Distance: 18 miles one way plus ferry ride
Elevation gain: 490 ft

(A Best of the Best ride)

This is a flat, easy recreational ride with lots of company through many of the Bay tourist’s favorite haunts: the San Francisco waterfront, Pier 39, Fisherman’s Wharf, the SF Marina, Crissy Field, the Bridge, Sausalito, the Mill Valley-Sausalito Mike Path, Tiburon, and the Bay ferries.  Each of these is a treasure worth hanging out in and exploring.  The centerpiece is the Golden Gate Bridge: the most photographed man-made object on Earth.  So this ride isn’t really about “cycling,” which is why you’ll be sharing the route with a few hundred wobbly tourists on rental townies.   If you want to expand the loop to include more work, there are five excellent ways to do that, detailed in the Adding Miles section.

I know riders who say they wouldn’t be caught dead riding on the Golden Gate Bridge.  Granted, you’re riding on a sidewalk that’s usually full of hordes of pedestrians stopping to gawk and take selfies, not to mention hordes of cyclists riding rental bikes and staring out over the water as they ride.  To these naysayers I say, crossing the Bridge under your own power is the archetypal Bucket List experience.   Just go do it.   Walk it if you’d rather.  I’m a cyclist, so I’m riding it. However, it’s true that at 10 AM of a weekend morning in good weather the bridge is packed shoulder to shoulder with rental bikes, and it’s intolerable, so get there c. 8 AM if you can.

The Bridge is open to cyclists every day of the year during daylight hours, but beyond that the schedule is shifty.   The Bay (east) side is closed to bikes on weekend days because of the crowds.  The ocean (west) side is open to bikes on weekdays after 3:30 only.  At least I think so.  The rules governing bikes on the Bridge are a bit complicated.  If both sides are open to you, you must make a decision.  The west side is much less crowded, but the views are only grand, not cosmically marvelous like on the east side.  I’m pretty sure that the “no bikes on the east side on weekends” rule isn’t strictly enforced (like the Pirates’ Code, it’s more like a guideline) so if you want that Bay view you might try to poach it.  Or ride the west side and accept second-best.  Or ride on a weekday.   The east side isn’t usually crowded in the morning (see photo below).

Navigating this route is pretty tricky throughout, so take along some mapping capability.  For the City portion of the loop, the SF Bicycle Coalition has made a great bicycle map of San Francisco, and it will guide you.  For the Marin leg, there’s the Marin Bicycle Map.  Remember, electronic maps often won’t show you bike paths, which is half the ride.

Time management is critical on this ride, because on some days the Tiburon ferry stops running in the late afternoon, and if you miss the last one it’s a long ride back (or a trip to Sausalito to catch the ferry there).  Check the ferry schedule for the last run of the day, and calculate backwards to find your starting time, remembering to factor in lots of time for a leisurely pace and lots of lingering and snacking.  I would guess you’ll want at least 4 hours elapsed time.

About a quarter of this loop, the leg from the Pier 41 ferry dock to the Bridge, duplicates a leg of our other SF ride, San Francisco’s Wiggle Loop.

Don’t try to park near the bridge.  Park at Crissy Field or next door at the Marina Green, where the parking is usually easy and free, and ride to the Bridge (by the way, our map starts at Pier 39, because I wanted to show you the whole route and I can’t map the ferry ride, but don’t try to park there either).  For details on Crissy Field or any of the route between Pier 39 and the Bridge, see the San Francisco’s Wiggle Loop ride, which shares this leg.

Navigation here is tricky, because the road system leading to the Bridge is complicated.  There are signs, and you can just follow the stream of rental bikes (any bike with a sign that says Blazing Saddles).

The Bridge has fascinating stuff at both ends.   At the south end there’s a visitor center (at South Vista Point) with interesting interactive displays about the history and physics of the bridge, a statue of Strauss the builder, and a section of suspension cable that awed me as a child and still does.   Fort Point, well worth your time, is under the bridge a short ride below you.  At the north end there’s a parking lot/viewing area with an iconic view of the City and a touching Lone Sailor Statue.

Cross the Bridge, stopping often to gawk in wonder.  Exit ASAP on the R and ride Alexander Ave. into Sausalito, one of the world’s more charming artist communities.  It’s full of shops, galleries, excellent restaurants, and other points of interest, including a huge model of the Bay (built for studying tidal flow) you can visit.  As you approach the town you ride along the breakwater, which has a breath-taking view of SF across the Bay—stop and ogle.  Stop on your way out of town at Bicycle Odyssey to salivate over high-end bikes and shop for jerseys (they have hundreds).  As you exit Sausalito you’ll see bobbing in the water on your R the world-famous community of house boats, a curious mix of waterman and bohemian cultures.  Many of them are show palaces of interior design on the inside (there’s an annual fund-raiser house boat tour when you are allowed to enter a select few).

