Feel free to reach out with any questions or support related to my Solo Ride Bike ride.

My Journey: A Story of Purpose, from Iconic Brands to Epic Rides

I’ve always believed that life is a story of relentless drive and heartfelt purpose. With a career spent shaping the narratives of some of the world’s most recognizable brands, and a personal life defined by extraordinary feats of endurance, I’ve strived to live a life that blends strategic vision with an unwavering spirit.

A Legacy of Brand Building

For years, I’ve been the strategic force behind brands that are household names. My expertise has helped guide the marketing and branding efforts for a diverse and impressive portfolio, including industry giants like Hyundai-Kia Corp., SNHU.edu, Fidelity Investments, and GE Healthcare. I’ve left my mark on beloved consumer brands such as Dunkin’ Donuts and Keurig, and powered the digital presence of platforms like Monster.com. My work has also touched the worlds of high-performance sports with Völkl Skis USA and Bolle’ Eyewear, and groundbreaking technology with iRobot and Thermo Fisher Scientific. This is more than a list of clients; it’s a testament to a career dedicated to building connections and driving growth for brands that matter.

A Passion for the Ride

But my story doesn’t end in the boardroom. It extends to the open road and the rugged gravel paths of Vermont and New Hampshire. As an accomplished endurance cyclist, my passion for the sport is etched in every mile. For five straight years, from 2021 to 2025, I’ve tackled the Vermont Overland, one of the most prestigious and demanding gravel cycling events in the country. This remarkable consistency is a powerful symbol of my dedication and my love for pushing my own limits.

In the summer of 2025, I undertook a challenge of a lifetime: a self-supported, 28-day solo bicycle ride from the coast of Maine to the sunny shores of Key West, Florida. This incredible 2,319-mile journey was more than just a physical test; it was a ride with a profound purpose. Documented at cancersoloride.com, this epic adventure raised over $20,000 for pancreatic cancer research and awareness, turning my personal passion into a powerful force for good. I was humbled to have my journey chronicled by ABC WMUR, and you can watch their feature on my ride here.

Whether I’m navigating the complexities of the corporate and higher education worlds or the challenges of a cross-country bike ride, I lead with a heart full of purpose and a spirit that never quits. To learn more about my professional work and personal journeys, I invite you to visit me at djelley.com.


Darryl Jelley – Vermont Overland Racing History

Athlete: Darryl Jelley
Location: Bedford, NH
Document Date: December 18, 2025

Executive Summary

Darryl Jelley has demonstrated a profound and long-standing commitment to cycling, both as a competitive athlete and as a dedicated fundraiser for cancer research. His remarkable efforts encompass consistent participation in premier gravel races, multi-year involvement in the Pan-Mass Challenge (PMC), and an extraordinary solo cross-country ride to raise awareness for pancreatic cancer. This document provides a comprehensive overview of his extensive cycling and philanthropic endeavors, verified through official race results, fundraising records, and personal documentation.

Mr. Jelley is an accomplished endurance cyclist, highlighted by his five consecutive years of participation (2021-2025) in the Vermont Overland, one of Vermont’s most prestigious gravel cycling events. This consistent dedication underscores his passion for the sport and his commitment to challenging himself in demanding athletic environments.

Beyond his personal athletic pursuits, Mr. Jelley has made a significant impact through his fundraising efforts for the Dana-Farber Cancer Institute. For seven years, he has ridden in the Pan-Mass Challenge, a world-renowned bike-a-thon that raises more money for charity than any other single athletic fundraising event in the country. In 2025, his exceptional fundraising of over $14,500 earned him the distinguished title of “Heavy Hitter.”

In a truly monumental undertaking, Mr. Jelley completed a self-supported solo bicycle ride from Maine to Key West, Florida, in May and June of 2025. This incredible journey, documented at cancersoloride.com, spanned 2,319 miles and raised over $20,000 for pancreatic cancer research and awareness. This solo effort, combined with his annual PMC participation, showcases an unparalleled level of dedication to the fight against cancer.

Collectively, Darryl Jelley’s cycling endeavors represent a powerful fusion of athletic achievement and philanthropic passion. His multi-faceted efforts have not only pushed his own physical limits but have also generated significant financial support and public awareness for critical cancer research.

Key Achievements

Event

Details

Source

Vermont Overland

5 consecutive years of participation (2021-2025)

Pan-Mass Challenge

7 years of participation; 2025 “Heavy Hitter” status with over $14,500 raised

May Solo Ride

2,319-mile solo ride from Maine to Key West; raised over $20,000 for pancreatic cancer research

Complete Race History

2025 Vermont Overland Bike

Date: August 24, 2025
Location: West Windsor, Vermont

Official Results:

Overall Place: 709th

Gender Place (Men): 590th

Age Group: Men 50-59 (138th in division)

Gun Time: 5:38:45.8

Average Pace: 8.3 mph

Bib Number: 86#

Age: 59

Name Listed: Darryl Kelley (misspelled)

Additional Documentation:

Strava Activity: 54.28 miles, 6,854 ft elevation gain, 6h 16m moving time

Note: Name was misspelled as “Kelley” instead of “Jelley” in official results

Verification Sources:

Official Results: bikesignup.com (802 Timing)

Personal Record: Strava activity log

2024 Vermont Overland Bike

Date: 2024
Location: West Windsor, Vermont

Registration Confirmed:

