Four Peninsula towns in one day

Palo Alto's neighbors to the west look nothing alike. Menlo Park has a small, walkable downtown and a famous bookstore. Woodside is horse country with a country store from 1854. Portola Valley put its town hall in a meadow below Windy Hill. Los Altos keeps a village downtown with free parking behind the shops. All four sit within a short loop of Palo Alto, so you can see them in one easy day by car.

This plan runs clockwise: Menlo Park in the morning, Woodside at lunch, Portola Valley in the afternoon and Los Altos for dinner. It assumes a Thursday or Saturday, when every stop below is open. Our Palo Alto as a base page covers longer trips if you want to go farther.

The route at a glance

Without a car of your own, compare rental cars for the day. Cyclists can ride the classic Sand Hill, Portola and Alpine loop for the middle section, though the hills and the traffic make it a ride for confident riders.

Morning: Menlo Park

Menlo Park sits directly north of Palo Alto across San Francisquito Creek. Park in one of the eight free public plazas behind Santa Cruz Avenue, which have three-hour limits enforced on weekdays. Start at Kepler's Books at 1010 El Camino Real, the independent bookstore that became a gathering place for the 1960s counterculture. Cafe Borrone next door is the town's living room, with a big patio and good coffee.

Walk west along Santa Cruz Avenue past the boutiques, then drive a few minutes to Allied Arts Guild at 75 Arbor Road. Delight and Garfield Merner founded it in 1929. Its 3.5 acres of courtyards, fountains and tiled walls now hold small shops whose proceeds benefit Lucile Packard Children's Hospital. It is free and open Monday to Saturday from 10 a.m. to 5 p.m. Café Wisteria serves lunch there Tuesday to Saturday from 10:30 a.m. to 2 p.m. and recommends booking ahead.

On a Sunday, swap the guild for the Menlo Park farmers market, which runs from 9 a.m. to 1 p.m. at Santa Cruz and Menlo avenues year-round. Our Menlo Park food guide lists more places to eat.

On the way: Sand Hill Road

Take Sand Hill Road west toward Interstate 280. This short stretch through Menlo Park holds the most famous addresses in venture capital: Kleiner Perkins at 2750, Sequoia at 2800 and the low office campus at 3000 Sand Hill Road. There is nothing to visit, but it is worth the drive to see how modest the buildings are. Rosewood Sand Hill sits at 2825 and its restaurant, Madera, serves breakfast and dinner. Our Sand Hill Road guide tells the story behind each address.

Midday: Woodside

Cross Interstate 280 and follow Woodside Road into Woodside's village center, a short stretch of low wooden buildings around Whiskey Hill Road. Woodside incorporated in 1956 to stay rural and it has. Town Hall is at 2955 Woodside Road and the small Woodside Community Museum sits next door.

Lunch

Buck's of Woodside, opened in 1991 by Jamis MacNiven, serves breakfast, lunch and dinner daily in a dining room full of oddities, from a Soviet space suit to a giant shoe. Its booths were long known for founder and investor breakfasts. The Village Pub across the road says it has held a Michelin star every year since 2009. It lists lunch on Fridays only, so save it for dinner on another day. Roberts Market is the place for picnic sandwiches.

The Woodside Store

Drive a few minutes west to 3300 Tripp Road at Kings Mountain Road. The Woodside Store was built in 1854 and served the logging district as a store, post office, bank and dentist's office. It is California Historical Landmark No. 93 and now a county museum stocked with goods of the 1880s. In October 2026 its hours were Tuesday and Thursday from 10 a.m. to 4 p.m. and weekends from noon to 4 p.m. Check historysmc.org before you go.

Drive slowly here. Riders share Woodside Road, Kings Mountain Road and Cañada Road with cars. Pass horses wide and slow and never honk near them.

Afternoon: Portola Valley

Head south on Portola Road, about 15 minutes through oak meadows. Portola Valley, a town of about 4,500 people, incorporated in 1964. Its Town Center at 765 Portola Road is a cluster of wood-sided buildings around a plaza, rebuilt in 2008 after the old school buildings on the site were found to sit on a trace of the San Andreas Fault. The new library, Town Hall and community hall earned a LEED Platinum rating. Look down as you cross the plaza: leaf imprints were pressed into the wet concrete. The 1909 Historic Schoolhouse, on the National Register, now serves as the council chambers.

From the Town Center, the Portola Trail leads about 0.4 miles to the lower Windy Hill lot. The Sausal Pond loop from there runs about 1.6 miles, an easy walk with views up the bald ridge. Midpen asks visitors not to park along Portola Road and enforces it, so leave the car at the Town Center. Bring a layer. The ridge earns its name.

Evening: Los Altos

Take Alpine Road to Interstate 280 south and exit toward Los Altos, about 20 minutes. Downtown Los Altos is a triangle bounded by Foothill Expressway, San Antonio Road and Edith Avenue, with about 1,400 free public parking spaces in plazas behind the shops. Time limits stop being enforced at 6 p.m. Walk Main Street to see the 1910 Shoup Building and the 1913 Craftsman railroad depot at 288 First Street, whose front was moved to the rear when the expressway replaced the tracks. The free Los Altos History Museum is at 51 S. San Antonio Road if you arrive in daylight.

For dinner, State Street Market is a food hall where everyone can order something different. For a sit-down meal, choose The Post on Main Street, Hiroshi for omakase, Aurum for contemporary Indian cooking or Los Altos Grill. Many kitchens close around 8 or 9 p.m. on weeknights, so do not linger too long in Portola Valley. Our Los Altos food guide has details. From late April to late October a Thursday farmers market fills State Street, so in season Thursday evenings get busy.

Variations

• Gardens. Add Filoli on Cañada Road between Menlo Park and Woodside. It uses timed tickets and runs holiday lights from November 14, 2026 to January 10, 2027.
• Redwoods. Swap Windy Hill for Huddart Park up Kings Mountain Road, 973 acres of redwood canyons. San Mateo County parks charge $6 per vehicle.
• Wine. From Woodside, drive up to Skyline Boulevard for a tasting at Thomas Fogarty Winery, listed open daily from 11 a.m. to 5 p.m. Only if someone else is driving.
• An overnight. To make it a weekend, compare hotels in Menlo Park and Los Altos. Hotel Nia, the Stanford Park Hotel and Enchanté in Los Altos are all close to this loop.

Frequently asked questions