7 Best Kept Maryland Destinations — Travel Like a Local

With beautiful landscapes, a rich history, and seafood galore, there’s no shortage of Maryland destinations to tempt adventurous travelers. However, you don’t want to get caught up in crowds of tourists. So if you’re looking to travel like a local with a custom charter sightseeing tour, here are a few great locations off the beaten path you’ll surely want to add to your must-list.

Eastport (Annapolis)

There are plenty of reasons to visit Annapolis proper, but if you want the local experience when it comes to Maryland destinations, consider crossing the bridge into eastern Annapolis. You can take a water taxi or even walk on over the Spa Creek Bridge. Eastport is the place to be if you’re interested in boating, even if you just want to rent a canoe and paddle around the harbor. Afterward, you can enjoy live music and dine on the water at many local restaurants.

Gunpowder State Falls

Established in 1959, this state park is an excellent alternative to more popular tourist destinations like Sandy Point State Park. You’ll find playgrounds and picnic spots at the Hammerman Area, and Jerusalem Mill Historic Village offers a must-see glimpse of living history. Experience this beautiful park via hiking, biking, or horseback ride. It is located in Kingsville, Maryland, just northeast of Baltimore.

Boordy Vineyards

While Maryland has many remarkable wineries, its first commercial winery, Boordy Vineyards, is a great place to kick back and sample handcrafted local vintages. Sip on crisp, fruity Vidal Blanc or Boordy Blush from the Chesapeake Icons collection. Or try citrusy Albariño and rich, complex Cabernet Franc Reserve from the Landmark Series. Located in northeastern Baltimore County, there are many events throughout the year to enjoy.

Old Town Bowie Farmers Market

Many people visit Bowie for golf, biking, summer concerts, and other outdoor events. But if you want to travel like a local, pop by the farmers’ market on summer Sundays. You can pick up fresh-from-the-farm produce, meats, baked goods, gorgeous flower arrangements, and handcrafted goods. But, of course, if you aren’t in Bowie, there are plenty of other Maryland Farmers Markets to choose from.

Ellicott City

Located just 13 miles west of Baltimore, this suburb offers a small-town experience with rich history and legitimately outstanding dining opportunities. Outdoor adventures abound at Patapsco Valley State Park and Centennial Park. You can also scratch your shopping itch at a range of funky boutiques. From there, enjoy creative Mexican cuisine and margaritas at La Palapa Grill & Cantina, or order a pitcher at Manor Hill Beer Garden. This is one stop you’ll definitely want to add to your brew tour bachelor weekend.

Bengies Drive-In Theater

When was the last time you went to a drive-in theater? If you’re under 40, the answer might be never. Bengies Drive-In is a throwback to a bygone era — and a can’t-miss experience in Baltimore County. So pop the hatchback, grab some snacks, and cuddle up to watch a current release from the comfort of your car. It remains the largest movie screen remaining in the U.S.!

Assateague Island

Much of beautiful Assateague Island is overrun with tourists, and it’s not hard to see why — this 37-mile peninsula offers up endless ocean views and, no joke, herds of wild horses. If you want to travel like a local, stick to the northern end. The Maryland horse herd roams free here. If you camp at Assateague State Park, you’re likely to see them wandering around and frolicking on the beach. You’ll also enjoy sandy beaches, truly outstanding sunsets, and well-maintained facilities.

Getting to Your Maryland Destinations in Style

Wherever you want to go in Maryland, you can find safe and reliable transport for your entire group with Chesapeake Charter. Contact us today to request a quote and get your trip underway.