01
Best overall pick
Alice's Restaurant
Skylonda Junction • Iconic Mountain Roadhouse • Road-Trip Classic
The beloved stop where riders, hikers, and Sunday drivers converge for hearty plates and a cold drink under the redwoods.
Perched where Highway 84 meets Skyline Boulevard, Alice's feels like the unofficial clubhouse of the Santa Cruz Mountains. The menu leans into big, satisfying comfort food—think burgers, tri-tip sandwiches, and all-day breakfasts that actually fuel you for another climb. Grab a table on the deck for the full mountain-roadhouse experience and some great people-watching as bikes roll in and out.
02
Worth the coastal detour
Duarte's Tavern
Downtown Pescadero • Historic Coastal Tavern • Best For Comfort Food
A century-old tavern famous for artichoke soup, fresh pies, and generously portioned coastal classics.
Duarte's is the kind of place where you settle into a wooden booth and lose track of time over bowls of artichoke–green chile soup and slabs of warm sourdough. The menu runs from sand dabs and cioppino to prime rib and daily specials, all served in a room that feels unchanged in the best way. Save room for pie—ollalieberry if it is on the board is non-negotiable.
03
Family-friendly choice
Parkside Grille
Portola Valley Village Center • Casual American Restaurant With Patio • Best For Groups
Relaxed, neighborly spot with a broad menu and a sunny patio that works just as well for kids, cyclists, and post-hike meetups.
Tucked into Portola Valley's small commercial center, Parkside Grille is where locals go when they need something easy and reliably good. Burgers, pastas, salads, and flatbreads cover most cravings, and portions are generous without trying too hard. The outdoor seating is especially nice after time on the nearby trails, with plenty of room for groups to linger over another round.
04
Live-music hangout
San Gregorio General Store
San Gregorio Crossroads • Rustic Café And Bar In A Historic Store • Laid-Back Weekend Stop
A creaky-floored general store turned café and bar, serving simple fare, beer, and frequent live music just minutes from the beach.
Part mercantile, part saloon, San Gregorio General Store feels like stepping into a Western movie set—only the sandwiches and local beers are very real. The short menu covers basics like chili, grilled cheese, and deli-style sandwiches that pair nicely with an afternoon beer. On weekends, live bands set up in the corner, and the mix of surfers, locals, and day-trippers gives the place a loose, friendly energy.
05
Upscale splurge
The Village Pub
Woodside Town Center • Refined New American Restaurant • Best For Special Occasions
A polished, farm-driven dining room offering seasonal New American cooking and a serious wine list in tiny, leafy Woodside.
If you want to trade dusty hiking boots for white tablecloths after a day in the redwoods, The Village Pub is the move. The kitchen builds elegant, seasonal dishes around local produce and pristine meats, with a level of execution you would more often expect in the city. Attentive service and a deep wine program make it a natural pick for anniversaries, celebrations, or simply a well-earned splurge.