The Preppy Redneck

By Morgan Buckingham

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The Preppy Redneck
photo credit: Morgan Buckingham

Over the bridge.Growing up in Maryland there has always been this sense of credulous hopefulness driving to the Eastern Shore. As I have grown up and my trips over the Maryland Bay Bridge have become more frequent, going over that bridge has become a symbol of nostalgia as well as excitement.

I’ve also learned over the years that I love most things that other people cannot stand, such as airports, car rides, and driving over this bridge.  As we approached the Bay Bridge on this particular trip, I was excited and commented on how clear and beautiful the sight of the sailboats on the bay looked. My mom’s knuckles were white before we even paid the toll.

I asked her why she hated it so much and she simply said, “Talk about something else, please, or I may cry.”

Being my snarky self, I responded, “Isn’t it awesome that the woman who crashed her car off the bridge was able to swim to those rocks and survive?”

She hit me, but I managed to make her laugh and all her nerves were eased.  Like crossing the bridge, traveling can be terrifying, but instead of letting the fear of the unknown give you white knuckles, embrace the beauty of it and what it has to teach you.

I’ve crossed this bridge what feels like a million times now. Most times our destination is the beach, for relaxation and a week of thinking about nothing but sunscreen, but this time we were headed for St. Michaels, MD.  St. Michaels is a small town in Talbot County, Maryland, tucked along the Chesapeake Bay.  It is steeped in history and charm. Known as “the town that fooled the British,” in the War of 1812, the town has an ability to preserve history for generation after generation. We drove into St. Michaels, and right away I felt amity. The day was clear, a light chill in the air, and I was happy to get away from my everyday woes for a few days of serenity with my mom.

“I’m glad you asked me to come with you this weekend,” my mom said as we drove off of route 50. “It’s times like these that as parents you treasure. I spent every day with you until you moved out, and now I see you once or twice a week. You don’t get these moments back. You could have come down here with anyone, but you asked me.”

My mom has always been my backbone, and as I set out on this trip, she knew I had to go to write an article, what she didn’t know is that it meant so much more to me, especially just having her there.

Our first stop was to the Chesapeake Bay Maritime Museum. The museum is a beautiful and nautical themed museum on the Chesapeake that walks visitors through the history of the town and the bay. Looking out across the bay, you see the lovely, gigantic and charming Inn at Perry Cabin, where they filmed “Wedding Crashers.”

The Inn at Perry Cabin

The Inn at Perry Cabin
photo credit: Morgan Buckingham

We began our self-guided tour with a short “how-to” from a tour guide, Nick Green.  He explained the importance of St. Michaels to the War of 1812. The town turned out all the lights and hid lanterns in the trees, so the British thought the town was in a different location.  “It could all be legend, but we’re proud of our way of fooling outsiders,” he said.

We spent the rest of the day walking through the Hooper Strait Lighthouse, reading about oyster dredging, boat repairs, Frederick Douglas and the appeal of the bay. As you walk through it, you can almost feel the past, as you walk up the creaking stairs of the lighthouse and imagine sleeping there in the harshest of Maryland winters in the 1700 and 1800s. There is so much to read and so much to learn, it can be a tad overwhelming. My mom and I got distracted all too often by the beauty of the bay.

This was my fourth time in St. Michaels, and I fall more in love with the town every time I go. Each time I have gone, it has been for a different reason and with a different person. My agendas for going always change, but St. Michaels never does.

The last time I was in this beautiful, quaint, small town, that can be best described as cute, I was with my ex-boyfriend. We were on our way home from a rainy weekend in Ocean City, MD. We made it to St. Michaels and were stranded there overnight because all the roads were flooding. The main road into the town was pretty vacant with water rushing through the street,  and I remember saying to him despite the awful weather conditions, the town still seemed alive and happy.

Completely drenched and exhausted from a weekend without an ounce of sun, we went to Macroritaville Tiki Bar and Restaurant. Ask any local in the town, and their first recommendation will probably not be Macroritaville, but it’s fun, different, and it’s sure to make you smile. With fake grass skirts draped as coverings on the sushi bar and regular bar, Bud Light signs on the walls and a menu ranging from Maryland seafood to Asian cuisine, you can’t help but think this place has an identity crisis. It’s eccentric, you expect Its Five O’clock Somewhere by Jimmy Buffett to be playing – instead there’s dim romantic lighting, but that’s what gives it charm.

