The Gulf Winds Summer Trail Series takes place May 30, 2026, in Tallahassee, Florida, at various venues. This trail running event offers two distances: a 5-mile option and a 6-mile option, giving runners flexibility in their race choice. The event starts at 8:00 AM, a practical early-morning window that helps athletes avoid the day's heat. Entry fees range from free to $89.00 depending on your registration timing and distance selection. With multiple trail locations across the area, participants should confirm their specific venue assignment upon registration. This series format provides trail runners a chance to test themselves over early-summer distances on Tallahassee's terrain.
From the Race Organizer
2026 Gulf Winds Summer Trail Series This four-race series takes place on the most scenic and challenging trails in Tallahassee. Each course offers a little bit of everything: rolling terrain, single track trails, multi-use trails, and technical sections with rocks, roots, and tight twisty turns. This is a great off-road running experience. Registration is limited to 150 runners. Don't miss out! May 30 - Oak Hammock Trail (~5.0 mi), 8:00 a.m. June 20 - Redbug Trail (~5.0 mi), 6:00 p.m. July 18 - Cadillac Trail (~6.0 mi), 8:00 a.m. August 22 - Maclay Gardens State Park (~6.0 mi), 8:00 a.m. Race History: Trouble Afoot! by Herb Wills Race shirt : One shirt is available for the race series. Shirts are unisex short sleeve t-shirts (60% combed ringspun cotton/40% polyester, laundered for reduced shrinkage) Runners who register for the series will receive a race shirt with registration. Shirts are not guaranteed for late registration (if offered). Series Championship Awards : Series championship awards will be presented at the last race. A point system will determine the series champion. If there is a tie at the end of the series, the winner will be determined by the fastest overall time at the last run. Your best three races count towards the series standings. Points awarded for the finish of each race: 1st place ‐ 20 Points 2nd place ‐ 15 Points 3rd place ‐ 12 Points 4th place ‐ 10 Points 5th place ‐ 8 Points 6th place ‐ 6 Points 7th place ‐ 4 Points 8th place ‐ 2 Points 9th place & Up ‐ 1 Points Race Age : Your race age will be your age as of May 30, 2026. That will keep you in the same age category for the entire series. Water Stations : Water stations may be set up approximately halfway through each course. Runners are encouraged to carry a water bottle at each event for hydration and will be notified in advance if a water station will not be available. Packet Pick‐up : Race day bib pick up is from 7:00 to 7:45 AM for the morning races and 5:00 to 5:45 PM for the evening race. Runners will receive a new bib for each race. Additional Information : Emails with details go out the Monday of each race week. Race Director : Bobby York
Hotels Near This Race
Find accommodation close to the start line in Tallahassee, FL. Sorted by distance from the race venue. Book early — race weekend hotels fill fast.
RaceHotelFinder earns a small commission when you book through links on this page, at no extra cost to you. Results are sorted by distance from the race venue.
Gulf Winds Summer Trail Series 2026 — Tallahassee, FL
Race weekend dates pre-loaded on Booking.com. RaceHotelFinder may earn a commission at no extra cost to you.
Race Travel Insurance
Don't forget travel insurance for May 30.
You've trained for months and booked a trip to Tallahassee, FL.
A pre-race injury, a delayed flight, or a family emergency can derail the whole thing.
Travel insurance can help cover your race entry fee, hotel, and flights if you can't make it,
and may cover medical costs if something goes wrong on the course. Plans typically only run
5-7% of your total trip cost — and running events are covered under standard plans with no
additional coverage needed.
Trip cancellation up to 100% of prepaid costs
Running events covered under standard plans — no add-ons needed
Trip interruption up to 150% of non-refundable costs
When is Gulf Winds Summer Trail Series 2026 — Tallahassee, FL?
Gulf Winds Summer Trail Series 2026 — Tallahassee, FL takes place on May 30, 2026. The race is held in Tallahassee, Florida.
Where is Gulf Winds Summer Trail Series 2026 — Tallahassee, FL held?
Gulf Winds Summer Trail Series 2026 — Tallahassee, FL is held at Various in Tallahassee, Florida.
Where can I find hotels near Gulf Winds Summer Trail Series 2026 — Tallahassee, FL?
RaceHotelFinder shows hotels sorted by distance from the race venue in Tallahassee. Use the map or list view on this page to compare options and book race weekend accommodation.
