Georgetown
Trail Running Calendar near Georgetown 2026-2027
Explore the top trail runs near Georgetown for 2026-2027! We've gathered 12 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.
October 2026
A farm-based 5K run and walk at Hopkins Farm in Lewes on October 10, 2026, with chip timing, awards, participant shirts, and fundraising for ag education.
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.
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.
A community 5k run/walk and a separate competitive walking 5k at Killens Pond State Park on November 28, 2026. The event supports Milford High School Cross Country and features chip timing, awards, shirts, and post race refreshments.
January 2027
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
A multi-distance event in Lewes, Delaware with 5K, 10K and half marathon options plus race walk and heavy march categories. The weekend includes an educational exhibit, vendors and live music while supporting wounded warriors and homeless veterans.