8 Most Photogenic Towns In Maryland

Maryland is a state with dynamic small towns and stunning landscapes. From the craggy cliffs and quiet coves of the Chesapeake Bay to tree-lined rivers and bustling harbors, Maryland’s towns are as diverse as they are picturesque. Wander through historic districts that date back to colonial times, where cobblestone streets and centuries-old architecture whisper tales of the past. Explore lush state parks, wildlife refuges, and serene waterfronts perfect for kayaking, birdwatching, or simply taking in the scenery. Whether you’re drawn to maritime heritage, peaceful outdoor escapes, or charming main streets, these eight photogenic Maryland towns showcase the best of the state’s rich history and natural wonders.

St. Michaels

Nestled on the Chesapeake Bay’s Eastern Shore, St. Michaels captivates with its coastal appeal and maritime past. The Chesapeake Bay Maritime Museum, complete with boats and a working shipyard, gives visitors an in-depth look at the region’s nautical heritage. St. Michaels Harbor, with its tranquil waters and sailboats, provides the setting for a leisurely stroll or a meal at waterfront favorites like The Crab Claw Restaurant, where diners can enjoy fresh seafood while taking in the bustling harbor scene. For outdoor enthusiasts, a boat ride along the Miles River reveals lush marshlands and secluded coves. For a memorable stay, the Inn at Perry Cabin, known for its timeless elegance and bayfront location, has luxurious accommodations.

Chestertown

Chestertown, located along the Chester River, is a colonial gem with a legacy dating all the way back to 1706. The town’s well-preserved 18th-century architecture, including the iconic White Swan Tavern and the Courthouse Square, transports visitors to a bygone era. The waterfront is a hub of activity. Kayaking or sailing on the Chester River is popular with visitors to the area. Wilmer Park, with its expansive green space and scenic river vistas, is a lovely spot to relax and take in the town. Chestertown also hosts the annual Chestertown Tea Party Festival, celebrating its revolutionary roots with reenactments and lively events.

Oakland

Tucked into the Allegheny Mountains, Oakland is a haven for outdoor enthusiasts, but it also has a rich history. The town’s historic B&O Railroad Station, a beautifully restored landmark, speaks to Oakland’s role in Maryland’s railroading. Just a short drive from town, Deep Creek Lake is a year-round destination for boating, fishing, and hiking, with trails providing vantages of the water and surrounding forests. Swallow Falls State Park is home to Maryland’s tallest waterfall, Muddy Creek Falls. It is a must-visit for its rushing water cascades and forested trails. In the fall, the area’s foliage transforms Oakland into a brightly colored wonderland, drawing in visitors from across the state and beyond.

Berlin

Berlin is often celebrated as "America's Coolest Small Town," and for good reason. Its lively Main Street boasts beautifully preserved Victorian architecture, including the iconic Atlantic Hotel, a charming 19th-century building that now operates as a boutique inn.

Beyond the town, Assateague Island National Seashore beckons with its pristine beaches, salt marshes, and the chance to see the island’s famous wild ponies. The nearby Pocomoke River provides opportunities for kayaking the many waterways framed by towering cypress trees. Berlin’s active arts scene also comes alive through local festivals and events, such as the Berlin Fiddlers Convention and the 2nd Friday Art Stroll.

Havre de Grace

The town of Havre de Grace sits where the Susquehanna River meets the Chesapeake Bay. The town is home to the Concord Point Lighthouse, one of the oldest in the United States, which provides stunning views of the bay. Stroll along the Havre de Grace Promenade, a scenic boardwalk that winds past marinas, parks, and landmarks like the Havre de Grace Maritime Museum. The nearby Susquehanna State Park features forest areas and trails like the Rock Run Trail, which has beautiful river views and glimpses of the Rock Run Grist Mill, a structure dating back to the early 19th century. The town also boasts a charming downtown area filled with antique shops and cozy cafés like The Vineyards Restaurant & Winery, where visitors can enjoy local wine and fresh seafood in a quaint setting.

Boonsboro

Nestled at the base of South Mountain, Boonsboro is a history-rich town with stunning surroundings. The Appalachian Trail passes just outside the town, offering hikers scenic vistas and peaceful tree-lined paths. Washington Monument State Park, home to the first completed monument dedicated to George Washington, is also a great place to take in the Maryland countryside from its hilltop perch. Downtown Boonsboro endears visitors with its locally owned shops, including Turn the Page Bookstore, a haven for book lovers. The town’s proximity to the Antietam National Battlefield, a significant Civil War site, adds an extra layer of historical intrigue.

Snow Hill

Snow Hill, located on the banks of the Pocomoke River, is a peaceful Eastern Shore town brimming with natural beauty and small-town allure. The town’s historic district features stately homes and landmarks like the 19th-century Bishop's Stock Fine Art Gallery and the beautiful, historic All Hallows Episcopal Church, a stunning example of Gothic Revival architecture.

For nature enthusiasts, Pocomoke River State Park is a must-visit, with opportunities to kayak and canoe the river. Birdwatchers will love spotting a variety of species, including herons, egrets, and bald eagles, as they soar above the marshlands. Snow Hill also hosts an array of festivals, such as the Snow Hill Arts & Crafts Festival, making it a lively destination throughout the year with art, music, and local vendors adding to the town’s charm.

Rock Hall

Known as the “Pearl of the Chesapeake,” Rock Hall is a quintessential waterfront town on the bay. The town’s marinas and seafood restaurants make it a haven for boaters and food lovers alike, with places like Waterman’s Crab House serving up fresh local catches. Eastern Neck National Wildlife Refuge, located nearby, features miles of trails and observation points. Travelers can spot migratory birds, such as tundra swans and ospreys, as well as other wildlife. The Rock Hall Beach, with its calm waters and golden sunsets. Relax, swim, or capture photographs on the shore. Rock Hall also celebrates its maritime culture through lively events like the Rock Hall FallFest and Waterman’s Day, which highlight the community’s rich heritage.

Maryland’s small towns are brimming with scenic beauty, fascinating history, and vibrant local culture. From tranquil riverside retreats to bustling historic districts, each of these towns offers something unique. Whether exploring the lush trails of Oakland, strolling through Berlin’s charming streets, or enjoying the maritime heritage of Rock Hall, visitors will discover the photogenic charm that makes these destinations unforgettable.