We were the only two in the restaurant. It was peaceful, and despite how crazy that weekend had been, we both felt at ease. St. Michaels has a way of doing this to you. You enter the town and feel immediately calm, as if stress was never an aspect of your life and the time you spend there will allow you to slow down That’s what I remember from that weekend. Not the monsoon or my truck getting damaged from rushing waters. I remember sitting in that restaurant and feeling like I was discovering a new chapter in my life. A chapter that I could fall in love with. A chapter that would begin to define who I am.  A chapter that looking back now would hurt, put me through hell, and it would be my return to St. Michaels that would help heal me.

I came back to St. Michaels in search of an answer to my crossroads. Would it reveal something to me? Would it change how I was currently feeling? Walking down the brick sidewalks surrounded by buildings, circa 1800s, there is something overwhelmingly nostalgic and delightful about this town. Each house, which most have now been converted into shops or boutiques on Talbot Street, has a character all its own. The smell and crisp feel of fall in the air and the blissful sound of water crashing into the side of sailboat, the closer I approached the water, everything seemed to make me smile.

Part of the allure of St. Michaels is that it is so inviting, in all seasons of the year. But, in the four times I had been there, I think October was the best. Even though it wasn’t prime fishing or boating season, there was still plenty to do.

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The Hooper Strait Lighthouse at the Maritime Museum
photo credit: Morgan Buckingham

My first encounter with St. Michaels was when I was 18. At 4 a.m., we drove to Tilghman’s Island, an island just south of the town of St. Michaels. I think the only one excited was my friend’s father, from whom I learned one of the most important lessons of my life on that fishing trip; take every day as an adventure to indulge in and reel in a great catch. It wasn’t until we stepped onto the boat to set sail out onto the Chesapeake that I felt enthusiastic. I’ll never forget that day, it was the day I fell in love with being on the water. There is no better feeling in the world than being in the middle of the Chesapeake as the sun rises and the cool wind from the water hits your face. Catching rockfish isn’t like catching small bass in a pond; it’s challenging and catching my first was such a rewarding feeling.

While in St. Michaels this most recent time, I couldn’t help but reminisce about that trip to my mom.  Telling her this story, we were in one of the jewelry shops on Talbot Street; all the pieces in the store were handmade sterling silver. I was telling her the story of rock fishing, when a certain piece caught me eye, and I couldn’t help but comment on how beautiful the detailing of it was. The man working there, Steve, said, “It’s no wonder you found that piece. It was inspired by a day fishing off of Tillman’s Island.” I smiled, knowing that I wasn’t the only person who is unable to forget that breathtaking view.

“I hope you’re enjoying your time in St. Michaels. You seem to appreciate our little town. But, why would you not? It’s said to be one of the top 1,000 places to visit before you die,” said Steve.

This came as no surprise that other travelers would feel the same way about this place as I do. Of all the exotic places in the world, one of the picks is St. Michaels, Maryland. Known as the “town that fooled the British,” during the War of 1812, it still has a way of fooling those who come there today by making you think that one trip is enough, but you keep coming back for more.

After the Maritime museum and a little shopping, my mom and I walked further into town and ate at Marcoritaville. We were the only ones in the restaurant; this was now becoming a trend.  We ordered conch fritters and each got a salad, mine with Rockfish, of course, and hers with salmon. It was a salad, so simple, but it was crisp and fresh and tasted like a lovely memory Like a song can bring back memories, so does St. Michaels, for me.

Our next visit was to the Eastern Shore brewery, which is next door to the St. Michaels winery. The two places are side by side and have a completely different feel and energy; a true reflection of the town it self. The Eastern Shore brewery has a very rustic feel with vintage sofas and antler racks on the walls.  The bartender matched the scenery with his handlebar mustache and laid-back demeanor. When we walked into the brewery, he was having a vibrant conversation with a couple at the one and only bar there. They were discussing music genres and the changes their musical taste have taken throughout their lives. The hipster bartender said, “Music allows you to return to where you were. Music is a journey that you go through. Through life’s changing paces you change what you like, and make a complete circle and come back to the start.”

