Leave Your Heart in San Mateo

Fall in love with the beautiful coastline, attractions and charming small towns in this Bay Area destination that boasts luxury and farm tours, side-by-side.

One of the great things about planning a San Francisco vacation is that there are so many terrific nearby destinations to include in your itinerary just beyond the city borders. San Mateo County is one such place. I’ve had the pleasure of exploring this destination while living in the Bay Area for the past 15 months, and whether you’re into history and small-town exploration, outdoor activities, culinary excursions, family festivals or a Northern California beach vacation at a seaside resort, San Mateo can meet your needs.

A Sense of Place

San Mateo County, formed in 1856, covers most of the peninsula directly south of San Francisco and is bordered by the San Francisco Bay to the east, Silicon Valley to the south, and the Pacific Ocean to the west. Fly into the San Francisco International Airport, and you’re on its doorstep.

San Mateo County’s northern and eastern areas are composed of abutting suburban towns, but get beyond those and suddenly you’re among the rolling foothills of the Santa Cruz Mountains, equestrian estates and working farms. Beginning in the late 19th century, the peninsula became a popular place for many of San Francisco’s elite to build their country homes, following the economic boom sparked by the 1849 Gold Rush.

Half Moon Bay

Arguably the best known of San Mateo’s sights is Half Moon Bay, the coastal resort town about 25 miles south of San Francisco. Spend time chilling out on one of its gorgeous beaches, then stroll down Main St. to browse the many craft shops, European-style boutiques and art galleries. Be sure to visit Pillar Point Harbor, about four miles north along the coast, and check out (or even buy!) fresh crabs and other goodies brought in by commercial fishermen, or sign up for a kayak adventure at Half Moon Bay Kayak Company (read more in our Bay Area Hike, Bike and Kayak article).

The annual Half Moon Bay Art & Pumpkin Festival takes place Oct. 18 to 19 this year. Last year’s giant pumpkin winner came in at 1,524 pounds. Visit Farmer John’s Pumpkin Farm to see some of these stunners, along with dozens of other types of pumpkins and gourds of all shapes and sizes, during the fall, if you can’t make the festival. The farm opens mid-September, Mon. to Fri., 9:30 a.m. to 5:30 p.m., Sat. and Sun., 9 a.m. to 6 p.m.

Perched on a cliff south of Half Moon Bay is Pigeon Point Lighthouse, which at 115 feet is one of the tallest lighthouses in the United States. In operation since 1872, the lighthouse is no longer open due to structural concerns, but you can visit the grounds and often spot sea lions and whales from the deck over the cliff rocks.

Where to Eat

There are plenty of excellent places to eat in town and nearby along the coast. For some of the freshest Italian dishes you’ll find anywhere—most ingredients are sourced from local farmers—enjoy a meal (or three) at Pasta Moon. If you’re familiar with wine-pairing meals, consider a beer pairing at the Half Moon Bay Brewing Company at Pillar Point Harbor. It offers more than 120 types of beers, and its homemade brews compliment the California Coastal Cuisine served in its restaurant. Another favorite is Café Gibraltar, for its flavorful Mediterranean dishes, with influences from Morocco to Turkey. Families with teens might prefer the more casual Cameron’s Restaurant, Pub and Inn, south of town. Fish-and-chips are the specialty.

Where to Stay

Half Moon Bay has long been a popular vacation spot—as well as the location for the famous Mavericks Surf Contest—and is even more so now since the 2001 opening of the Ritz-Carlton Half Moon Bay. Set on a bluff overlooking the Northern California coastline, with its fabulous spa and access to two neighboring championship golf courses, the resort’s popular Kids Night Out program, available Friday and Saturday evenings, keeps children occupied with dinner, movies and arts and crafts, while parents enjoy a quiet dinner together at the resort’s Navio restaurant, or one of the picks above.

