Distance: 51-mile loop
Elevation gain: 5900 ft (RWGPS)

(A Best of the Best ride)

(Update: the recent Stage Road construction is completed and the road is now open.  jr)

About a quarter of this route is covered thoroughly in words and pictures at toughascent.com, enough to give you the look of the ride.

Before we begin, let me raise two red flags.  First, as several commenters make clear below, many people simply won’t ride Skyline Blvd because of the danger from car traffic.  I’ve never found it problematic (nerve-wracking, yes, dangerous, no), but it’s certainly one of the most hazardous roads in Bestrides.  Second, there are differing opinions about the quality of the road surface on Tunitas Creek Rd.  Two commenters below say it’s been recently repaved and now “sucks.”  I haven’t ridden the new surface yet, but it looks to be a smooth chipseal, which some people hate and some don’t mind.  I asked a rider doing the route how the surface was for riding and he said it was superb.  So I stand by the original route, but if either issue worries you, you can try the route in the Shortening the route section below, which avoids both while retaining most of the good stuff.

This ride is one of the harder rides in Bestrides—50 miles, none of them flat, and almost  6000 ft. of vert.  It’s a big climb through forest that’s as pretty as forest gets, then a leg up and down along the ridge spine down the middle of the San Francisco Peninsula, with a stop-over at an iconic California hippie/biker cafe, then one of the great descents in California and Oregon.  The ridge leg isn’t an A-level ride, because it’s straight and trafficky with no shoulder, but you’re going to have to do it to get to that descent, so what the hell.

(To see an interactive version of the map/elevation profile, click on the ride name, upper left, wait for the new map to load, then click on the “full screen” icon, upper right.)

https://ridewithgps.com/routes/37965821

Start in the bustling metropolis of San Gregorio, which is nothing but a four-way intersection and a cute, friendly country store worth exploring (a sign asks you to remove your cleats, which means you’re welcome).  Look east to the top of the ridge, as far as you can see—that’s where you’re going.  Ride south, paralleling Hwy 1, on Stage Road.  This road is a lovely up and down canter on a charming, quiet road through grassy coastal hills.  (If you don’t want to climb on cold legs, start in Pescadero and do Stage Road last.)  Watch for a nice view of an ocean beach midway.  Don’t miss the magnificent colonnade of huge old eucalyptus trees lining both sides of the road as you near the town of Pescadero.

Roll into town, a charming, energetic hamlet with good restaurants, B and B’s, and other signs of life.  If you want to do the tourist thing, have the famous artichoke soup at Duarte’s Tavern (the sign says only “tavern,” but it’s a conventional restaurant).  On your R as you enter town you pass Arcangeli’s Grocery Co., a fun and friendly old store with gigantic fresh cookies, water from the vegetable mister, and, behind the store, out of sight down the side alley, a picnic area with tables, outhouses, and a bike repair stand with tools and a pump!

Turn L onto Pescadero Creek Rd., which climbs first through pretty farmland and then through forests and redwoods as gorgeous as anything in Bestrides.  At first the grade is imperceptible, then the road rolls up and down pleasantly, and finally it turns 10%-pitch serious in the last couple of miles before the summit.

At the bottom of an unexpected, short, and wonderful 2-mile descent, you come to an intersection and you have a choice.  If you’re looking to cut off some miles and/or minimize the climbing pitch, take the cutoff (still called Pescadero Rd.) over to La Honda Rd. and the community of La Honda, then ascend to Skyline Blvd. via La Honda Rd.  This route is about 7 miles shorter and cuts out a good chunk of climbing, but it’s also much less dramatic.  La Honda Rd. is a large, wide, relatively unvarying shoulder slog with traffic.  Not awful, just not nearly as nice as staying right at the intersection and ascending on Alpine Rd.  Alpine is steeper, smaller, deserted (except for bikes), much more scenic, and with a nicely varied road contour.  We’re going R.  There’s a sign as you start up the road reading “Gravel—bicycles not advised.”  It’s just there to make you feel burly—ignore it.

Alpine’s scenery is superb and varied.  You’ll do thick redwoods, maple forests, and open grassy hillsides with expansive vistas of the Pacific Ocean and all the country you’ve ridden through so far.   Which is a good thing, because you are going to do some serious work here and will need something to take your mind off the pain.  At first it’s easy, almost flat, but then it isn’t.   For the first miles you’re riding right alongside Pescadero Creek, but the foliage is so thick you’ll rarely see it.

At 3.6 miles up, the road T’s, and you have to go L because, as the sign says, R is a dead end, but the new road is still called Alpine.  Remember this turn if you decide to ride from Pescadero to Skyline as an out and back.  By the way, near the bottom of Alpine is a sign reading “(Winding road icon) next 4 miles.”  Don’t misread this and think it’s 4 mi. to Skyline—it’s 7.5 mi.  These last 3.5 miles are a slog—unvarying up in a straight line on an exposed hillside—but the vistas are grand.

