Trail

Operation Outdoor Freedom Event - Middleburg

📅 October 18, 2026📍 Middleburg · United States

Available distances

10 mi5 mi

About

The Operation Outdoor Freedom Event - Middleburg takes place on October 18, 2026, in Jennings State Forest near Middleburg, organized by Sombrero Running Events LLC. Runners can choose a 10 Mile Trail Run (16.1 km) or a 5 Mile Trail Run (8 km), both starting at 8:00 a.m., on routes that use the new Sawyer Trail and the Many Seeps Bridge.

The aid stations are well stocked, and the event is cupless, so participants must bring their own water containers. Awards go to the overall and masters winners, along with a unique “Slow A$$” category, and every finisher receives a custom medal. The event supports Operation Outdoor Freedom, with all proceeds going to the cause. Alcohol is not allowed on site.

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