When people are thinking of doing a U.S. road trip, they think of route 66 or the vastness that is Texas, and both of those places are great for car-based trips that you will never forget, but you know what? Smaller places like Maryland, are great for seeing the spirit of America too. In fact, Maryland is one of the best road trip destinations in the country due to its spooky lighthouses, blue crabs by the bucket and sweeping mountain views.
Sound good? Here’s how to do Maryland right by road.
Start Strong in Baltimore
Baltimore is basically that friend who’s cooler than they let on. You roll in expecting rowhomes and a harbor, and suddenly you’re knee-deep in street art, world-class museums, and some of the best seafood of your life.
Kick off at the Inner Harbor – touristy? Maybe. Worth it? Absolutely. Hit the National Aquarium, then wander up Federal Hill for skyline views that’ll have you whispering “Okay Baltimore, I see you.”
Food stop? Grab a crab cake (you legally can’t leave the city without one). Then treat yourself to a romantic finale at the best hotel in Baltimore for a romantic getaway – The Ivy Hotel, because sometimes you deserve to live your elegant, candle-lit fantasy for a night.
Detour Into History: Annapolis
Next stop on your itinerary has to be Annapolis, aka Colonial Instagram Heaven. If brick streets, sailboats, and history make your heart flutter, you’ll be smitten here. Tour the U.S. Naval Academy (bring comfy shoes), browse cozy boutiques, and take a peaceful harbor cruise.
Bonus points if you time your road trip for sailing season so you can watch the boats glide in like a lifestyle commercial you suddenly want to star in.
Go Bay-Side: Kent Island & Chesapeake Trivia
Cross the Chesapeake Bay Bridge (deep breath, bridge worriers, you’ve got this) and coast into Kent Island. This is picnic-by-the-water territory, so pack snacks. Or do the sensible thing and stop at a dockside restaurant for steamed crabs and Old Bay everything.
Want to feel like a local?
Say, “Yes, I do want extra Old Bay,” and don’t look back.
While you digest, explore the Chesapeake’s quiet parks, kayak the calm waters, and keep an eye out for ospreys and herons living their best life.
Small-Town Sweetness in St. Michaels
A little farther down the coast lies St. Michaels, which feels like someone bottled pure coziness and turned it into a town. Sip wine at a waterfront winery, hop on a sailing tour, or explore the Chesapeake Bay Maritime Museum.
This is your slow-down, stroll-hand-in-hand, “maybe we should move here?” portion of the trip.
(Pro tip: Don’t look at real estate prices unless you’re ready to fall deeply, financially in love.)
Mountains and Quiet Magic in Western Maryland
Time for a scenery plot twist: head west. Deep Creek Lake and Savage River State Forest swap out coastal vibes for mountain air and pine trees that whisper, “Delete your email app.”
Hike, kayak, ski in winter, or just sit by a fire and wonder why you don’t road-trip more often.
Maryland, you overachiever!