Other hotels in the area include the Half Moon Bay Lodge, with many of its spacious rooms facing the Half Moon Bay Golf LinksBeach House Hotel and including a balcony and fireplace; the , with loft suites; and the new Oceano Hotel & Spa Half Moon Bay Harbor. The spa at Oceano was not yet open during my stay, but is supposed to be by Fall 2008.


About 14 miles south of Half Moon Bay is the farming and art village of Pescadero. It’s pretty much a three-street town, but I’ve found reason to return several times this year. In town are a variety of antique and craft shops, two white-steeple churches and a hillside cemetery where you can get a sense of the town’s history by reading its worn headstones. One of my favorite places is Harley Farms Goat Dairy. Best goat cheese I’ve ever tasted. Take a tour, it’s great for kids (no pun intended); meet the goats and llamas; stock up at its cheese store.

Where to Eat

Duarte’s Tavern specializes in fish and seafood (lines are out the door on weekends), and the Pescadero Country Store (tel. 650-879-041) added a brick oven this year and serves tasty pizzas. There’s also the excellent Los Amigos Mexican taqueria at the corner gas station. Don’t miss Arcangeli Grocery Co., aka Norm’s Market, which makes amazing Italian gourmet bread—especially its melt-in-your-mouth Garlic Herb and Artichoke Bread flavor. You can even shop online! The store also sells Harley’s goat cheese in case the farm is closed when you visit.

Where to Stay

Hands down, one of the coolest hotels I’ve seen lately is the Costanoa Lodge & Camp. It’s an eco adventure resort with accommodations ranging from tents and cabins with communal “comfort stations” (bathrooms, showers, saunas and fire pits) to a luxurious lodge and spa. Its grounds are connected to three state parks, with 40,000 acres of hiking, a wildlife reserve, tide pools and coastal dunes. Activities include horseback riding, kayaking, mountain biking and the Costanoa Kids Camp for 5- to 12-year olds. Rates start at $125 per night.

There’s also the charming Pescadero Creek Inn Bed & Breakfast in town, a renovated turn-of-the-century farmhouse with four rooms, each with an antique claw-foot tub. Rates start at $175 per night.

San Gregorio

Blink and you’ll completely miss San Gregorio, located about seven miles north of Pescadero and two miles east from San Gregorio Beach on Hwy. 84. Just about everything you could need or want is at the one-stop-shop San Gregorio General Store: groceries, restaurant, bar, bookstore, clothing, outdoor gear, housewares, maps, games, souvenirs, live music and the post office. Friends I’ve brought here love it, as do I, and many of the motorcyclists you’ll often see parked out front on weekends.

Woodside and La Honda

Those above-mentioned bikers most likely just came through Woodside and La Honda, two towns with interesting histories along Hwy. 84, which precariously winds its way from the flat inland part of San Mateo up and over the Santa Cruz Mountains via switchbacks, hence the popularity with the biker crowd.

Home to the native Ohlone/Costonoan people, the buttoned-down town of Woodside is one of the oldest English-speaking settlements on the south peninsula. Today it’s also one of America’s wealthiest, with residents including tech biggies Steve Jobs and Larry Ellison.

Filoli, built from 1915 to 1917, is one of the county’s older estates now open to the public. You might recognize it from the opening of the TV show Dynasty. The 36,000 square feet of interior space boasts massive marble fireplaces and period furnishings. Equally impressive are the grounds of the surrounding 16-acre formal garden. Special events are held throughout the year, and for families, there are education programs geared for 8- to 12-year-olds, children’s teas ($25 for kids ages 6 to 12), and the popular annual Easter Egg Hunt, which takes place the week before Easter.

Where to Eat

In town, eat at Bucks Restaurant, a popular place for breakfast, then check out Independence Hall and other historic structures in town, such as the Woodside Store, (tel. 650-851-7615 ) which also houses a museum with displays from the town’s early lumber days, and the Pioneer Saloon, established in 1880. To feast on succulent, locally sourced seasonal dishes, dine at The Village Pub, otherwise for more casual fare, grab a juicy burger and amazing garlic fries at Alice’s Restaurant on your way out of town at Skyline Blvd. and La Honda Rd. toward the town of La Honda.

