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29 Oct 2026
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Oak Island Trip Planning

Fall in Oak Island is a magical experience filled with exciting events! Sure, summer gets all the glory, but there’s something special about the breeze when autumn rolls around. Let’s set the scene: fewer crowds, perfect-beach walking weather, a mix of salty air with a touch of fall crispness. If you've only visited us during the summer months, you're in for a treat! From local festivals to cozy holiday gatherings, Oak Island’s  fall events calendar is packed with activities that'll make you wonder why you didn't discover autumn at the beach sooner.

Fun Oak Island Fall Events

Pumpkin on the beach

NC Festival by the Sea (Holden Beach)

Oct. 24 -25, 2026

Every fall, the NC Festival by the Sea returns to Holden Beach with exciting events lined up. Enjoy live entertainment, local food vendors, and kid-friendly activities. Enjoy the talent showcased by local artists through a diverse array of arts and crafts. From live entertainment to delicious food vendors, you’ll have a blast participating in contests and experiencing the spirit of the coast.

Haunted Fishing Derby

Oct. 29, 2026 from 5:30 PM - 7:00 PM

Head over to the Oak Island Pier in your favorite Halloween costume to participate in the Haunted Fishing Derby. Bring your fishing gear and join the community for an exciting annual event. What will be your next catch?

Trunk or Treat

Oct. 31, 2026, from 5:00 PM - 7:00 PM

Get in the holiday spirit with the annual Trunk or Treat at the OKI Recreation Center. Join the fun by seeing how spooky you can decorate your car as you hand out scares and treats to the kids of Oak Island. You can also join the fun by bringing your family to collect delicious treats in the parking lot for the ultimate sugar rush! There will be a contest for the best decorated car, so don’t hold back!

Fall into the Holiday Spirit Early with these Oak Island Events

As fall passes us by, the holiday spirit fills the air, breathing life into the community. Get a head start on your Christmas gifts by checking out one of the many holiday craft sessions. You’ll put a smile on your family’s face with Oak Island’s holiday traditions.

Holiday cookies on a plate

Holiday Craft Market

Dec. 6, 2026, from 12:00 PM - 4:00 PM

Skip the shipping deadlines and shop local this holiday season on Oak Island! Browse a variety of area vendors offering locally made goods, unique gifts, and homegrown finds perfect for everyone on your holiday list. Holiday Craft Market is located in the Middleton Park Complex, 4610 E. Dolphin Dr.

Flashlight Candy Cane Hunt

Dec. 17, 2026 at 6:00 PM - 8:00 PM

The Flashlight Candy Cane Hunt is a fun event that your small kiddos will love! For children 10 and under, this scavenger hunt will tire out your little tikes and give them the chance to get a photo with Santa. This is a free event taking place at Bill Smith Park. Come collect as many candy canes as you can so you can fill stockings and fill your tree back home!

Tree Lighting

Dec. 4, 2026 from 5:00 PM - 7:00 PM

Towards the end of fall, the annual tree lighting tradition prepares Oak Island guests and residents for the winter! The Middleton Park Complex will be filled with live music from The Ford Project, a train ride, craft stations to create gifts, and a station to leave letters for Santa. Stop by and join the Oak Island community as we count down to the tree lighting!

Make the Most of Your Fall Vacation in Oak Island

Autumn in Oak Island is filled with endless fun as we welcome the wondrous Winter season. Experience coastal living after the rush of summer and experience great fall and winter savings with Margaret Rudd! Whether you're planning a weekend festival escape or an extended autumn retreat, we’ll help you find the perfect Oak Island vacation rental for your fall adventure.

Stay right on the beach with oceanfront Oak Island vacation rentals or bring your pet along and stay in a pet-friendly vacation home. No matter where you choose to stay in Oak Island, you'll find the perfect vacation rental for the perfect price with us! Don't miss out on these seasonal savings – book your dream vacation home today and fall in love with Oak Island's autumn charm.