If Half Moon Bay's historic Main Street could talk, it would share its long and captivating history with every sightseer and passerby.  From the earliest settlers of Native-American, Spanish, and Portuguese decent, through the Gold Rush, whaling and agricultural booms, Main Street promises to reveal the very soul of San Mateo County’s first town, Half Moon Bay.  

The old town district of Main Street serves as the very gateway to this magnetic seaside town. The historic motorway intersects highway 92, offering a nostalgic jaunt into the earliest established region of Half Moon Bay. Enveloped in rolling country side, evidence of a robust past is peppered throughout the downtown architecture, the retail establishments and unique cultural events.

Today’s modern Main Street maintains its quaint and relaxed atmosphere, offering some of the best-in class dining and unique shopping experiences, while maintaining much of its original character. It’s where locals go to eat, shop and socialize. It’s where the world-famous Half Moon Bay Pumpkin Festival takes place. It’s where people come to embrace local culture, celebrating and revitalizing Half Moon Bay’s history through unique events, landmarks, and the heritage of this aptly named thoroughfare. 

We encourage you to stay awhile, take in all the sights and experiences that this Main Street offers!

Main Street Inns

1855 Zaballa House

324 Main Street Half Moon Bay, CA 650-726-9123
Established as Main Street’s very first building, the Zaballa House was home to Mexican settler Estanislao Zaballa who also opened the first markets, saloons and stables on Main Street. Zaballa also mapped streets, blocks, and lots of the town. When you visit the iconic 12 room bed and breakfast, be sure to see their History Room’s collection of artifacts and an early Main Street diorama of the1860’s. 

San Benito House

356 Main Street Half Moon Bay, CA 650-726-3425
The charming San Benito House is one of the earliest hotels. Rooted as the town’s first namesake, this hotel includes one of the town’s best delicatessens with homemade breads, a beautiful period cocktail bar and sprawling outdoor deck with fire pit for casual dining. The inn reminds its visitors that it’s not for light sleepers!

Mill Rose Inn

615 Mill Street Half Moon Bay, CA 650-726-8750
This 1901 cottage is one of the first bed and breakfasts on the coastside, offering opulent décor and period furnishings in a beautiful country garden setting. The current Innkeepers have owned the Mill Rose Inn for nearly 40 years, welcoming visitors into their beloved and charmed establishment for overnight stays, special events and business meetings.

Nantucket Whale Inn

779 Main Street Half Moon Bay, CA 650-726-1616
This 1898 Victorian was featured in the January 2016 issue of Travel & Leisure Magazine's "Five Winter Getaways We Love Near San Francisco". Extensive renovations provide for a delightfully updated décor that’s modern and tasteful but comfortable and cozy inn.

Other Points of Interest

Half Moon Bay Jail, established in 1911 is now the location of the Spanish Town Historical Society Museum and Mary Vallejo History Center. 505 Johnston Street

Giuseppi Boitano’s General Merchandise Store and Saloon (1873) – This is the oldest place of continuous retail business in town.

The Historic Bridge over Pilarcitos Creek, located at the north end of Main Street, was among the first steel-reinforced concrete bridges in the world. Built in 1900, it was the very first in San Mateo County. The steel used for reinforcing was the used cables from the San Francisco Cable Car system. 527 Main Street.

Mac Dutra Park/The Bells of Half Moon Bay (corner of Main Street and Kelly Avenue)
In the early years of the 20th century, school children responded to the toll of this original bell located at Mac Dutra Park. Mac Dutra Park has recently been renovated serving as an outdoor stage venue for scheduled Music in the Park.

Half Moon Bay City Hall c1922, this quaint building looks like a bank because it once was. It was first the Bank of Half Moon Bay, then Bank of Italy, and later Bank of America. 501 Main Street
Community United Methodist Church - Built in 1872, it is the oldest church still standing today and with a thriving community of parish. 777 Miramontes Street

The Johnston House c1855, the beautifully restored home is at the south end of Main Street, and is open for tours and annually opens its doors as a Holiday boutique. The Johnston House was among the first built on the coast, by Mr. James Johnson who settled here from the east.

Half Moon Bay Bakery - Originally established by Italian immigrant Nat Castiglione (c1929), this bakery become famous for its delicious Italian bread, baked in its original brick ovens, which are still in use today. 514 Main Street, Downtown Half Moon Bay.

Dining, Retail and Recreation

The Downtown area boasts numerous retailers and restaurants, ranging from art galleries, bakeries, and one-of-a-kind boutiques offering unique apparel and fine quality home goods. 

As you stroll through town, stop in for some tastings at the Half Moon Bay Wine & Cheese, or drop over the southern end to Sacrilege Brewing for bites and home brews. Outdoor dining options at several of the Main Street restaurants, such as its Italia, and San Benito provide for a pet friendly and a relaxed atmosphere.

The shopping experience on Main Street is as diverse as the town’s earliest settlers. Visit the many boutique clothiers such as the Crow’s Nest, or the alluring hand-crafted furniture at Cottage Industries or you can opt to grab some picnic items from Historic Cunha’s Market before visiting the local beaches.

Historic Main Street includes plenty of recreational activities for the little ones. Oddyssea provides opportunities for creative play. La Petite Baleen Swim School offers swim lesson opportunities and the new and beautifully constructed Boys and Girls Club Gymnasium on Kelly Avenue offers additional options for your youth to experience in a day.

Whether its souvenirs to take home, the latest in coastal fashion, or stunning jewelry for a loved one, Main Street offers something for everyone and at every budget. The small-town hospitality of this old town district promises to deliver everything a visitor might want to experience in the very special beach town of Half Moon Bay.