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 championships, waterfall hikes, and alpaca farms are just a few of the experiences that await. If you want to mix up your routine and visit a town with one-of-a-kind attractions, keep reading to find your next adventure.

Berlin

Bathtub races, honky-tonks, and colonial mansions are a few of the things that set Berlin apart, and the town has collected national recognition for it, including a turn as America's Coolest Small Town. Its strangest tradition is the summer bathtub race, when competitors tear down Main Street in tubs and barrels mounted on wheels, competing for the title of fastest tub racer. Check the town calendar for the date, which moves. The Globe is another draw, working as a restaurant and bar while doubling as a live music venue, comedy club, or movie theater depending on the night.

The Rackliffe House, a brick plantation house built in the 1740s on Sinepuxent Bay, is now a museum, and its windows look out over the water toward Assateague Island. Keep an eye out for the shops and restaurants downtown, including Fins Ale House and Raw Bar, the Blacksmith Restaurant, and Jeffrey Auxer Designs Glass Studio, where you can watch glassblowing in progress.

Oakland

There is always something going on in Oakland, a Garrett County seat that packs an unusual number of annual events into the calendar. The Maryland State Banjo, Mandolin and Fiddle Championships, Oakland Winter Fest, the Little Yough Summer Music Festival, and the Autumn Glory Grand Feature Parade are just a few worth checking.

Ever wanted to meet an alpaca? You can book a meet-and-greet at Alpaca Acres Farm and Fun, which also runs family activities and a gift store. To see the tallest free-falling waterfall in the state, spend a day hiking at Swallow Falls State Park, home to the 53-foot Muddy Creek Falls and a stand of old-growth hemlock that is among the last in Maryland.

Chestertown

Anyone who loves eclectic finds should base themselves in Chestertown and drive the twelve miles east to Crumpton for Dixon's Furniture Auction, universally known as the Crumpton Auction. It is a third-generation operation founded in 1961 by Norman Dixon and now run by his grandson, and it moves at a pace that has to be seen. Several auctioneers work simultaneously, each selling around 200 items an hour, with thousands of lots consigned in the morning and gone by evening. Check the schedule before you drive out, since sale days have changed over the years.

Chestertown's own arts and entertainment district is another good place to walk away with something unusual, full of studios, galleries, and art centers. Barn Artist Studio, Hegland Glass Gallery, and the Garfield Center for the Arts are a few worth a look. For exercise, start the morning running, walking, or biking the 2-mile Wayne Gilchrest Rail Trail.

Leonardtown

Leonardtown divides into several distinct districts, among them the Leonardtown Wharf, Fenwick Street, Leonardtown Square, and the Arts and Entertainment District. At the Wharf, visitors can take in waterfront views over Breton Bay and rent a kayak or canoe to get out on the water.

Fenwick Street holds the independent shops and boutiques, with Board & Brush, North End Gallery, and David's Flowers among them. The War Memorials Garden sits in Leonardtown Square, one of the few surviving colonial-era town squares in the state, while the Arts and Entertainment District is where to find a class, a workshop, or the occasional town market.

St. Michaels

Set on a narrow neck of land along the Miles River near the Chesapeake Bay, St. Michaels is a working coastal town with a long maritime memory. Local legend holds that residents hung lanterns in the trees during the War of 1812 so British gunners would overshoot the town, which is why it is sometimes called the town that fooled the British. Visitors can explore the harbor by renting a paddleboard or kayak, booking a sailing charter, or taking an afternoon cruise.

To learn more about the bay itself, spend a morning at the Chesapeake Bay Maritime Museum on its 18-acre waterfront campus, where the 1879 Hooper Strait Lighthouse is the piece most people climb. For a meal with a view there are several waterfront restaurants, Stars and Blu Miles among them. Through December the town runs holiday events including a Christmas parade and a lighted boat parade, so check the calendar before booking.

Sykesville

Sykesville has one of the state's more interesting downtown districts, a designated Main Street community with a historic core listed on the National Register. Landmarks worth finding include the Old Main Line Visitors Center and Post Office, the Sykesville Town House, and the Gate House Museum of History, which occupies the former gatehouse of the state hospital that once dominated the hill above town.

The Little Sykes Railway Park is the other draw, a miniature train dating to 1949 that still runs through the town's 2-acre park. Anyone wanting to get outdoors can head for the Patapsco River, popular for tubing and fishing, with the Patapsco Valley State Park trail network just across the water.

Thurmont

Locals call Thurmont Maryland's gateway to the mountains, and the Catoctins start more or less at the town line. Catoctin Mountain Park has around 25 miles of hiking trails, historic exhibits including the sawmill and the Blue Blazes Whiskey Still, and places to camp, picnic, climb, and fish. The park also contains Camp David, the presidential retreat, which is why the ridgelines here are better protected than most.

The historic village of Catoctin Furnace is another Thurmont attraction, built around an 18th-century iron furnace whose surviving workers' houses, church, and stone stack can be walked in an afternoon. To see a 78-foot cascading waterfall, Cunningham Falls State Park is the other outdoor option, and it also holds the 43-acre Hunting Creek Lake with a sandy swimming beach.

Chesapeake City

Set along one of the world's busiest canals, Chesapeake City is a waterfront town of around 700 people with bars, 19th-century buildings, and a brewery. Ocean freighters pass within yards of the restaurant decks, which is the whole appeal. Explore the waterway on the Ben Cardin C&D Canal Trail, a roughly 17-mile path running the length of the canal, and stop at the C&D Canal Museum, housed in the original stone pumphouse.

Bayheads Brewing Company, founded in 2016, is a local brewery with a rustic taproom serving craft beer, cider, whiskey, and wine. For chocolates and candy, check out Chesapeake Candy Works. Want to get on the water? Chesapeake Water Tours runs cruises out of the harbor.

Final Thoughts

These eight towns share a habit of leaning into whatever makes them odd rather than smoothing it over. Berlin races bathtubs down Main Street. Crumpton sells several thousand lots in a day to buyers who drove in from three states. Sykesville runs a 1949 miniature train through a two-acre park. The geography helps you plan: Oakland and Thurmont sit in the western mountains, Berlin is out on the coastal bays near Assateague, and Chestertown, St. Michaels, and Chesapeake City work the Eastern Shore, with Leonardtown and Sykesville in between. Pick a corner of the state and you can reach two or three of them in a weekend.