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Skyline Boulevard and Alice’s

3 passes in 302 km, topping out at 1099 m

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302 kmDistance
5 h 29Riding time
150 mHigh point
85Curve score

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Why this ride

Scenery first, traffic last, with checkpoints that make sense on a bike. Out of Kensington and back again: 302 km, roughly 5 h 29 in the saddle. On the way it passes Petaluma, Bolinas and South San Francisco. The climbs: El Granada, near Newark and Scenic stretch near Castro Valley. Long stretches are under trees.

Roadbook

  1. Fuel stop near Kensington fuel

    Fuel at 0 km.

  2. Near Petaluma, on the way back swim

    Eggs made Petaluma famous. In the early twentieth century this town in southern Sonoma County, an hour north of San Francisco, called itself the egg basket of the world, thanks to hundreds of chicken farms around it and an incubator invented here that helped revolutionise poultry farming. Today the chickens are fewer, but the town still has a strong farming identity, with dairies, cheese makers and creameries in the hills around it.

    Petaluma's downtown is a pleasure: a row of nineteenth-century iron-fronted buildings along the river, many of which survived the 1906 earthquake that wrecked so much of the region. Film directors love it for its period look, and scenes from American Graffiti and Peggy Sue Got Married were shot here. The Petaluma River, technically a tidal slough, winds through town toward San Pablo Bay, and the old riverfront warehouses now hold shops and restaurants.

    As for swimming, the honest answer is that the ocean nearby is cold and rough, with big waves and strong currents, and the town's river is not for swimming. Dillon Beach, about forty minutes west, and the beaches around Tomales Bay are the closest places to get in the water, but the Pacific here rarely gets above the mid-teens Celsius, so it is a quick, brave plunge rather than a lazy swim. Many people settle for wading.

    The real treat is the riding. West of Petaluma, roads such as the Point Reyes–Petaluma Road, Chileno Valley Road and the Bodega Highway wind through rolling grassland and dairy farms toward the coast. These are narrow, quiet roads with plenty of corners, short climbs and sweeping views of golden hills dotted with oaks and black-and-white cattle. The surface varies, and you will meet cyclists and slow farm traffic, but on a clear day it is wonderful riding.

    Petaluma has everything you need, from fuel and motorcycle shops to excellent restaurants and cafes. On the way back south toward San Francisco, the 101 freeway gets crowded, especially on weekend evenings, so an early return or a slower route along the backroads through Nicasio and Lucas Valley makes a gentler end to the day.

  3. Bolinas food

    Bolinas does not want to be found, and it has made that clear for decades. Locals have a long tradition of removing the road sign that points to the town from Highway 1, so you may have to watch for the unmarked turnoff at the end of Bolinas Lagoon. The reward is a small, eccentric, salt-weathered village at the tip of a mesa on the Marin coast, with a few streets of old wooden buildings, a beach, surfers and an atmosphere that feels decades removed from the Bay Area just over the hill.

    Geology explains the setting. The San Andreas Fault runs straight through Bolinas Lagoon and up the Olema Valley to Tomales Bay, and the land to the west, including the Point Reyes peninsula, sits on a different tectonic plate, moving slowly northwest relative to the rest of California. The lagoon is a haven for wildlife: harbour seals haul out on the sandbars, and herons, egrets and pelicans fish in the shallows. Duxbury Reef, off the end of the mesa, is one of the largest shale reefs in North America, with tide pools at low tide.

    The road in is the reason to come. Highway 1 from Mill Valley and Muir Woods climbs over the shoulder of Mount Tamalpais and drops down to Stinson Beach on a sequence of tight, twisting bends above the ocean, with sheer drops and spectacular views. It is narrow, often bumpy, frequently foggy and shared with cyclists and tourist cars that stop without warning. The Panoramic Highway and the Ridgecrest Boulevard over Mount Tam are equally twisty and even more scenic. North of Bolinas, Highway 1 follows the lagoon and the Olema Valley toward Point Reyes Station, through rolling pastures and eucalyptus.

    Fog is a constant companion, especially in summer, and the coast can be cold and damp even when the inland valleys are hot. Spring brings green hills and wildflowers, and autumn is often the clearest season.

    Bolinas has a couple of places to eat and drink, but do not count on filling the tank here. Fuel up in Mill Valley or Fairfax before heading out, or at Point Reyes Station further north. Respect the locals' wish for quiet: park considerately, keep the revs down in town and enjoy the beach, the lagoon and the strange, independent spirit of the place.

  4. El Granada pass

    Mavericks, one of the most fearsome big-wave surf breaks in the world, breaks over a reef off Pillar Point, a few hundred metres from El Granada. On the biggest winter swells, waves rise to fifteen metres or more, and only the best surfers in the world dare to ride them. From the bluffs above, with binoculars, you can watch them drop down faces the size of buildings.

