A weekend of cycling, running, rucking, and supporting local non-profits, ending with a festival of music, food, fun, and community!
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Cycling the Series+ will comprise three different events on the weekend it is put on (October 24th and 25th) The events will be a road challenge, dirt division {gravel}, event. and ruck/running event. Each event will have different categories. The road event will be a challenge with timed KOM's/QOM's.
The weekend will be a festival. There will be music (local band), food from local restaurants, catered . drawings for great prizes, all participants will have a chance to win prizes, just by participating. You do have to be present at the drawing to win. THE PARTY IS ON THE 25TH AFTER THE ROAD CHALLENGE
For details of the after party each day, see the description of the days below.
Relentless Run & Ruck Challenge is a timed, competitive-style endurance event built for runners and ruck athletes.Choose to run it normally (no weight) or take on the course ruck-style with weight. Either way, you're on the same trail course, pushing yourself and getting after it!
One approximately 5K loop on trails.
Awards/categories will be finalized based on participation
Mandatory ruck weigh-in will take place before the start and at the finish line.
The Relentless Run & Ruck Challenge is for runners who want a simple, timed event, ruck athletes who want a legit course and standards, and anyone who wants to push themselves and have some fun.
Whether you’re chasing a time, carrying weight, or just here to test yourself - this challenge is for you.
All fitness levels are welcome - come push yourself and see what you’re capable of.
For each participant of the Relentless Run & Ruck Challenge $20.00 will be donated to to Heroes in Transition thanks to our community impact sponsor Alquist 3D.
The ride starts at 10am and will start and finish at Sandy Pond in Yarmouth.
View the Dirt Division course on Ride with GPS
A hydration and nutrition stop will be available near the midpoint of the route. SAG cyclists on e-bikes will patrol the course to assist riders as needed. Medical and physical therapy personnel will also be available along the course, at the hydration and nutrition stop, and at the start/finish area.
Every participant in the Dirt Division Gravel Ride will automatically be entered into a drawing for a Pinarello Gravel Bike.
The Dirt Division will award a $1,000 scholarship to a Cape Cod student who will be attending college beginning in the fall of 2027.
Additional scholarship details will be announced.
The Road Challenge is an approximately 41-mile cycling event featuring three divisions based on riding pace. Each division will be limited to 100 riders.
Riders must complete the full course without stopping and should carry sufficient hydration and nutrition with them on their bikes.
Each division will be accompanied by a medical van or EMT vehicle. Medical and physical therapy personnel will also be available at the start and finish.
The course will feature four King of the Mountain (KOM) and Queen of the Mountain (QOM) segments for each division.
Riders will be ranked based on their lowest combined time across the four segments. Prizes will be awarded five deep to both male and female riders in each division.
All riders participating in the KOM/QOM competition must use Strava to record their segment times.
View the Road Challenge course on Ride with GPS
Every participant in the Road Challenge will automatically be entered into a drawing for a Pinarello X.
The Road Challenge will support four beneficiaries:
$40 per rider will be donated, with the proceeds divided equally among the four beneficiaries. Donations will be funded through rider registration fees and event sponsorships.
There is no required fundraising for participants, although riders will have the option to raise additional funds if they choose.
Every rider will receive an event T-shirt. Participants will also have the opportunity to purchase an event cycling jersey for $50, discounted from its $80 retail price.
After the ride, participants and volunteers are invited to stick around for the after party, featuring:
Each participant and volunteer with receive $30 in coupons to use are they choose at the after party.
Stay at the Irish Village Aiden by Best Western for just $122.10 nightly, October 23–25. Reservation code emailed after registration. Book by September 30, limited availability.
All 2027 college-bound entrants are eligible for a $1,000 scholarship drawing. Four event organizers will select the winner. Requirements arrive with your registration confirmation email before the drawing.
The following local non-profits will directly benefit from your participation. Thank you!
Katie Ward, coach and multi-sport athlete, created the Relentless Run & Ruck Challenge to inspire confidence, resilience, and growth through challenge
KB is a former sub-four-minute miler turned elite cyclist, holding numerous Strava records and helping lead Cycling the Series+, inspiring others to achieve their best.
Tim, co-founder of Bike Zone, turned a BMX-focused shop into Cape Cod’s premier cycling retailer and has helped launch and support leading regional cycling events.
Pat has spent 54 years building businesses, banks, and sporting events. Nearing 80, he remains passionate about creating premier cycling events on Cape Cod.
