Cape to Cape

From the Atlantic Ocean to the back bays of Chincoteague, Sinepuxent and Assawoman, set your sights on a seaside rendezvous amid some of Maryland’s most beautiful and historic beaches and islands.
Maryland’s Section: Ocean City to Stockton
79 Miles
Drive Time: 5 - 7 Hours
Best Done in 2 - 3 Days
Best for: outdoor adventure enthusiasts, relaxation, nature lovers, families, romantic getaways, foodies
Cape to Cape
Enjoy sightseeing, small-town warmth and the Delmarva Peninsula’s famous fresh seafood along this water-laced route — and bring your gear for fishing, camping, paddling or biking while exploring scenic trails once traveled by Native Americans.
Enjoy sightseeing, small-town warmth and the Delmarva Peninsula’s famous fresh seafood along this water-laced route — and bring your gear for fishing, camping, paddling or biking while exploring scenic trails once traveled by Native Americans.
Ocean City to Assateague Island
Including MD 378, MD 528, US 50, & MD 611
Drive south along the coast to OCEAN CITY. This dynamic family resort invites byway travelers to relax on a 10-mile strip of wide beach and enjoy nearby waterslides and amusement park rides on the wooden boardwalk. Steamed crabs, ice cream and miniature golf are must-dos for many vacationers. Fifteen area golf courses, the OCEAN DOWNS racetrack-casino and an outlet mall round out the fun.
See the historic HENRY HOTEL, once a full service facility catering to African-American tourists and entertainers, like Cab Calloway, Duke Ellington, Count Basie and Willie Harmon. These musicians stayed here during years of strict segregation among the boardwalk hotels.
Ocean City is also a well-known destination for anglers and outdoor adventure enthusiasts. Charter captains are waiting to guide you to hook a prized catch. Try paddleboarding, or parasailing over the Sinepuxent Bay, or embark on a guided eco-tour of nearby Assateague Island aboard a pontoon boat or by kayaks.
ASSATEAGUE ISLAND, an undeveloped, 37-mile-long barrier island, showcases the best of the Mid-Atlantic’s oceanfront and barrier island natural habitat. Swimming, crabbing, surfing, fishing, kayaking, and biking are favorite activities here, and most visitors come to see the wild horses roaming among the dunes. Camping on the island’s state and national parks is a special treat where the beach is just steps away.
Nature lovers find the interpreted trails and waterways a birders paradise year-round. The SINEPUXENT BAY WATER TRAIL weaves through open water, small coves and salt marshes. Several local guide services are available, and birding tours are offered on DELMARVA BIRDING WEEKENDS.
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Assateague Island to Snow Hill
Including MD 611, MD 376, US 113
Just across the Bay on the mainland you’ll find the charming town of BERLIN with historic brick buildings that offer antiques, jewelry, art galleries and gift shops, as well as restaurants and museums. Popular stops include THE MERMAID MUSEUM and JEFFREY AUXIER DESIGNS BLOWN GLASS GALLERY AND STUDIO. Explore CALVIN B. TAYLOR MUSEUM in a restored, early-19th-century house, which is among nearly 50 structures on the National Register of Historic Places. Spend the night in the famed HOTEL ATLANTIC, the setting for the movie Runaway Bride.
Continue south on the byway to the town of SNOW HILL, known for its ARTS AND ENTERTAINMENT DISTRICT full of galleries, music venues and shops. The JULIA A. PURNELL MUSEUM explores over 500 years of local history through Native American artifacts to Civil War relics. The town is graced with several bed and breakfasts in historic mansions for a perfect night’s rest.
Nearby parks provide boat landings, dockage and public facilities. Rent a canoe or kayak from POCOMOKE RIVER CANOE AND KAYAK COMPANY to paddle through one of the northernmost stands of Bald Cypress trees. It will feel like another world - Jurassic Park anyone?
For the outdoorsy types, a stay in a mini-cabin at Shad Landing in POCOMOKE RIVER STATE PARK will let your cares slip away with the tides. Fishing and boating opportunities are plentiful from the marina and their swimming pool is a great place for the kids to cool off.
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Respect wildlife:
Keep your distance (40 feet) from wild ponies and never feed them. Wild animals can become aggressive when habituated to people. Keep your camp clean and secure food in your vehicle.
SNOW HILL TO STOCKTON
MD 12 & MD 365
From Snow Hill the byway continues southeast past the EA Vaughn Wildlife Management Area. Side tracks on MD 365 and local roads take you to the bayfront communities of Public Landing and George’s Island Landing for gorgeous views. The E. A. VAUGHN KAYAK AND CANOE TRAIL offers 3 paddling routes ranging from 3 to 6 miles, which provide an up-close look at coastal plant and animal life.
Back on the byway, continue south through Stockton and into Virginia, toward Chincoteague.
Follow the Storyways: A Journey of Faith & Freedom on Maryland’s Eastern Shore driving tour to explore sites and stories about the pursuit of civil rights, freedom and equality for African Americans.
Trip Tip
Take a day bike trip for an unforgettable experience. The back roads and flat lands of Maryland’s Coast offer easy pedaling. Pick up a map of the View Trail 100 through Worcester County for the best rides.
Enjoy Every Season
Spring/Summer
Spring/Summer
- Go birding by boat with a guide during Delmarva Birding Weekend
- Watch choreographed kite flying demos on the beach at the Maryland International Kite Festival
- Paddle through Bald Cypress trees from Shad Landing on the Pocomoke River
- Swim, surf or paddle board in the ocean
- Charter a fishing excursion from OC
- Try crabbing or clamming on a Ranger-guided tour at Assateague
- Sample some succulent peach pie at the Peach Festival in Berlin
- Photo: Ocean City Fishing Charter
Fall/Winter
Fall/Winter
- Rock out at the Oceans Calling music festival
- Hit the links at 15 area golf courses
- Rent a kayak in Snow Hill and wildlife watch on the Pocomoke River
- Join the festivities and merriment at the Christmas in Berlin Festival
- Watch for flocks of waterfowl at the Ocean City inlet
- Walk the Ocean City Boardwalk and see the holiday lights
- Photo Credit: Worcester County Tourism