7 Fairy-Tale Small Towns In Maryland
Maryland hides a run of small towns that look lifted from a fairy tale. Their historic architecture, cobblestone streets, and Chesapeake Bay waterfronts set the scene. Berlin sits near the eastern shoreline with a whimsical downtown. Chesapeake City straddles the Chesapeake and Delaware Canal, while Thurmont backs up against the Catoctin Mountains. These seven fairy-tale small towns in Maryland each carry their own tales to tell.
Berlin
The city of Berlin maintains its fairy-tale reputation with a unique Victorian downtown, mischievous landmarks, and a thriving arts and boutique scene. A fantastic place to begin the quirky adventure is the Mermaid Museum, a magical place honoring the queens of the sea, with sculptures, a fun bathtub with a mermaid's tail for tourists to take pictures with, and a giant clam with a pearl in it with its own mermaid's tail for photos. A short walk north of the Mermaid Museum is the Ghost Museum, which honors these supernatural beings with art, historical accounts of spiritualism, and ghostly artifacts. There's also a communal wall where guests share their own ghost stories for others to read about.
Just a short walk from Main Street is the Holland House Bed and Breakfast, a welcoming turn-of-the-century house that provides its guests with five comfortable rooms, a common room, coffee on demand, and a freshly made continental breakfast in the mornings. The front porch has a couch and some chairs to relax in, and the den in the back stands out, with its wooden walls and brick fireplace. A great spot to enjoy hot meals and refreshing drinks is Blacksmith, a gastropub serving patrons market fish stuffed with crab, jumbo lump crab cakes, spicy steak frites, and ice-cold house cocktails like the Blacksmith or the ultimate gin and tonic. When out on the town, this is an incredible spot to go out to dinner, on a date, or to celebrate a birthday with friends and family.
Havre de Grace
The city of Havre de Grace earns its fairy-tale-like look from its storied waterfront setting on the Chesapeake Bay, rich maritime history, and quaint architecture. A quirky place to visit in town is the Havre de Grace Decoy Museum, which showcases hunting decoys, hunting rifles, and row boats on display, along with teaching people how local ecology, migration patterns, and community artistry shaped the community into what it is today. Another museum that's close by is the Havre de Grace Maritime Museum, which further dives into the region's maritime history with exhibits showcasing model boats, Underground Railroad artifacts, and ice-harvest artifacts, and hosts local events that bring the community together.
On the northern part of town is the Tidewater Grille, where patrons can enjoy elegant views of the bay and delicious meals and drinks like Maryland Crab Soup, a signature crab cake, the Chesapeake burger, and a refreshing strawberry mule. Tidewater hosts weekly trivia nights, a daily happy hour, and live entertainment on weekend evenings. Right in the heart of downtown is La Banque de Fleuve. This event venue is perfect for that real-life fairy-tale wedding, as it's set in a fully restored 1905 First National Bank, with elegant balconies, allowing visitors to soak in the views of the bay and the landscape, an extraordinary ballroom, and a waterfront deck for up-close views of the waterfront while celebrating an unforgettable wedding or event.
Thurmont
Set near the foothills of the Catoctin Mountains is Thurmont, a town that has an old-world reputation due to its historic Main Street with 19th-century buildings, quiet forests, waterfalls, and trails, and is a real-life retreat with Camp David nearby. The Wolf Rock and Chimney Rock Trail is a rugged 3.9-mile-long loop showcasing two glorious vistas, Wolf Rock and Chimney Rock, as the trail is marked by an orange blaze, and the trail is 600 feet above elevation. Dogs are allowed on the trail, but must be on leashes and cannot go near the Wolf and Chimney Rocks. Right in the timeless downtown is 10Tavern, a modern sports bar serving patrons Maryland Crab Dip, bone-in and boneless wings, crab cake sandwich, wines, and domestic draft beers. The tavern has a daily happy hour, trivia nights, watch parties for sporting events, and other events that bring the community together.
On the southern end of town is the Maple Run Golf Course, an 18-hole par-72 public golf course providing golfers of all skill levels a fun yet challenging course with bunkers, sand traps, and water hazards, while also being scenic. The course has a practice range, a pro shop, and a clubhouse with outdoor seating for golfers to enjoy after a round on the green. Back in town is the Thurmont Community Park, a relaxing green space that has a playground, basketball courts, tennis courts, a fitness trail, and grills for barbecues and cookouts with friends and family.
Chesapeake City
Just near the Delaware State Line is Chesapeake City, a community renowned for the Chesapeake and Delaware Canal flowing through where people can view boats and yachts with ease, timeless amenities, and perfectly preserved 19th-century architecture. On the northern side of town is the Ben Cardin Chesapeake and Delaware Canal Trail, a 1.8-mile-long trail that's considered an easy route for quiet walks and bike rides next to the waterfront. The trail also provides free ferry service between April and October to the southside of town on the opposite side of the canal. A wonderful place to enjoy a lavish dinner and memorable events is the Chesapeake Inn Restaurant and Marina, as it provides its guests with alluring views of the waterfront, while serving diverse menus for brunch, lunch, and dinner, with delicious options like crab cake sandwiches, brick oven pizzas, Maryland Catfish, and speciality rolls. The restaurant has a marina for boaters to explore the open waters and is the premier place to host a wedding, corporate event, or reunion.
