January | February | March | April | May | June | July | August | September | October | November | December
| May | ||
| May 28 | Coastal Running League Cross Country Meet | Falmouth |
| May 26 | 13th Annual Memorial Mile & Half Mile Race | Cumberland |
| May 26 | Snowy Egret 5K | Scarborough |
| May 25 | Pineland Farms Trail Challenge 50M, 50km, 25km, &4km Canicross | New Gloucester |
| May 24 | RUN FOR THE SUN 5K ROAD RACE | Brunswick |
| May 21 | Weekly Back Cove 5K | Portland |
| May 18 | 2nd Annual Kittery Fire Association 5K Run/Walk | Kittery |
| May 18 | Dragonslayer 6K | York |
| May 18 | Sugarloaf Marathon & 15 K | Kingfiled |
| May 17 | HOPE TO HOUSE RACE/WALK | Gorham |
| May 17 | 3rd Annual SPRING SPRINT Sloan Critchfield Memorial 5K Run/Walk | Portland |
| May 17 | Laura Vogel Memorial 5K | Portland |
| May 14 | Weekly Back Cove 5K | Portland |
| May 14 | Coastal Running League Cross Country Meet | Topsham |
| May 14 | Weekly Back Cove 5K | Portland |
| May 11 | 8th Portland Sea Dogs Mother’s Day 5K | Portland |
| May 10 | McAuley 5k Run for Hope | Portland |
| May 4 | Kennebunk Beach Classic 5 miler and 3 miler | Kennebunk |
| May 4 | Hot Pursuit 5K Road Race | Brunswick |
| May 3 | 28th Annual Rocky Coast Road Race 10K | Boothbay Harbor |
| May 3 | Fort Foster 4-Miler | Kittery |