This Tiny Town Is The Best-Kept Secret On Maryland's Eastern Shore

Key Takeaways

Berlin, Maryland’s historic downtown is the hub for shopping, arts, dining, and architecture.

Visitors have their pick of food options, including coastal cuisine, farm-to-table meals, and casual spots with live music.

Take a break from the town’s many festivities and events and stay at one of Berlin’s historic inns.

In the South, nicknames are earned, not given. You can’t just wake up one day and decide to go by Speedy. You’ve got to win a race or two first. Just 10 miles inland from Maryland’s famed Ocean City, the village of Berlin has more than earned its moniker as America’s Coolest Small Town. When the weather warms, folks flock to coastal towns like St. Michaels, Easton, and Cambridge, but Berlin remains comfortably sheltered from the crowds. However, the hidden gem destination is more than worth a detour from the sandy shores.

Boasting one of the country’s most vibrant Main Streets, with more than 60 shops, plus a dozen art galleries and bountiful dining options, Berlin’s residents and visitors never tire of things to do. The walkable town is a haven for artists of all types, which means you can hear live music, shop at galleries, take an art workshop, or delight in the culinary arts whenever you please.

One of the best things about Berlin is its community. At 5,000 locals strong, you’ll find small-town sensibilities but more than enough passionate people to produce nearly 50 events a year. Classic Americana events include yearly bathtub racing, a peach festival, and a fiddler's convention. Pair that with a rich history dating to the 1700s and beautiful historic buildings and homes, and you’ve got all the makings of a community befitting of its distinction as the Coolest Small Town in America. Here’s how to spend a weekend in Berlin, Maryland.

Courtesy of Town of Berlin

What To Do In Berlin, Maryland

Head Downtown For Shopping And More

Life in Berlin revolves around its historic downtown. Characterized by picturesque tree-lined streets, colorful shop awnings, and Victorian, Greek, and Gothic Revival architecture, the heart of the town is found on Main Street. The area is divided into six distinct districts, four quadrants around Main Street, plus offshoots at Broad Street and Old Ocean Boulevard. Start your visit by exploring shops like Sound Storm Records for new and vintage vinyl, Bruder Hill & Home for women’s apparel and gifts, and the effortlessly chic European-style flower shop Bleached Butterfly. Find calming scents at the whimsical Honey Water Candles and written and visual art at indie bookstore The Greyhound. On Sundays from May through September, join the gathering of talented area makers, producers, and farmers at the Berlin Farmers Market.

Courtesy of Honeywater Candles

Don't Miss The Mermaid Museum

After you’ve spent time popping in and out of shops throughout town, make a longer stop at one of the town’s most unique and newest attractions, The Mermaid Museum. Opened in 2020, the museum features interactive exhibits dedicated to the mythical sea creature. History buffs and those who appreciate beautiful architecture should take time to stroll through Berlin’s quaint neighborhoods where every house has its own irresistible character, and the flowering trees are centuries old. If the area looks familiar, romcom aficionados might not be surprised to learn that Berlin was a major filming location for 1999’s Runaway Bride starring Richard Gere and Julia Roberts.

Admire Local Art

One-half of Berlin’s town motto is “artistically alive”. You can experience the arts from multiple avenues in Berlin, but one of the easiest entry points is the Worcester County Arts Council. Visit the local nonprofit’s headquarters, a tiny white clapboard home, where they host a rotating exhibit and regular art classes. After, take a walking tour of the town’s best galleries. Find glasswork at Beach Memories and Jeffrey Auxer Designs. For art on two ends of the spectrum, head to The Dusty Lamb for whimsical modern works, then visit Henry Fine Arts Gallery for more traditional creations. At working gallery Wooden Octopus, visitors can see four artists in action and purchase their work. In Berlin, art isn’t limited to its designated spaces, several businesses like On What Grounds? coffee house and Baked Dessert Cafe host in-house galleries featuring the works of local artists.

Courtesy of Mandala Pies

Where To Eat In Berlin, Maryland

Start The Day At A Classic Diner

Rayne's Reef Soda Fountain and Grill has a throwback feel that's genuine. The place opened in 1901, after all. While it's beloved for its burgers and milkshakes, the diner also offers a breakfast menu with all the classics, from pancakes to omelets to French toast.

Have An Afternoon Picnic

For a light and artisanal midday meal, prepare your own picnic spread with gourmet goodies from Gilbert’s Provisions. If they have a lunch special on the day you visit, don’t hesitate to order it. Complete your meal with a slice of from-scratch pie from Mandala Pies. The Banana Cloud is like your favorite barbecue joint’s banana pudding—but better—and the The Old Farmer’s Almanac puts a new spin on the classic apple pie with top and bottom crusts made from cinnamon rolls.

Go Global Or Get BBQ For Dinner

For dinner, farm-to-table favorite Blacksmith is your spot. Entrees range from Shrimp Risotto to Black Lentil and Vegetable Thai Curry. The Stacked Crispy Eggplant with herb Boursin cheese and slow-cooked tomato sauce is a must-try appetizer. Another great place to eat (and play!) is Oaked at the Globe, a music venue and gastropub located in a historic building in the heart of downtown Berlin. Inside, find a simple menu of sandwiches and barbecue served with mac and cheese and curry potato salad. If the weather is nice, snag a seat on the outdoor patio for an entirely different concept known as Tiki Tim’s. Live music happens inside on Friday and Saturday nights.

Courtesy of Town of Berlin

Enjoy A Nightcap

If you’re not ready to head back to your hotel after dinner, find a sweet treat at Island Creamery. Looking for something stronger? Find craft beer at local favorite hangout Burley Oak Brewing Company and honey-brewed mead at The Buzz Meadery.

Courtesy of The Inn Berlin

Where to Stay in Berlin, Maryland

Check In To A Historic Hotel

Berlin may be a small town but its lodging options are far superior to your average side-of-the-road lodges or unexciting hotel chains. The Atlantic Hotel is one of Berlin’s crowned jewels. The hotel welcomed its first guests in 1895. Today, new owners have chosen to pay homage to the building’s roots by restoring its 15 rooms to their former Victorian-era glory. Sit for a spell on the gracious front porch or have a meal in the elegant onsite eatery.

Another historic property, The Inn Berlin transforms a grand Victorian estate into an elegant, modern retreat. Perched on a grassy knoll on the edge of downtown, The Inn sits comfortably away from bustling Main Street while maintaining easy walking distance to all of Berlin’s shops, restaurants, and galleries. With five spacious guest rooms, each outfitted with luxury furnishings and thoughtful antique touches, you’ll feel perfectly at peace in your private retreat. Gourmet breakfast from a 100% gluten-free kitchen is served daily. For those who aren't staying at The Inn, breakfast and lunch items are available for purchase from the in-house café known as Boulangerie Berlin. Options range from sweets like Lemon Pistachio Cake and Chocolate Mousse Tart to Quiche Lorraine and homemade baguettes.

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