How to Organize a Day on the Eastern Shore, MD

How to Organize a Day on the Eastern Shore, MD

Whether you’re a history buff, a nature lover, or beach bum, the Eastern Shore has something for everybody. The travel experts at Metropolitan Shuttle have rounded up the area’s must-see spots in a perfect itinerary that combines cultural highlights, outdoor adventures, and entertainment.

Assateague Island National Seashore

Situated on Maryland and Virginia state lines, the beautiful, secluded beaches of this 37-mile long barrier island offer the perfect setting for getting away from the hustle and bustle. Plus, the wild horses of Assateague Island add a unique and dreamy quality to the natural setting. A fun and relaxing way to see the island is by biking along the paved bike path on Bayberry Drive, which takes you on a 4-mile trek across dense island habitat on the Maryland side. In Virginia, the bike path goes from Chincoteague to Assateague Island, giving you plenty of opportunities for nature viewing.

How to Organize a Day on the Eastern Shore, MD

If you and your crew are ready to fully embrace the great outdoors, the Maryland side offers camping in the barrier island habitat. Each campground is equipped with a picnic table and fire ring, so make sure to bring all the necessary camping gear. The campsite also includes rustic facilities, including cold showers, drinking water, and chemical toilets.

Another way to see Assateague is by kayaking or canoeing, which allows you to explore the sheltered waterways on the backside of the island that can only be accessed by boat. The kayaking tour starts in the historic town of Chincoteague Island, Virginia, next to southern half of Assateague Island and the Chincoteague National Wildlife Refuge. Once you’re on the water, you’ll have a chance to take in all the natural wonders, like dolphins, eagles, shorebirds, and a view of the Assateague Lighthouse.

With all this fresh air and activity, you’ll need some fuel to keep you going on your big day out, so we recommend packing a picnic or eating before you go at the variety of cafes and restaurants nearby the park.

Travel Tips: If you’re traveling with a party of five or less, rideshare services or car rental is a budget-friendly choice for getting from the mainland to the island. For a day trip, a charter bus is the most affordable and convenient option, especially for groups of six or more.

Ocean City, MD

An insanely popular tourist destination, Ocean City makes an ideal spot for a vacation because it’s where you’ll find all the action. With an iconic boardwalk, shops, and condos, it brings the best aspects of the city right up to the shoreline. It’s one of the few places on the Eastern Shore where you can enjoy a lively city vibe while taking in the natural wonders of the ocean.

Before you set out on a day of exploring, we recommend a substantial breakfast to get your day started. Head over to the Satellite Coffee Shop on 24th St., a local favorite for breakfast and coffee on the boardwalk.

After breakfast, enjoy a walk down the boardwalk, a cultural icon of Ocean City. You’ll find a delightful variety of shops, including The Kite Loft, which is the best spot in the city for all things kite related. Ocean City beaches are known for an abundance of ocean breezes, which is why kite flying is a fun activity if you find yourself on the shoreline.

The boardwalk is also known for its famous treats, including Fisher’s Popcorn, which has been serving the best caramel corn in Ocean City for 80 years. They also offer other flavors like white cheddar, cinnamon, and caramel chocolate drizzle. Another spot that’s famous for its carnival classics is The Golden Plate, which serves up some of the best funnel cakes and gyros on the boardwalk. For a snack you can only get in Ocean City, The Wrapper doesn’t disappoint with their local delicacy— a delicious soft pretzel filled with chicken, melted cheese and Old Bay seasoning.  

At sunset, take a break from the boardwalk action at Harrison’s Harbor Watch, a casual sit-down restaurant known for beautiful ocean views, plus a fresh raw bar, the best seafood in town, and dishes showcasing local produce. For dessert, take a short walk to Dumser’s Dairyland for an old-fashioned ice cream cone, which has been made in-house since 1939.

If you forgot your beach gear, Malibu’s Surf Shop is situated conveniently on the strip, so not to worry. You’ll find a variety of boards, clothing, and accessories, plus surfing lessons for the sporty and adventurous travelers. Another must-see of the boardwalk is Marty’s Playland, a retro style arcade with classic games like skeeball, air hockey, and more.  

You might be in the east but once you enter Frontier Town, get ready to be immersed in the Wild West. Lasso your entourage, head to this western themed amusement park and unleash your inner cowboy. The Western Theme Park is like stepping back in time, so giddy up cowboy and don’t miss their classic Wild West Shows and Native American Village. The park also features a Lazy River, which makes for a leisurely and relaxing day of floating on the water. Or, get your adrenaline pumping at the waterslides for the more adventurous at heart.

At Frontier Town, you’ll find activities for the whole family, including 18 holes of Mini-Golf set against a lovely backdrop of shade trees and waterfalls. For a bird’s eye view of the estate, take a zip line through the forest in the High Ropes Adventure Park, which offers an exciting obstacle course situated in the treetops.

Are We There Yet? Getting from Point A to Point B

Wherever you’re traveling from, getting to Ocean City with large groups is easy and hassle free when you book a charter bus for your travel needs. Choose the best bus for your budget, sit back in reclining seats, and get ready for fun in the sun at Ocean City, the favorite vacation destination on the Eastern Shore.

Rehoboth Beach

While it might be a little quieter compared to Ocean City, Rehoboth Beach is a favorite Southern Delaware getaway. The sandy beaches have some of the cleanest water in the country, making Rehoboth a popular vacation spot for fleeing the heat in Maryland, Washington D.C. and inland Delaware.

Start your day with breakfast at The Crystal Restaurant and then enjoy some retail therapy at the variety of charming boutiques along the boardwalk. Once you’ve hit your shopping sweet spot, enjoy the ocean view while eating at one of the many restaurants and cafes. Or, feel right at home during your beach stay and make your own meal with fruits and veggies from the local farmer’s market. While you’re in the area, take the short walk to the Rehoboth Beach Museum and discover the coast’s surfing and skim boarding heritage.  

You haven’t had the complete boardwalk experience in Rehoboth until you’ve spent time at Funland, which features carnival rides and a vintage style arcade. Keep it casual and budget-friendly with an inexpensive lunch at Grotto Pizza close by.

The Dogfish Head pub on Rehoboth Avenue is another popular spot for dinner and craft brews. Afterward, if you’re visiting in the summer, make sure not to miss the summer concert series at Rehoboth Beach Bandstand. Good times, good tunes, and the ocean breeze—the trifecta of summertime fun.  

Now that you’ve experienced the best of the boardwalk and nearby attractions, it’s time for some much-needed Vitamin “Sea” on the most pristine beaches in the U.S. For a spacious beach without the crowds, get your toes sandy at the Cape Henlopen State Park entrance, which features hiking trails and parking for your convenience. If you bring beach gear and a cooler stocked with drinks and snacks, you can easily fill your entire day with fun in the sun. After all, life is always better in flip-flops.

After a day at the beach, show off your sun-kissed glow at the Summer House Saloon, a low-key place for pre-dinner cocktails. Stay for casual dining or head to Eden for an upscale dinner with an haute cuisine twist.

With itineraries packed full of fun activities for everybody in your entourage, take a vacation on the Eastern Shore and get ready to celebrate the leisurely way of life.


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