Oddly, when Alpine T’s into Skyline Blvd. there is no road sign marking Skyline, but you’re obviously at the spine of the ridge and there’s a large sign reading

Palo Alto
San Francisco
Santa Cruz

with arrows pointing straight ahead, L, and R respectively.  Go L, toward SF.

Skyline is a series of mostly straight, moderately steep rollers along the ridge spine, sometimes through dark, pretty woods and sometimes through open fields with huge vistas of the coast to your L and the south Bay to your R.  If it weren’t for the traffic, which is speedy and indifferent to your needs for space, and your tiredness level, it wouldn’t be a bad ride.

From our intersection, the rollers are 80% downhill all the way to the intersection of Skyline and La Honda Rd., where you should stop at Alice’s Restaurant, not Arlo’s place but a local institution nonetheless, with nice outside bathrooms and a big front porch that’s a great place for a breather if the sun is shining.

Now you will pay for all that downhill.  From Alice’s to the Tunitas Creek Rd. turnoff it’s 5.3 miles of 90% uphill, most of it at a significant pitch.  Get this in your head or the unexpected work will kill you.

Watch your mileage, because Tunitas Creek Rd. is hard to see (there’s a crossroads sign as you approach, and a road sign at the intersection).  It’s 5.3 miles from Alice’s, after you pass Corte de Madera on your L and a rock-walled vista turnout on your R., at the bottom of a fairly fast descent.  Turn L on Tunitas Creek Rd. and enjoy, as promised, one of the best descents in California and Oregon.  It’s perfection—sweeping, banked corners, next-to-no traffic, not too steep, through pretty forest but with good sight lines so you can see the nonexistent cars ahead of time, and it just keeps coming.  I usually have to stop midway just because I need a break from the non-stop giddiness.  Two readers (below) say the recent repaving of TCR has spoiled the road surface; others say it hasn’t.  YMMV.

At the bottom of Tunitas Creek Rd. you encounter one of life’s kinder gestures, the Bike Hut.  Leave a buck or two, then turn L on Hwy 1.  You are not done climbing.  You will immediately have to slog up one final pitch, a typical Hwy 1 mega-roller that goes on far too long.  Stare at the ocean and it will pass.  Right after, get off the highway onto Stage Rd. (small but signed) on your L and descend to San Gregorio and your car.

Shortening the route: If you have qualms about traffic or road surfaces, or just want to ride less, starting in Pescadero and riding Pescadero Creek Rd./Alpine as an out-and-back gives you all the beauty of the longer ride and a fine descent as well.  You can do it two ways: 1) ride to the T at the end of Alpine and return the way you came—this gives you a stiff 2-mile climb where that sweet 2-mile descent was on the way out (funny how it always works out that way); 2) Ride to the T, descent to the Alpine/Pescadero Creek intersection, go R to La Honda and down La Honda Rd. (#84) to San Gregorio, then back to Pescadero via the Stage Road.  This cuts out the 2 miles of climbing entirely and allows you to ride Stage Road, which is well worth going out of your way to work in.  The only drawback to this second route is that La Honda Rd. is mediocre riding.

If you want still less, I’d say Pescadero is a prettier ascent/descent than Alpine.

Locals certainly do ride Tunitas Creek as an out-and-back.  I haven’t, because it looks like a grind.

Adding miles: All the nearby back roads in the Half Moon Bay area are good.  There’s our Purissisma Creek Road ride, but also Lobitos Ridge Rd., Irish Creek Rd., and Lobitos Creek Cut-Off.  A few miles down Hwy 1 (or, from Pescadero, a few miles down the unspectacular but quiet Cloverdale Road) and particularly beautiful is Gazos Creek Road (see photo below), which runs for about 5 relatively flat miles through gorgeous redwood canopy before reaching a gate, turning to dirt, and continuing on all the way to the Big Basin Visitor Center (all well worth doing if you’re set up for dirt).  The riding on the east side of Skyline Blvd is very popular with Peninsula riders—Kings Mountain Rd., Bear Gulch Rd., Old La Honda.  A Friend of Bestrides who lives in the area asked me to give special praise to riding up Old La Honda, eating at Alice’s, and down Hwy 84 (plain La Honda Road), so I am.  See other possibilities in the Adding Miles section of the Purissima Creek Road ride.  This stretch of Hwy 1 to Santa Cruz is mostly ruler straight with some enormous rollers—not great riding, but lots of interesting places to stop.  See the Purissima Creek ride for details.

Afterthoughts: The weather in the Half Moon Bay area is drippy.  I wouldn’t want to come down Tunitas Creek Rd. in the wet (I did it once, when the road was only damp, and it was pretty hairy).  If at all possible, do this ride in dry conditions.

I’ve never ridden this loop in the other direction, but many people do.  Of course you’d be losing that wonderful Tunitas Creek Rd. descent, and TCR as an ascent is pretty monochromatic compared to Pescadero/Alpine.