ENTERPRISES

Cycling, The Series+

October 24th & 25th, 2026

Cotuit, MA
Cycling the Series+ will comprise three different events on the weekend it is put on. The events will be a road event, 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 bands), food from local restaurants, either catered or at the restaurant. 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. For details of the after parties each day, see the description of the days below.

Event Details

Road event (Challenge)-October 25th, 2026

The road event will be approximately a 46 mile event. The event will be comprised of three different divisions: the divisions will be comprised of 75 riders each. Division 1-riders who can ride 22 mph +; Division 2, riders who can ride 18-21 mph; Division 3, riders who can ride 15-17 mph. The ride will be approximately 46 miles. The riders will have to ride the complete distance without ever stopping. 


There will be a police escort for each of the divisions with 6-8 motorcycle police escorting the division around the course. 


We will have a medical van or EMT vehicle accompanying each division, along with Medical and PT personnel at the start and finish.


There will also be KOM’S/QOM’S throughout the course. There will be 4 for each road ride (race). The riders with the lowest combine times in the KOM's/QOM's in each division (5 deep, male and female) will receive a prize, 


The riders will all have to subscribe to Strava and record their times for each of the KOM’s/QOM’s on Strava. 


Special drawing: Every participant in the Road Event (Challenge)will be entered into a drawing for a Canondale Super Evo, value $5,500.00.


The road event will have three beneficiaries, the Youth Athletic Foundation, Real Eyes Truth, and the Barnstable Land Trust. The event will donate $50.00 per rider to the beneficiaries. The monies will be split between the beneficiaries equally. The monies to donate to the beneficiaries will come from either the rider fees or from sponsorships. There will not be any required fundraising, however, there will be a fundraising option for the riders.


Map: https://ridewithgps.com/routes/53720153


Swag: Every Road Event (Racer) rider will receive a cycling jersey worth approximately $85.00


After Party: There will be food Catered by Kidd's Hill Kitchen/Courtside Cafe, Music by a local band (to be named), and beer and wine provided by Barnstable Brewing. Each participant and volunteer will receive coupons worth $30.00 to be used as they choose at the after party. 



Gravel Event-October 24th, 2026

A ride through the trails and woodlands of Mashpee, Massachusetts. 


There will be three different divisions of the Gravel Ride ? miles, ? miles, ? miles. The course will be a loop course. The longer distances will ride the course multiple times, i.e ……………..


This is a ride not a race.


The starts and finishes for each course will be at the same spot.


There will be a Hydration and Nutrition stop at the midpoint of the loop.


There will be SAG Cyclists on e-bikes patrolling the course in case a cyclist needs assistance. We will have medial and PT personnel available to assist riders on the course, stationed at the Hydration and Nutrition stop and also at the Start/Finish. 


A special drawing: Every participant in the Gravel Ride will be entered into a drawing for a ____________ frame.



The Relentless Run & Ruck Challenge-October 24th, 2026

The Relentless Run and Challenge is a timed competitive-style endurance event built for runners and ruck athletes. 


You can choose to run it normally (no weight) or ruck style with weight. 


Either way you're on the same trail course, pushing yourself and getting after it!! 


Course Format and Event Options: 

The Course: One, approximately 5K loop on trails.
 

Event Options: 

5K: One loop. Great for first timers, fast runners, or anyone who wants to send it.

10k: Two loops. The sweet spot- competitive, challenging, and super doable.


Relentless 6-Hour Endurance Challenge: Complete as many 5K loops as possible in 6 hours. This is the long game option: pacing, grit, and staying disciplined when it gets hard. Perfect for anyone who wants to test themself at a longer time domain/distance.


Divisions (All Distances) 

Choose a division when you register: 

Run: Run it like a normal 5K, 10K, or 6 Hour Race. No weight, just run. 


Ruck: 30lb (Men)/ 20lb (Women) 

All Ruck weights are dry weight and do not include water. See additional details below.


Scoring and Results: 

  • 5K/10K: Ranked by fastest finish time 
  • 6-Hour Endurance Challenge: Ranked by total distance completed. Tie breaker: final fastest complete loop


Awards/categories will be finalized based on participation 


Ruck Standards & Rules (Weighted Divisions)

Mandatory ruck weigh-in will take place before the start and at the finish line.


Weight Rules & Approved Ruck Set Up
  • Required ruck weight must be non-consumable and non-wearableNo food, water, or clothing used as required weight
  • You can carry extra supplies (food, water, layers, etc.) Just know this counts as additional weight on top of the required division weight
  • Required weight must be carried on your back as a traditional ruck. Any backpack/ruck is acceptable. Plate carriers are NOT allowed
  • No sling bags or duffel bags
  • No trekking poles allowed
  • If you have questions about your ruck set up, email katie@stay-relentless.com

Who This Is For

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.


Non-Profit Donations: Cycling, the Series will donate funds from each of the events to the non profit Heroes in Transition


For the Road event (race) $50.00 from the registration fee will be paid to a pool of funds that will be shared by three different non-profits (Beneficiaries)on an equal basis.


Beneficiaries: Road event (race) - Youth Athletic Foundation, Real Eyes Truth, Inc


For the Gravel event ? From the registration fee will be donated to the non-profit(s) associated with this particular event on an equal basis.


Beneficiaries: Gravel event - 


For the Ruck/Running event ? From the registration fee will be donated to Heroes in Transition


Sponsors