For the next 30 days—Monday, August 24 through Wednesday, September 23, 2026—the confirmed large/community run I can verify in Pensacola is:

• Saturday, September 5 — Rock4Vets 5K
  A Pensacola 5K sponsored by Peoples Hospice Foundation, with registration listed at roughly $38.96. Race listing / registration details

• Every Saturday — Rec Plex North parkrun (free 5K)
  August 29; September 5, 12, and 19, 7:30 a.m. A free, timed, community 5K—walkers and runners are welcome.
  Where: Rec Plex North Field, University of West Florida, 11000 University Pkwy, Pensacola, FL 32514. Course and weekly-event details

Important date cutoff

The big fall kickoff event many people are already planning for—Pensacola Seafood Festival and its Don McCloskey 5K—is September 25–27, so it falls just outside your September 23 cutoff. The festival is in downtown’s Seville Square, and the race is September 26. Festival date listing

I’m not seeing another confirmed major Pensacola festival in the August 24–September 23 window from the current listings. For concerts, smaller markets, tours, and pop-up community events that get added closer to the date, the most reliable live source is Visit Pensacola’s event calendar.

👉 Would you like me to make this into a weekend-by-weekend calendar, including Pensacola Beach and nearby Gulf Breeze/Navarre events?