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16 Mar 2025Updated last time
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Ocean City, MD Weekend Getaway Itinerary

Ocean City, MD Weekend Getaway Overview

Embark on a delightful weekend getaway to Ocean City, Maryland, and experience a perfect blend of relaxation, adventure, and entertainment. Begin your trip at the pristine Ocean City Beach, where you can indulge in activities such as swimming, sunbathing, and surfing along the scenic shoreline. Following a refreshing beach day, take a leisurely stroll down the vibrant Ocean City Boardwalk, filled with an array of shops, restaurants, and entertainment options that promise a lively atmosphere and memorable experiences.

Next, venture to the breathtaking Assateague Island National Seashore, known for its natural beauty and wild horses. Engage in nature-centric activities like hiking, birdwatching, and kayaking, allowing you to connect with the serene environment. For those seeking thrills, head to Jolly Roger Amusement Park, where a diverse selection of rides, water slides, mini-golf, and go-karts await visitors of all ages.

As the sun sets, unwind at Seacrets Jamaica USA, a unique bayfront venue that offers a tropical atmosphere, delicious Caribbean-inspired cuisine, and live music. Whether you're relaxing by the beach, exploring the boardwalk, or enjoying the vibrant nightlife, Ocean City, MD promises an unforgettable weekend filled with fun and relaxation.


Recommended Activities

  • Trip Point Pin1

    Ocean City Beach

    Ocean City Beach offers a perfect blend of relaxation and adventure with its pristine sandy shores, clear waters, and numerous water activities like swimming, sunbathing, and surfing.
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  • Trip Point Pin2

    Ocean City Boardwalk

    The Ocean City Boardwalk is a must-visit for its vibrant atmosphere, featuring a variety of shops, restaurants, and entertainment options, making it an ideal spot for a leisurely stroll and people-watching.
    Open Google Maps Button
  • Trip Point Pin3

    Assateague Island National Seashore

    Assateague Island National Seashore is renowned for its stunning natural beauty and wild horses. It's an ideal destination for nature enthusiasts offering activities like hiking, birdwatching, and kayaking.
    Open Google Maps Button
  • Trip Point Pin4

    Jolly Roger Amusement Park

    Jolly Roger Amusement Park is a great destination for families and thrill-seekers alike, offering a variety of rides, water slides, mini-golf, and go-karts for all ages.
    Open Google Maps Button
  • Trip Point Pin5

    Seacrets Jamaica USA

    Seacrets Jamaica USA provides a unique dining and nightlife experience with its bayfront setting, tropical atmosphere, live music, and delicious Caribbean-inspired cuisine.
    Open Google Maps Button

Restaurants

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    Fager's Island

    4.4
    $$$$

    Fager's Island

    This bayside restaurant offers a magical dining experience with stunning sunset views, live music, and a diverse menu featuring seafood and American cuisine.
    4.4
    $$$$
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    The Hobbit Restaurant

    4.5
    $$$$

    The Hobbit Restaurant

    Known for its elegant ambiance and panoramic views of the bay, this restaurant offers a fine dining experience with an inventive menu of seafood and steaks.
    4.5
    $$$$
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    Harborside Bar & Grill

    8.2
    $$$$

    Harborside Bar & Grill

    Famed for its laid-back atmosphere and signature Orange Crush cocktail, this waterfront venue provides a delightful mix of seafood dishes and pub fare.
    8.2
    $$$$
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    Liquid Assets

    4.5
    $$$$

    Liquid Assets

    A unique combination of restaurant, bar, and package goods store, offering an eclectic menu and an extensive selection of wines and craft beers in a cozy, rustic setting.
    4.5
    $$$$
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    The Shark on the Harbor

    4.4
    $$$$

    The Shark on the Harbor

    Located right on the harbor, this restaurant emphasizes fresh, locally sourced ingredients in its creative seafood and American dishes, with a focus on sustainability.
    4.4
    $$$$
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Hotels

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    The Edge Hotel at Fager's Island

    4.6

    The Edge Hotel at Fager's Island

    This boutique hotel offers luxurious suites with contemporary decor, beautiful bay views, and a peaceful atmosphere perfect for a romantic getaway.
    4.6
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    The Lankford Hotel

    4.2

    The Lankford Hotel

    Steeped in history, this charming hotel provides a unique old-world experience with quaint rooms and a prime location right on the boardwalk.
    4.2
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    The Commander Hotel & Suites

    4

    The Commander Hotel & Suites

    Offering oceanfront suites with private balconies, this hotel combines modern amenities with retro charm, providing easy access to both the beach and the boardwalk.
    4
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    The Lighthouse Club Hotel

