Participate in the Tom Simpson Cycling Festival in the U.K. and Choose Between Two Events or Ride Them Both

Have you been looking for a reason to get over to the U.K. and do some cycling while immersing yourself in English culture? Then the Tom Simpson Cycling Festival might just be that reason. This will be the second time this event will be held, with the inaugural event occurring in 2025.

Sponsored and supported by Cycling Legends, a U.K. magazine and media outlet that celebrates the riders and events in cycling’s long history, the festival is a eight day event (from 6th of Septembet to the 13th of September) that includes two rides in England’s East Midlands along with a six day community event that explores Simpson’s association with the area and his time as a pro cyclist during the 1950s and 1960s.

Who Was Tom Simpson?

Tom Simpson is considered one of England’s most successful professional pro cyclists. He won races such as Milan-San Remo, the Giro di Lombardia, two stages of the Vuelta a España, and Paris-Nice. Unfortunately, at 29, Simpson died on the 13th stage of the 1967 Tour de France. Supposedly, his death was due to heat exhaustion.

Cycling Festival Rides: The Simpson Sportive

In addition to the community events, the festival features two cycling events. The first, which begins the festival, is known simply as the Simpson Sportive with three distances: 63 kilometers (39 miles), 100 kilometers (62 miles), and 161 kilometers (100 miles).

According to the Cycling Legends website, each route “… explores the quiet, scenic roads of North Nottinghamshire, Lincolnshire and South Yorkshire – many of which were part of Tom’s training ground growing up.” The cost to ride the event is 20 pounds (around $30) for the 63 kilometer ride and goes up a little bit from there for each route. The sportive takes place on September 6th, 2026.

Your entry for the event includes the following:

• Exclusive Tom Simpson Cycling Festival Musette – filled with a race brochure full of historical stories, and goodies from our sponsors
• Feed Zones (one for 63km and 100km, 2 for 161km) with complimentary food and drink
• Event photography – images without watermark available for purchase after the event
• Fully signed route, finishers medal and free parking
• Broom wagon and mechanical support
• Supports the Tom Simpson Memorial Fund

Cycling Festival Rides: The Simpson Retro for Pre 1995 Bikes

The second cycling event, which takes place on the last day of the festival, is called The Simpson Retro. Whereas the Simpson Sportive is more of a traditional event ride open to everyone on any kind of bike, the Simpson Retro is for riders with bikes built before 1995.

Along with the ride itself, Cycling Legends sponsors a “Best in Show Competition.” The winner receives a trophy to be kept for one year. Second and third place winners receive trophies that they can keep. Fourth to sixth place winners receive medals.

There are also awards for “Best Original Bike” for pre 1995 bikes in the best original condition. Lastly, the “Best Team” celebrates a group of four riders who have the same bike and are wearing identical team kits. A trophy is also awarded to the volunteer of the year called the Paul Edmonds Trophy for helping to organize the cycling festival.

The Simpson Retro has two routes. The first route is 63 kilometers (39 miles) and is called the “Chemin de Simpson.”The second route is the “La Grande Classique” and is 83 kilometers (51 miles).

Included with your entry to the Simpson Retro:

• Exclusive Tom Simpson Cycling Festival Musette – filled with a race brochure full of historical stories, and goodies from our sponsors

• A Feed Zone (Sunday ride) with complimentary food and drink

• Event photography – images without watermark available for purchase after the event

• Fully signed route, and free parking

• Supports the Tom Simpson Memorial Fund

• Entry to the Best in Show Competition

The cost to participate in the Simpson Retro is 36 pounds ($48.00), which also enters your bike in the “Best in Show” competition. Participants in the festival can also buy a weekend ticket for 100 pounds that includes the Simpson Retro as well as, what the organizers state, are “… engaging talks, vibrant social events, and the ever-popular retro bike ride along the same roads Tom Simpson once trained on.”

Last Thoughts

The Tom Simpson Cycling Festival sounds like a fun way to explore the U.K. via bike rides and weeklong events to celebrate the region where Simpson grew up and trained for races. The cost for the festival and rides seems very affordable for all that is included.

So, I’d say book some tickets, book a flight, and plan for an adventure in early September later this year. And if you have a pre-1995 bike, pack that up and bring it along. You might just win the “Best in Show.”