There's a reason cyclists make the drive over Highway 92 just to ride here. The San Mateo Coastside has everything: car-free coastal paths with ocean views, quiet canyon roads winding through redwoods, and enough variety in terrain and distance that whether you're a Sunday cruiser or a serious road rider, there's a route with your name on it.
Here's our local guide to the best rides on the Coastside — organized by effort level so you can find the right fit.
Easy Rides — For Families, Casual Riders & First-Timers
The Half Moon Bay Coastal Trail
Distance: 7.5 miles one way (15 miles out-and-back) · Surface: Paved & Some Gravel · Difficulty: Easy
This is the Coastside's signature family ride and one of the most scenic car-free paths in the entire Bay Area. The California Coastal Trail follows the former Ocean Shore Railroad route and welcomes bikers, runners, walkers and those in wheelchairs.
For cyclists, the best stretch extends 7.5 miles from Pillar Point Harbor to the Ritz Carlton. Without stops, the one-way journey clocks in at an average 45–60 minutes and makes a great out and back! But you'll want to stop — often. The multi-purpose paved trail passes through numerous beach communities including Kelly Beach, Poplar, Venice, Dunes, Roosevelt, and Surfer's Beach, crossing a charming footbridge along the way.
If you need a destination to ride toward, make it Pillar Point Harbor. Visit the famous Mavericks Surf Company, grab clam chowder at Sam's Chowder House, watch the fishing boats come in, and ride back with the Pacific at your side.
Best for: Families with kids, beginners, e-bike riders, dogs (on leash)
Devil's Slide Trail, Montara
Distance: 2.8 miles out-and-back · Surface: Paved · Difficulty: Easy
This one is short but unforgettable. The former Highway 1 segment was converted into a dedicated trail with 12 feet striped for walking and 12 feet for bicycling, offering spectacular views of the Pacific Ocean and its coastal cliffs. Waves crash on the rocks far below, there is interesting geology to explore and a series of informational signs introducing the history and local wildlife.
The trail can be accessed from one of two small parking lots on either side of the Tom Lantos Tunnel, about 2.5 miles south of Pacifica. Parking fills fast on weekends, so arrive early. The ride itself takes about an hour round trip and is suitable for all ages.
After your ride or to pick up picnic supplies, stop by one of several tasty places in Montara. We highly recommend the Gherkin’s sandwiches and the Sage Bakehouse savory pies and coffee.
Best for: Families, visitors, anyone who wants maximum drama for minimum effort
Moderate Ride — For Weekend Warriors & Regular Riders
Purisima Creek Road & Higgins Canyon Loop
Distance: 20 miles · Elevation: ~1,000 feet · Difficulty: Moderate
This is the Coastside's most beloved road cycling loop, combining coastal riding with inland climbs through scenic canyon roads. Park near the Coastside Firehouse or downtown.
Purisima Creek Road winds through all the classic features of the region: small, hand-tended fields of row crops, unpretentious horse or goat farms, rolling coastal hills, eucalyptus groves, and a few redwoods. The climb up Higgins Canyon Road rewards you with a long, satisfying descent back toward the popular Purisima Creek Trailhead, then winds you out to the coast. Locals do this loop on Saturday mornings and end up downtown Half Moon Bay for breakfast, and you should too. Moonside Bakery, Cafe Society, and Johnny’s offer excellent options for a stop to fill up after the ride. If it’s lunch and a beer you are looking for, make sure to stop in the new Main Street location of the Half Moon Bay Brewing Company.
Best for: Intermediate road cyclists, those who want coast AND canyon in one ride
Challenging Rides — For Strong Riders Who Want to Work for the View
Higgins - Lobitos - Tunitas Loop
Distance: 30+ miles · Elevation: 3,032 feet · Difficulty: Moderate - Hard
This is a local’s loop that never leaves the coast hills. Roll out from the Firehouse and climb Higgins Canyon Road, then drop through Purisima to Verde Road and over the Lobitos Creek Cutoff to Tunitas Creek Road. Head up Tunitas through farmland and into the redwoods, then turn onto Lobitos Creek Road for the climb to the top. After a fast descent back down to Verde, you go up and over Higgins one more time on the way home. You’ll see more cows than cars, and the reward at the end is downtown Half Moon Bay. Insider tip: you can make it harder by heading up Lobitos Creek and descending down to Tunitas, looping back on Lobitos cut-off.
Best for: Experienced road cyclists, those who want a half-day adventure
Pescadero & La Honda Loop
Distance: ~31.9 miles · Elevation: 2,349 feet · Difficulty: Moderate to Hard
This classic half-day ride starts in Pescadero and heads inland on Pescadero Creek Road, climbing over Haskins Hill through redwood groves toward the old mountain town of La Honda. From there, Highway 84 takes you on a long, sweeping descent through the San Gregorio valley. The return follows quiet Stage Road, rolling over two short climbs through open ranchland and back into Pescadero. Traffic moves fast on 84, so stay alert and ride single file.
Post ride you will find two excellent options for lunch: the classic Duartes with it’s famous artichoke soup, and the best mexican food you weren’t expecting at Mercado & Taqueria Des Amigos.
Best for: Riders wanting a mix of coastal scenery and agricultural backroads
A Few Tips Before You Ride
Layers are mandatory. The Coastside can be 15 degrees cooler than the Peninsula and the marine layer rolls in without warning. Even on a sunny morning, stash a windproof layer in your jersey pocket.
- Morning is best. The coastal wind picks up significantly in the afternoons, especially in summer. An early start makes for a much more pleasant ride in both directions.
- Parking for the Coastal Trail. Start from Half Moon Bay State Beach or Pillar Point Harbor — both have parking and drop you directly onto the trail.
- Devil's Slide fills fast. The parking lots can fill fast in the summer months, so make sure to get there early. Arriving before 9am makes a real difference.
- Bring more water than you think you need. There are limited water sources once you leave the harbor area, especially on the canyon roads.
The Coastside is one of those rare places where the commute and the adventure are the same ride. If you're curious about what it's like to live somewhere this beautiful, we'd love to show you around. Reach out to the Ocean Element team anytime.
