Sat, Oct 24, 2026
Brewster, NY
Entry is $17.92 now and rises to $30 after Oct 23, 2026, so registering before then saves $12.08.
The course starts at an intermediate school and winds through the surrounding neighborhood and school district. It is a road race with a local feel, the kind of morning where you will recognize the streets even if you have never run them before. There is a shorter fun run option alongside the main distance for those who want something less demanding.
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Going by the 2025 results, this is a small, friendly field, with a competitive front end and a big recreational middle.
5K · 2025 results
Top 3: Ueder Magalhaes (23:08) · Jim Bail (24:13) · Erik Smith (25:09)
The 2nd Annual Brewster Grin 'N Bear It 5K and 1 Mile Fun Run is in its 2nd year.
Enter a finish time to see where it lands against the most recent 5K results.
How we calculate these stats: RunSesh calculates these figures from the most recent published results of past editions, sourced from RunSignup. We show aggregates only: field size, winning and median times, and the cutoff. We never publish individual finisher tables. Last updated Jul 27, 2026.
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Almost certainly not. Half the 5K field finished slower than 43:14, and the last recorded finisher came in around 1:13:15, so there is a long tail of runners behind the middle of the pack. Most fields are far slower than people expect.
It is a small race (100 finishers), which is friendlier and less intimidating than a big-city event, though the field thins out. There is no qualifying time, and the finish-time spread above shows how varied the field really is. If it is your first 5K, that spread matters more than the winner's time.
The 5K winner ran 23:08 while the median finisher took 43:14. That spread points to a mixed field, with a competitive front and a big recreational middle.
