Events in Woodbury, Connecticut | 2026-2027

4th Annual Sail to the Finish 2M Run [runsignup.com]

Sat, May 02, 2026 at 1:00 PM

Description

The race is to benefit the Quassapaug Sailing Center, a nonprofit organization designed to provide sailing instruction and encourage and promote good fellowship between persons actively interested in...

The race is to benefit the Quassapaug Sailing Center, a nonprofit organization designed to provide sailing instruction and encourage and promote good fellowship between persons actively interested in sailing and water sports. Sails to trails summer camp is operated every summer to encourage sailing and outdoor activities for children. Scholarships are offered for children in need.

Race is an out and back road course starting at the Quassapaug Sailing Center. First mile is downhill, then you run back up the hill (no complaining- it’s not that steep!). No Dogs allowed!

Parking is limited- carpooling is encouraged. Race entries will be limited due to space limitations (likely that the race will sell out- sign up early!).

Awards: Overall Male and female finishers & top three in age groups 19 & under, 20-29, 30-39, 40-49, 50-59, 60-69 & 70 & up.

Race day is international Harry Potter day - come with your best costume and try to win an award.

2 Miles Run Trail

30 W Lake Rd, Woodbury, Connecticut, 06762, United States
OpenStreetMap Google Maps

5K Walk/Jog/Run for Jon [runsignup.com]

Sat, May 23, 2026 at 10:00 AM

Description

As many of you may already know, a valued member of our Nonnewaug school community, Jon Cheung, was recently diagnosed with Leukemia. Just as he always has done in the classroom, on the sports...

As many of you may already know, a valued member of our Nonnewaug school community, Jon Cheung, was recently diagnosed with Leukemia. Just as he always has done in the classroom, on the sports fields, and in life, Jon is giving his all in this fight and the whole community is behind him. Our chapter of the Math Honor Society, of which Jon is a member want to show support and help raise funds to assist with the medical costs that his recover process involves so that him and his family can focus their attention on his health. To that end, we have planned a charity 5K walk/jog/run on Nonnewaug's campus for the 23rd of May. We hope you will show your support by signing up and enjoying a fun race with music, games, food, and more. If you have any questions, please email rrobillard@ctreg14.org or text 860-605-3730.

5k Run Walk

5 Minortown Rd, Woodbury, Connecticut, 06798, United States
OpenStreetMap Google Maps

11th Annual Flanders Field & Forest 5K Trail Run/Walk [runsignup.com]

Fri, Jun 05, 2026 at 6:00 PM

Description

Flanders is excited for its 11th Anniversary Field & Forest 5K Trail Run/Walk on its property in Woodbury, CT. The 5K run/walk is a fun event, which exposes community members to the Flanders Van...

Flanders is excited for its 11th Anniversary Field & Forest 5K Trail Run/Walk on its property in Woodbury, CT. The 5K run/walk is a fun event, which exposes community members to the Flanders Van Vleck Farm & Nature Sanctuary. It promotes health and fitness, capitalizes on the growing interest in trail running/walking, and raises funds to support Flanders' mission to provide opportunities to appreciate nature’s wonders and preserve land, inspiring lifelong learning about our natural world.

Walk/run through the woods and fields of Flanders, officially timed by Fast Track Timing. Celebration after the run includes live music, food trucks, and more!

Register by May 5th to receive a FREE race shirt!

2026 Flanders Field & Forest 5K Trail Course Map

This event is rain or shine; however, Flanders reserves the right to cancel in the event of lightning. We apologize, due to the terrain this event cannot accommodate strollers or pets on the course. Registration fees are non-refundable.

2026 Flanders 5K Race Day Important Information/Instructions

3.1 Miles 5k Run Trail Walk

Woodbury, Connecticut, 06798, United States
OpenStreetMap Google Maps

Quassapaug Sailing Center Open Water Swim [runsignup.com]

Sat, Sep 05, 2026 at 1:00 PM

Description

20th ANNUAL QUASSAPAUG SAILING CENTER OPEN WATER SWIMMING FESTIVAL

Sponsored by and to Benefit the Quassapaug Sailing Center

3 Mile

$40.00 Postmarked before 5/1/26

$45.00 Postmarked before 7/1/26...

20th ANNUAL QUASSAPAUG SAILING CENTER OPEN WATER SWIMMING FESTIVAL

Sponsored by and to Benefit the Quassapaug Sailing Center

3 Mile

$40.00 Postmarked before 5/1/26

$45.00 Postmarked before 7/1/26

$50.00 After 7/1/26

$55.00 Day of Race

Awards Categories:

Male and Female Awards by 10-year age groups 1st, 2nd, 3rd places

5 Mile Swimmers Awards- 1st, 2nd, 3rd Male and Female

Wetsuit Competitors- 35 & Under and 36 & Over- 1st, 2nd, 3rd Male and Female

1 1⁄2 Mile Race

$35.00 Postmarked before 5/1/26

$40.00 Postmarked before 7/1/26

$45.00 After 7/1/26

$50.00 Day of Race

1⁄2 Mile Race

$30.00 Postmarked before 5/1/26

$35.00 Postmarked before 7/1/26

$40.00 After 7/1/26

$45.00 Day of Race

Five Miles of Open Water Swimming Water

Entry Fee for All 3 Races

$80.00 Postmarked before 5/1/26

$90.00 Postmarked before 7/1/26

$95.00 After 7/1/26

100.00 Day of Race

Swimmers will be removed from the water based upon the following time limits:

3 Mile Swim – 2 1⁄2 Hours

1 1⁄2 Mile Swim – 1 1⁄2 Hours

1⁄2 Mile Swim – 1 Hour

Tickets for Post Race Food for Family, Relatives & Friends are on sale for $10.00 and can be Purchased at QSC on Day of Race Only.

1.5 Miles 2 Miles 3 Miles 3.5 Miles 4.5 Miles 5 Miles Open Water Swim

30 W Lake Rd, Woodbury, Connecticut, 06762, United States
OpenStreetMap Google Maps

4 running and walking events in Woodbury, Connecticut

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