Ocean City, Maryland Travel Itinerary: A Comprehensive Guide

Ocean City, Maryland, is a bustling seaside resort town known for its beautiful beaches, vibrant boardwalk, and family-friendly attractions. This itinerary will guide you through the best landmarks, food, entertainment, culture, outdoor activities, shopping, history, beaches, and festivals in Ocean City. Each section offers a unique glimpse into what makes Ocean City a top travel destination.

Landmarks

Ocean City Boardwalk

The Ocean City Boardwalk, a 3-mile long wooden promenade, is one of the most iconic landmarks in Ocean City. Established in 1902, the boardwalk stretches from the Inlet to 27th Street and is lined with shops, restaurants, amusement parks, and arcades. Stroll along the boardwalk to take in the ocean views, enjoy street performances, and indulge in classic boardwalk treats like Thrasher’s French Fries and Fisher’s Popcorn. The boardwalk also features historic sites such as the Ocean City Life-Saving Station Museum, which offers exhibits on local maritime history.

Assateague Island National Seashore

Located just a short drive from Ocean City, Assateague Island National Seashore is a must-visit landmark known for its wild horses and pristine beaches. The island offers a variety of outdoor activities, including hiking, kayaking, bird watching, and camping. The Assateague Island Visitor Center provides educational exhibits and information about the island’s wildlife and natural history. Don’t miss the opportunity to see the famous Assateague ponies, which roam freely across the island.

Trimper’s Rides and Amusements

Trimper’s Rides and Amusements, located at the southern end of the boardwalk, is a historic amusement park that has been entertaining visitors since 1893. The park features a mix of classic and modern rides, including a vintage carousel, Ferris wheel, and roller coasters. Trimper’s is a beloved family destination that offers fun for all ages. Be sure to explore the Haunted House, a dark ride that has been thrilling visitors since the 1960s.

Food and Cuisine

Breakfast at Happy Jack Pancake House

Start your day with a hearty breakfast at Happy Jack Pancake House, a local favorite known for its delicious pancakes and friendly service. The menu offers a variety of breakfast options, including classic buttermilk pancakes, Belgian waffles, and omelets. Try the signature Jack’s Special, which features a stack of pancakes topped with fresh fruit and whipped cream. The restaurant also offers gluten-free and vegetarian options to cater to all dietary needs.

Lunch at Fish Tales

For a laid-back lunch with a view, head to Fish Tales, a waterfront restaurant and bar located on the bay. The menu features fresh seafood, sandwiches, and salads, along with a variety of tropical cocktails. Enjoy dishes like the crab cake sandwich, fish tacos, or the seafood platter while taking in the scenic views of the bay. The restaurant also has a playground for kids, making it a great spot for families.

Dinner at The Shark on the Harbor

For a more upscale dining experience, visit The Shark on the Harbor, a farm-to-table restaurant that focuses on sustainable and locally sourced ingredients. The menu changes daily based on the freshest available ingredients, offering dishes such as seared scallops, crab-stuffed flounder, and roasted duck. The restaurant’s waterfront location provides stunning views of the harbor, making it a perfect spot for a romantic dinner or special occasion.

Desserts at Dolle’s Candyland

No trip to Ocean City would be complete without a visit to Dolle’s Candyland, a historic candy store that has been serving sweet treats since 1910. The store is famous for its saltwater taffy, caramel popcorn, and homemade fudge. Choose from a wide variety of flavors and enjoy a nostalgic candy-shopping experience. Dolle’s also offers gift boxes, making it easy to bring a taste of Ocean City back home with you.

Entertainment

Jolly Roger Amusement Park

Jolly Roger Amusement Park, located on 30th Street, is a premier entertainment destination in Ocean City. The park offers a wide range of attractions, including roller coasters, water slides, mini-golf, and go-karts. Splash Mountain, the park’s water park, features a variety of water slides, wave pools, and a lazy river. Jolly Roger at the Pier, located on the boardwalk, offers additional rides and attractions, including a giant Ferris wheel and a looping roller coaster. The park is a great place for families and thrill-seekers alike.

Ocean Downs Casino

For a night of excitement, visit Ocean Downs Casino, located just a short drive from Ocean City in Berlin, Maryland. The casino features over 800 slot machines, electronic table games, and live horse racing. Try your luck at the slots or enjoy a live harness race at the racetrack. The casino also offers dining options, including a buffet and a sports bar. Live entertainment and special events are held regularly, providing a fun and vibrant atmosphere.

