Exploring Small Maryland Towns | Wander With Wonder

Sometimes tiny towns have the best food. That’s what we discovered—and more—while exploring the small Maryland towns of Charlestown and North East.

Taking the road less traveled often provides one with tasty and memorable rewards. As a curious traveler, I had driven by Charlestown and North East, MD, several times, and I barely wondered what they might offer me. It took food—a visit to Woody’s Crab House in North East—to get me to veer off the highway to begin exploring two small Maryland towns. I quickly realized how much I had missed by not visiting sooner. Here are some of the things you can find when you explore the small Maryland towns of Charlestown and North East.

It All Begins with Food

I had seen a billboard on the Pulaski Highway advertising Woody’s and figured it was worth a try. As soon as I got into the core of downtown North East, time slowed as I looked at the bustling and historic main drag. After securing a free parking spot next to Town Hall, I walked to Woody’s where the lunch crowd spilled onto the patio. Several customers were whacking the steamed crabs with wooden mallets and feasting on the succulent crab bits as if they were in a feeding frenzy.

Although I love crab, the menu included lobster rolls, and I have a weakness for an easier meal than steamed crabs. The weather was fine for outdoor dining, and I enjoyed the lobster roll and watching the pedestrians and cars roll by. I noted the full bar for future happy hour stops as I was sure to return. I’ve also returned to Woody’s Ice Cream next door, which is always busy on summer days. Over the eight years since I first stopped at Woody’s, I’ve been back to North East numerous times. My favorite activities are: hiking Elk Neck State Park, shopping at Main Street merchants, and eating at the restaurants this small town offers.

Lobster rolls at Woody’s Crab House are one of my favorite menu items. Photo by Kurt Jacobson

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Take a Hike in These Small Maryland Towns

Elk Neck State Park is probably one of the most popular parks in Coastal Maryland. There’s something for everyone, including a boat launch, a camping area, picnic tables, a beach, and a historic lighthouse. I love the 1.8-mile round-trip hike from the trailhead to the Turkey Point Lighthouse. Be aware that the trailhead parking lot fills up quickly with only about 20 spaces. If you go on weekdays or early on weekends, you can get a parking spot.

Turkey Point Lighthouse stands watch over the Upper Chesapeake Bay. Photo by Kurt Jacobson

The trail is well-marked and a great place to bring your leashed dog. Along the way to the lighthouse are a few overlooks just off the main trail near very steep cliffs. Charlestown is visible off to the west on clear days. About halfway to the lighthouse is an open area with a sign proclaiming Hawk Watch. From this spot you can see hawks on most days in spring and fall as they migrate along this flyway. At the trail’s end, the lighthouse stands tall as it has since 1833. Turkey Point Lighthouse sits on a 100-foot high bluff and has helped mariners navigate the shipping channels for years. An interesting side note to the Turkey Point Lighthouse is that it had more female lighthouse keepers than any other Chesapeake Bay lighthouse.

A History Lesson

The Revolutionary War and the War of 1812 brought British ships past Elk Neck on their way to battle or to harass the locals. On August 25, 1777, General Howe led a force of 15,000 troops to attack Philadelphia. This British force landed on the shores of the Elk River, about halfway between Turkey Point Lighthouse and the town of North East. They took Philadelphia without a fight; this was a powerful army. Then on April 28, 1813, British Admiral Cockburn arrived with a force of some 450 men after attacking towns along the Chesapeake Bay during the War of 1812. They left towns like Havre de Grace, MD, mostly in ruins after looting, burning, and terrorizing their way up the Chesapeake Bay. Imagine the American locals having to go through another war after the one with the British in 1777!

A sign depicting the landing of General Howe during the War of 1812. Photo by Kurt Jacobson

Back in town, a more peaceful historic site awaits the intrepid traveler. Saint Anne’s Church was built in 1742, and it is one of the oldest churches in Maryland. Take a walk among the gravestones in the church’s cemetery, and you might find some weathered tombstones with names of the families still living in the area. The Elk River borders the church and makes for a quiet place to experience the vibe of this historic town.

St Anne’s Church in North East Maryland is one of Maryland’s oldest churches. Photo by Kurt Jacobson

Steak and Other Food Options

While there aren’t a lot of restaurants in North East, I find enough for a town this size. Steak and Main is an above-average eatery. As the name indicates, it’s on Main Street. Open for lunch and dinner, they have a good selection of sauces to top your steak, my favorite being the brandy peppercorn sauce.

I don’t think I’ve ever seen a filet mignon meatloaf on the menu at any other restaurant. This ultimate meatloaf comes with bacon, signature steak sauce, and whipped potatoes. Paired with an excellent red wine like their Patz and Hall Pinot Noir, this is living large. Steak and Main also has a sushi bar and oyster bar for seafood lovers.

A perfect-looking New York strip steak at Steak and Main. Photo by Kurt Jacobson

Other restaurants of note are Pier 1 Restaurant on Main Street, Bay Crawlers Crab Shack on the way to Elk Neck State Park, Woody’s Crab House, and Woody’s Tacos and Tequila. Out on the Pulaski Highway is North East Family Restaurant. I haven’t dined there since it changed hands some three to four years ago, but I often see many cars parked out front when I pass by.

Wine, Gifts, and Chocolate

One of the cutest little chocolate shops in Maryland is located on Main Street. I usually stop at North East Chocolates for a treat and love the dark chocolate-covered pretzels. They have an excellent selection for such a small shop and have an adoring fan base.