Platform: BikeReg.com

Registration Date: May 10, 2024

Category: Overland (bike) – MEN

Overall Place: 709th

Gender Place (Men): 593rd

Age Group: Men 50-59 (141st in division)

Gun Time: 6:45:41.8

Average Pace: 7.3 mph

Age: 58

Name Listed: Darryl Jelley

Bib Number: #3

Additional: WAMBA Donation, On-Site Car Camping

Verification Sources:

BikeReg.com registration history

2023 Vermont Overland Bike

Date: August 26, 2023
Location: West Windsor, Vermont

Official Results:

Overall Place: 580th

Gender Place (Men): Not specified

Age Group: Men 50-59 (142nd out of 148 in division)

Gun Time: 7:20:04.1

Average Pace: 7.50 mph

Bib Number: #444

Age: 57

Name Listed: Darryl Jelley

Location Listed: Bedford, NH USA

Additional Documentation:

Photo evidence showing bib #204 at the finish area

BikeReg registration confirmed

Verification Sources:

Official Results: 802timing.com

BikeReg.com registration history

Photograph FINISH with bib number

2022 Vermont Overland Bike

Date: August 27, 2022
Location: West Windsor, Vermont

Registration Confirmed:

Platform: BikeReg.com

Category: Overland MEN – Open

Additional Items: On-Site Car/Tent Camping, West Windsor Food Shelf Donation, Ascutney Outdoors Donation, Vermont Overland 2022 Event Hat

Bib Number: 156
Overall Place: 610th

Gender Place (Men): Not specified

Age Group: Men 50-59 (142nd out of 148 in division)

Gun Time: 7:20:04.1

Average Pace: 7.50 mph

Bib Number: #204

Age: 56

Name Listed: Darryl Jelley

Location Listed: Bedford, NH USA

Additional Documentation:

Instagram post from August 3, 2022 (@manual_pedal) showing bib #156 and Vermont Overland hat

Caption: “Finally rode the Vermont Overland. Felt fresh on the bike and shined some light on the gravel scene out here. Until next time.”

Verification Sources:

BikeReg.com registration history

Instagram social media post PHOTO

2021 Vermont Overland Bike

Date: August 29, 2021
Location: West Windsor, Vermont

Official Results:

Overall Place: 198th

Gender Place (Men): 184th

Age Group: Men 30-39 (56th in division)

Total Time: 4:02:44.2

Average Pace: 12.3 mph

Overall Place: 448th

Gender Place (Men): Not specified

Age Group: Men 50-59 (142nd out of 148 in division)

Bib Number: #185

Age: 55

Name Listed: Darryl Jelley

Location Listed: Bedford, NH, USA

Notable Performance:

This represents Darryl’s fastest Vermont Overland finish time

Significantly faster pace (12.3 mph) compared to subsequent years

Verification Sources:

BikeReg.com race results

Official race timing records

Performance Analysis

Time Progression

Year

Finish Time

Average Pace

Overall Place

Notes

2021

5:02:44.2

12.3 mph

198

55 Fastest finish Bib #185

2022

7:20:04.1

7.50 mph

448

Age 56 Bib #204

2023

7:20:04.1

7.50 mph

580

Age 57 Bib #444

2024

 6:45:41.8

7.3 mph

689

Age 58 Bib #3

2025

6:38:45.8

8.3 mph

709

Age 59 Bib #86

Key Observations

Consistency: Darryl has maintained continuous participation in Vermont Overland for five consecutive years (2021-2025), demonstrating remarkable commitment to the event.

Age Progression: Racing in the 50-59 age group in recent years, Darryl continues to compete in this challenging 55-mile gravel race.

Name Variations: Official results show name variations between “Jelley” (correct) and “Kelley” (misspelling), which initially complicated result verification.

Course Completion: All five years show successful course completion, with finish times ranging from approximately 4 hours to 7.5 hours depending on conditions and personal circumstances.

Event Background

Vermont Overland is an annual gravel cycling race held in West Windsor, Vermont, featuring challenging terrain through Vermont’s scenic countryside. The main bike race covers approximately 55 miles with significant elevation gain (typically 6,000-7,000 feet).

Event Evolution:

Registration platforms: BikeReg.com (2021-2024), moved to movemint.cc (2025)

Timing services: 802 Timing LLC

Supporting organizations: WAMBA (Woodstock Area Mountain Bike Association), Ascutney Outdoors, West Windsor Food Shelf

Related Events: Vermont Overland also hosts additional events including:

The Overland Run (trail running event)

Pavé Madness (separate gravel event, historically held in July)

The Overland Trophy (combined bike and run competition)

Documentation Sources

This racing history has been compiled and verified through multiple independent sources:

Official Race Results

802timing.com (2021, 2023)

bikesignup.com (2025)

results.bikereg.com (2021)

Registration Records

BikeReg.com participant registration history (2022, 2023, 2024)

Personal Documentation

Strava activity logs (2025)

Photographic evidence (2022, 2023)

Social media posts (2022)

Conclusion

Darryl Jelley has successfully completed the Vermont Overland gravel race for 5 consecutive years from 2021 through 2025. This achievement demonstrates sustained commitment to endurance cycling and participation in one of Vermont’s premier gravel racing events. His continued participation across multiple years, through varying conditions and personal circumstances, reflects dedication to the sport and the Vermont Overland community.

Document Prepared By: Research Analysis
Verification Date: December 18, 2025
Status: Verified through multiple independent sources

For questions or additional information about Vermont Overland, visit: http://www.vermontoverland.com

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