Oakley’s Farm Market

If you’ve ever rolled down Route 50 through Hebron and spotted a roadside market bursting with color, that’s Oakley’s. The farm itself goes back generations. Allie and her husband both hold degrees in agribusiness, and his grandfather is the one who started it all. That heritage shows up in everything they do, from the way the fields are tended to the care put into each growing season.

Every spring, the main market on Ocean Gateway comes alive with U-pick strawberries, hanging baskets, and fresh cut flowers. As the season moves along, so does the produce: corn, watermelons, cantaloupes, green beans, and eventually U-pick pumpkins in the fall. They even make their own strawberry jam right on the farm.

Fresh Local Produce Markets in Wicomico County

Oakley’s home base has been on Route 50 in Hebron since 2000. They’ve since expanded to two additional locations, one on Rockawalkin Road and a smaller market on Snow Hill Road in the Moose Lodge parking lot. When you want to know what’s ready to pick or when the fields are open, their Facebook page is the place to check. They keep it updated throughout the season so you’re never making a wasted trip.

Family-Friendly Farm With Playground and Seasonal Events

Two events draw big crowds every year. The Berry Bash, held the day before Mother’s Day, is a springtime celebration worth putting on your calendar. Come fall, their Trunk or Treat brings the whole community together. They also welcome school field trips for little ones during strawberry and pumpkin season, and a well-equipped playground keeps kids entertained long after the baskets are full.

Oakley’s also donates excess produce to the local food bank each season, and they’re proud members of the Maryland’s Best program. This is a farm that genuinely gives back to the community it’s been part of for decades.

If you’re looking for a real slice of Eastern Shore farm life, Oakley’s is worth the stop. Whether you’re loading up on fresh produce for the week, letting the kids loose in the patch, or picking out the perfect fall pumpkin, there’s always something in season and something to look forward to.

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