This ride is about 28 miles and includes one very challenging hill (Old LaHonda), but can be shortened to 19 miles bit by simply lopping off the ride up the hill and instead heading back the way you came (on Mountain Home Road).
You start in Woodside, at the corner of Canada and Woodside Road. Head south on Mountain Home Road and pass by Fort Ellison (Oracle chief Larry Ellison's estate, complete with underground parking!), shown in the photo on the right. Looks like a summer camp, but don't let that fool you! Mountain Home has a few little rises and drops, but the most challenging aspect is the choppy pavement and narrow shoulder. Fortunately, it gets very light car traffic.
Mountain Home dead-ends into Portola/Sand Hill Road. We head east (the Sand Hill side) up a small rise, then descend a bit and then climb quite a bit until...
The killer descent with the view! You drop down to the 280 overpass (be careful here, as there are some pretty nasty cracks in the pavement on the overpass), climb slightly and then descend to Alameda/Junipero Serra.
Coming up on Page Mill Road. If you head straight for 7.5, you'll be at the doorstep of our Los Altos store!
But today we take a right turn (head west) up Page Mill. Fortunately, we don't deal with the traffic for long, as you immediately turn right onto Old Page Mill, a virtually car-less little cruise that bypasses the big hill.
The contrast between the idyllic car-free Old Page Mill and the real thing is immediately apparent as soon as you merge back onto it. Just ahead is one of the most dangerous obstacles to safe cycling on the Peninsula- the 280/Page Mill interchange. It's worse than it looks. After you get past the north-bound freeway onramp, you end up with two lanes on the right that both turn! No allowance has been made for bikes, and you essentially have to fend off cars for a couple hundred yards that think you're in their way.
But once you get past 280 you take the first right onto Arastradero, a very scenic little road with rolling hills (and not much shoulder).
At the end of Arastradero you make a left turn up Alpine and head past the Alpine Inn, known as Rosatti's Beer Garden, or just simply "Zotts" by some.
Alpine Road is one of the "main drags" for cycling. Nicely paved, wide shoulder and not too steep.
At the "top" of Alpine Road you turn right on Portola Road. There's a convenience store here where you can refuel if needed.
A pair of cyclists enjoying the unchallenging terrain and beautiful day (on Portola Road).
But if a ride's on this website, it probably does have a hill! In this case, Old La Honda Road, about 1200 feet of climbing over 4 or so miles. Three pretty steep sections, but this is still the most pleasant climb to Skyline due to its beauty and relative lack of cars.
Bicyclists aren't the only ones enjoying a nice day! SkyLonda, at the corner of Skyline Blvd and 84, is a very popular hangout for all manner of 2-wheelers.
Highway 84 is a reasonably safe descent with great views, a couple of which are worthwhile stopping to admire. Much safer than taking pictures from a bike at 35mph!
At the bottom of 84 you head north, and take a slight detour on Tripp Road to the base of King's Mtn.
At the end of Tripp Road is the Old Store, an historic landmark (and not just because it's the timing point for beginning the climb up Kings Mtn!).
At the end of Tripp Road you make a right onto King's Mtn, which will take you back to 84 (Woodside Road), where you make a left and ride a very short distance back to Woodside. Alternately, you can take a left turn at Manuella (which is what's shown on the map at the top of this piece), and wind your way around to Canada Road and then back to Woodside.
Last updated 01/24/14 since 05/06/05
Chain Reaction Bicycles is your local bicycle shop for the San Francisco Bay Area! Unlike some other shops, we are dedicated 100% to serving the needs of local cyclists; our offerings are exclusively available for in-store pickup. You will find us at 1451 El Camino Real, Redwood City CA, 94063. 650 366 7130. Our Los Altos location closed on September 24th, 2017; we have consolidated all operations within our Redwood City flagship store. Our hours and directions may be found here. We look forward to taking care of all of your cycling needs, including service! Mike & Steve Jacoubowsky, Partners, Chain Reaction Bicycles. Serving you since 1980!