2nd Annual Brewster Grin ‘N Bear It 5K and 1 Mile Fun Run 2026 — Brewster, NY

Date
October 24, 2026
Location
Brewster, NY
Venue
20 Farm to Market Road
Start Time
10:00 AM
Entry Fee
$17.92 – $40.00
Events
5K Run, 1 Mile Fun Run
Includes
T-Shirt
Register NowRegistration Open

The Brewster Grin 'N Bear It 5K starts at 10:00 AM, giving you a reasonable morning window if you're traveling in from nearby areas. The race takes place on October 24, 2026, at 20 Farm to Market Road in Brewster, New York. Entry fees range from $17.92 to $40.00 depending on registration timing and options. This second annual event offers a 5K distance for runners looking for a straightforward road race experience in the Hudson Valley region. With a moderate entry price and mid-morning start time, it's an accessible option for local and regional runners planning a fall race weekend.

From the Race Organizer
Join us for the Second Annual Brewster Teachers' Association 5K and inaugural 1 Mile Fun Run! This is a community event designed for runners and walkers of all ages and abilities! Set at our very own C.V. Starr Intermediate School, this 5-kilometer race will take you through the heart of our Brewster community and school district! It will offer both a challenge and enjoyable experience for participants. Whether you're an experienced runner looking to set a new personal record or just want to enjoy a fun, active day outdoors, this event is perfect for you! All proceeds will be used to add to our BTA Scholarships through the Brewster Education Foundation! Shirts are guaranteed for the first 200 participants!

Hotels Near This Race

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2nd Annual Brewster Grin ‘N Bear It 5K and 1 Mile Fun Run 2026 — Brewster, NY

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Race Travel Insurance

Don't forget travel insurance for October 24.

You've trained for months and booked a trip to Brewster, NY. A pre-race injury, a delayed flight, or a family emergency can derail the whole thing. Travel insurance can help cover your race entry fee, hotel, and flights if you can't make it, and may cover medical costs if something goes wrong on the course. Plans typically only run 5-7% of your total trip cost — and running events are covered under standard plans with no additional coverage needed.

  • Trip cancellation up to 100% of prepaid costs
  • Running events covered under standard plans — no add-ons needed
  • Trip interruption up to 150% of non-refundable costs
  • Emergency medical up to $250,000
  • Cancel For Any Reason add-on available
  • 24/7 real-time support
Get a Quote — Faye Travel Insurance

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Frequently Asked Questions

When is 2nd Annual Brewster Grin ‘N Bear It 5K and 1 Mile Fun Run 2026 — Brewster, NY?

2nd Annual Brewster Grin ‘N Bear It 5K and 1 Mile Fun Run 2026 — Brewster, NY takes place on October 24, 2026. The race is held in Brewster, New York.

Where is 2nd Annual Brewster Grin ‘N Bear It 5K and 1 Mile Fun Run 2026 — Brewster, NY held?

2nd Annual Brewster Grin ‘N Bear It 5K and 1 Mile Fun Run 2026 — Brewster, NY is held at 20 Farm to Market Road in Brewster, New York.

Where can I find hotels near 2nd Annual Brewster Grin ‘N Bear It 5K and 1 Mile Fun Run 2026 — Brewster, NY?

RaceHotelFinder shows hotels sorted by distance from the race venue in Brewster. Use the map or list view on this page to compare options and book race weekend accommodation.