8 Most Eccentric Towns in Maryland

Although Maryland is the ninth smallest state by size, it is surprisingly diverse in festivals, history, and natural landmarks, particularly in its small towns. Antique auctions, bathtub races, banjo competitions, waterfall hikes, and alpaca farms are just a few of the exciting experiences that await. If you want to mix up your routine and visit a town with one-of-a-kind attractions, keep reading to discover your next adventure.

Berlin

Named by the Smithsonian as one of the “20 Best Small Towns to Visit”, bathtub races, honkey tonks, and colonial mansions are just a few of the attractions that set Berlin apart. One of the town’s strangest traditions takes part on July 7th, a bathtub race where competitors dash through the streets in tubs and barrels, vying for the title of fastest tub racer. The Globe is another unbeatable attraction, serving as a restaurant and bar while doubling as a live music venue, comedy club, or movie theater, depending on the night.

The Rackliffe House is a fascinating historic landmark, a brick mansion over 300 years old that has witnessed the passing of Barbary Pirate Ships, Spanish Galleons, and the Revolutionary War, serving as a museum today. Keep your eye out for funky shops and restaurants downtown, including Fins Ale House and Raw Bar, Blacksmith Restaurant, and Jeffery Auxer Designs Glass Studio.

Oakland

There is always something going on in Oakland, with the town hosting countless annual events throughout the year. The Maryland State Banjo, Mandolin & Fiddle Championships, Oakland Winter Fest, Little Yough Summer Music Festival, and Autumn Glory Grand Feature Parade are just a few to check out.

Ever dreamed of meeting an alpaca? You can do so at Alpaca Acres Farm and Fun by scheduling a meet and greet, as well as enjoy the farm’s family-friendly activities and gift store. To see the tallest free-falling waterfall in the state, spend a day hiking at Swallow Falls State Park, home to 53-foot tall Muddy Creek Falls.

Chestertown

Those who love eclectic finds and antiques must spend a few days at Chestertown, home to the renowned Dixon’s Crumpton Auction. Crumpton’s, a third-generation auction company, hosts fast-paced antique auctions. It is not uncommon to sell 200 antique items per hour, allowing visitors to nab a vintage treasure.

Chestertown’s arts & entertainment district is another great place to walk away with a one-of-a-kind souvenir, full of art studios, galleries, and art centers. Barn Artist Studio, Hegland Glass Gallery, and Garfield Center for the Arts are just a few artsy spots worth checking out. Those wanting to get some exercise can start their morning off running, walking, or biking on the 2-mile Wayne Gilchrest Rail Trail.

Leonardtown

Leonardtown can be divided into several diverse districts, the Leonardtown Wharf, Fenwick Street, Leonardtown Square, and the Arts & Entertainment District, being just a few. At the Wharf, visitors can admire waterfront views and rent a kayak or canoe to explore the waters.

Fenwick Street is home to eclectic shops and boutiques, Board & Brush, North End Gallery, and David’s Flowers being just a few to check out. Check out the War Memorials Garden in Leonardtown Square, one of the few provincial town squares remaining, while the Arts & Entertainment District is perfect for attending a class, workshop, or occasional town market.

St. Michaels

Located on a narrow strip of land along the Miles River, near the Chesapeake Bay, St. Michaels is a lively coastal town. Visitors can explore the harbor by renting a paddleboard or kayak, going on a sailing charter, or enjoying an afternoon cruise. To learn more about the Chesapeake Bay, travelers can spend a morning at the Chesapeake Bay Maritime Museum, situated on an 18-acre waterfront campus.

For a meal with a view, there are several waterfront restaurants to choose from, including Stars and Blu Miles. All December long, visitors can enjoy St. Michael’s holiday events, including a Christmas and Lighted Boat Parade, Breakfast with Santa, and New Years Eve celebrations, so keep your eye on their calendar!

Sykesville

Sykesville boasts one of the state's most fascinating downtown districts, recognized as both a National Trust for Historic Preservation District and a National Main Street District. A few of the historic landmarks to check out include the Old Main Line Visitors Center and Post Office, the Sykesville Town House, and the Sykesville Gate House Museum.

The Little Sykes Railway Park is another fun attraction, a miniature train from 1949 that runs through Sykesville’s 2-acre park. Those wanting to head outdoors can make their way to the Patapsco River, popular for both tubing and fishing.

Thurmont

Locals in Thurmont often refer to it as being Maryland’s “Gateway to the Mountains”, conveniently situated near the Catoctin Mountains. Those wanting to explore these nearby mountains must visit Catoctin Mountain Park, home to 25 miles of hiking trails, historic exhibits such as the Sawmill and Blue Blazes Whiskey Still, and places to camp, picnic, rock climb, and fish.

The historic village of Catoctin Furnace is another one of Thurmont’s attractions, featuring 65 houses, a church, a school, and a store to explore. To see a 78-foot cascading waterfall, Cunningham Falls State Park is another outdoor recreational option, also home to a 43-acre man-made lake.

Chesapeake City

Located along one of the world’s busiest canals, Chesapeake City is a lively waterfront town with many bars, 19th-century historic buildings, and a brewery to discover. Explore the canal up close along the Ben Cardin C&D Canal Trail, a 17-mile trail that winds along the entirety of the canal.

Bayheads Brewing Company, founded in 2016, is a local brewery with a rustic-style taproom where visitors can enjoy craft beer, cider, whiskey, or wine. For luxury chocolates and candies, check out Chesapeake Candy Works. Want to get on the water? Consider a tour with Chesapeake Water Tours, who will take you on an exciting cruise through the bay.

Final Thoughts

Concluding our tour of these eight eccentric towns, it is clear that Maryland has a unique side that sets it apart. No matter where your interest lies, whether it be in hiking, maritime history, or souvenir shopping, each of these towns will give you an unforgettable vacation or weekend away. So, dust off your suitcase and prepare to explore the quirky, unforgettable side of Maryland!