s Restaurant, Ridge

This out of the way, way, way Southern St. Mary’s County “slow food” Mom and Pop spot – Courtney’s Seafood Restaurant – is right on the waterfront. With its own fishing boat. So, you know your fish is fresh caught that day. Far from any industry or development, this restaurant is as low key as it gets.

St Inies Coffee bookshop MD

COFFEE: St. Inie’s Coffee, Lexington Park

This local roaster/coffee shop/bookstore, St Inie’s Coffee, is the passion project of mother of 4, Catherine Grube, who created this super popular community hub in 2017. A comfy blast from the past meeting place on an otherwise commercial strip, St. Inie’s excels in Cold Brew coffee. A must-go in St. Mary’s County.

EAT: PAX River Alehouse, Lexington Park 

A popular spot for people who work on Base, PAX River Alehouse has good brews on tap, of course, but also gooey bites like Bavarian Pretzel Sticks and Onion Ale Soup made with onions stewed in ale and sherry, topped with toasted croutons and gruyere cheese.

Ruddy Duck Seafood St Georges Island MD

EAT: Ruddy Duck Seafood and Alehouse, St. George’s Island

Right next door to the Island Inn and Suites, this second Ruddy Duck Seafood and Alehouse outpost is all about the water views on both sides. The place is jumpin’ every night of the week. For a quiet corner of the Southern Shore, this is a happening place.

Best Places to Stay in St. Mary’s County

Beach at Pier450 Ridge MD

STAY: Pier450, Ridge

If you ever need to escape “real life” – to feel a bay breeze on you face, sipping wine with your toes in the sand of a makeshift beach while watching a glorious sunset – wend your way down to Pier450 in teeny Ridge MD. A Maven Favorite – we provide a full write up in this Pier450 Review.

Swanendele Inn St Marys County MD
Swanendele Inn St Marys County MD

STAY: Swanendele Inn, Ridge

The Swanendele Inn sits on a promontory at the Southern tip of St. Mary’s County MD, where the Potomac River meets Chesapeake Bay, just five miles from Point Lookout State Park. It’s the perfect hideaway for stressed out intellectuals, nature lovers, and really anyone seeking a slow-paced few days away from the grind. Another Maven Favorite – find our complete coverage in this Swanendele Inn Review.

STAY: Inn at Leonardtown

The 43-room Inn at Leonardtown – a Choice Hotel – brings needed full-service lodging options to St. Mary’s County. Its brick Federalist exterior belies the clean-lined inviting modern rooms inside.

Island Inn and Suites Solomons MD

STAY: Island Inn and Suites, Ascend Collection St. George’s Island

Cross the causeway (where a sign states: “British Landing Prevented”) onto this arrow thin entrance to St. Mary’s County’s least commercially developed island, St. George’s.  Check in to this 28-room Island Inn and Suites, and you’ll be forced to answer one question: “do want sunrise or sunset views?” Wedged between the Potomac River and St. George’s Creek, you can’t really go wrong with either one.

Romantic Things to do in St Mary's County MD Pin

Author

  • Malerie Yolen-Cohen

    Malerie Yolen-Cohen is the Author of the cross-country travel guide, Stay On Route 6; Your Guide to All 3562 Miles of Transcontinental Route 6. She contributes frequently to Newsday, with credits in National Geographic Traveler, Ladies Home Journal, Yankee Magazine, Shape.com, Sierra Magazine, Porthole, Paddler, New England Boating, Huffington Post, and dozens of other publications. Malerie’s focus and specialty is Northeastern US, and she is constantly amazed by the caliber of restaurants and lodging in the unlikeliest places.

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