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Grin 'N Bear It: Brewster 5K

📅 October 23, 2027 (estimated date)📍 Brewster · United States

⚠️ 2027 edition: provisional information

The date is estimated from the 2026 edition (October 24, 2026), on the same day of the week. Courses, start times, fees and description are carried over from the previous edition: check them on the official website. This page will be updated as soon as the organizer publishes them.

Available distances

3.1 mi

About

Grin 'N Bear It: Brewster 5K is on October 24, 2026 in Brewster, New York, with the 5K starting at 10:00 a.m. Put on by the Brewster Teachers' Association, it welcomes runners and walkers of every age and ability. The route takes in the Hudson Valley setting around town, mixing trails, tree-lined streets and open space within the Brewster community. Proceeds fund BTA scholarships through the Brewster Education Foundation.

Those mixed surfaces make it less of a pure road 5K and more of an all-around effort — trail shoes are not required, but a shoe with some grip helps. Experienced runners still use the race to go after a personal best, while anyone newer can walk-run the distance comfortably. A month of three to four runs a week, one of them including a few faster intervals, is a solid way in.

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