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Outsider Endurance Triathlons

A multi-sport & adventure racing company

Outsider Events

Outsider Endurance offers an event for every multi-sport athlete. We encourage you to browse our events below and find one that fits your goals. 

July 21, 2024

New Englands most beginner-friendly triathlon.

June 15, 2024

New England’s favorite half distance triathlon! 

August 25, 2024

Now 22 years strong, offering sprint and olympic distance multisport races

Cranberry Trifest

September 7, 2024

A late season multisport event offering sprint and half distance races.

Pilgrimman Triathlon
Patriot Half Triathlon
Whaling City Triathlon
Clutch Rescue

September 15, 2024

A brand new adventure triathlon. Details and registration are coming soon. 

2024 Official Charity Partner

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About Big Brothers Big Sisters of Eastern Massachusetts
Big Brothers Big Sisters of Eastern Massachusetts is as an innovative, energetic organization that is making a real difference in the lives of nearly 4,000 youth annually by providing them with an invested, caring adult mentor in long-term, professionally supported relationships. With research and proven outcomes at its core, Big Brothers Big Sisters of Eastern Massachusetts is working to defend the potential of children facing adversity and ensure every child has the support from caring adults that they need for healthy development and success in life. The organization’s vision is to inspire, engage and transform communities in Eastern Massachusetts by helping youth achieve their full potential, contributing to healthier families, better schools, more confident futures and stronger communities. Throughout its 75 years, the largest Big Brothers Big Sisters affiliate in New England has created and served more than 25,000 youth. For more information about the agency and its mission, visit
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About Outsider Endurance

Jeff & Kristin Smith

Outsider Endurance is an athlete-first event production company, founded by Jeff & Kristin Smith. Our focus is to provide a series of multi-sport and adventure races that prove to be safe, challenging and rewarding. Outsider Endurance was founded to promote a year-round lifestyle obsessed with all things outside.

Outsider Endurance Triathlons
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