“Wow, that was deep,” was all I could muster to my mom.

Music, like travel is a journey, you start at one point and life takes you places you never expected, yet you return back to who you were and where you were in the beginning with more knowledge, wisdom, and appreciation.  After our beer tasting of chocolate coffee flavored beer we walked through town and we entered a small store called “The Preppy Redneck.”

I fell in love with the store right away. Each store along Talbot Street is unique and packed with merchandise in the small 1800 style houses with merchandise lining the narrow old staircases and using every corner of the home for displaying pieces. This store, however, stood out to me the most.

The woman working there told us that when the owner married the biggest redneck in town and when she had children, she didn’t know how to dress her kids, thus coining the term the “preppy redneck.”  She said her kids quickly learned it’s all right to be who you are, not defined to one word or stereotype.  You are who you want to be. That’s St. Michaels too; it is exactly what you make it to be. On one trip there, I was trapped and learned to find love in chaos, and this time around, St. Michaels has given me a huge emotional smack in the face.

St. Michaels, MD- "The Town that fooled the British"

St. Michaels, MD- “The Town that fooled the British”
photo credit: Morgan Buckingham

I suddenly had an “a-ha” moment that showed me that I can run from hurt and pain, I can leave it behind, or I can use it to direct and propel me to embrace the preppy redneck that I am. It is so easy to get lost in a place and even easier to get lost in a relationship. I had lost direction, but St. Michaels has this way of preserving history; n:not only its own but mine too. Walking down the street after being inspired at the “preppy redneck,” I was able to readjust my sails back to myself. This rocky period in my life was a roadblock, but it doesn’t define who I am or who I am becoming anymore.  St. Michaels is a combination of so many things, why can’t we as humans be a combination of so many things?

We spent the rest of the day shopping and wine tasting at the winery in the afternoon. We spent more money than we probably should have but neither one of us really cared.

“Mom, thanks for always spending so much time and money on me.”

“You know when I had kids, I didn’t say to myself: now this is a great way for us to save money. I know you and your sister don’t expect us to spend money on you, but I do it because I love to see you happy. I enjoy seeing my preppy redneck happy,” she laughed. I couldn’t have asked for a better person to come on this weekend of self-discovery with me. My mom has been there through every heartache, every tear and every time I struggled with being a preppy redneck.

After shopping, we decided to look for the St. Mary’s museum where there was promised to be more history of the town. Well, we never found what we were looking for, but we ended up walking down Mulberry Street. With narrow brick sidewalks and landscaping spilling over, it was picturesque. We walked until the end of the road, where it dumps into the water. All of the houses were built in the1800s and there is nothing cookie-cutter about them. It looks like a scene right out of movie.

After never finding the museum, we went to the Inn at Perry Cabin. The Inn is breathtaking and so inviting. The once horse farm is now a Victorian colonial mansion resort and spa.  From guests relaxing on the water in Adirondack chairs, riding bikes down the brick driveway or getting a massage and facial at the spa, the Inn is a perfect match with the charm of St. Michaels. At the spa, the woman at the front welcomed us in a friendly St. Michael’s tone.  Standing in the warm foyer of the spa, the scents of jasmine and lavender filled the air.

The beautiful St. Michaels, the pride of the Chesapeake. It’s a hidden gem of the Eastern Shore that many over look on their way to the beach. Whether you want to spend a day on the water or a day walking down Talbot Street or tasting wine or beer, St. Michaels is a town of history and charisma that will stay with you long after you leave.

I came to St. Michaels in an attempt to forget the past, only to leave feeling thankful for it. As I left and walked away feeling more like myself than I had in months,. We met a couple walking along the docks named Bob and Stacy on their way into the Martime Museum.  We asked Stacy to take our photo in order to capture our weekend in St. Michaels and Bob made his impression by photo-bombing the picture. This was their fifth time there, and this time they came with friends to enjoy a weekend away. I asked them why St. Michaels? Bob said, “ it may be a small town and you think one weekend is enough to renew your spirits, but the town has a way of always drawing you back. Each time you come, you enjoy something new every time, but in fact the town itself never changes.”

This is when I realized that St. Michaels will always be a part of who I am, and every time I return, I learn something new about myself from the alluring, quiet town by the bay, just over the bridge.

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