Ocean City at Night

How to Spend A Few Days on the Eastern Shore

Stroll the Boardwalk in Ocean City, dine on crab in Crisfield, and experience the Eastern Shore’s maritime legacy. 

Share
Ocean City at Night

The Eastern Shore is full of warm, welcoming waterfront towns, each perfect for a getaway. When you make the trip, give yourself a few days to explore all the area has to offer and make sure you check out these Eastern Shore favorites!

Spend A Day By The Water

Ocean City is a perfect introduction to the Eastern Shore. You’ll find a party pretty much every season—from Winterfest to Springfest, Sunfest and beyond. While in Ocean City make sure you fit in a stroll along the award-winning Boardwalk. You’ll find amusements, arcades, and plenty of snacks—like Fisher’s famous caramel popcorn and Thrasher’s french fries. You’ll definitely want to stay the night in Ocean City so you can enjoy a delicious dinner overlooking Assateague Island at Harrison’s Harborwatch Restaurant.  

Drive to Crisfield for Crab Cakes

Once you’ve done all things Ocean City, hop in the car and drive just over an hour to Crisfield. The town of Crisfield is known as the “Crab Capital of the World”—and for good reason! It’s home to tons of real deal crab houses and proudly presents annual events for crab lovers, including the National Hard Crab Derby and the J. Millard Tawes Crab & Clam Bake. If your trip happens to fall between event dates, don’t worry! You can always get your crab fix at The Crab Place, Linton’s Seafood or Waterman's Inn, among others.  

Visit Salisbury and Whitehaven

After a night in Crisfield (or two, or three—so much delicious food to enjoy!), double back to Salisbury and immediately take a step back in time at Poplar Hill Mansion, a Federal-style home. Then take a walk through the Salisbury Zoo, which has been called "one of the finest small zoos in North America" or visit the Ward Museum of Wildfowl Art, where art meets nature. Once your stomach starts rumbling for dinner, take a short ride through the lovely countryside to the sleepy waterfront village of Whitehaven. Grab a table at The Red Roost and fill up on steamed hard crabs, shrimp, corn on the cob and much, much more. Some evenings at Red Roost also offer sing-alongs, banjo playing and entertainment!  

Experience Maritime Traditions

When your voice needs a rest from too much sing-along-ing, fuel up for a 1.5 hour drive from Whitehaven to Tilghman, one of the last small fishing villages left on the Chesapeake Bay. Tour the Phillips Wharf Environmental Center to learn about the life of a crab and meet some native bay animals in the estuarium. Meander over to nearby St. Michaels (about a 20 minute drive) and stop by the Chesapeake Bay Maritime Museum. After learning the traditions of boat building, fishing, water fowling and visiting a 100-year old screw-pile lighthouse, board the Patriot for a tour of the Miles River. It’s the perfect way to end your Eastern Shore getaway—and psych yourself up for the next visit!

Family at the Beach Watching Wild Horses
Family Watches Wild Horses at the Beach

Slide

Ice Cream at Sweets & Treats in Cambridge
Ice Cream at Sweets & Treats in Cambridge
Kayaking at Blackwater National Wildlife Refuge
Kayaking at Blackwater National Wildlife Refuge
Chesapeake Bay Maritime Museum
Chesapeake Bay Maritime Museum
Sail Selina II Boat Tours
Sail Selina II Boat Tours