Seacrets Jamaica USA

Seacrets Jamaica USA is a unique entertainment complex located on the bay in Ocean City. The venue features multiple bars, restaurants, and nightclubs, offering a lively atmosphere and stunning waterfront views. Enjoy live music and DJs, dance the night away, or relax with a tropical cocktail in one of the beachside lounges. Seacrets also offers boat rentals and water sports, making it a great spot for both day and night entertainment.

Culture

Art League of Ocean City

The Art League of Ocean City is a non-profit organization dedicated to promoting the visual arts in the community. The Ocean City Center for the Arts, located on 94th Street, features rotating exhibitions of local and regional artists, as well as art classes and workshops for all ages. The center also hosts special events, such as the annual Plein Air Painting Competition and the Sand Castle Home Tour. Visit the gallery to appreciate the diverse range of art and support the local art community.

Ocean City Life-Saving Station Museum

The Ocean City Life-Saving Station Museum, located at the southern end of the boardwalk, offers a fascinating look into the history of Ocean City’s maritime heritage. The museum is housed in a historic life-saving station and features exhibits on the U.S. Life-Saving Service, shipwrecks, and local marine life. Visitors can learn about the heroic efforts of the life-saving crews and explore the museum’s collection of artifacts, photographs, and interactive displays. The museum also offers educational programs and special events throughout the year.

Performing Arts at the OC Performing Arts Center

The OC Performing Arts Center, located within the Roland E. Powell Convention Center, hosts a variety of cultural events and performances. The center features a state-of-the-art theater that seats over 1,200 people, making it a premier venue for concerts, theater productions, dance performances, and comedy shows. Check the schedule to see what’s playing during your visit and enjoy a night of live entertainment in a comfortable and modern setting.

Outdoor Activities

Fishing at the Ocean City Fishing Pier

Fishing is a popular activity in Ocean City, and the Ocean City Fishing Pier, located on the boardwalk, is a great spot to cast a line. The pier offers rod rentals, bait, and tackle, making it easy for both novice and experienced anglers to enjoy a day of fishing. Catch species such as flounder, bluefish, and striped bass while taking in the beautiful ocean views. The pier also offers a tackle shop and snack bar, making it a convenient and enjoyable fishing destination.

Biking on the Ocean City Bike Path

Exploring Ocean City by bike is a fun and healthy way to see the sights. The Ocean City Bike Path runs parallel to the beach and boardwalk, offering a scenic and safe route for cyclists. Rent a bike from one of the many rental shops in town and enjoy a leisurely ride along the path. The bike path extends from the Inlet to 27th Street, with additional bike lanes and routes available throughout the city. Biking is a great way to experience the fresh ocean air and enjoy the beautiful coastal scenery.

Watersports on the Bay

Ocean City offers a wide range of watersports for adventure seekers. The calm waters of the bay are perfect for activities such as kayaking, paddleboarding, jet skiing, and parasailing. Several rental shops and tour operators offer equipment and guided tours, making it easy to get out on the water and enjoy the thrill of watersports. Whether you’re a beginner or an experienced water enthusiast, there’s something for everyone to enjoy on the bay.

Shopping

Ocean City Outlets

For a great shopping experience, visit the Ocean City Outlets, located just a short drive from the beach. The outlets feature a variety of stores, including popular brands such as Nike, Under Armour, and Coach. Find great deals on clothing, accessories, and home goods while enjoying the convenience of an outdoor shopping center. The outlets also offer dining options, making it easy to take a break and refuel during your shopping spree.

Ocean Gallery World Center

Ocean Gallery World Center, located on the boardwalk, is a unique art gallery and shop that offers a wide variety of artwork, prints, and collectibles. The gallery’s eclectic exterior, covered in colorful murals and decorations, is a landmark in itself. Inside, you’ll find a diverse collection of art, from local and regional artists to famous prints and posters. Ocean Gallery is a great place to find a special piece of art to take home as a memento of your trip.

Tanger Outlets

Tanger Outlets, located in nearby Rehoboth Beach, Delaware, is another great shopping destination for those looking for deals on name-brand merchandise. The outlets feature over 130 stores, including designer and brand-name outlets such as Michael Kors, Polo Ralph Lauren, and Calvin Klein. Take advantage of tax-free shopping in Delaware and enjoy a day of retail therapy just a short drive from Ocean City.

