May Classic Races within 100 miles of Fairfield, CT on Sundays
West Windsor, NJ
Good Grief 5K Run & Walk
May 19, 2024
Port Jervis, NY
Delaware River 5K
May 5, 2024
Jamaica, NY
JFK Rotary Club 5K Runway Run
May 5, 2024
Huntington, NY
YMCA 5K in Memory of Marcie Mazzola
May 5, 2024
Pittsfield, MA
Mother's Day Women's 5K
May 12, 2024
Steel Rail Race
May 19, 2024
Stratford, CT
Miles for Margaritas & Cinco de Mama 5K
May 5, 2024
Montclair, NJ
Doug Williams Memorial Run
May 26, 2024
Hamden, CT
Spring into Spring Glen 5K
May 19, 2024
Wilbraham, MA
Jack Rome Memorial 5K
May 5, 2024
Oyster Bay, NY
Cinco de Mayo 5K
May 5, 2024
Staten Island, NY
Spring Meltdown 5K
May 5, 2024
Greenwich, CT
Breast Cancer Alliance 5K
May 5, 2024
Syosset, NY
West Side Run
May 5, 2024
New Rochelle, NY
Cinco de Mile
May 5, 2024
Bridgewater, NJ
Bridgewater Donut Chase 5K
May 4, 2025
Wayne, NJ
Run for the Last Mile 5K
May 4, 2025
Madison, NJ
Madison 5K
May 5, 2024
Rocky Point, NY
PFC Joseph P Dwyer PTSD Memorial 5K
May 26, 2024
Marlborough, CT
Memorial Day Weekend Round the Lake 5K
May 26, 2024
Weehawken, NJ
Lincoln Tunnel Challenge 5K
May 5, 2024
Jersey City, NJ
Running Is Back 10K + 5K
May 12, 2024
Jersey City Half
May 19, 2024
Westfield, NJ
Greta's Run for Imagine
May 19, 2024
Freehold, NJ
Paulette's C of Hope
May 19, 2024
Roxbury, CT
Mine Hill Half Marathon
May 26, 2024
Carmel, NY
CTA Scholarship 5K
May 5, 2024
Lawrenceville, NJ
Big Red Race
May 5, 2024
Monroe, CT
M and T Bank Mile Down the Pike
May 26, 2024
Brookfield, CT
WeCare-Mother's Day 5K
May 12, 2024
Glen Ridge, NJ
Blue Jean Mile
May 19, 2024
Tenafly, NJ
Rubin Run
May 11, 2025
East Hampton, NY
OMAC May Day 5K
May 5, 2024
Darien, CT
5K Run For Ukraine
May 12, 2024
New York, NY
Bridge the Gap 5K
May 5, 2024
NYC Spring 10K & 5K
May 5, 2024
NYPD Memorial 5K Run
May 19, 2024
Westfield, MA
Miles for Mary Run/Walk
May 19, 2024
Longmeadow, MA
Spring Shuffle - Run, Walk, Roll
May 19, 2024
West Islip, NY
Mama Bear Run
May 5, 2024
Summit, NJ
Mother's Day 5K
May 5, 2024
East Meadow, NY
NSRF Comic Run
May 12, 2024
Howie Levy Cross Country 5K
May 19, 2024
Holmdel, NJ
HFEE 5K
May 19, 2024
Wyckoff, NJ
Friends of TJ 5K
May 19, 2024
Bloomfield, NJ
Family Promise of Essex County 5K Run/Walk
May 5, 2024
Geo Foundation 5K
May 19, 2024
Nutley, NJ
Nutley Chamber of Commerce 5K
May 5, 2024
Ridgefield, CT
Run Like a Mother
May 12, 2024
Washington, CT
Rossiter Run 5K Race & Fun Run
May 19, 2024
Yorktown Heights, NY
Mother's Day 5K
May 12, 2024
Beacon, NY
Breakneck Point Trail Runs
May 4, 2025
Kingston, NY
Woodstock 15K
May 26, 2024
Poughkeepsie, NY
Great Donut Run
May 19, 2024
Cranford, NJ
Cranford Pizza Run
May 18, 2025
Long Beach, NY
City Manager's Race to Remember
May 26, 2024
South Orange, NJ
South Orange Rescue Squad 5K
May 19, 2024
Springfield, MA
Celebrate Kate 5K
May 19, 2024
Outrun Hunger
May 19, 2024
Mystic, CT
Mystic Half Marathon
May 19, 2024
Mahwah, NJ
MRCC 5K/3K
May 19, 2024
Stafford, CT
Soapstone Mountain Trail Races
May 19, 2024
Morristown, NJ
Superhero Half Marathon & Relay
May 4, 2025
Brooklyn, NY
Cinco de Mayo 5K
May 5, 2024
Brooklyn Mother's Day Half
May 12, 2024
I.S. 223 Running for Success 5K
May 19, 2024
Newington, CT
Newington Library 5K Challenge
May 19, 2024
Waldwick, NJ
Waldwick Chamber of Commerce 5K
May 5, 2024
Manhattan, NY
NYC Teen Race of Hope 5K
May 18, 2025
Woodhaven, NY
Vaisakhi 5K
May 5, 2024
Forest Park Runners Classic 4 Mile Road and Trail Race
May 26, 2024
Asbury, NJ
MWA Run for the River
May 5, 2024
Woodland Park, NJ
Anthony 'Blues' Barbato Memorial 5K Run/Walk
May 19, 2024
Hadley, MA
Dandelion Dash and Mushroom Mile
May 4, 2025
Vernon, NJ
Vernon Spring 5K and Kid's Mile
May 5, 2024
Little Silver, NJ
Ridge Road Run
May 5, 2024
Monroe Township, NJ
Om Memorial 5K
May 19, 2024
Lindenhurst, NY
Beat Lives On 5K
May 19, 2024
Fair Lawn, NJ
Radburn PTA 5K
May 5, 2024
HIghland Park, NJ
Run in the Park - Highland Park 5K
May 5, 2024
Mount Sinai, NY
Robert Grable Memorial 5K
May 5, 2024
Katonah, NY
Spring Run The Farm
May 19, 2024
River Vale, NJ
Spring Fling 5K
May 19, 2024
Demarest, NJ
Demarest 5K
May 19, 2024
Terryville, CT
Edmund Ganem Memorial 5K Run/Walk
May 5, 2024
Old Westbury, NY
Levathon 5K
May 19, 2024
Burlington, CT
Burlington to Collinsville Classic 10K
May 5, 2024
Ellenville, NY
Run Like the Wind
May 18, 2025
Baldwin, NY
Friedberg JCC 5K
May 19, 2024
Ocean Township, NJ
Ocean Parks 5K
May 19, 2024
Amenia, NY
RattleSnakeRun
May 5, 2024
New Hartford, CT
Race Around The Lake
May 26, 2024
West Babylon, NY
Rhiannon's Run
May 5, 2024
Goshen, CT
Run With The Animals
May 19, 2024
Hopkinton, RI
Race for Raymond
May 5, 2024
Dalton, MA
Dalton CRA May Day Races
May 4, 2025
Wall Township, NJ
Superhero Sprint
May 19, 2024
Governors Island, NY
New York Harbor Oyster Classic 5K
May 4, 2025
Bohemia, NY
Using our Voices Mental Health Run
May 19, 2024
Sat | Sun | Mon | Tue | Wed | Thu | Fri | Multiple |
1. Breakneck Point Trail Runs
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May 4, 2025Sunday
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26.2M, 13.1M trail run
More Information
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Beacon, NY
44 miles point to pointDutchess County, NY
2. Bridgewater Donut Chase 5K
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May 4, 2025Sunday
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5K run
More Information
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Bridgewater, NJ
79 miles point to pointSomerset County, NJ
3. Dalton CRA May Day Races
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May 4, 2025Sunday
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10K, 5K run
