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Trail Running Calendar near Parsonsburg 2026-2027

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Explore the top trail runs near Parsonsburg for 2026-2027! We've gathered 9 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

September 2026
Run a new 5K every hour for 24 hours at Pemberton Park in this unique point based endurance festival for solo runners and teams of four.
A 5K fundraising run/walk at Paradise Grill in Long Neck on September 20, 2026, offering a choice of water or woods courses that rejoin near the finish.
October 2026
A 2 mile walk and 5K run at Assateague State Park on October 17, 2026 benefiting the Macky & Pam Stansell House; includes a shirt and medals.
A 5K on Gravel Hill Road in Georgetown DE on October 17, 2026 benefiting the Delaware Aerospace Education Foundation with timing, awards, and postrace photos.
Community trail event at Camp Barnes in Frankford, Delaware offering 6.2 and 3.1 mile runs, 1 to 3 mile family walks, and a Kiddie Color Run. Post race lunch and live bluegrass music support Mariners Bethel youth ministries.
A nighttime trail 5K on October 30, 2026 at Pemberton Historical Park in Salisbury, MD with chip timing, costume prizes, and Halloween decorations.
November 2026
A 10K run and a 1.5 mile non-competitive walk at Bethany Brewing Company with trails in Fresh Pond State Park to benefit the Delaware Center for the Inland Bays.
February 2027
A trail 5K on February 20, 2027 at the Wicomico Ranger Station in Parsonsburg, MD that raises funds for 4STEPS therapeutic riding programs, with age/gender prizes in Amazon gift cards and a $32 registration fee.
May 2027
Test your endurance at The Ripper, a 14 hour timed race on a 3.3 mile trail loop in Pocomoke where runners complete as many laps as possible from sunrise to sunset.
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