Grin 'N Bear It: Brewster 5K

More races nearby

• TriRidgefield Sprint Triathlon and Duathlon [runsignup.com]

  Sun, May 31, 2026 at 7:00 AM

  Description

  ▼ Show more Show less

  We are pleased to present TriRidgefield and DuRidgefield. First held in 2007, the races wind their way through the bucolic countryside of Ridgefield, Connecticut. There will be a Sprint Triathlon,...

  We are pleased to present TriRidgefield and DuRidgefield. First held in 2007, the races wind their way through the bucolic countryside of Ridgefield, Connecticut. There will be a Sprint Triathlon, consisting of a half-mile swim in pristine Great Pond, a rolling 13-mile bike ride, and a challenging 5K finishing run. For you non-swimmers, we will also have a Sprint Duathlon held concurrently with the Tri, consisting of a 2-mile run, followed by the same 13-mile bike ride, and finishing 5K run.

  NOTE: For registrations received after May 1, we cannot guarantee you will receive a shirt.

  17.6 km from Village of Brewster
  19 Great Pond Road, Ridgefield, Connecticut, 06877, United States
  OpenStreetMap Google Maps

  Duathlon Run Sprint Swim Triathlon

• Run the Race 5K [runsignup.com]

  Sat, Jun 06, 2026 at 10:00 AM

  Description

  ▼ Show more Show less

  AOC Run The Race 5K

  Starts at Rogers Park, Danbury, CT

  Race Time 10am

  T shirt for the first 100 runners Awards:

  First, second and third place men and women

  Pre registration $35 dollars | Race day...

  AOC Run The Race 5K

  Starts at Rogers Park, Danbury, CT

  Race Time 10am

  T shirt for the first 100 runners Awards:

  First, second and third place men and women

  Pre registration $35 dollars | Race day registration $40 dollars

  Refreshment will be serve after the race (Provided by: Elmer's Diner), fruits, water and more.

  For more information contact Jon L. [email protected]

  Athletes of Christ: Supporting youth scholarships for AOC Soccer and Basketball programs.

  13.6 km from Village of Brewster
  Danbury, Connecticut, 06810, United States
  OpenStreetMap Google Maps

  5k Run

• TRI the PARK [runsignup.com]

  Sun, Jun 07, 2026 at 8:00 AM

  Description

  ▼ Show more Show less

  Date: Sunday, June 7th, 2026 at 8:00am

  Join us for TRI the PARK at Bedford Hills Memorial Park, a youth triathlon designed for fun, challenge, and community spirit! Participants will compete in a...

  Date: Sunday, June 7th, 2026 at 8:00am

  Join us for TRI the PARK at Bedford Hills Memorial Park, a youth triathlon designed for fun, challenge, and community spirit! Participants will compete in a POOL swim, followed by a park bike and run. Whether your athlete is tackling the long course or giving the short course a go, it’s a great way to race into summer.

  The entire race should take athletes anywhere from 10 to 30 minutes as it is a beginner course, and each participant will receive a finisher’s medal!

  Long Course: 100m swim, 2mi bike, 0.50mi run

  Short Course: 50m swim, 1mi bike, 0.25mi run

  Participants can compete in either distance race and must be between the ages of 6-16.

  Register by noon on May 10th to guarantee your event T-shirt! After that, shirts will be available on a first come, first served basis while supplies last. Registration closes on May 31st.

  23.5 km from Village of Brewster
  60 Haines Road, Town of Bedford, New York, 10507, United States
  OpenStreetMap Google Maps

  Run Swim Triathlon

• Brookfield Lions Strides to Cure Diabetes 5-Miler [greystoneracing.net] [Register at runsignup.com]

  Sun, Jun 07, 2026 at 9:00 AM

  Description

  RACE DAY REGISTRATION IS AVAILABLE ONSITE STARTING AT 7:30 A.M.

  The Brookfield Lions Club is proud to once again sponsor this event to promote diabetes awareness and research. Bring the whole family to participate in this flat, fast and scenic 5-mile run, and generously support this charitable fundraising event.

  17.6 km from Village of Brewster
  Brookfield, Connecticut, 06804, United States
  OpenStreetMap Google Maps

  5 Miles Run

• Hat City Dash [runsignup.com]

  Sun, Jun 07, 2026 at 9:30 AM

  Description

  ▼ Show more Show less

  This race will start and finish on Kenosia Avenue. Runners will begin the race heading northbound until they reach Christopher Columbus Avenue. From there, runners will continue around the cul-de-sac...

  This race will start and finish on Kenosia Avenue. Runners will begin the race heading northbound until they reach Christopher Columbus Avenue. From there, runners will continue around the cul-de-sac and head back towards the start/finish line. The course is flat and will have a hydration table set up around the halfway point. There will be a post race party and awards at Elicit Brewery following the race.

  Every dollar raised from this race will go toward supporting an officer’s child’s higher education fund. At the end of the event, a recipient will be randomly chosen by an independent third party.

  A free beer from Elicit Brewing will be given to any runner age 21+, with valid proof of sign up.

  There will be plenty of parking available on race day at the Elicit Brewery lot, located at 15 Backus Avenue.

  Early bib pickup will be available on Saturday, June 6th at Elicit Brewery

  12.4 km from Village of Brewster
  15 Backus Avenue, Danbury, Connecticut, 06810, United States
  OpenStreetMap Google Maps

  3.1 Miles Run