Oakland, located in Northwest Orange County, is a quaint, unhurried town that will take you back to the Florida of Yesterday. Our partnership with the Town began in 2022, where OBMco. became the exclusive provider of quality vendors for the community events and farmers market.
Since then, we have worked tirelessly to ensure that only the best vendors are selected to participate in these events. Our goal is to provide a unique and enjoyable experience for both residents and visitors alike.
Oakland's community events are a great way to get to know your neighbors and experience the town's rich history. From the annual Oakland Heritage Festival to the twice a month farmers market, there is always something fun and exciting happening in Oakland.
At OBMco., we are proud to be a part of Oakland's vibrant community and look forward to continuing our partnership for years to come. Whether you're a long-time resident or a first-time visitor, we invite you to come and experience all that Oakland has to offer.
Every 2nd and 4th Thursday, from 9:00am-2:00pm along the West Orange Trail
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On January 31, 2026 Healthy West Orange will open the event at Speer Park with up to 1000 guest finishing the annual 5k. After the race guest will enjoy live music from Lucky to Live and Sean Holcomb, vendors, food trucks, games, and much more!
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On March 28, 2026 guest will enjoy live music, DJ, vendors, food trucks, games, and much more!
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April 16th - One food tent or truck, sweet treat, and specialty drink set up outside the Healthy West Orange Arts and Heritage Center
May 2nd - One food tent or truck, sweet treat, and specialty drink set up outside the Healthy West Orange Arts and Heritage Center
October 11th lets rock out at Music Under the Oaks. Food trucks, Drink vendors, desserts, and activity based vendors only.
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Join OBMco. for Santa’s Lane in Oakland December 5th, 2026 from 1:00-5:00pm.
Celebrate the holiday season with us at the Town of Oakland’s Santa’s Lane as we proudly participate for the fifth year!
Expect the same fantastic entertainment you love, plus a few extra surprises to make this year even more magical.
Once approved, vendors will have the opportunity to select their preferred row based on availability. On event day, spaces within the chosen row will be assigned on a first-come, first-served basis.
Don’t miss this cherished holiday tradition—join us and be part of the magic!
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A vendor application must be submitted for review to become a vendor. Submission of an application is not acceptance to the market. All applications will be reviewed, and an emailed approval will be sent if you are accepted as a vendor. We do our best to review applications weekly. Once you are a vendor of the market you no longer need to apply, simply pay your fee through the payment link provided in your original approval email with the event date noted.