The eastern side of the state shares the Delmarva Peninsula with Delaware and Virginia, offering cushy white shores and breezy beach towns like Ocean City. A bit inland, the enormous Chesapeake Bay shimmies its way past bustling cities like Annapolis and Baltimore – and along the western portion of the state, the Appalachians cut through the land, creating a rolling landscape of forestry. No matter where you land, Maryland is brimming with history and homey pleasures, like blue crabs and beer, just waiting to be enjoyed campside with friends.
Your inner 5 year-old may still desperately want to see a pony – a dream you can actually bring to fruition at beautiful Assateague Island, a pristine barrier island just south of Ocean City. Nicknamed "Pony Island" by locals, Assateague State Park is home to wild horses that make regular appearances on the park’s nature walks. And the island’s bayside waters feature twisty hidden inlets, perfect for exploring by canoe.
Nearby at Smith Island, you’ll discover one of the last inhabited islands in the Chesapeake. The island is only accessible by ferry, and once you arrive – visitors typically either walk the history-laden streets or rent a golf cart to zip around in. Don’t leave without sampling the island’s famous layered cake, available at Smith Island Cakes by the slice.
Speaking of food, you can’t shake a stick in the Chesapeake Bay without hitting a great crab shack, but one of the best-in-show is Kentmorr, which offers gorgeous bay sunsets, a sandy beach for the kids to play in before dinner, and award-winning seafood.
A mild climate and rich piedmont soil come together on the Maryland Wine Trail, which crosses this region via the Piedmont and Carroll Wine Trail. In spring and summer, the vineyard grounds light up with weekend concerts, festivals and wine tastings.
Mountain bikers can get their fill at hilly Patapsco Valley State Park, one of Maryland's oldest state parks. Less experienced riders can head for the flatter trails near the top, and enjoy some waterfalls along the way. Lighthouse Trail in Elk Neck State Park offers an easy loop that culminates in a 100-foot cliff at Turkey Point Lighthouse overlooking the Chesapeake Bay.
From Pen-Mar to the Potomac River, Western Maryland is home to 40 beautiful – and somewhat flat – miles of the Appalachian Trail. The fairly chill hike, which hugs the ridge of South Mountain, is easily broken up into a few days; or you can challenge yourself with some intense climbing and bouldering at Carderock or Rocks State Park. Adventurous rafters can head out with a guide along the Youghiogheny River (nicknamed “Yok”), which boasts Class V rapids, not for the faint of heart.
If biking’s your jam, you’ll find 28 miles of smooth, paved bike trails along the Chesapeake & Ohio Canal on the Western Maryland Rail Trail. It’s not Montana, but there’s some excellent fly fishing to be had in the 30-mile long Savage River, which is filled with trout.