It’s easy to find reasons to celebrate in beautiful Ocean City, Maryland! Our scenic stretch of paradise hosts everything from wine festivals to car shows, and you’re always invited to join the excitement. Will you RSVP and enjoy some remarkable experiences this year? We hope so! Check out these upcoming events in Ocean City, MD, for 2020 and see why so many people love them. You’ll have a blast and leave with memories to last a lifetime. We’ll help you make the most of every event with our list of fantastic vacation rentals nearby. Find your ideal property and get ready to celebrate!

Find Your Happy Place!

Mark Your Calendars for These Ocean City, MD, Events

An easter basket with candy at the Art and Craft Show & Kids Fun Fair


Easter Art and Craft Show & Kids Fun Fair | April 10 to 11

Children can hunt for eggs and parents can hunt for treasures of their own at the Roland E. Powell Convention Center this spring! There will be arts and crafts displays, juggling contests, egg hunts, and an appearance by Beanny the Easter Bunny!

Restaurant Week | April 19 to May 3

Enjoy tasty cuisine at fantastic prices throughout Ocean City. You might discover your new favorite place to eat!

Maryland International Kite Expo | April 24 to April 26

Let your excitement soar to new heights at this year’s Maryland International Kite Expo. Head to the beach and join the fun as the sky fills up with colorful kites.

Crab Soup Festival | May 2

Bring the whole family to Somerset Plaza on May 2 to taste some of the best crab soup you’ve ever had. It’s an excellent activity for celebrating Mother’s Day Weekend!

Springfest | May 7 to 10

Admission is free, and so are the memories at Springfest 2020. Come and check out the Inlet Lot in Downtown Ocean City, Maryland, to enjoy four full days of live music!

Cruisin’ Ocean City | May 14 to 17

Cruisin’ Ocean City is an annual favorite, bringing talented artists and breathtaking car shows to Ocean City, MD. When you’re not checking out hot rods and muscle cars, head to the Ocean City Performing Arts Center for a performance by Jay Leno.

OC Car & Truck Show | June 13 to 14

Which automobile will win the Best in Show award this year? Find out in June! You can even stay an extra day for the Shoreline Showdown Show!

OC Air Show | June 13 to 14

Watch in awe as skilled aviators race across the sky and showcase impressive aerial maneuvers! The U.S. Navy Blue Angels headline at the OC Air Show in 2020.

Young baseball players cheering at the Youth Baseball Nationals in Ocean City, MD


July 4th Concert and Fireworks | July 4

The Independence Day celebrations take place at not one, but two locations in Ocean City. Whether you’re Downtown or at Northside Park, you can enjoy free live music and spectacular fireworks.

Ocean City Tuna Tournament | July 10 to 12

See if you can reel in a cash prize at the Ocean City Tuna Tournament! This local event features outstanding entertainment, tasty food, and fun for all.

White Marlin Open | August 3 to 7

Take your vacation to the seas this August when the White Marlin Open returns. This fishing competition began in 1974, and it has grown into one of the most popular events in Ocean City!

Youth Baseball Nationals | August 6 to 9

Coaches, players, and fans are all in for an incredible time at the Youth Baseball Nationals. Register your team and compete against athletes from all over the world to see if you can take home the championship trophy. Even if you don’t win, you receive free passes to Ocean City attractions and get to enjoy a fun vacation with friends and family members!

OC BikeFest | September 16 to 20

Hop on your favorite two-wheel vehicle and head to Ocean City from September 12 to 15 for the biggest motorcycle rally on the East Coast! There will be concerts, food, fun, and more. Don’t forget to grab some official OC BikeFest merchandise!

Women toasting with white wine in Ocean City, Maryland


Wine on the Beach | September 25 to 26

The Wine on the Beach festival is an opportunity to welcome the fall season with delicious local Maryland wines and plenty of craft beers as well. The list of exhibitors this year includes Cove Point Winery, Linganore Winecellars, Bordeleau, and many more.

Sunfest | October 1 to 4

Sunfest features fun for the whole family — and a lot of it! Enjoy activities at the Inlet Lot by the Ocean City Boardwalk, like hayrides and must-see concerts over four days. It’s a wonderful way to end the summer on a high note!

Free State Corvette Weekend | October 16 to 17

If you love cars, especially the iconic Corvettes that Chevrolet has made famous, the Free State Corvette Weekend is for you. Cruise into Ocean City in October and check out car shows, rallies, and a parade. Proceeds help support charities!

Endless Summer Cruisin’ | October 8 to 11

It may be fall, but the summer fun lives on at Endless Summer Cruisin’. Enjoy entertainment and games at the Inlet Lot and a variety of more activities throughout town. You can even explore stunning show cars at Endless Summer Indoors in the Convention Center.

Making Strides Against Breast Cancer | October 24

Support a great cause while having an incredible time at this year’s Breast Cancer Walk. Fundraising efforts go toward the American Cancer Society, promoting awareness, research, and support to anyone affected by breast cancer. It’s a truly inspirational experience taking place at the Ocean City Boardwalk.

O.C.toberfest | October 24 to 25

Check out O.C.toberfest and have a spooky good time with the whole family! It’s a favorite among locals and visitors with the popular Beach Maze, Howl-O-Ween Pet Parade, and the Great Pumpkin Race.

Northside Park full of holiday lights for the Winterfest of Lights celebration

Holiday Celebrations

Winterfest of Lights | November 19 to January 2

Every year, Northside Park comes to life with holiday cheer at the Winterfest of Lights. Festivities continue from the end of November to New Year’s Eve with enchanting holiday lights, merry sing-alongs, rides on the Winterfest Express, and plenty of hot chocolate to go around. Santa Claus will also journey from the North Pole to take pictures and invite you inside his Ocean City workshop!

Light Up Downtown Winter Festival | TBA

Another great event to kick start the holiday season is the Light Up Downtown Winter Festival. Get a head start on your shopping, win prizes, and check out the tree lighting!

Holiday Shoppers Fair | November 27 to 29

Find the perfect gifts for everyone this holiday season! The Roland E. Powell Convention Center hosts dozens of vendors showcasing everything from candles to jewelry with an abundance of activities and face painting for kids.

Ocean City Christmas Parade | December 5

Santa Claus is coming to town for everyone’s favorite Christmas parade. Gather along the Coastal Highway as marchers and floats fill attendees with holiday cheer!

Local tip: Make sure you arrive early to get a good view of the excitement.

New Year’s Eve Celebration | December 31

Join us at Northside Park as we wave goodbye to 2020 and hello to 2021! Fireworks begin at midnight with hot chocolate and live entertainment. The park will be full of lights for Winterfest as the fireworks light up the sky. It’s a magical experience for all!

Local tip: Remember to take advantage of the town’s free bus service on New Year’s Eve!

Penguin Swim | January 1

There’s nothing like jump-starting the new year by leaping into ice-cold water at the beach! It’s all for a great cause, supporting the Atlantic General Hospital Foundation, with prizes and games for swimmers.

Stay Near All the Excitement This Year!

The living room inside Belmont 810 in Ocean City, Maryland

Lodging tends to fill up quickly for these events in Ocean City, Maryland, and we don’t want you getting left out of the fun. Book early, and book direct with Vantage Vacation Rentals to secure excellent properties in the area. Whether you’re attending a concert by the boardwalk or the holiday lights at Northside Park, we have the perfect property nearby to help you enjoy it to the fullest. Find your happy place today and stay steps away from some of the best celebrations of 2020. See you there!