Organised for the first time in 1998 as a preparation ride for some of the club members going to take part in the "Raid Pyrenean" in France, the Five Hills Challenge was considered such a success that in 1999 it was included in the clubs events for the national leisure calendar.

The challenge takes place in August so that A. people are most likely well trained up during the summer and B. in the hope of good weather. The course starts in Carlow town and goes out the Wexford road to the "Fighting Cocks" before turning for Fenagh. After Fenagh is Myshall and then a short trip to the first heart stopper of the day " the Corribut Gap"(Hill #1). This comes so early on that it catches the muscles by surprise on a very steep but short climb. After a short descent its on to the Nine Stones (Hill #2) on Mount Leinster this is more of a drag, and on a good day there's some nice scenery on the right, this is also a favourite haunt for Hang Gliders.

At the nine stones there is an optional hill climb up the notorious Mount Leinster climb to the Mast. This is not to be taken lightly, as it is an extremely hard push with some gradients between 10% to 20%. After the nine stones its downhill until "TomDuff", a drag not counted in "the 5", and then on through Bagnalstown to Royal Oak where there is a planned stop to allow most to re-group and grab some sustenance. After crossing the Main Kilkenny road we take in the third! Climb of the day "Mile Bush"(Hill #3). Once again it's a steep little sucker that'll put hairs on yer chest. The descent from this is dodgey! And should be taken very easy as it has unannounced switch back turns, while going down almost vertically. Then its narrow farming roads before meeting the small village of Old Leighlein at the foot of the next climb "The Butts"(Hill #4). This climb has featured in "The Ras" and also in the "Des Hanlon memorial" races and is a drag culminating in a steep finish.

On then through more farm roads to meet up on the Ballanabranagh to Rosmore road, climbing up until the statue to Our Lady, again not included in "the 5". Descending from Rosmore almost to Kileshin church you take a sharp left and begin the final climb of the day "the Cuts"(Hill #5). This again is a tester being at the back end of a hard cycle, but once over it, its down hill onto the Castlecomer - Carlow road, and a good descending run-in back to the town of Carlow. There everyone has awakened since we left earlier in the morning, and you can get some well-deserved refreshments, which are laid on, in the local pub. Certificates, Slagging, and Compliments are then dished out to all that deserve them.