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Fall Festival Season Picks Up As Summer Winds Down

There was once a time when Labor Day weekend marked the death knell of the summer season in Ocean City, Maryland. It marked the transformation from bustling tourist town to boring ghost town, and putting an end to the majority of excitement and activities as period of winter hibernation crept in. Simply put, those days are long gone and Ocean City now offers nearly as many amazing festivals and experiences in the fall and winter as it does between Memorial Day and Labor Day. If you think Ocean City is just for summer vacations, you’re wrong.

Check out these annual highly-anticipated fall festivals.


6 Things You Need to Know About Sunfest

Labor Day may mark the end of summer in some places, but Ocean City, Maryland is not one of them. In Ocean City, summer is a state of mind that can’t be located on a calendar or constrained to certain months.

When Ocean City held the first ever Sunfest four decades ago as a way to delay the inevitable onset of winter, no one imagined it would blossom into the most popular festival of the entire year. Now well into its 40s, Sunfest continues its tradition of attracting thousands to town each fall for a weekend of national music acts, amazing food and great times with family and friends. And it’s free to attend (aside from headline concerts). 

Wine on the Beach

Wine on the Beach hasn’t experienced quite the longevity of Sunfest, but in its second decade, it’s asserted itself as a post-summer mainstay in Ocean City. As always, this year’s Winefest will feature dozens of the finest wines from the best local and regional vineyards and wineries for your tasting pleasure. In addition to locally produced libations, Winefest provides favorite local food vendors, handmade arts and crafts and live music to the Inlet parking lot.

Endless Summer Cruisin’ 

Endless Summer Cruisin’ rolls into Ocean City – OceanCity.com

Custom and classic cars, hot rods and trick trucks will be out in Ocean City this weekend for the 16th annual Endless Summer Cruisin’ event at the inlet parking lot and 40th Street convention center. Events kicks off Thursday with car shows, vendor showings and awards presentations and continue through Sunday, with more than 2,000 automobiles on the streets and on display.

Ocean City may be known for its widely popular car and truck shows throughout the summer, but its fall festival dedicated to cruisers, muscle cars, hot rods and trick trucks offers as much tire burning, engine revving excitement as its June and July counterparts. The Endless Summer Cruisin’ weekend (usually the first weekend in October) draws over 2000 classic cars and thousands more spectators for a weekend of car shows, national vendors, live music, celebrity meet-and-greets and parades along the Boardwalk each morning. It’s still unclear whether or not the combination of exhaust, custom paint jobs and celebrity appearances help extend endless summer, but they will certainly help you take your mind off of cold weather blues for a few days in early October.

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Ocean City Restaurant Week 

4 reasons to eat, drink and be merry at Ocean City’s Restaurant Week

Historically, Ocean City has always been a vacation destination for food enthusiasts–if your idea of a good meal is limited to crabs, pizza and bar peanuts. Thankfully, the Ocean City restaurant scene has been expanding greatly in the last decade, and the town’s Restaurant Week has gotten bigger along with it.



5 great ways to celebrate OCtoberfest in Ocean City – OceanCity.com

It breaks our heart to say it, but we’ve probably seen the last of 90 degree temperatures for 2016. That said, it still will get warm and there still are a ton of things to do at the beach. Why not give Autumn a proper welcome and give the Indian summer a thankful sendoff by …


Winterfest of Lights

Ocean City Winterfest 2017! Celebrating 25 Years of Lights

The 35th Annual Ocean City Christmas Parade will march up Coastal Highway from Old Landing Rd to the judges at 120th St. The event will feature more than 50 units, including high school bands, horses, antique cars, colorful holiday floats, and more. Bring your chair and blanket and enjoy the day in Ocean City!

No matter how hard we try  to delay it, winter eventually takes hold over the town. Rather than dwell on cold weather and short days, Ocean City celebrates with a 2 ½ month-long celebration known as Winterfest of Lights. From mid- November to January, Ocean City is covered in over 1,000,000 light bulbs and hundreds of eye-popping displays that bring thousands of eager onlookers to town. The amazing lights at Northside Park are one of the main attractions, but a ride aboard the Winterfest Express or a stroll down the Boardwalk allows you to see many unique holiday themed displays that have won national awards and recognition in past years.  Words and pictures on a page cannot do the Winterfest spectacle justice; this is truly an event you must see for yourself to fully appreciate.

With numerous festivals and celebrations taking place after summer gives way to the colder seasons, Ocean City can be just as exciting after Labor Day as it is before. The fall and winter months are no longer a period of hibernation–they’re full of exciting experiences to keep you occupied until summer strolls back into town.

*This page was updated 9/22/17. 

We love sharing all things Ocean City, Maryland! From Beach Photos to Day Trips, we're always up for something fun. Reach out to info@OceanCity.com to share your favorite photos and stories.

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  1. Every time I have been to Ocean City this past year has been a AWESOME
    AWESOME TIME!!!! First time was with the Women of ” Life Community Church ” for a beautiful time a womens Bible retreat… It was for 2days 1 night
    not long enough for me lol we stayed at the Dunes Oceanfront I couldnt
    leave so me n Steph stayed another night.
    Second time was a gift to my one and only Sisters 50th Birthday
    Once again at the Dunes and we stayed a week!!! And I still wanted to stay
    longer but my Sister couldnt at the time anymore vacation time :-(. Now I just had my second neck surgery ( soo painful worst surgery ever had!! Soon as as I am able.. I hope I will be there once again.. God willing.


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