Take a chocolate break in North East on Main Street. Photo by Kurt Jacobson

Staying on the same side of the street, find Kathy’s Corner Shop, a gift shop my wife loves to visit. Kathy’s has a good selection of local art, books about the area, wind chimes, gourmet foods, and more. I like to chat with H.L. Mahan, a photographer in the back of Kathy’s Corner Shop. H.L. has an impressive selection of photos including ones of East Coast wildlife.

Look for the colorful mural to find Kathy’s Corner Shop on Main Street in North East. Photo by Kurt Jacobson

If you like sweet wines give Turkey Point Vineyard a try. They are easy to find on the way to Elk Neck State Park on the right side of the road. Turkey Point is dog friendly and has a private event space for weddings, family reunions, etc. Although I prefer dry wines, I found their Lighthouse White, a blend of Vidal Blanc and Chardonnay, a good summer sipper.

Charlestown, Big Fun in one of the Small Maryland Towns

I don’t remember how I found Charlestown, MD. What matters is that I did find this tiny town on the west shore of the Upper Chesapeake Bay. With a population of just 1,496, per the 2020 census, this is a popular place to escape city life.

There are good reasons to visit Charlestown: fishing, picnicking, taking a ride on the Upper Chesapeake Bay on the former Wellwood Water Taxi (now owned by North East Cruises), dining at the Wellwood Restaurant, or getting a history lesson. The first time I came to Charlestown I saw a historical marker telling of its founding in 1742. History runs deep here as many influential people have traveled through or settled in Charlestown.

This is one of several historical markers in Charlestown, MD. Photo by Kurt Jacobson

Spring, summer, and fall are the best seasons to visit Charlestown. Bring your binoculars and telephoto camera if you want to see and photograph osprey flying, nesting, and fishing. A local fishing jetty, about two blocks southwest of the Wellwood, usually has several anglers hoping to catch rockfish or other game fish in these waters.

An osprey squawks a warning while watching over its four hunkered-down chicks. Photo by Kurt Jacobson

A Historic Restaurant

The Wellwood has been around for a long time, especially considering that most restaurants close within the first five years of operation. The Wellwood’s website tells of the restaurants beginning in the late 1800s: “The Wellwood Club was originally a private hunting and fishing club that was established as an organization of optimists and humanitarians in the broadest sense.”

I love the next line: “Its purpose is to promote the ‘happy habit’; to reduce the friction of life to a minimum and increase the pleasure of existence to the maximum; to discourage strife and promote food fellowship.”

The Wellwood was once a private Country & Yacht club with a 9-hole golf course and other amenities. It is currently a restaurant, marina, and event center. Many famous politicians have been to the Wellwood. The owner Larry Metz told me, “Back when railroads were the main source of transportation, politicians and businessmen from New York City and Washington DC would meet at the Wellwood due to its location.”

The view at sunset from the Wellwood Marina. Photo by Kurt Jacobson

The Wellwood has four dining areas for customers to enjoy their meals and hang out for a while. The Wellwood Club is their casual dining room open year-round; the River Shack is a laid-back summer dining area outside. The formal dining room is for special occasions. The formal dining room has gifts from politicians, including a hand-carved wooden eagle given by President Roosevelt. Larry’s family bought the Wellwood in 1958 and treasures the eagle and other gifts from appreciative politicians.

Crab Dining Outdoors

The River Shack is a great place for the whole family in the outdoors that includes a sandy area, picnic tables, some of the best steamed crabs in Maryland, and a bar. Open only during the warm months, The River Shack is a fun place to let your hair down and party like a local.

Five gorgeous blue crabs await the mallet. Photo by Kurt Jacobson

Their outdoor dining area in front of the main building is the fourth dining area available to customers. This is where my wife and I love spending 2-3 hours having lunch while listening to live music.  After lunch, we walk the waterfront and take our dog for a water taxi ride on the scenic Upper Chesapeake Bay.

What About the Food?

The first time I stepped into the Wellwood, I approached the hostess counter and asked for a menu to peruse. I noted the sign behind the hostess counter saying, “World Famous Fried Chicken.” In my line of work, I often see a restaurant boasting the best this or that, and I’m often suspicious of such lofty claims. I asked the hostess, “Is it really that good?”

The Wellwood’s fried chicken pairs well with a glass of white wine. Photo by Kurt Jacobson

Little did I know that the owner, Larry Metz, was in earshot and came around the corner to tell me, “Yes, it is. The recipe is an old family favorite, and we use quality ingredients to make it the best fried chicken it can be.”

I tried the fried chicken and agree it’s one of the best I’ve ever had. Since then, my wife and I have been back several times for the fried chicken, steamed crab, baked oysters Rockefeller, and to listen to the live music on their patio.

The Wellwood is popular for private events inside the main building or in a tented banquet pavilion. The Wellwood Water Taxi was sold to Northeast River Cruises in 2022 and can be booked for private tours with pickups available at the Wellwood Marina. All Wellwood restaurants are closed on Mondays. See the website’s hours and days of operation for all of the Wellwood dining areas.

A fun time from days gone by on the water taxi with our dog Sophie. Photo by Kurt Jacobson

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Both of these towns are just minutes off I-95. Now that you know more about these cool places, it’s time to visit. When planning your trip to Small Maryland Towns, other small towns, or Maryland destinations, let Wander with Wonder be your guide.

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Exploring Small Maryland Towns of Charlestown and North East