Exploring Saint Mary’s County Maryland: Rural Charm and Hospitality

Exploring Saint Mary's County Maryland

One of the pitfalls of being well-traveled is a tendency to look too far beyond your front door. Truth is any new adventure, no matter how near, is still worth having. Embracing that idea is how I found myself a few hours from home exploring Saint Mary’s County Maryland.

Much of the county is dotted with bucolic encampments of cattle and fields of corn. Formerly a seat of tobacco cultivation, some of that land has been converted to wine production. Which brings us to our first stop, a winery!

Port of Leonardtown Winery

This small winery boasts a bevy a awards and accolades for its small batches of surprisingly sophisticated {surprising to me that is because much of my experience with Maryland wines has fallen a bit short of a trip to Montepulciano} wine. Setting it apart from most wineries is the fact that Port of Leonardtown is a cooperative of growers. Each producer tends to their growth and harvest, the bounty is then turned over to an in-house vintner. The resulting product is uniquely, Saint Mary’s County Maryland.

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Just outside the tasting room is a small park with a beautiful, copper roofed gazebo. Making this stop family-friendly. Wine + Family Time = Bonus

Up next, I go back to the Navy…

Patuxent River Naval Air Museum

Have you ever walked into a place you’ve never been before and been overwhelmed by a sense of déjà vu? … all over again. This is that place for me.

The lobby of the newly redesigned museum is designed just like a hangar bay.  A bay that was so reminiscent of the one I worked in daily as part of Helicopter Sea Combat Squadron Two known as the Circuit Riders back in my day. Standing at the wheel of a vintage Navy helicopter that is the focal point of the room, completed the sense of having been there before.

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Tucked along side the helicopter you’ll find a brief history of naval aviation dating back to the days of the brothers Wright and forward into space travel. It’s both an informative and adventurous visit when combined with a stroll down the tarmac outside the building. 

You’ll find historical and unique aircraft along that tarmac and even a very cool prototype or two. There are hands on exhibits and flight simulators as well.

I can’t tell you how wonderful it was to share this part of my history with our kids. They’ll have some epic fodder for essays this school year, for sure.

Historic Leonardtown

While we’re on the subject of time travel, fans of Marty McFly and Doc Brown will fall in love with the historic section of Leonardtown. Standing in the town square it’s as though you’ve stepped back in time, or onto a movie set.

Red bricked buildings boast painted marquees of businesses long gone. Quaint shops and small eateries line the cobblestone streets. At the center, a town square dedicated to Leonites who’ve served their country, completes the Mayberry-like vibe.   

One of our favorite stops was Heritage Chocolates – for obvious reasons… like, um… handcrafted confections of chocolate covered bliss. Bonus points for the entertainment value of watching someone making these sweet treats – I-Love-Lucy-Style.

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The historic jail is a must-see for history nuts, like us. Hold up behind the stone walls of this small building is a chronology of crime and punishment, the history of a local doctor and philanthropist and a treasure trove of period items donated by residents for the preservation of the town’s history. 

Into the paranormal? Fancy yourself a bit of a ghost hunter? Be sure to make time to learn about Moll Dyer, her rock and the rumors of witchcraft that still linger in the air. 

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Where to Stay 

Where you stay can be the biggest factor in the success of nearly and adventure. On our Saint Mary’s County expedition our base camp was perched on a tiny strip of land just big enough for two way traffic and buildings (mostly on one side,) called Saint George Island. Just driving to the Island Inn & Suites is an adventure as the tide laps at the grass that hugs the road. 

Hospitality here is the hidden gem of Saint George. The staff is warm, welcoming and excited to share their home with you. Borrow a beachcomber bicycle for a ride down to the park at Piney Point or take to the water with one of the kayaks they offer. Our favorite activity was watching the sun set from the balcony after a walk down the boat pier behind the hotel. They also have a public fire pit and will even supply wood and marshmallows for roasting. 

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Saint George Island is fairly isolated, but that is part of the charm. You won’t find a grocery store or gas station on the island but both are easy driving distance. Next door to the hotel is The Ruddy Duck a nice little eatery offering local favorites and some very good craft beer, which by far makes up for the lack of “night life” on the island. 

Though it may not be a place that gets huge marque in the travel space, exploring Saint Mary’s County Maryland is certainly worth the trip. 

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One thought on “Exploring Saint Mary’s County Maryland: Rural Charm and Hospitality”

  1. Isn’t it funny when you find something so close to home and you never really thought about it before? Maryland is a bit of a trek for me (San Diego), but one day I have plans to visit the East and I’m eager to make a stop here!

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