Follow the Mill Valley-Sausalito Bike Path out of town, going straight as the main road bends L and under Hwy 101—take the path through interesting tidal meadows to Blithedale Ave. and take Blithedale R.  It turns into Tiburon Blvd., which goes to Tiburon (“Shark” in Spanish), where your ferry awaits.  Tiburon Blvd. is heavily trafficked shoulder riding, and you can avoid almost all of it by using a system of bike paths that is hard to find on your own but which is laid out for you in the Marin Bike Map.  Or use the Belvedere detour detailed in Added Miles.

Tiburon is a small, charming little town with one short main street, the unpretentious sibling to Old Money’s posh Belvedere adjacent.  If you want the full Bay Area experience you’ll eat at Sam’s.  Check out the galleries, then find the ferry to San Francisco and take it to Pier 39 (strictly speaking, Pier 41 next door).   The ferry terminal is peculiarly hard to find, but the town is tiny and the terminal has to be on the water so you’ll run it to ground eventually.  Do not get on the ferry to Angel Island, which is next door and much more prominent.

You can buy your ticket on the ferry—they’re used to bikes and make it easy.  The ferry ride across the Bay may be the best part of the loop, and it’s something you should do even if you left your bike at home.  From Pier 39 work your way west along the waterfront through Fisherman’s Wharf, Fort Mason, the Marina, and finally Crissy Field and your car.  Again, for route details see San Francisco’s Wiggle Loop.

If you’re BARTing in from the East Bay you’ll start the ride at the Ferry Building and follow the San Francisco’s Wiggle Loop route to the Bridge.  In that case, you have four options for ending the ride: 1) ride the Tiburon ferry back to Pier 39 and ride back to the Ferry Building; 2)  ride back to Sausalito and ride the Sausalito Ferry back to SF—it goes alternatively to Pier 39 and the Ferry Building, so if you take the latter it drops you back at Market Street, so you won’t have to ride the waterfront twice; 3) ride the Tiburon-to-Pier-39 ferry to Sausalito (it always stops there), get off, and get on the Ferry Building ferry; 4) finally, take the brand-new (as of 11/2019) bicycle path crossing the Richmond-San Rafael Bridge—continue north from Tiburon to the RSRB via Option 4 in Adding Miles below, cross it, then ride or BART back to your starting point.  The Bridge itself isn’t particularly attractive riding, but the views are great.

Shortening the ride:  Ride to Sausalito and jump on the ferry there.

Adding miles: There are at least five good ways to expand this loop, three of them Bestrides rides and the other two worthy of being Bestrides rides:

1. The San Francisco portion is shared by the San Francisco’s Wiggle Loop ride around the City, which will add some miles but not much work to your ride.

2. At the north end of the Bridge you’re at the beginning of Bestrides’ Conzelman Loop.

3. From Tiburon you can take the ferry to Angel Island, another low-key, flat bike stroll on the paved road that circumnavigates the island.   Angel Island was the Ellis Island of the West Coast, a processing station for Asian immigrants, and had an active military presence, all fascinatingly documented in Angel Island State Park.  Of course the views of the Bay and the Bridge are outstanding.

4. Tiburon, where you pick up the ferry, is on the route of our Paradise Drive ride.

5. To avoid the stressful shoulder ride that is Tiburon Blvd./Blithedale Blvd, or to do a bit of real work, break off the Sausalito Bike Trail midway and cut over to Seminary Drive.  Ride it (continuing on when it becomes Strawberry Drive) around the shoreline of little Strawberry peninsula, which juts out into Richardson Bay—check out the spectacular shoreline views of SF and the Bridge along the way.  Follow Greenwood Beach Rd. and the Tiburon Bike Path to San Rafael Ave, skirting the edge of Belvedere Lagoon, which since I was age 10 has always been my absolute top fantasy place to live.  Continue onto Belvedere Ave. and Beach Rd., which will take you up and over Belvedere Island, which is the loop part of the Paradise Drive lollipop.  You’re now surrounded by some of the most exclusive and prestigious property in the Bay Area.  Beach Rd. debouches at the entrance to the town of Tiburon.

This route is pretty much impossible to follow on either a street map or google maps, but the Marin Bike Map leads you right through it.

Afterthoughts:

Wind and fog are always possibilities on this ride—pack accordingly.  The last time I did it, in August, it was a cold, damp 55 degrees.  Fog also impacts the view—it’s not unusual to cross the Bridge on a foggy day and look out on an impenetrable wall of gray.

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.

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.