    4.7

    The Lighthouse Club Hotel

    With an elegant nautical theme, this hotel offers serene and spacious rooms overlooking the bay, creating a perfect retreat for relaxation.
    4.7
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    The Atlantic Hotel

    4.6

    The Atlantic Hotel

    Located in nearby Berlin, this historic hotel features Victorian-style decor and a boutique atmosphere, offering a unique and charming stay a short drive from Ocean City.
    4.6
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Local Events & Happenings

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    Oceans Calling

    Oceans Calling

    The event will take place at Ocean City Inlet in Ocean City.
    Map IconOcean City Inlet in Ocean City (5.21 mi)
    Calendar IconN/A
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    Country Calling

    Country Calling

    The event will take place at Ocean City Inlet in Ocean City.
    Map IconOcean City Inlet in Ocean City (5.21 mi)
    Calendar IconN/A
    Picture for Country Calling
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    Michael Franti & Spearhead - 21+

    Michael Franti & Spearhead - 21+

    The event will take place at Seacrets in Ocean City.
    Map IconSeacrets in Ocean City (6.58 mi)
    Calendar Icon16 Sep 2025
    Picture for Michael Franti & Spearhead - 21+
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    Oceans Calling Festival

    Oceans Calling Festival

    The event will take place at Ocean City Inlet in Ocean City.
    Map IconOcean City Inlet in Ocean City (6.58 mi)
    Calendar Icon26 Sep 2025
    Picture for Oceans Calling Festival
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    Country Calling Festival

    Country Calling Festival

    The event will take place at Ocean City Inlet in Ocean City.
    Map IconOcean City Inlet in Ocean City (6.58 mi)
    Calendar Icon3 Oct 2025
    Picture for Country Calling Festival
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    Lake Street Dive

    Lake Street Dive

    The event will take place at Freeman Arts Pavilion in Selbyville.
    Map IconFreeman Arts Pavilion in Selbyville (11.96 mi)
    Calendar Icon4 Sep 2025
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    Alison Krauss and Union Station w/ Jerry Douglas

    Alison Krauss and Union Station w/ Jerry Douglas

    The event will take place at Freeman Arts Pavilion in Selbyville.
    Map IconFreeman Arts Pavilion in Selbyville (11.96 mi)
    Calendar Icon14 Sep 2025
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Travel Gems from Reddit


Music for Your Journey

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    The Beach Boys - Good Vibrations - Remastered 2001

    The Beach Boys - Good Vibrations - Remastered 2001

    This song will instantly lift your spirits with its upbeat tempo and feel-good lyrics, perfect for a beach trip.
    Listen on Spotify
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    The Beach Boys - Surfin' USA - Live

    The Beach Boys - Surfin' USA - Live

    An iconic surf rock anthem that complements the ocean vibes and enhances your beach experience.
    Listen on Spotify
    Picture for The Beach Boys - Surfin' USA - Live
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    Katrina & The Waves - Walking On Sunshine

    Katrina & The Waves - Walking On Sunshine

    Its energetic and happy tune is perfect for a bright sunny day at the beach or boardwalk.
    Listen on Spotify
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    Bryan Adams - Summer Of '69

    Bryan Adams - Summer Of '69

    A classic rock song that captures the nostalgic feeling of summer adventures.
    Listen on Spotify
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    Weezer - Island In The Sun

    Weezer - Island In The Sun

    This mellow track creates a relaxing atmosphere, ideal for unwinding by the beach.
    Listen on Spotify
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    The Drifters - Under the Boardwalk

    The Drifters - Under the Boardwalk

    A nostalgic tune that fits perfectly with the boardwalk environment, creating a laid-back vibe.
    Listen on Spotify
    Picture for The Drifters - Under the Boardwalk
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    The Beatles - Here Comes The Sun - Remastered 2009

    The Beatles - Here Comes The Sun - Remastered 2009

    A timeless classic that brings warmth and positivity, making it great for a scenic drive or beach day.
    Listen on Spotify
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    Jimmy Buffett - Margaritaville

    Jimmy Buffett - Margaritaville

    This laid-back, tropical tune will make you feel like you’re in paradise while enjoying Seacrets Jamaica USA.
    Listen on Spotify
    Picture for Jimmy Buffett - Margaritaville
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    Katy Perry - California Gurls

    Katy Perry - California Gurls

    A fun pop song that will add excitement to your summer road trip and beach outings.
    Listen on Spotify
    Picture for Katy Perry - California Gurls
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    Jake Owen - Beachin'

    Jake Owen - Beachin'

    A country song that captures the essence of a carefree day at the beach, making it a great addition to your trip playlist.
    Listen on Spotify
    Picture for Jake Owen - Beachin'