6 Best Maryland Towns For A Weekend Trip
Maryland may be one of the smallest states in the country, but it’s packed with picturesque small towns that boast unique attractions and memorable experiences. Whether you’re drawn to historic charm, waterfront tranquility, or the beauty of the countryside, Maryland’s hidden gems offer something for everyone. Take Oakland, where outdoor enthusiasts can marvel at the cascading waterfalls of Swallow Falls State Park, or explore St. Michaels, a quaint harbor town rich in maritime history and scenic views. These towns and more showcase the diverse appeal of Maryland, making it the perfect destination for a rejuvenating weekend escape.
Saint Michaels
St. Michaels is one of those towns that feels like it was crafted with weekend escapes in mind and has the accolades to prove it. In 2007, Coastal Living Magazine named it #8 on their list of the Top Ten Romantic Escapes in the USA, and in 2018, Forbes declared St. Michaels “The East Coast Weekend Getaway You’ve Been Missing.”
From April through November, the town comes alive with its Saturday farmer’s market, where you’ll find fresh produce and artisanal goods from across the region. May draws runners to the St. Michaels Running Festival and Half Marathon, while summer brings a festive Fourth of July celebration with fireworks over the harbor. Fall is no less lively with the “Fall into St. Michaels Weekend” featuring the crowd-favorite Jack Russell dog race.
History aficionados can dive into the past at the St. Michaels Museum, Chesapeake Bay Maritime Museum, and Classic Motor Museum or visit nearby Tilghman Island and the 1879 Hooper Strait Lighthouse. For a taste of local craftsmanship, stop by Eastern Shore Brewing, Saint Michaels Winery, or LYON RUM Distillery. celebrate your weekend at Wades Point Inn On The Bay or the Inn at Perry Cabin, where relaxation meets stunning waterfront views.
Chestertown
Chestertown is an ideal destination for those seeking a weekend escape filled with history and artistic charm. Visitors can delve into its rich past with a tour of Washington College, one of the nation’s oldest colleges, set on a picturesque campus. History enthusiasts will also enjoy the Historical Society of Kent County, while art lovers can explore MassoniArt Gallery and Art on High. For live entertainment, the Garfield Center for the Arts at the Prince Theatre hosts captivating performances that add to the town’s cultural appeal.
If you’re planning your visit, try to align it with Chestertown’s First Friday celebration, a monthly event that sees shops on Main Street welcoming guests with open doors and special displays. This lively tradition draws residents and visitors from neighboring towns and is especially popular with Washington College students, creating a vibrant community atmosphere.
After a day of strolling and shopping, stop by Luisa’s Cucina Italiana for a hearty Italian meal served in a warm, inviting setting. To complete your weekend, stay at the White Swan Tavern, a restored 18th-century inn featuring period-style furnishings and a cozy ambiance, all conveniently located in the heart of downtown.
Havre de Grace
In Havre de Grace, visitors flock year-round for its blend of history, allure, and outdoor adventure. A journey through the town often begins in the bustling Havre de Grace Main Street district, where locally owned shops and eateries create a warm and inviting atmosphere. Stepping into one of these establishments, you’ll find everything from handmade crafts to delicious meals that reflect the community’s welcoming spirit.
Nature lovers will find plenty to explore at Susquehanna State Park, with its scenic trails and breathtaking views of the river, making it an ideal spot for hiking, fishing, or a peaceful picnic. For a dose of local history, the Steppingstone Farm Museum offers insight into the area’s agricultural past with its interactive exhibits and restored buildings. A walk along the Havre de Grace Promenade delivers stunning waterfront views and a relaxing way to cap off your day.
To complete your visit, consider staying at the Vandiver Inn, a quaint Victorian-style bed-and-breakfast known for its beautifully appointed rooms and gourmet breakfasts. Alternatively, the Travelodge by Wyndham Aberdeen provides a convenient and comfortable option for those seeking modern accommodations near all the action.
