3 running, swimming, and triathlon events in Dover, Massachusetts

From big races to Saturday morning group runs—find running, swimming, and triathlon events and connect with the local endurance sports community.

• Powisset Farm Trail Run - Spring [barntorun.com] [Register at runsignup.com]
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  Mon, May 25, 2026 at 8:00 AM

  Description

  The Powisset (pronounced “po-wiss-it”) Farm Trail Run is part of the Barn to Run Trail Race Series and the spring edition of this event takes place Memorial Day, Monday, May 26, 2025 at Powisset Farm in Dover, MA. The event includes running the trails of Powisset Farm and neighboring Noanet Woodlands and offers 4 race distances to choose from — 8.6, 5.6, 3.1 and 1.5 miles.

  1.5 Miles 3.1 Miles 5.6 Miles 8.6 Miles Run Trail

  37 Powisset Street, Dover, Massachusetts, 02030, United States
  OpenStreetMap Google Maps
• Dover Sherborn Boosters Triathlon [runsignup.com]
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  Sun, Sep 13, 2026 at 8:00 AM

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  The 19th Dover Sherborn Boosters Triathlon is back for 2026! The organizers of this race are honored to be your beloved September sprint distance triathlon and looking forward to seeing everyone on...

  The 19th Dover Sherborn Boosters Triathlon is back for 2026! The organizers of this race are honored to be your beloved September sprint distance triathlon and looking forward to seeing everyone on Sunday, September 13th, 2026 @ 8am.

  2026 Course Map: For a detailed course map click here

  2026 Run Route: Map My Run Run Route here

  2026 Bike Route: Map My Run Bike Route here

  2026 Athletes Guide: Click here

  Want to volunteer? Student and adult volunteer sign ups below!

  • Student volunteer sign up here

  • Adult volunteer sign up here

  The Dover Sherborn Boosters Triathlon offers:

  1. Swim: .25 mile swim at Farm Pond, an immaculate and crystal clear kettle pond.

  2. Bike: 14.3 mile bike through the hills and backcountry, sought after by cyclists from all over the state.

  3. Run: 3.4 mile run through the challenging yet welcoming backroads of Sherborn and Dover.

  For those new to the race and for our valued alumni please see below on what makes this Triathlon so special:

  1. The cleanest fresh water, rolling swim start within 20 miles of downtown Boston

  2. A well designed, double transition style course that winds through the scenic roads and farms of Dover and Sherborn and finishes Olympic stadium style at Dover-Sherborn High School

  3. The best post race Breakfast Brunch Buffet this side of the Rocky Mountains - sponsored by a huge outpouring of support from local merchants

  4. A community organized, volunteer driven event developed to benefit the Dover-Sherborn Boosters - a non-profit focused on providing quality athletic experiences for our children while promoting health and exercise

  DS Boosters Triathlon past years photos: Click here

  DS Boosters Triathlon results: Click here

  Swim Triathlon

  Farm Street, Dover, Massachusetts, 02030, United States
  OpenStreetMap Google Maps
• Powisset Farm Trail Run - Fall [barntorun.com] [Register at runsignup.com]
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  Sun, Oct 25, 2026 at 8:00 AM

  Description

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  The Powisset (pronounced “po-wiss-it”) Farm Trail Run is part of the Barn to Run Trail Race Series and the fall edition of this event takes place Sunday, October 25, 2026 at Powisset Farm in Dover,...

  The Powisset (pronounced “po-wiss-it”) Farm Trail Run is part of the Barn to Run Trail Race Series and the fall edition of this event takes place Sunday, October 25, 2026 at Powisset Farm in Dover, MA. The event includes running the trails of Powisset Farm and neighboring Noanet Woodlands and offers 4 race distances to choose from — 8.6, 5.6, 3.1 and 1.5 miles. This is a popular event with experienced and novice trail runners alike.

  Come for the race... stay for the cider donuts! Post-race cider donuts are a staple of the fall races in the Barn to Run series. Bring the kids to see the animals, free pumpkin painting and to see all the farm has to offer!

  Run.com ranked the Powisset Farm Trail Run one of the Top 12 Runs for Fall Color in 2025. Read about it here.

  1.5 Miles 3.1 Miles 5.6 Miles 8.3 Miles Run Trail

  37 Powisset Street, Dover, Massachusetts, 02030, United States
  OpenStreetMap Google Maps