Brewster
Walking Events Calendar near Brewster 2026-2027
Monthly updates for Brewster
Get new running races (and updates) in your inbox every month.
Explore the top walking events near Brewster for 2026-2027! We've gathered 69 great walks in the area. Check out our detailed list below to find your next local walk.
October 2026
Walkers are welcome on the 1/2 Marathon and 5K starting at Philipstown Recreation Department in Garrison NY, on Hudson Highlands single and double track trails with river views; 5K has no cut off.
Walkers may follow the 3.1 mile course or the shorter 1.7 mile route from Mineola Lake through scenic cemetery paths with lakes and fall foliage. Water stations and restrooms are provided and the course is stroller and dog friendly.
Walkers can take the 5K course starting at 5 Van Wyck Lane in Wappingers Falls, NY. A 1K kids fun run runs alongside the running races and proceeds benefit Blood Cancer United.
November 2026
Walkers can choose 26.2 Miles or 13.1 Miles routes that start and finish at Rockwood Hall in the Rockefeller State Preserve. Routes follow wide groomed carriage roads and trails with no pavement or cars, pass rivers, forests and stone walls,..
Walkers can choose the 5K or Kids 1K at Westchester Community College in Valhalla NY on a campus course; all finishers receive a medal and free finish line photos.
Walkers can enter 10K or Half Marathon at Tarrywile Park Danbury on technical single track near 3K elevation with lake views, aid stations and cupless hydration.
Walkers are welcome on the 13.1 miles trail at Roosevelt Forest, 700 Peters Lane, Stratford CT, consisting of eight 1.64 mile wooded loops on marked singletrack and doubletrack with roots, rocks and rolling hills. Aid station and porta potties ar..
Walkers can choose 10 km or 5 km routes at Westchester Community College in Valhalla, NY, with an untimed 5 km option alongside the running races. Both in person and virtual options are offered.
Walkers follow the 5K road loop starting at Bethel Municipal Center in downtown Bethel, with a moderately uphill first half and a downhill second half on neighborhood streets.
December 2026
The 2 Mile walk begins on the Bethlehem Town Green in front of Memorial Hall and follows the 5K course on rolling country roads, turning back at the one mile mark. Parking is at the Bethlehem Fair Grounds with shuttle buses to the Green, and the..
Walkers can do the 5K from 2900 Purchase Street in Purchase NY alongside the running races; participants receive a shirt, jingle bells and a medal.
Walkers can complete the 5K out and back course starting at 10 Washington Parkway in Stratford along a flat scenic waterfront in the Lordship section. The family friendly route suits all abilities and collects new, unwrapped toy donations at bib..
Walkers can complete the 5K on forest trails at Roosevelt Forest, 700 Peters Lane, Stratford CT, following an off road wooded route that requires a little trail experience. The pavilion is the sole aid station; parking is limited and larger vehic..
February 2027
Walkers may register to walk the scenic 7.8 miles loop around glacial Lake Waramaug, starting and finishing at Hopkins Vineyard with lake shore views. The course is mainly flat with gentle rolling hills and a final 0.2 miles ascent up Hopkins..
March 2027
Walkers have up to 6 hours on the 2.3 miles loop at Roosevelt Forest, Stratford CT, on roots, rocks and rolling hills with a pavilion aid station, lap chip and food.
April 2027
The 4k Jay Walk offers a 4 km non competitive route starting at the John Jay Middle School field that follows the wooded John Jay Community Trail. It skips the first out and back loop, starts after the 5k runners enter the woods, and finishes at..