A 240 km loop
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Scenery first, traffic last, with checkpoints that make sense on a bike. Out of Pacifica and back again: 240 km, roughly 4 h 22 in the saddle. It goes by way of Montara, Daly City, Scenic stretch near Kentfield and near Lucas Valley-Marinwood. Long stretches are under trees.
For decades the most nervous stretch of Highway 1 south of San Francisco was Devil's Slide, a ledge carved into crumbling cliffs above the Pacific between Pacifica and Montara, which slid into the ocean so often that the road was closed for months at a time. In 2013 twin tunnels finally bypassed it, and the old road became a walking and cycling trail where you can stand on the cliff edge and see what the engineers were up against. Pacifica sits at the northern end of that story, a string of beach neighbourhoods tucked into coves and valleys between the coastal hills and the surf.
It is a good place to start and finish a long ride. The town has fuel, supermarkets and the famous Taco Bell on Linda Mar beach, built in timber with an open-air terrace over the sand, which may be the only fast-food restaurant anywhere that surfers would call a destination. Pacifica Pier stretches far out into the waves and is a favourite spot for anglers and pelican watchers.
History is here too. In 1769 the Spanish soldiers of the Portolá expedition, searching for Monterey Bay, climbed Sweeney Ridge above the town and became the first Europeans known to have seen San Francisco Bay. The site is now part of the Golden Gate National Recreation Area, and the walk to the top gives a view of both the bay and the ocean.
The ride to Yosemite and over the Tioga Pass is a long one, crossing the Central Valley and climbing into the Sierra Nevada to one of the highest road passes in California. The Tioga road is closed by snow for much of the year, usually opening in late May or June and closing in autumn, so check before you leave.
Pacifica's weather is the joke of the Bay Area. Fog rolls in most summer afternoons, the wind blows hard off the ocean, and the temperature can drop by fifteen degrees in a few minutes. Carry warm layers, whatever the season.
For years, the stretch of Highway 1 just north of Montara was the road everyone worried about. Devil's Slide, a crumbling headland of rock above the Pacific, kept sliding into the sea and closing the highway, sometimes for months. Since 2013 the traffic has passed through a pair of tunnels bored through San Pedro Mountain, and the old road along the cliff has become a walking and cycling trail with some of the wildest views on the San Mateo coast. If you have twenty minutes, walk a piece of it.
Montara itself is a small, quiet coastal community at the foot of Montara Mountain, with wooden houses scattered up the slope and a wide, sandy state beach below the highway. The Point Montara lighthouse, a slender white tower, stands on the bluffs just south of town. A little further on, at Moss Beach, the Fitzgerald Marine Reserve protects rocky reefs and tide pools where, at low tide, you can see anemones, crabs and starfish, and sometimes harbour seals hauled out on the rocks.
The ride along this part of Highway 1 is classic Northern California coast. The road winds along the cliffs and through small towns, with the Pacific on one side and green hills on the other. In summer, fog often hangs over the coast in the morning, burning off by midday, and the temperature can be ten degrees lower than in the Bay Area just over the hills. The road is busy on weekends with cars and cyclists, and the surface varies from smooth to bumpy. Watch out for sudden stops near the beaches and viewpoints.
Montara is too small to have much in the way of services, but El Granada and Half Moon Bay, a few miles south, have fuel, restaurants and cafés, and Pillar Point Harbor is the place for fish and chips by the boats. The beach here is beautiful but the water is cold, the surf can be powerful and rip currents are common, so swim only if you know what you are doing. Sitting on the sand with a coffee, watching the surfers and pelicans, is a safer pleasure.
South of San Francisco's city limits, the land runs out abruptly. Daly City's houses, the ones with the colourful matching boxes that inspired the song Little Boxes, cover the hills right up to the edge of high, crumbling sea cliffs, and below them the Pacific pounds a long empty beach.
The fog is the local character. In summer it rolls in from the ocean in the afternoon and often stays all day, pouring over the hills like a slow wave while the inland valleys bake. A sweater and a good jacket are essential even in July. Riding in it can be damp and chilly, with wet patches and limited visibility on the coast road, but when it lifts the light over the ocean is gorgeous.
Geology is everywhere here. The San Andreas Fault runs right under this coast, heading out to sea at Mussel Rock just south of Daly City, and the cliffs keep sliding and collapsing. Further south, the old Highway 1 route around Devil's Slide fell apart so often that it was replaced by tunnels, while the former roadway became a walking and cycling trail. At Fort Funston, the old military batteries sit on top of the bluffs and hang-gliders launch into the steady onshore wind.
The rides from here go two ways. Skyline Boulevard, Highway 35, begins nearby and runs south along the ridge of the peninsula, through the Santa Cruz Mountains, famous for its curves, redwoods and the gathering of bikes at Alice's Restaurant. It starts suburban but grows wilder and more beautiful the further you go. The Napa rides head north instead, across the city and over the Golden Gate Bridge, through Marin and into the wine valleys, where the morning fog burns off and the Silverado Trail runs between the vineyards.
