Brewster
Walking Events Calendar near Brewster 2026-2027
Monthly updates for Brewster
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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.
July 2026
Walkers can choose 3.1 Miles or 8 Miles routes starting on New Milford Town Green. The course follows scenic rural roads with rolling hills including Canterbury Hill, provides water stops, and welcomes walkers and dogs.
Walkers have an untimed 1 mile Holiday Stroll from 10 Washington Pkwy, Stratford, through the scenic, mostly flat Lordship seaside neighborhood. Roads are open so walkers should stay left facing traffic, parking may fill and water tables may not..
An untimed 1 mile walk around scenic & tranquil Twin Brooks Park on an easy course. The walk starts at the same place as the 5K run, has a $30 online registration fee and no paper or cash entries on the day.
August 2026
Walkers can take part in a 5K health walk that starts at Holy Trinity Orthodox Church on Joe's Hill Rd in Danbury, CT, alongside the running races. Race day registration and check in are at the church and pre registered walkers may receive a T sh..
Walkers can choose the untimed 1 Mile walk or walk the 3.1 Miles 5K course at Seaside Park in Bridgeport, CT. The 1 Mile is untimed, strollers are welcome, shirts are included for 1 Mile and 5K registrants and advance registration is required..
Walkers can join a 90 minute indoor walk and stair climb at Sacred Heart University Martire Family Arena around the ice rink. Each lap is 0.20 miles with about 80 stairs and 450 steps; a one week virtual 40,000 steps challenge is at participa..
Walkers use a certified 5k (3.1 Miles) course starting at Pent Rd Recreational Complex in Beacon Falls. Entry fees are $25 for adults and $10 for 16 and under, and the walk takes place alongside the running races.
Walkers can choose a 1.5 Miles route or tackle the 5K course starting and finishing at Millbrook Vineyards & Winery, across mostly grass cross country terrain with some mildly challenging sections. Registration includes a post walk pour of wi..
The event offers a 5K walk starting at The Amber Room Colonnade in Danbury, with a scenic route across the Amber Room grounds. Walkers join alongside the running race and can enjoy a post race barbecue and refreshments on site.
Walkers can take part in the 5K run walk through Mill River Park in Stamford, CT, on a park course. Medals are handed out to in person finishers, T shirts are subject to availability after July 17, and the event is rain or shine.
Walkers can join the 5K walk on a scenic, flat course starting at 6 Youngs Field Rd, New Milford CT, alongside the running races. The route includes a hydration station and post race refreshments, and registration is free.
September 2026
Walkers follow a 2 Miles route from downtown Ossining on Main Street north along the scenic Old Croton Aqueduct Trail, alongside the 5K, with a $35 registration fee.
Walk the 5K course at FDR State Park Lot 1, 2957 Crompond Road in Yorktown Heights in a park setting alongside the running races. Race day registration is available and festivities include vendors, food trucks, live music and pet adoptions.
Walkers can join the certified 5K course at Fairfield Hills, 3 Primrose St, Newtown, CT, on event day. Entry is $30 plus three canned goods for the main walk and $5 plus three canned goods for the kids walk, held alongside the running races.
12K, 25K and 50K walks at Macedonia Brook State Park on single track forest trails with steep climbs and views; aid stations supply water, snacks; walkers carry own cup.
Walkers can complete a 5K in person at St Francis Episcopal Church, 2810 Long Ridge Rd, Stamford CT, on a USATF certified course with canine companions welcome. A virtual 5K is available Sept 14 to 20 for remote participation.