6 Best Maryland Towns For First-Time Visitors

Few states can pull off the balancing act of diverse experiences like Maryland. It was the seventh to ratify the US Constitution and now offers more than 3,000 miles of shoreline, 53 state parks, and 18 sites managed by the National Park Service. There is so much to see across the state that visiting for the first time often feels daunting! If you are considering a trip to the Old Line State, these six towns are great starting points, featuring waterfront resorts, 18th-century mansions, and seafood festivals that showcase everything Maryland has to offer.

Ocean City

If you are craving a beach trip, Ocean City is a worthwhile contender, featuring 10 miles of pristine beaches. You’ll find several beach districts throughout town, each with its own personality. The Historic Downtown beach district is where a lot of the action takes place, home to a boardwalk, Ferris wheel, arcade, and museum.

On the boardwalk, you’ll find plenty of local businesses and restaurants, including The Angler, a waterfront restaurant that has been operating in the community for over 85 years, offering plenty of delicious dishes like mussels, crab dip, fried flounder, and calamari. If you prefer to catch your own fish, several companies offer fishing charters. Chasin Tides Charters, for example, offers a variety of fishing excursions, all of which are led by licensed United States Coast Guards.

Chesapeake City

Chesapeake City sits along one of the world’s busiest canals, giving it a surprisingly lively atmosphere for a town of fewer than 1,000 residents. It is also filled with historic, 19th-century buildings to explore! Travelers can begin their adventure in town by taking a stroll on the Ben Cardin C&D Canal Trail, a canal-side trail that extends for 17 miles, eventually connecting to Delaware City. After your afternoon on the trail, stop by Bayheads Brewing Company for a pitstop, where you can enjoy craft beers, whiskeys, bourbon, cider, and wine, among other spirits.

Visitors with a sweet tooth can also get their sugar fix at Chesapeake Candy Works, which sells gourmet candies, luxury chocolates, and frozen yogurt. To complete your Chesapeake City tour, consider spending the night at the Inn at the Canal, which perfectly exemplifies the town’s architecture, set in an elegant home that dates back to around 1870.

Cumberland

Moving up to northwestern Maryland, travelers will find Cumberland, an Appalachian Mountain town. This town is famously home to the Western Maryland Scenic Railroad, a historic railway that operated between 1852 to 1983, now offering scenic excursions into the countryside. Throughout the year, the railroad offers thematic rides, including a Polar Express ride, dinner train, and winter express.

For even more scenery, make sure to visit the C&O Canal National Historical Park & Towpath, which extends for 184.5 miles, passing through Cumberland and winding through the county’s Potomac River, parks, and forests. Hungry? Grab a bite and enjoy a performance at The Balcony, a restaurant and bar that doubles as a music venue. It is currently offering some delicious fall drink specials, including apple cider sangria, pumpkin spice margaritas, and caramel apple mimosas to get you right into that fall spirit!

St. Michaels

Sitting along the Miles River and Chesapeake Bay, St. Michaels is filled with fascinating maritime history. The Chesapeake Bay Maritime Museum is one of the best places to experience it all, preserving the entire bay’s history, culture, and environment. A few of the experiences that visitors can appreciate at the museum include river cruises, a historic floating fleet, as well as a variety of long-term and special exhibitions.

On October 25 this year, the museum will also host the famed annual OysterFest. Celebrating this bay delicacy, activities during the festival include plenty of fresh oysters, an oyster stew competition, demonstrations and presentations, boat rides, and more. Wrap up your trip with a stay at the Inn at Perry Cabin, a luxurious 25-acre waterfront resort that began as a farm following the War of 1812. The inn offers an array of experiences, including sailing charters, golfing lessons, yoga sessions, garden tours, and more.

Hagerstown

Hagerstown offers the best of both worlds: an exciting Arts & Entertainment district, along with several nearby state and national parks in the area. South Mountain State Park, only a short drive away, runs 40 miles along the South Mountain ridge to the Potomac River and is perfect for hiking and picnicking.

Those interested in the performing arts scene can check out the calendar at The Maryland Theatre, which dates back to 1915, and today hosts a range of events, from orchestra performances and ballets to touring musicians. The Washington County Museum of Fine Arts is another cultural highlight, developing over the years into a museum that today holds over 6,500 paintings, sculptures, drawings, prints, and other pieces in its permanent collection. A few of the focal points you’ll find in the museum include American artworks, 19th-century European pieces, and other art from around the globe.

Annapolis

Last on the list is none other than the state’s capital: Annapolis! Home to just over 40,000 residents, this town has received numerous distinctions, including being ranked among the prettiest and best to visit in the United States. You will definitely want to check out the Historic Annapolis District, home to historic landmarks like the William Paca House & Garden. This Georgian mansion, which dates back to the 1760s, was built for William Paca, one of the state’s Declaration of Independence signers.

As another beloved Chesapeake Bay town, the area has a great appreciation for boating. The Annapolis Boat Shows are a key part of the city’s maritime culture, featuring an extensive lineup of in-water sail and powerboats across two weekends each year. Not able to visit the city during one of the boat shows? No problem! You can still enjoy a sailing excursion with a local charter, such as Schooner Woodwind Sailing Cruises, which provides rides on its gorgeous wooden 74-foot schooners.

A Good Starting Point For Your Maryland Adventure

While choosing only six towns is a challenge, these are some of the most incredible places to begin your exploration, largely thanks to their large variety of experiences. Some towns have a maritime focus, due to their position along waterways and the Chesapeake Bay, while others, like Cumberland, are beautiful mountain towns. So whether you explore them all or just one, prepare to experience the best of Maryland’s scenery and attractions.