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.
Free race emails
Get races near Brewster in your inbox. Every Monday we send the races coming up, and every Thursday we send the ones happening that weekend.
Two helpful emails per week. No spam. Unsubscribe anytime.
Going by the 2025 results, this is a small, friendly field, with a competitive front end and a big recreational middle.
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 Oct 23, 2026.
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.
Not sure what to aim for? The 5K pace chart lists the pace for every finish time.
Traveling for this race? The map shows hotels and rentals in and around Brewster — 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.
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.
Want more races like this delivered straight to your inbox?