The Fiendish Fortymile (formerly The Hellion’s Metric Half-Century) takes you on a trip along the San Mateo County coastline where you’ll be treated to spectacular views of the Pacific Ocean and get off the beaten path to explore the peaceful and picturesque countryside.

With a moderate elevation gain of 2510′, this ride is geared towards advanced-intermediate cyclists looking to push through to the next level and advanced cyclists who ride regularly and are looking for an invigorating medium distance workout. Riders under 18 must be accompanied by a parent or guardian.

For 2019, all three of our road ride routes have been enhanced for your safety and enjoyment, and now include a scenic detour through the peaceful, winding backroads of Half Moon Bay. This change has added an additional 2 1/2 miles to the distance from previous years’ rides, hence the name change. See map below for more details.


There are two aid stations along the course (see map below for exact locations). You can take a shuttle from the second aid station in Montara to the southern entrance of the Devil’s Slide Recreational Trail which allows you to bypass the 2.4-mile stretch of Highway 1 North between Montara and the Lantos Tunnels, notorious among cyclists for its uncomfortably narrow, rocky shoulder. We strongly urge you to take advantage of this service! 

We’ll be running two vans, equipped with bike racks all morning, but please be aware that there may be up to a 20 minute wait between shuttles depending on the amount of traffic on Highway 1, which is beyond our control. To make your wait as pleasant as possible, snacks and drinks will be available while you wait.

If you opt to ride back the entire way instead, your total route length will be 42.4 miles.

Check our Event Day Schedule & Parking for starting times and additional details. You can also Follow us on Twitter and Facebook.

If you have specific questions about the course, please email us at or use the Contact Us form below.


  • Routes are subject to change based on CalTrans and local government requirements and/or weather conditions.