    El Granada is a small community on the coast north of Half Moon Bay, laid out in the early twentieth century by Daniel Burnham, the Chicago architect, in a pattern of semicircular streets fanning out from the shore. It was meant to be a resort town on the Ocean Shore Railroad, which never got further than this stretch of coast. The harbour at Pillar Point is busy with fishing boats, and the restaurants on the waterfront serve fresh fish and crab.

    Half Moon Bay, to the south, is famous for pumpkins, and every October the town holds a festival with a weigh-off for giant pumpkins that can top a tonne.

    For riders, the ride inland on Highway 92 climbs over the hills to Skyline Boulevard, a winding road along the ridge of the Santa Cruz Mountains, and Alice's Restaurant, at the crossroads of Skylonda, is a famous biker meeting point. The roads are winding and scenic, with redwoods, fog and views over the ocean and the bay.

    Pack a warm layer whatever the forecast says. In summer the marine fog sits on this coast for days, damp and grey, while ten minutes inland the ridge basks in sunshine; the transition on Highway 92 happens in a single bend. Fuel and food are in Half Moon Bay, and the harbour at Pillar Point sells crab straight off the boats in season.

  5. Near South San Francisco finish

    The dead outnumber the living in Colma by a margin of more than a thousand to one. In the early twentieth century, San Francisco banned new burials within city limits and then evicted most of its existing cemeteries, and the graves were moved a few kilometres south, to this small town just over the county line. Today Colma is a quiet, green landscape of memorial parks and monument workshops, where Wyatt Earp lies in a Jewish cemetery and Joe DiMaggio in a Catholic one. Locals like the joke on the town's own slogan: it's great to be alive in Colma.

    The start is close by, on the slope between Daly City, South San Francisco and the ridge of San Bruno Mountain, an island of wild coastal scrub surrounded by suburbs. Daly City's tightly packed hillside houses inspired Malvina Reynolds's satirical song Little Boxes in the early 1960s, and from certain angles you can see exactly why.

    The rides that start and finish here go south along Skyline Boulevard, State Route 35, which follows the crest of the Santa Cruz Mountains for many kilometres above the Bay Area, through redwood forests and open grasslands, with views over the Pacific on one side and the bay on the other. It is a classic Bay Area riding road, with a mixture of fast curves and tight bends, and at its heart, at the junction with Highway 84, Alice's Restaurant has been a gathering place for riders for decades. On weekend mornings the car park is a rolling motorcycle show.

    The weather here is dominated by fog. On summer mornings it rolls in from the Pacific and wraps the ridge in grey mist, dropping the temperature and wetting the road, while a few kilometres inland the sun is shining. Ride with care in the fog, and with an extra layer. Skyline is also popular with cyclists and has a reputation for speed enforcement and accidents, so keep it sensible. There are plenty of fuel stations, taquerias and diners in Daly City and South San Francisco.

  6. High point near Newark pass
  7. Scenic stretch near Castro Valley pass

    You top out here; the road stops climbing.

  8. Back to Skyline Boulevard finish

    This is the East Bay, the side of the bay that gets less attention than San Francisco and has more hills to ride. The point is in the hills above Berkeley, near Kensington and Orinda, where narrow streets climb steeply past eucalyptus trees and houses perch on slopes with views of the bay and the Golden Gate. A line of ridges, the Berkeley Hills, runs along the whole east side of the bay, and the Hayward Fault lies at their foot, which is something people here think about more than they mention.

    The road along the crest is Grizzly Peak Boulevard, which curves through Tilden Regional Park and gives a series of views over the bay, with the city skyline and Mount Tamalpais on the far side. Tilden has a small steam train for children, a botanic garden of California native plants, and tracks through eucalyptus and bay woods. The road is narrow with sharp bends, and cyclists and hikers share it.

    Further south, Skyline Boulevard continues along the ridge through Oakland, through Redwood Regional Park, where a grove of coast redwoods stands on slopes that were logged heavily in the nineteenth century. The park's second-growth trees have grown tall, and the road beneath them is dark, cool and quiet. In 1991 a firestorm swept across the Oakland and Berkeley hills, destroying about three thousand homes, and the rebuilt neighbourhoods carry that memory.

    Berkeley, down below, is worth a stop. The university campus, with its bell tower, the cafés of the Gourmet Ghetto and the lively Telegraph Avenue make for a vivid, slightly chaotic afternoon, and the town was where the California food movement was born, around a restaurant opened in 1971. Fuel and food are easy in the flat part of the city and in Orinda.

    The best time to ride is a weekday morning, when the fog has lifted from the hills and traffic is light. In summer the fog often rolls through the gaps in the ridge in the afternoons, dropping the temperature sharply, so a layer is useful. Autumn can bring hot, dry winds and fire warnings, and winter rain makes the hillside roads slippery, with mud and leaves on the surface.

Where this sits

🇺🇸 United States San Francisco Bay Area Forest Long days, 250–400 km Lowland and coast Mountain passesSwim stopsFuel on routeFood stops

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