Wiggle Chiltern Classic – Saturday August 5

The Chilterns are a popular cycling hub in the South East, with plenty of rolling terrain to get your legs stuck into.

The undulating terrain of the Wiggle Chiltern Classic is typical of the area, with the climbing starting early in the ride on all three routes – Epic (101 miles), Standard (73 miles) and Short (33 miles).

After crossing under the M40, the terrain eases and you can enjoy the ‘quaint and quiet’ village backdrop, but keep something in reserve as you hit the Chilterns once more before returning to the Henley base.

Late entry closes on Friday (August 4) at 4pm, so be quick!

Entry fee: £38 (Epic, Standard); £29 (Short)
Website: UK Cycling Events

Evans Cycles RIDE IT Peak District – Sunday August 20

Oldgate Nick, Bunsal Cob, Mam Tor, Snakes Pass… Evans Cycles’ Peak District sportive is one of the toughest on their RIDE IT calendar, rated the top level for difficulty.

Set in the Peak District National Park, the ride showcases the best of the beautiful area – but that means plenty of tough climbs to negotiate, hence the slightly shorter routes compared to normal.

The Long Route packs 10,000ft of climbing into the 80-mile course, with Mam Tor – a 2.1km slog at ten per cent average gradient, with a steepest pitch of 15 per cent – among the highlights.

Even the 55-mile Medium Route features 5,900ft of climbing – it’s as tough as they come on the RIDE IT calendar, but it is also an incredibly rewarding ride.

Entry fee: £25 (Long, Medium); £20 (Short); £7.50 (Fun)
Website: Evans Cycles

Tour de Mon – Sunday August 20

The Tour de Mon takes place on the North Welsh island of Anglesey, with the terrain lending itself to a lumpy tour of ‘one of Britain’s best kept secrets’.

The climbs are tough, with the roads joining Trefor and Carmel kicking up to 12 per cent from the off, but it is not just the climbs to test your legs on – the sportive also includes a timed ‘flying mile’ at Mona Airfield.

You have a choice of three routes in all, with the 107-mile Mawr, 77-mile Canol and 46-mile Bach available to enter.

Entry fee: £39.99 (Mawr); £37.99 (Canol); £35.99 (Bach)
Website: Always Aim High Events

The Hertfordshire 100 – Sunday August 27

Fancy taking advantage of the Bank Holiday weekend by booking in for a 100? Sportive UK’s original sportive, the Hertfordshire 100 is back for its fifth year with an improved route.

You can choose 100 miles, 100km or 33 miles with the rural Hertfordshire routes serving up rolling countryside roads and a couple of climbs to keep the legs working.

While the longer two routes head out into the rolling countryside too, all three pack the climbs in with the short, sharp hills of ‘Little Switzerland’ demanding you keep something back for the last ten miles.

Entry fee: £25 (100 miles, 100km); £20 (33 miles)
Website: Sportive UK

The Winking Sheep Sportive, Sunday August 27

Taking in the best roads the North Pennines, the Roof of England, has to offer, the Winking Sheep Sportive is now in its third year.

With the closed-road Etape Pennines no longer run, the Winking Sheep Sportive has taken up the mantle as the ultimate North Pennines sportive, with a choice of 90, 75 and 55-mile courses.

Starting and finishing in St John’s Chapel, the sportive heads out into Middleton-in-Teesdale, Stanhope, Allenheads and more to tackle the quiet, rolling roads.

There are plenty of climbs to negotiate, but the views on the top of the moorland are unparalleled – the perfect way to spend a Bank Holiday.

Entry fee: £25
Website: Winking Sheep Sportive

With a new 100-mile option added to the line-up too, the event then finishes with a lap of the Velodrome, Paris-Roubaix style, for an authentic Hell of the North tribute.

Also passing Celtic Manor and the Newport Velodrome, the event is promoted by Cycle Classics, who also count the Flanders-inspired Cheshire Cobbled Classic and Strade Bianche-esque White Roads Classic in their stable.

Entry fee: £30
Website: Cycle Classics