Tucked just ten miles inland from the bustling shores of Ocean City, Berlin, Maryland has rightfully earned its nickname as “America’s Coolest Small Town,” according to this article from Southern Living. While nearby destinations like St. Michaels, Easton, and Cambridge often attract seasonal crowds, Berlin remains a serene retreat, rich in character and creativity. From its vibrant Main Street to its historic architecture, this Eastern Shore gem invites exploration at every turn.
One of Berlin’s biggest draws is its artistic energy. The walkable downtown is home to over 60 boutiques, more than a dozen galleries, and numerous venues showcasing the culinary and visual arts. Visitors can drop into local shops, hear live music drifting through open doors, or sign up for a creative workshop. The Worcester County Arts Council serves as a cornerstone of the community’s cultural scene, offering rotating exhibits and public art classes inside a charming white cottage. Nearby, galleries like Jeffrey Auxer Designs, Wooden Octopus, and Henry Fine Arts Gallery showcase works ranging from whimsical to classical. Even cafes like On What Grounds? and Baked Dessert Cafe double as art spaces, supporting Berlin’s motto: “artistically alive.”
The town’s architectural charm is a constant visual delight. A stroll through its neighborhoods reveals well-preserved buildings dating back to the 1700s, many framed by ancient flowering trees. It’s easy to understand why Berlin was chosen as a filming location for the 1999 romantic comedy Runaway Bride, starring Julia Roberts and Richard Gere. For a unique museum experience, visit The Mermaid Museum, a quirky and interactive destination celebrating the myth and magic of mermaids.
Events are a major part of Berlin’s identity, fueled by its close-knit community of about 5,000 residents. Despite its size, the town hosts nearly 50 events each year, from a summer Fiddler’s Convention to bathtub races and peach festivals. These traditions, paired with the town’s heritage and welcoming atmosphere, contribute to its nationwide acclaim.
Berlin’s lodging options blend historical elegance with modern comfort. The Atlantic Hotel, built in 1895, remains a crown jewel of the town. Lovingly restored, its 15 Victorian-era rooms and gracious front porch offer a timeless sense of hospitality. Not far away, The Inn Berlin transforms a grand estate into a boutique retreat with luxury furnishings, antique details, and gourmet breakfasts from a dedicated gluten-free kitchen. Even if you’re not an overnight guest, its in-house café, Boulangerie Berlin, welcomes walk-ins with decadent treats like Lemon Pistachio Cake and savory Quiche Lorraine.
Dining in Berlin ranges from nostalgic to globally inspired. Rayne’s Reef Soda Fountain & Grill has been serving classic American fare since 1901, offering everything from milkshakes to French toast in a retro setting. For a more casual midday meal, gather artisan provisions from Gilbert’s Provisions and enjoy a slice of pie from Mandala Pies under the open sky. Come dinnertime, Blacksmith delivers farm-to-table excellence with dishes like Shrimp Risotto and Black Lentil Thai Curry. For live entertainment and a bite, head to Oaked at The Globe, where music meets comfort food, or relax on the patio at Tiki Tim’s for a breezy evening atmosphere.
No trip to Berlin is complete without a deep dive into its downtown shopping scene. The six distinct districts branching off Main Street feature everything from vintage vinyl at Sound Storm Records to fashionable finds at Bruder Hill & Home and floral artistry at Bleached Butterfly. The town’s indie bookstore, The Greyhound, offers a thoughtful selection of literature and gifts. On Sundays from May through September, the Berlin Farmers Market transforms downtown into a showcase for local growers, makers, and bakers.
Berlin may be modest in size, but its offerings are anything but small. With its artistic soul, historic charm, and welcoming pace, the town continues to prove why it deserves its title as America’s Coolest Small Town.
For more travel-related news and information, click here.