Berlin
A community steeped in character and appeal, Berlin is a must-visit gem on Maryland’s Eastern Shore. Named “America’s Coolest Small Town” by Budget Travel in 2014, Berlin is celebrated for its quaint Main Street, lined with boutique shops, unique eateries, and historic architecture. The town’s inviting personality and walkable downtown make it an ideal spot for exploration and discovery.
Nature seekers will appreciate Berlin’s proximity to outdoor treasures like Assateague Island National Seashore, home to wild horses and serene beaches, and Pocomoke State Forest, offering hiking and kayaking opportunities amidst lush landscapes. For a touch of whimsy, don’t miss The Mermaid Museum, a quirky and one-of-a-kind attraction that sparks curiosity and fun.
Dining in Berlin is as delightful as the town itself, with cozy spots like Baked Dessert Cafe and The Sterling Tavern serving up something to satisfy every palate. To round out your visit, choose from accommodations like the Atlantic Hotel, a beautifully restored 1895 property featuring antique furnishings and a central location on Main Street, or Holland House, a quaint bed-and-breakfast housed in a turn-of-the-20th-century home that exudes warmth and hospitality.
Cambridge
Much of the appeal for those planning a weekend visit to Cambridge lies in its rich heritage and natural beauty. This Maryland town is deeply connected to its waterways and history, making it a fascinating destination. The Harriet Tubman Museum and Educational Center provides an in-depth look at the life of the famous abolitionist and her role in the Underground Railroad, while the Choptank River Lighthouse highlights the maritime history that has shaped the area. For nature enthusiasts, the Blackwater National Wildlife Refuge offers miles of scenic trails, wildlife observation, and a serene escape into the great outdoors.
Local festivals add even more reasons to visit Cambridge. In January, the Cambridge Ice and Oyster Festival showcases icy sculptures and local seafood, while May brings the Flower Fair, filling the streets with vibrant blooms and community celebrations. Dining here is just as enjoyable, with fresh, locally sourced seafood being a highlight.
When it’s time to unwind, accommodations like the Hyatt Regency Chesapeake Bay Golf Resort, Spa, and Marina promise a relaxing retreat with stunning river views and luxurious amenities. For a more intimate stay, the Cambridge House Bed and Breakfast offers fascinating, historic accommodations right in the heart of town.
Oakland
Maryland is home to many delightful towns, but Oakland stands out for its breathtaking landscapes, rich history, and undeniable allure. Start your adventure at the Oakland B & O Railroad Museum, where the town’s railroading legacy comes to life through interactive exhibits and captivating stories of the region's past. For outdoor lovers, Oakland is a dream. Deep Creek Lake State Park features endless opportunities for kayaking, hiking, and soaking up the serene lake views. A visit to Swallow Falls State Park is a must; prepare to be awestruck by the majestic Muddy Creek Falls, Maryland’s tallest free-falling waterfall, framed by lush forest trails.
After a day of adventure, dive into the local flavors. Sweitzers BBQ serves up mouthwatering smoked meats, while the 3rd Street Diner dishes out comforting classics in a welcoming atmosphere. For a memorable stay, the Haley Farm Bed & Breakfast and Retreat Center boasts spa treatments, scenic grounds, and farm-fresh breakfasts. Alternatively, The Garrett Inn provides cozy, rustic accommodations that feel just like home. Oakland is where adventure and relaxation come together beautifully.
From waterfront escapes to historic towns, Maryland offers an array of destinations for a memorable weekend. Whether it’s strolling along the scenic promenade in Havre de Grace, savoring local wines in Saint Michaels, or immersing yourself in the arts and culture of Chestertown, these six towns deliver a blend of history, nature, and relaxation. Maryland's diverse offerings cater to every traveler, from delightful bed-and-breakfasts to gourmet dining and unique attractions. With its stunning landscapes and rich heritage, Maryland invites visitors to slow down and savor the small-town charm that makes it an ideal state for a peaceful weekend retreat.
