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Events
5K Kent Pumpkin Run
Kids Fun Run
🎃 ＫＥＮＴ ＰＵＭＰＫＩＮ ＲＵＮ ２０２６ 🎃
50 Years. Thousands of Runners. Countless Costumes. One Incredible Tradition.
For fifty years, runners have gathered in Kent on a crisp autumn morning to celebrate fitness, friendship, community, and fun. What began as a small local race has grown into Kent's largest one-day community event and one of the most beloved fall traditions in Connecticut.
On Sunday, October 25, 2026, join us as we celebrate the 50th Annual Kent Pumpkin Run and write the next chapter in this incredible story.
Whether you're chasing a personal record, competing for a prize, running in costume, or simply soaking in the festive atmosphere, you'll be part of a tradition that has brought generations together.
🏃♀️ 5-Mile Road Race
🕛 Race Starts Promptly at Noon
🎭 Award-Winning Costume Contest
💰 Cash Prizes for Overall Winners
🏅 Age Group Awards
👧🧒 Kids Fun Run at 11AM
🍂 Beautiful Fall Scenery
❤️ A Celebration of Community
From superheroes and pumpkins to pirates and princesses, costumes have become just as famous as the race itself. So gather your friends, put together your best costume, and join hundreds of runners as they take on one of Connecticut's most scenic courses.
Online registration remains open until race time at noon on Sunday, October 25, 2026.
After the race, spend the afternoon enjoying Kent's unique shops, restaurants, galleries, and small-town charm.
The Kent Pumpkin Run is proudly organized by the Kent Chamber of Commerce and hosted by the Kent Green Shopping Center.
A heartfelt thank you to our volunteers, sponsors, local businesses, and runners. Because of your support, this tradition has thrived for 50 years.
🎃 Run the Course.
🎃 Wear the Costume.
🎃 Celebrate the Tradition.
🎃 Celebrate 50 Years.
Contact Form
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50th Kent Pumpkin Run
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Kent Green
41 Kent Green Blvd
Kent, CT 06757 US
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The Story of the Kent Pumpkin Run
In the fall of 1977, a small group of runners gathered in Kent for what would become one of Connecticut's most enduring and beloved traditions. Nearly five decades later, the Kent Pumpkin Run has grown from a local road race into Kent's largest annual community event, welcoming thousands of runners, families, volunteers, and spectators through the years.
Held each autumn against the backdrop of the spectacular Litchfield Hills, the five-mile course has become legendary. Beginning in the heart of Kent, runners wind through the rolling countryside along Cobble Road, Segar Mountain Road, and South Kent Road before returning to a cheering crowd at the finish line. The challenging hills, stunning scenery, and small-town atmosphere have made the Pumpkin Run a favorite among generations of runners.
Along the way, the race developed a personality all its own. What started as a competitive road race evolved into a celebration of community, costumes, and fall fun. Pirates, pumpkins, superheroes, skeletons, and countless creative characters have crossed the finish line alongside elite athletes and first-time runners alike. The result is a race unlike any other in New England.
Over the years, traditions have come and gone, but the spirit of the Pumpkin Run has remained the same. The blast of the traditional starting cannon, the laughter of costumed runners, the excitement of the Kids Fun Run, and the dedication of hundreds of volunteers have become part of the fabric of Kent.
The Kent Pumpkin Run has weathered changing times, welcomed new generations, and created memories for thousands of participants. For many families, it has become an annual reunion and a cherished part of the Halloween season.
As we celebrate the 50th Anniversary in 2026, we honor everyone who has made the Pumpkin Run possible since 1977 — the runners, volunteers, sponsors, local businesses, community organizations, and spectators who have helped transform a small-town road race into a Kent tradition.
For fifty years, the Kent Pumpkin Run has been more than a race.
It has been a celebration of community.
And the next chapter starts this October.
50 Years. Thousands of Runners. Countless Costumes.
One Incredible Tradition.
Running for Robby
This year, the Kent Pumpkin Run is proud to support the Robby Kennedy Fund, helping continue the legacy of one of Kent's most beloved community members.
Known to many as the unofficial "Mayor of Kent," Robby Kennedy was a familiar face throughout town, always ready with a smile, a wave, a kind word, or a helping hand. Whether riding his bicycle through town, volunteering with local youth programs, supporting the Kent Volunteer Fire Department, or simply brightening someone's day, Robby embodied the spirit of kindness, generosity, and community.
In honor of Robby's remarkable legacy, 20% of all Kent Pumpkin Run ticket proceeds will be donated to the Robby Kennedy Fund to help support the construction of a new community shelter project in his memory. This shelter will serve as a lasting tribute to the kindness, warmth, and community spirit that Robby shared with everyone he met.
The Town of Kent recently proclaimed May 9 as "Be Kind Day" in honor of Robby Kennedy, recognizing the lasting impact his compassion and generosity had on our community.
As we celebrate the 50th Annual Kent Pumpkin Run, we invite runners, walkers, volunteers, and supporters to join us in honoring Robby's memory. Every registration helps ensure that his legacy of kindness continues to inspire future generations.
Run for the tradition. Run for the community. Run for Robby.
