Races near Orlando in May 2027
Updated
18 races are on the calendar near Orlando in May 2027, starting with Sunshine Double (Two Days, Five Distances to choose from) on Saturday, May 1 in Winter Park. Listed by date, with prices and early-bird deadlines where the race publishes them.
Nov 2026Dec 2026Jan 2027Feb 2027Mar 2027Apr 2027May 2027Jun 2027Jul 2027Aug 2027Sep 2027Oct 2027
By date
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Sat May 1 · 6:00 AM · Winter Park · Orlando & Winter Park
5K10KHalf marathonMarathon50K
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Sat May 1 · 7:30 AM · Clermont · Kissimmee, Clermont & Winter Garden
5K
from $35Sign up ↗ -
from $20Reg. closed
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Sat May 1 · 8:30 AM · DeBary · Seminole County & West Volusia
5K10KHalf marathon
from $30Sign up ↗ -
Sat May 8 · 7:00 AM · Sanford · Seminole County & West Volusia
5K
from $35Reg. closed -
Sat May 8 · 7:30 AM · Clermont · Kissimmee, Clermont & Winter Garden
5K
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Sat May 8 · 8:30 AM · Deland · Seminole County & West Volusia
5K10KHalf marathon
from $30Sign up ↗ -
Sun May 9 · 7:30 AM · Clermont · Kissimmee, Clermont & Winter Garden
5K
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Sat May 15 · 7:00 AM · Orlando · Orlando & Winter Park
1 mile5K10KHalf marathon
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Sat May 15 · 8:30 AM · DeBary · Seminole County & West Volusia
5K10KHalf marathon
from $30Sign up ↗ -
Sat May 22 · 8:30 AM · Deltona · Seminole County & West Volusia
5K10KHalf marathon
from $30Sign up ↗ -
Sat May 29 · 5:00 AM · Winter Park · Orlando & Winter Park
5K10KHalf marathonMarathonTrail
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from $30Sign up ↗
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from $75Sign up ↗
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Sat May 29 · 8:30 AM · Deland · Seminole County & West Volusia
5K10KHalf marathon
from $30Sign up ↗
Quick answers
How many races are near Orlando in May 2027?
18 races are listed near Orlando in May 2027. The first is Sunshine Double (Two Days, Five Distances to choose from) on Saturday, May 1 in Winter Park, and the last is Medal Madness 5K, 10K, & 13.1M at Deland, FL (22) on May 29.
What is the cheapest race near Orlando in May 2027?
First Journey 5k on May 1 has the lowest listed entry fee: $20. Prices are before the registration platform's processing fee.
When does the next early-bird price end for races near Orlando?
Ole Ole 5K - Orlando: the 5K goes from $37 to $42 after November 15. 7 more of these races publish a later price increase.
Are there half marathons or marathons near Orlando in May 2027?
Yes: 8 half marathons and 2 marathons. The first is Sunshine Double (Two Days, Five Distances to choose from) on May 1.