Daly City is a big suburban city and has every service: fuel, supermarkets, fast food and plenty of Filipino restaurants, a reminder of one of the largest Filipino communities in the United States. The Serramonte area by the freeway is the easiest stop. If you have a few minutes, walk out to the cliffs at Fort Funston and watch the waves, but keep well back from the edge; it has a habit of falling into the sea.
Scenic stretch near Kentfield, about halfway.
Photo stop near Lucas Valley-Marinwood sits at 147 km, about halfway.
Mount Diablo dominates everything here. The mountain rises alone to 1,173 metres above the eastern side of San Francisco Bay, its brown summer slopes dotted with dark oaks, and on a clear winter day, after rain, the view from the top is said to be one of the widest in the world, reaching the Sierra Nevada to the east and the Golden Gate to the west. San Ramon, Danville and the gated enclave of Blackhawk spread along its western foot, a valley of tidy suburbs, office parks and golf courses.
The valley has a few surprises. In Danville, the playwright Eugene O'Neill built Tao House in the 1930s with his Nobel Prize money and wrote Long Day's Journey into Night and The Iceman Cometh there; it is now a National Historic Site, visited by shuttle. At Blackhawk, a museum houses a collection of classic and rare automobiles, a fine detour on a hot afternoon for anyone who cares about engines.
The swimming is a short ride south. The Tri-Valley summer is hot and dry, often well over thirty degrees, and locals cool off at Shadow Cliffs, an old gravel quarry near Pleasanton turned into a lake with a swimming beach, or at Lake Del Valle, in the hills south of Livermore, a long reservoir with sandy beaches, lifeguards in season and oak-covered hills all around. Check whether swimming is open before you go, because the parks close beaches when water quality is poor.
The riding is the main draw. The roads up Mount Diablo, North Gate and South Gate, climb through grassland and chaparral to the summit with tight bends, steep grades and big views, and they are popular with cyclists, so be patient. Morgan Territory Road, a narrow single-lane road over the hills east of the mountain, is a classic for riders who like it slow and twisty. Crow Canyon and Norris Canyon Roads cross the hills to the west with nice curves. Watch for gravel, deer and summer fire closures.
San Ramon has fuel, food and services everywhere, and Danville has a pleasant old downtown with cafés and restaurants. Fill up here, drink plenty of water, and if the day is hot, find that lake.
The hills behind Hayward rise steeply from the flat bay plain, and Fairview sits right on top of them, a semi-rural community of ranches, winding lanes and houses with long views across San Francisco Bay. On a clear day, you can see the bridges, the city skyline and the Peninsula hills beyond. It is a peaceful spot above one of the busiest urban areas in the country.
For riders, the area is a gateway to some of the best backroads of the East Bay. Palomares Road twists through a narrow canyon of oaks and sycamores towards Niles Canyon, where Highway 84 follows Alameda Creek through a gorge with an old railway line. Further east, Calaveras Road and the roads towards Sunol and Livermore offer more curves and quiet. The hills turn green in winter and spring after the rains, then golden brown in the dry summer, when the smell of dry grass and bay laurel fills the air.
These are narrow, technical roads with blind corners, gravel, and often cyclists, so ride with care. Fog can roll in from the bay in the morning, while summer afternoons inland can be hot. Watch for deer and cattle on the rural stretches, and for fast local traffic on the main roads.
Fairview itself is residential with few services. For fuel and food, head down to Hayward or Castro Valley, where there is plenty of choice, from gas stations to taquerias and diners. From here, the routes lead north towards Marin and Point Reyes, or south towards Big Sur, two of the great rides of California. Fill up below, enjoy the view from the top, and pick your direction.
Pacifica is the last proper coastal town before San Francisco, a long strip of fog, surf and low houses squeezed between the Pacific and the steep ridge of the Coast Range. It is a place that feels slightly overlooked, which is part of its appeal. The beach at Linda Mar is one of the Bay Area's best-known surf spots, and on a gray winter morning you can watch wetsuited figures bobbing in the breaks while commuters stream by on Highway 1.
For riders, the real story here is the road. For decades, Highway 1 south of Pacifica crossed the cliffs at Devil's Slide, a notorious stretch where winter storms sent the pavement into the sea and traffic closed for weeks. A pair of tunnels opened in 2013 and now carry the highway through Montara Mountain, with a tidy view of the sea at either end. The old road was kept as a quiet bike and walking path, and you can still stand where the cliffs fall away beneath you. The result is a much calmer ride, though the tunnel exits expose you to crosswinds and fog.
North toward San Francisco, the Great Highway and Skyline Boulevard offer long, fast curves above the surf, and in the opposite direction the coast road to Half Moon Bay is a classic. Come early on a weekday if you can, because summer weekends bring a slow line of cars, and the fog tends to hold on until midday. Wear a warm layer even when the Bay is hot.
Pacifica has everything a rider wants after a long day: gas stations along the highway, taquerias, a pier for fishing and a handful of coffee shops that open early for the surfers. Sharp Park's golf course, designed by Alister MacKenzie, sits right on the waterfront, and the wetlands behind it shelter a rare snake and a rare frog that have tangled the course in local politics for years.
If you are riding north from here, the road eventually rises over Fort Funston's dunes, and the city's hills come into view. It is a fine end to a coastal day, even with the traffic.