About the RTB Fair Winds 5k/Fun Run
The course runs through Quiet Waters Park on paved trails that wind through woods and meadows. It is a comfortable surface underfoot with natural scenery throughout, and the park setting gives the route a sheltered, tree-lined feel even on open stretches.
Costumes are a real part of the morning here. Prizes go to the best individual and best group or family costume, so some people show up having put in serious effort. The race raises money for academic and camp scholarships, so the crowd tends to be invested in the event beyond the running itself.
Free race emails
Get the Weekly RunSesh
In for this one or still deciding, keep race season near Annapolis on your radar: a Monday look ahead and a Thursday rundown of the weekend's races.
Two helpful emails per week. No spam. Unsubscribe anytime.
Distances & Start Times
3.1 Miles10/24/2026 10:00$35
5K10/24/2026 10:00$15
Going for a Time?
Set a goal and get a pace band: every mile split on a card sized for your phone lock screen, so race morning needs no math.
Where to Stay
Traveling for this race? The map shows hotels and rentals in and around Annapolis — pan or zoom to compare what's nearby.
The map is provided by Stay22. If you book through it, RunSesh may earn a commission at no extra cost to you — it never affects the races we list.