More Information
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Dalton, MA
93 miles point to pointBerkshire County, MA
4. Dandelion Dash and Mushroom Mile
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May 4, 2025Sunday
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5K, 1M run
More Information
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Hadley, MA
91 miles point to pointHampshire County, MA
5. Hudson Valley Marathon at the Walkway Over the Hudson
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May 4, 2025Sunday
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26.2M, 13.1M, 10K, 5K, 1M run
More Information
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Highland, NY
54 miles point to pointUlster County, NY
6. Long Island Marathon Festival of Events
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May 4, 2025Sunday
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26.2M, 13.1M run
More Information
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Challenge
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Long Island, NY
46 miles point to pointNassau County, NY
7. New York Harbor Oyster Classic 5K
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May 4, 2025Sunday
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5K run
More Information
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Governors Island, NY
50 miles point to pointNew York County, NY
8. Run for the Last Mile 5K
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May 4, 2025Sunday
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5K run
More Information
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Wayne, NJ
53 miles point to pointPassaic County, NJ
9. Superhero Half Marathon & Relay
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May 4, 2025Sunday
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13.1M run | 13.1M relay
More Information
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Morristown, NJ
68 miles point to pointMorris County, NJ
10. Aisling Center 5K
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Past DateMay 5, 2024Sunday
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5K run
More Information
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Bronx, NY
37 miles point to pointBronx County, NY
11. Big Red Race
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Past DateMay 5, 2024Sunday
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5K run
Virtual OptionMore Information
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Lawrenceville, NJ
96 miles point to pointMercer County, NJ
12. Breast Cancer Alliance 5K
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Past DateMay 5, 2024Sunday
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5K run
More Information
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Greenwich, CT
20 miles point to pointFairfield County, CT
13. Bridge the Gap 5K
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Past DateMay 5, 2024Sunday
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5K run
More Information
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New York, NY
48 miles point to point
14. Burlington to Collinsville Classic 10K
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Past DateMay 5, 2024Sunday
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10K run
More Information
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Burlington, CT
47 miles point to pointHartford County, CT
15. Cinco de Mayo 5K
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Past DateMay 5, 2024Sunday
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5K run
More Information
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Oyster Bay, NY
23 miles point to pointNassau County, NY
16. Cinco de Mayo 5K
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Past DateMay 5, 2024Sunday
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5K run | kids run
More Information
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Brooklyn, NY
47 miles point to pointKings County, NY
17. Cinco de Mile
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Past DateMay 5, 2024Sunday
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1M run | kids run
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New Rochelle, NY
31 miles point to pointWestchester County, NY
18. Circle of Care 5K
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Past DateMay 5, 2024Sunday
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5K run
Virtual OptionMore Information
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Wilton, CT
10 miles point to pointFairfield County, CT
19. CTA Scholarship 5K
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Past DateMay 5, 2024Sunday
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5K run
Virtual OptionMore Information
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Carmel, NY
29 miles point to pointPutnam County, NY
20. Delaware River 5K
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Past DateMay 5, 2024Sunday
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5K run
More Information
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Port Jervis, NY
76 miles point to pointOrange County, NY
For the love of all that Is good And moisture wicking...
Though we Try To be accurate And On top Of things... Race details can change When we aren't lookin. And once in a while we simply make a mistake.
ALWAYS visit the race's website for the most complete and accurate race information.
ALWAYS visit the race's website for the most complete and accurate race information.