Water Wonders Itinerary
A water-lover’s 5-day Eastern Shore adventure
If you crave water activities, you’ll want to tack on a few extra days to this road trip. Maryland’s diverse waterways and miles of oceanfront fun provide enough variety for any water lover to enjoy until their heart’s content. Check out this itinerary to get your fill.
Get in a Maryland state of mind right off the bat, with your toes in the sand and your eyes on the ocean. Ocean City’s 10 miles of white-sand beaches offer ample space to swim, surf, fish, play or simply admire the beauty of the Atlantic. For lunch, get some shade and crack into fresh steamed crabs at Harborside Bar & Grill or Crab Alley. Next, stroll the boardwalk and enjoy the nostalgia of vintage arcades and amusements while snacking on famous snacks from Fisher’s Popcorn or Thrasher’s French Fries.
Take advantage of the stunning views afforded by the many oceanfront or bayside hotels, but not before tracking down a homemade crabcake or mouthwatering raw oysters at your choice of dozens of renowned seafood destinations.
There are lots of reasons Berlin is “America’s Coolest Small Town” according to Budget Travel. For starters, Main Sreet is simply not to be missed with 60 independent shops and a handful of breakfast and lunch choices. These small businesses make it easy to pick up authentic, locally-crafted gifts for friends and family back in Philly. History buff? You’ll be in heaven in this Eastern Shore town, where you can indulge in a walking tour that boasts 47 buildings on the National Register of Historic Places.
As evening arrives, rest assured Berlin is dotted with an impressive lineup of dinner options. From charming cafés and seafood spots to quaint creameries and taverns, there’s truly something for any appetite. Finally, give your legs a rest at the historic Atlantic Hotel or any of the conveniently located hotels located just steps from downtown.
Just south of Ocean City, the protected Assateague Island National Seashore is an expansive and serene barrier island. Get a taste of Maryland’s Trail System Second-to-None by hiking or biking trails that run through the island’s marshlands, dunes and forests. Sign up for a ranger-led walk and keep an eye out for bald eagles, migratory seabirds and the island’s famous free-roaming wild horses.
Finish your day with a sunset kayak tour with Ayers Creek Adventure, followed by a bite at Assateague Crab House. For lodging, head back to Berlin or nearby Snow Hill for a hard-earned good night’s sleep.
Start off in the charming, nautical town of St. Michaels with visits to the Chesapeake Bay Maritime Museum Lighthouse and Foxy’s Harbor Grille For lunch. But be sure to leave enough time to head to Tilghman Island, where you can charter a tour aboard the historic Rebecca T. Ruark skipjack ship. This guided experience is led by Captain Wade Murphy, Jr., a certified Chesapeake Bay Storyteller.
Dine in style with a dinner at one of many beloved eateries that adorn the charming streets of St. Michaels. Finally, fall asleep and wake up to a picturesque view, with your choice of multiple hotels and inns on the water. Looking to live it up for a night? The Inn at Perry Cabin is a unique luxury property that was featured in the film “Wedding Crashers”.
Matapeake Clubhouse and Beach provides a peaceful and fun way to start off your Kent Island visit. Soak up the sun and water and then enjoy lunch at the picnic area. Explore the 1-mile trail that runs through lush forests and provides a stunning view of the Bay Bridge. Next, grab a chartered boat at Queen Anne’s Marina to experience the Chesapeake Bay from the water.
For dinner, dine like a local thanks to Kent Island’s unmatched seafood restaurants and crab houses, many of which provide waterfront views. Call it a night by staying over at the historic and inviting Kent Island Resort, or one of many other charming lodging options on Kent Island.