Planning a trip to Maryland? Overwhelmed by choices? You're not alone! Maryland offers a stunning array of experiences, from sandy beaches to majestic mountains, making it tough to decide where to start. But here's the secret: choosing the right town can unlock the very best of what this diverse state has to offer.
Maryland, the seventh state to ratify the US Constitution, boasts an incredible 3,000+ miles of shoreline, a whopping 53 state parks, and 18 National Park Service sites. That's a lot to explore! For first-time visitors, the sheer volume of options can feel overwhelming. That's why we've curated a list of six fantastic towns that serve as excellent starting points for your Maryland adventure, each showcasing a unique facet of the state's charm. Get ready for waterfront resorts, beautifully preserved 18th-century mansions, and unforgettable seafood festivals that capture the true essence of Maryland.
1. Ocean City: Your Beach Bliss Awaits
Craving sun, sand, and surf? Look no further than Ocean City, a classic beach destination with 10 miles of pristine shoreline. The town is divided into several distinct beach districts, each with its own unique vibe. The Historic Downtown beach district is where the heart of the action is – think iconic boardwalk, a towering Ferris wheel, buzzing arcades, and even a museum!
The boardwalk is a vibrant hub for local businesses and restaurants. For a truly classic Ocean City experience, check out The Angler, a waterfront restaurant that has been serving up delicious seafood for over 85 years. Their menu is packed with mouthwatering options like steamed mussels, creamy crab dip, crispy fried flounder, and perfectly cooked calamari. Prefer to catch your own dinner? Several companies offer fishing charters. Chasin Tides Charters, for example, provides a variety of fishing excursions led by licensed United States Coast Guard captains.
2. Chesapeake City: Canal-Side Charm & Craft Brews
Nestled along one of the world's busiest canals, Chesapeake City has a surprisingly vibrant atmosphere, especially considering its population of fewer than 1,000 residents. The town is also a treasure trove of historic 19th-century buildings just waiting to be explored! Start your adventure with a relaxing stroll along the Ben Cardin C&D Canal Trail, a scenic canal-side path that stretches for 17 miles and eventually connects to Delaware City.
After your walk, reward yourself with a visit to Bayheads Brewing Company, where you can sample a wide selection of craft beers, whiskeys, bourbons, ciders, and wines. But here's where it gets controversial... Some locals argue that the recent influx of breweries is changing the character of the town. What do you think?
Got a sweet tooth? Chesapeake Candy Works offers gourmet candies, luxury chocolates, and frozen yogurt to satisfy any craving. For the full Chesapeake City experience, consider spending the night at the Inn at the Canal, a beautifully preserved home dating back to around 1870 that perfectly embodies the town's historic architecture.
3. Cumberland: Appalachian Majesty & Scenic Railways
Head to northwestern Maryland and you'll discover Cumberland, a charming Appalachian Mountain town. Cumberland is famously home to the Western Maryland Scenic Railroad, a historic railway that operated from 1852 to 1983 and now offers scenic excursions into the countryside. Throughout the year, the railroad hosts themed rides, including a magical Polar Express ride, an elegant dinner train, and a festive winter express.
For even more breathtaking scenery, don't miss the C&O Canal National Historical Park & Towpath, which stretches for an impressive 184.5 miles, passing through Cumberland and winding along the county's Potomac River, parks, and lush forests. When hunger strikes, grab a bite and enjoy live music at The Balcony, a restaurant and bar that doubles as a popular music venue. They often have seasonal drink specials, and if you're visiting in the fall, be sure to try their apple cider sangria, pumpkin spice margaritas, or caramel apple mimosas!
4. St. Michaels: Maritime History & Oyster Delights
Located on the shores of the Miles River and Chesapeake Bay, St. Michaels is steeped in fascinating maritime history. The Chesapeake Bay Maritime Museum is the perfect place to dive into it all, preserving the bay's rich history, culture, and environment. At the museum, you can enjoy river cruises, explore a historic floating fleet, and discover a variety of long-term and special exhibitions.
If you're lucky enough to visit in late October, don't miss the famed annual OysterFest! This celebration of the bay's beloved delicacy features plenty of fresh oysters, an oyster stew competition, cooking demonstrations, boat rides, and more. To complete your St. Michaels getaway, treat yourself to a stay at the Inn at Perry Cabin, a luxurious 25-acre waterfront resort that started as a farm after the War of 1812. The inn offers a wide range of experiences, including sailing charters, golfing lessons, rejuvenating yoga sessions, and informative garden tours.
5. Hagerstown: Arts, Culture & Outdoor Adventures
Hagerstown offers the best of both worlds: a vibrant Arts & Entertainment district and easy access to several nearby state and national parks. South Mountain State Park, just a short drive away, stretches 40 miles along the South Mountain ridge to the Potomac River, making it ideal for hiking and picnicking.
For those interested in the performing arts, check out the calendar at The Maryland Theatre, a beautifully restored venue dating back to 1915 that hosts a variety of events, from orchestra performances and ballets to concerts by touring musicians. The Washington County Museum of Fine Arts is another cultural gem, boasting a permanent collection of over 6,500 paintings, sculptures, drawings, prints, and other artistic treasures. The museum's highlights include American artworks, 19th-century European pieces, and art from around the world.
6. Annapolis: History, Harbors & Hometown Charm
Last but certainly not least is Annapolis, the state's capital! Home to just over 40,000 residents, this charming town has earned numerous accolades, including being ranked among the prettiest and best places to visit in the United States. A must-see is the Historic Annapolis District, home to historic landmarks like the William Paca House & Garden. This stunning Georgian mansion, built in the 1760s, was the home of William Paca, one of Maryland's signers of the Declaration of Independence.
As a beloved Chesapeake Bay town, Annapolis has a deep appreciation for boating. The Annapolis Boat Shows are a cornerstone of the city's maritime culture, featuring an extensive lineup of in-water sail and powerboats across two weekends each year. Can't make it during the boat shows? No problem! You can still enjoy a sailing excursion with a local charter, such as Schooner Woodwind Sailing Cruises, which offers rides on its gorgeous wooden 74-foot schooners. And this is the part most people miss... Many visitors stick to the main tourist areas and never venture into the residential neighborhoods, where you can find hidden gems like locally-owned boutiques and cozy cafes.
Your Maryland Journey Begins Now
Choosing just six towns as starting points for exploring Maryland was no easy task, but these destinations offer a fantastic range of experiences. Some towns, like Ocean City and St. Michaels, have a strong maritime focus due to their location along the waterways and the Chesapeake Bay, while others, like Cumberland, are nestled in the beautiful Appalachian Mountains. Whether you explore them all or just pick one, get ready to experience the very best of Maryland's stunning scenery and unforgettable attractions.
Which of these towns sparks your interest the most? Do you agree with our choices, or would you add another town to the list? Share your thoughts in the comments below!