A staple in the community is the Chesapeake and Delaware Canal Museum, housed in the Old Lock Pump House, where visitors can learn more about the history of the canal, the functions of the pump house, and how the canal retains a strong impact on the community and region today. Right in the heart of downtown is the Inn at the Canal, a relaxing hotel offering guests comfortable rooms with views of the canal, a lovely front porch out of a fantasy novel, $10 off breakfasts at Cafe on the Bay, and a crisp, cool drink at the RummR Lounge.
St. Michaels
St. Michaels has an old-world feel with its well-preserved 18th-century buildings, timeless waterfront allure, and warm, welcoming resorts. Right on the waterfront is the Victoriana Inn, a pretty Victorian-style bed and breakfast providing its guests with elegant rooms to unwind in for the night or weekend, beautiful gardens on the premises, a deck to enjoy the views, a luxurious dining room with a fresh breakfast, and within walking distance of downtown and numerous museums, restaurants, and shops. Just nearby is the Chesapeake Bay Maritime Museum, an 18-acre campus that is home to a diverse collection of historic boats, buildings, maritime artifacts, and unique exhibitions like the 1879 Hooper Strait Lighthouse and Living Shoreline. The museum hosts various events throughout the year, like the Mid-Atlantic Small Craft Festival, and can host the occasional wedding and private event, making for a true Cinderella story.
A glorious restaurant on the town's waterfront is Foxy's Harbor Grille, serving indulgent seafood like cream of crab soup, crab cake entrees, Foxy's fish tacos, and Pacific Rim mussels in a tropical-like setting, truly symbolizing what paradise looks like without a passport. The restaurant can host events, as it has a gazebo, Main bar, and lookout lounge providing guests with ample views of the bay. Another museum to visit is the Classic Motor Museum of St. Michaels, a car enthusiast's dream come true, as there are 20 pre- and post-World War II-era cars to view, attend the weekly Cars and Coffee Pop Up car show every Saturday morning between April and November, and other major events that take place at the museum.
Cumberland
On the western end of the state is the city of Cumberland, which earns its fable-like appearance from being surrounded by the Appalachian Mountains, preserved 19th-century architecture, and a historic city center. In the heart of downtown is the Embassy Theatre, an Art Deco theater built in 1931, run by volunteers who stage plays, shows, live performances, and musicals. The theater has a timeless interior, making people feel as if they've been transported to the early 20th century, while providing an inclusive environment that welcomes everyone to enjoy an incredible show. Down the street is the Allegany Museum, showcasing the city's history and has exhibits honoring Native Americans who lived in the region, fossilized mammals 500,000 to 700,000 years old, and post-Civil War artifacts. The museum hosts fun and exciting local events that bring the community together, like the Murder at the Museum in March.
Another glorious sight to see in downtown is the Wills Hotel, a pleasant place welcoming guests with warm comfort in their 20 rooms, serving lavish and delicious meals at 1867 - A Modern Chophouse, which is found in the lobby, and is an alluring place to gather for reunions, corporate meetings, and events. Next to the Potomac River is the Canal Place Historical Park, a 58.1-acre park serving as the gateway to exploring the Chesapeake and Ohio Canal and the adjacent river. The park is surrounded by the Western Maryland Scenic Railroad, where people can enjoy scenic train rides, grab lunch from the Crabby Pig, and attend the Summer Market Fest in August, where there are food trucks, vendors, a DJ playing music, a cornhole tournament, and admission is free for all to enjoy.
Sykesville
Between Frederick and Baltimore is Sykesville, a small community with well-preserved 19th-century Victorian architecture, surrounded by natural beauty, and has a very walkable Main Street. On Main Street is the Local Motive, a cozy restaurant serving customers craft beer, quality meals like warm hoagies, paninis, and scrumptious appetizers. The interior is incredibly modern and welcoming, and it is a great place to gather with friends, co-workers, and family. Just south of the Local Motive is the Sykesville and Patapsco Railway, a small, quiet museum for model train enthusiasts with four different train layouts inside and old train cars displayed outdoors. The museum is free to enter, and it also hosts local events that welcome everyone.
South of town is the Hugg-Thomas Wildlife Management Area, a nature area with the mission of preserving the wildlife and habitats of the region. Visitors to the wildlife area can hike the 2.6-mile-long Hugg-Thomas Loop and view the peaceful forest and creek. It is a wonderful place to go bird watching, a place for nature photography, and a great spot to go fishing. On the northern end of town is the Gate House Museum, a public museum set in the former gatehouse of the Springfield Hospital Center, where the family of William Shipley lived until his death in 1954. The museum celebrates the town and has numerous artifacts and historic memorabilia displayed within the building, and tours are available outside of scheduled hours.
A Fairy-Tale Escape Across Maryland
Each of these seven small towns in Maryland invites visitors to a real-life fairy-tale adventure, thanks to their historic charm, natural beauty, and local amenities. Sykesville and Cumberland have deep railroad histories and offer access to scenic nature. Chesapeake City draws visitors with its connection to the Chesapeake and Delaware Canal. Berlin features amazing, quirky museums that welcome tourists from across the region. Taken together, these qualities make Maryland a fantastic place for a true fairy-tale experience.