History

Rackliffe House

The Rackliffe House, located near Assateague Island, is a beautifully restored 18th-century coastal plantation house that offers a glimpse into the history of the region. The house is open for tours and features exhibits on colonial life, the history of the coastal environment, and the lives of the people who lived and worked on the plantation. The surrounding grounds offer scenic views of the coastal landscape and are a great place for a leisurely walk or picnic.

Calvin B. Taylor House Museum

The Calvin B. Taylor House Museum, located in nearby Berlin, Maryland, is a historic home that has been preserved and restored to showcase life in the 19th century. The museum features period furnishings, artifacts, and exhibits on the history of Berlin and the surrounding area. Guided tours provide insights into the daily life of the Taylor family and the history of the region. The museum also hosts special events and programs throughout the year.

Ocean City Life-Saving Station Museum

The Ocean City Life-Saving Station Museum, located at the southern end of the boardwalk, offers a fascinating look into the history of Ocean City’s maritime heritage. The museum is housed in a historic life-saving station and features exhibits on the U.S. Life-Saving Service, shipwrecks, and local marine life. Visitors can learn about the heroic efforts of the life-saving crews and explore the museum’s collection of artifacts, photographs, and interactive displays. The museum also offers educational programs and special events throughout the year.

Beaches

Ocean City’s Main Beach

Ocean City’s main beach, located along the boardwalk, is a beautiful stretch of sandy shoreline that offers plenty of space for sunbathing, swimming, and beach activities. The beach is patrolled by lifeguards during the summer months, ensuring a safe and enjoyable experience for visitors. Rent a beach umbrella and chairs, or bring your own beach gear and enjoy a relaxing day by the ocean. The boardwalk provides easy access to food, drinks, and entertainment, making it a convenient and fun beach destination.

Assateague Island National Seashore

Assateague Island National Seashore, located just a short drive from Ocean City, offers a more natural and secluded beach experience. The island’s pristine beaches are perfect for swimming, sunbathing, and beachcombing. Visitors can also enjoy activities such as kayaking, fishing, and wildlife watching. The island is home to a variety of wildlife, including the famous Assateague ponies, which can often be seen grazing near the beach. The Assateague Island Visitor Center provides information on the island’s natural history and recreational opportunities.

Northside Park Beach

Northside Park Beach, located in the northern part of Ocean City, is a quiet and family-friendly beach that offers a more relaxed atmosphere. The beach is adjacent to Northside Park, a 58-acre park that features sports fields, a playground, walking paths, and a fishing lagoon. The park also hosts events and activities throughout the year, making it a great destination for families and outdoor enthusiasts. Enjoy a day at the beach and then explore the park’s amenities for a fun and active outing.

Festivals and Events

Sunfest

Sunfest, held annually in September, is Ocean City’s largest and most popular festival. The event takes place at the Inlet and features live music, arts and crafts vendors, food vendors, and family-friendly activities. Enjoy performances by local and national musicians, browse the arts and crafts booths for unique souvenirs, and sample delicious festival foods. Sunfest also includes a variety of free activities for kids, making it a great event for families.

Springfest

Springfest, held annually in May, is a four-day festival that celebrates the arrival of spring in Ocean City. The event takes place at the Inlet and features live entertainment, arts and crafts vendors, food vendors, and activities for all ages. Enjoy concerts by popular bands and artists, shop for handmade crafts and jewelry, and indulge in a variety of delicious foods. Springfest is a festive and fun way to kick off the summer season in Ocean City.

OC Air Show

The OC Air Show, held annually in June, is a spectacular event that features thrilling aerial performances by military and civilian aircraft. The air show takes place over the beach and boardwalk, offering stunning views of the high-flying action. Highlights of the show include performances by the U.S. Air Force Thunderbirds, the U.S. Navy Blue Angels, and other top aerobatic teams. The OC Air Show is a must-see event for aviation enthusiasts and families alike.

Ocean City, Maryland, offers a wealth of experiences for travelers, from its beautiful beaches and historic landmarks to its vibrant entertainment scene and delicious cuisine. Whether you’re exploring cultural attractions, enjoying outdoor activities, or attending a festival, this itinerary provides a comprehensive guide to making the most of your visit to this popular seaside destination.

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