Unlike conservative Woodside, La Honda was the birthplace of the psychedelic era. Ken Kesey lived in La Honda, which was the base for The Merry Pranksters. Bikers congregate at Apple Jack’s bar (tel. 650-747-0331) for live music, while the new Sullivan’s Restaurant & Bar (tel. 650-747-9664) opened this summer.

A Sampling of Inland Options

There are too many other attractions, restaurants and hotels in San Mateo County to name them all, but here are a few that stand out.

The Hiller Aviation Museum, in San Carlos on the Bay side of San Mateo County, is dedicated to the history of flight, particularly historical achievements that took place in Northern California. It’s a great stop for families, as there are interactive displays for kids, plus they (and you) can sit in the cockpit and manipulate the controls of a 747.

For a history lesson, visit the San Mateo County History Museum, located in Redwood City in the restored San Mateo County Courthouse, built in 1910. Don’t miss the impressive stained glass dome in the rotunda.

Where to Stay and Eat

Airport hotels have rarely (overseas only) impressed me, but my opinion changed after staying at both the Sheraton Gateway Hotel and the San Francisco Airport Marriott. Each is located in Burlingame along the San Francisco Bay and has recently been gutted and upgraded. The Sheraton is, dare I say, sleek, and even offers yoga mats. The Marriott includes the brand’s comfy new Revive bedding and a surprisingly excellent restaurant. Families can request cookies and milk at turndown, along with a plush stuffed Mr. Marriott teddy bear.

The hotels also are steps from a lovely running/walking path along the waterfront (had I known beforehand, I would have brought my gym shoes). If a convention or meeting isn’t in town, you should be able to find good value rates on weekends. San Francisco is 20 minutes away on U.S. 101, or take the complimentary shuttle from either property to the Caltrain station for a short ride into the city

Walking distance from the Sheraton is Kincaid’s Fish, Chop & Steakhouse. On the Friday I arrived it has a happening after-work bar scene to accompany its tasty dishes. Also reachable on foot is The Sherman, a new restaurant specializing in seasonal dishes and seafood, located on a restored army transfer ship build in 1922, docked in the Bay.

For luxury lovers, there’s also the Four Seasons Hotel Silicon Valley, technically in neighboring Santa Clara County, but just barely, and the new Rosewood Sand Hill hotel, located on venture-capital central Sand Hill Road near I-280, is scheduled to open in 2009.

Destinations: San Mateo County, Half Moon Bay, Woodside, Pescadero

Themes: Beach Vacations, Family Travel

Activities: Hiking, Golf, Horseback Riding, Kayaking, Shopping, Sightseeing, Wine Tasting

User Comments

I was lucky enough to grow up in Woodside, and it really is an amazing little town. Some my favorite places to eat in are Robert's Market (amazing deli), Woodside Deli (can you tell I love sandwiches?), Bucks (get a slice of their coffee cake!), Alice's Restaurant (in La Honda; it's a beautiful drive to get there), and Woodside Bakery.

Take the kids to Año Nuevo Get up close to giant elephant seals in the winter. The docent-led walking tours take about an hour. Appropriate for kids 5 and up. ?page_id=523

Fresh As It Gets Web site The SMCVB also has a Web site dedicated to fresh food in the county, www.freshasitgets.com. Find out where to buy fresh produce direct from farmers, when food events are taking place, interviews with local chefs and more.

San Mateo County CVB Another good source of information about upcoming events in the region is the San Mateo County CVB:

Event at Pigeon Point Lighthouse There's a free BBQ at the Pigeon Point Ligthhouse Hostel (to celebrate the anniversary of Golden Gate Hostels) this Sunday, 9/14, from 1-4 p.m. Surf-rockers, The Mermen, will play. You can take a tour through the grounds after the BBQ, then buy some strawberry desserts from Swanton Berry Farm. Sounds great to me!