Enjoy a day of family fun and Florida charm at the 26th Annual Oakland Heritage Day on January 31
- Alastair Mac
- 1 hour ago
- 2 min read
Heritage Day features Healthy West Orange 5k, Fresh Start Zone, Food Trucks, Arts & Crafts Vendors, Educational Demonstration, Live Music, Mechanical Gator, and more.
Join the Town of Oakland on Saturday, January 31, 2026 from 10 am - 2 pm for Heritage Day at Speer Park, 331 N. Tubb St.
The 26th Annual Oakland Heritage Day will kick off bright and early at 9.30 am with the free Healthy West Orange 5K.
At 10 am local favorites Lucky To Be will perform live, and at 11.30 am don't miss the Oakland Nature Preserve educational demonstration.
A highlight at 12 pm will be a live performance from local favorite, and Nashville recording artist Sean Holcomb, who will take the stage to entertain the crowd.
All this plus, Heritage Day features family fun throughout the park. Bring your lawn chairs and enjoy live entertainment, vendors, food trucks, arts & crafts, mechanical gator, batting cages, and more.
Don't miss the Fresh Start Zone with Healthy West Orange where you can get FREE health screenings. Plus, blood pressure and cholesterol screenings with Orange County Medical Clinic, skin cancer screenings with Advanced Dermatology & Cosmetic Surgery West Orlando, and check your temperature, pulse, blood pressure, cholesterol, and hemoglobin levels before donating blood at the OneBlood Big Red Bus.
Looking for more fun events and things to do in Central Florida? Check out our Events Guide. We also publish weekly and monthly event guides with the can’t-miss happenings throughout Central Florida.
Heritage Day 2026 will have a ton of great vendors to visit! Vendors include Winter Garden Vintage, Caribbean Moonshine, Tasty Doghouse Treats, Red Heart Candles, Anna Grace Boutique, Kizzy's Books & More, Sharon's Dutch Bakery, and many more.
The event will also feature a food court and beer garden, where you can discover great food from Smash Burger, The Avacado Lab, Green Pea Coffee, Ragazzi Pizza & Bar, and more.
For more information on the 26th Annual Oakland Heritage Day on January 31:
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