Road Cycling Events in May 2021

Living up to its name, this Hilly Hundred is one of the tougher routes in the cycling calendar. Riders can take on the full hundred, or opt for the shorter 67 miles. Everyone takes home a medal, and enjoys the breathtaking views along the way.

Challenging Events

Hampshire Hilly Hundred

Take on the Struggle Dales for a true cycling challenge. Traversing 108 miles, with plenty of climbs throughout, all abilities of cyclists will feel the burn. There will be stunning countryside scenery to take in throughout the ride, so come to race and earn your medal.  

Struggle Events

Struggle Dales

Pedal for victory and support the armed forces in your choice of three stunning routes for the Taunton Flyer. With a mixture of open, flowing, flat road and part of the route through the Blackdown Hills, an Area of Outstanding Natural Beauty, this event will treat you to some stunning views. 

Sportiva Events

Taunton Flyer

Tackle the Surrey Hills Classic to climb some of the highest points in Southern England. There will be 4 distances to choose from, that will definitely challenge your road cycling ability. Come to see stunning floral grasslands, woodlands, and earn your finishers medal. 

UK Cycling Events

The Surrey Hills Classic

This summer sportive is perfect for riders of all stripes. With scenic views, flat routes, and varied distances, all abilities are welcomed. Enjoy the summer weather as you ride through stunning countryside, pick up your finisher's medal after you cross the finish line, and push for a PB.

Beyond Events

Beyond Lincolnshire Sportive

Weaving through the breathtaking greenery of Chiltern Valley is sure to enhance your cycling experience. This scenic route provides both challenging climbs and rewarding sweeping descents. Beginning and ending at the Winery and Brewery means you can treat yourself to a post-race beer.

Let’s Go Velo

Chiltern Valley Winery & Brewery Sportive

Take on this unique sportive through the scenic countryside of Northamptonshire. You will ride from the Towcester Mill Brewery and glide through the country lanes which surround it. Race to the finish to enjoy a well-earned locally crafted beer.

Towcester Mill Brewery Sportive

Create unforgettable memories in this fantastic ride along the best back roads of the England. Choose between the 161k or 101k route, riding over glorious rolling terrain within the rural Cotswolds. Come along for the punchy climbs, stunning views and a bespoke finisher's medal.

Hardest 100

The Cotswolds Beast 

Embrace the fantastic scenery of the Jurassic Coast on this fantastic classic ride. Feel the cool sea air against your skin as you ride for fun on this hilly route. There will be plenty spots of outstanding beauty. Test your endurance to earn your finisher's medal. 

The Jurassic Classic

Take on the circa 120k course in the chance to ride with cycling legend Johan Museeuw. Reach the finish and be rewarded with a special evening dinner at the Hilton Hotel Cobham and the chance to hear about Johan's days in the Pro-Peleton.

European Cycling Events

Johan Museeuw UK Sportive

Take on this challenging cycling event through Settle, featuring the famous Trough of Bowland climb. These sweeping climbs and descents are one of the UK’s best kept secrets, so come along to witness the breathtaking natural landscapes. This is certain to be an adventure you'll always remember.

Forest of Bowland Epic

Starting at Swanmore Village Hall then heading east across the beautiful Meon Valley, this route bends in and around the stunning landscape of Swanmore. With 3 distances on offer, there is something for all abilities and riders. Come for the incredible views and the elation of completing this race.

BigFeat Events

Beast to the East

Be part of this incredible “Beast” Series to take on an adventure through the stunning landscapes of Somerset. Pick between the 148k or 110k route to witness cinematic views as you cycle. With some steep climbs and fast and flat sections, this event has something for every ability. 

The Somerset Beast

Test your cycling endurance in this fantastic bike ride as you traverse 175 miles in 3 days. Catering for all abilities, the journey will take you from Morecambe Bay to Bridlington Harbour, covering areas of natural beauty. Sign up for an adventure and 3 unforgettable days of cycling. 

Cycle Britain

Coast to Coast Cycling Tour - Way of The Roses - May

<p>The Bealach is the UK’s biggest road climb with an ascent of 626m from sea level in just 10km.  It is set in a fabulous unspoilt landscape with outstanding views of the sea and hills.  The Applecross Peninsula is renowned as a gem in Scotland’s crown of natural wonders. The idea of a sportive belongs to local cycling legend Clifford Davidson.</p>

Bealach Beag Sportive

The Dorset Dirt Dash 100, formerly know as the Dorset Gravel Dash 100, is a self-supported gravel event on the Isle of Purbeck around Swanage. Now in it's 7th year, this is the perfect way to experience the rugged beauty of Dorset and the Jurass

Dirt Dash

Dorset Dirt Dash 100

Beyond Events is bringing their popular Sportives to New Forest to give riders the perfect start of the season test. With the choice of a long route of 100 miles, or a shorter ride of 62 miles through the stunning New Forest area, it's an awesome way to get back in the saddle. 

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