Three Counties Cycle Challenge for Middlesex 2031

We are delighted to announce the return of this year’s Three Counties Cycling Event, taking place on Sunday 28th June 2026 - and you’re invited to be part of it. This year’s event is being organised as a joint effort of the Middlesex 2031 Festival and the Middlesex Masonic Sports Association (MMSA), bringing together fellowship, fitness, and fundraising in a spirit of friendly challenge.

Three Counties Cycle Challenge for Middlesex 2031

Come and join us for an incredible ride through the natural, wooded splendour of our beautiful countryside, crossing three counties on two wheels. Whether you’re a seasoned cyclist or just starting out, there’s a route designed for you.

Starting and finishing in the stunning grounds of the Royal Masonic School for Girls, Rickmansworth, this year’s sportive offers three carefully curated routes to suit all levels, and there will be a BBQ at the finish line:

Route 1 – 15 miles
A gentle, scenic ride with mild inclines—perfect for beginners, families, or those looking for a relaxed and enjoyable cycle.

Route 2 – 30 miles
A step up in challenge with a few moderate hills to get the heart pumping. Ideal for cyclists with a bit more experience—nothing too brutal, but definitely a good workout.

Route 3 – 60 miles
Designed for the seasoned rider, this is a challenging and rewarding route that demands both endurance and determination. Featuring the infamous Lilly Pink Hill, this leg-burning climb is not for the faint-hearted—but the views (and the sense of achievement) are well worth the effort.

Whether you’re cycling for fun, fitness, or to support a cause, this promises to be a fantastic day of camaraderie, countryside, and challenge. There is a £25 entry fee, payable on the day, with proceeds going in support of the Middlesex 2031 Festival and the charitable activities of the Middlesex Masonic Sports Association (MMSA).

Family and friends are warmly encouraged to join us to cheer riders over the finishing line and enjoy food from the BBQ, available to purchase on the day.

Bookings will open soon, so please return soon. £25 per Bike to enter such a popular event.

Save the date: Sunday, 28th June 2026.

Don’t miss this chance to ride with us through the heart of the Three Counties!