Grin 'N Bear It: Brewster 5K

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.