Dating back to 1840, Half Moon Bay is the oldest town in San Mateo County. Traces of its past are visible in the many historic buildings as you explore Main, Purissima, and Johnston Streets "downtown". Cabrillo Highway (Highway 1) on the Coast, and Highway 92 over the mountains follow original Indian trails of the Costanoan Indians who lived here for hundreds of years. The Coastside was the first part of the Peninsula discovered by foreign explorers. During 1776, the year the United States was formed, Captain Gaspar de Portola founded San Francisco's Mission Dolores, and within a short time, the Coastside became the grazing land for mission cattle, horses, and oxen. More than 200 years later, much of the land is still used for grazing livestock.

In the 1840's, land grants were deeded to early Spanish settlers. The Dons came to live on their grants during the Mexican War. Later, Mexican and Chilean laborers settled here, and the village was dubbed Spanishtown. The first small Catholic chapel (no longer standing) was built in Pilarcitos Cemetery, which is visible from Highway 92 just east of Main Street. In 1874, Spanishtown officially became known as Half Moon Bay. The city of Half Moon Bay was incorporated in 1959.

In the late 1800's the area's character was again altered by the arrival of Canadians, Chinese, English, Germans, Irish, Italians, Scots, Portuguese, and Pacific Islanders. With the diverse representation of cultures, the Coastside became a prime example of the American melting pot.

Half Moon Bay was a thriving community in the late 1800s. The historic business district still shows signs of what downtown was like in those days.

To the south of Half Moon Bay there were stagecoach stops at Purissima, Lobitas, and San Gregorio. To the north, there were wharves at Miramar known as Amesport Landing and at Pillar Point for shipping.

The 20th century brought dramatic changes. The 1906 earthquake destroyed the last of the Spanish adobes, although wooden structures still remain. Another turning point was the construction of the Ocean Shore Railway. In 1908, the Railroad hugged the shoreline from San Francisco to Tunitas Glen. Passengers marveled at the stretches of sandy beaches perfect for picnics, kite flying, horseback riding, and exploring. Due to financial problems and the increasing popularity of the horseless carriage, the railroad ceased operation in 1920.

The Coastside came alive again during Prohibition. With hidden ocean coves and thick fog for cover, the setting was ideal for rumrunners from Canada.

From the 1920's to the present, growth has been slow but steady. Present day "explorers" of the Coastside will still see original farms dating back to the 1800's as well as miles of deserted white sandy beaches, redwood forests, beautiful state parks, fields of wild flowers, and hiking and biking trails along ocean bluffs and mountain ridges as far as the eye can see.

A house built by a dashing Mexican Don - Main Street
Pablo Vasques, son of a Mexican ranchero, built this redwood house in 1869. Over one hundred years ago, his fast horses, bullfights, and festive parties were the talk of the town.
A historic bridge over Pilarcitos Creek - North end of Main Street
Built in 1900, the Pilarcitos Creek Bridge was the first steel-reinforced concrete bridge in San Mateo County, and many people considered it quite innovative.
The oldest building on Main Street - 326 Main Street
Not only did Estanislao Zaballa build one of the earliest houses in the area (1859), he also mapped out the town.
The Bells of Half Moon Bay - Corner of Main Street and Kelly Avenue
In the early years of this century, school children responded to the toll of this original bell located at Mac Dutra Park. Firemen responded to another old bell now located at our new Fire Station at the south end of Main Street. (Neither bell is in its original location.)
A City Hall that looks like a bank - Main Street
Half Moon Bay City Hall (built in 1922) looks like a bank because it once was -- first called Bank of Half Moon Bay, then Bank of Italy, and later Bank of America.
A tiny jail - Johnston Street
Two cells and a small office remind us of simpler days on the Coastside during the first half of this century. The jail was built in 1911 and is open to the public.
A church and a railroad depot - Corner of Johnston and Miramontes Streets
The small building joined to the Community United Methodist Church (built in 1872) was once an Ocean Shore Railroad depot. Between 1908 and 1920, the train ran along the ocean bluffs a mile west of town. In 1930, the derelict depot was dragged to the church to become its social hall.

Princeton-by-the-Sea
Pillar Point Harbor and Princeton-by-the-Sea, once frequented by rumrunners and prohibition agents, now serve commercial fishermen and recreational boaters.

The trail north from Johnson Pier takes you to the public fishing pier on the inner breakwater. From the pier, around dusk, watch kwawking night herons leave their roost in the Monterey Cypress tree behind the Princeton Crab & Brewery Company.
The town of Princeton-by-the-Sea, noted for its streets named after famous colleges, was laid out in 1908 to serve the throngs of visitors who rode the Ocean Shore railroad trains from San Francisco to explore Coastside beaches.

Pescadero
A New England town on the Coastside -- that's Pescadero. The old frame houses and steepled churches reflect the town's pioneer Yankee roots, although today people of many cultural backgrounds call Pescadero home. A stroll around Pescadero reminds you of American small towns everywhere. A few restaurants, grocery stores, and a hardware store serve the needs of residents and visitors alike. But there is a difference. Instead of having a Main Street, Pescadero has a Stage Road running through town. Years ago, Pescadero was on the main road along the coast, and stage coaches brought hundreds of visitors to enjoy the famous resort hotels (now long gone) and Pebble Beach, two miles away.

The Pescadero Community Church, its steeple standing tall above the town, is a California Registered Landmark. Built in 1867 in the classical revival style, it is the oldest church in San Mateo County on its original site.

Montara & Moss Beach
Today, Montara, the first village south of Devil's Slide, contains approximately 3,000 people. It was founded around the turn of the century on a portion of the old Rancho Corral de Tierra by Harr Wagner, a San Francisco publisher. Wagner's hopes of establishing an art colony foundered with the demise of the Ocean Shore Railroad in 1922 and the fires of 1916 and 1920. Even the Sequoia gigantic planted by Joaquin Miller ("The poet of the Sierras"), who rode into town on the first passenger train, soon died as did Wagner's dream. However, today's population does include a number of writers and artists.

El Granada, Princeton & Miramar
El Granada, on the east side of Highway 1, offers restaurants and shops. Originally planned by the Ocean Shore Railroad as the "Jewel of the Coast," a grandiose resort to rival Atlantic City, the town was laid out by architect Daniel Burnham in a Beaux-Arts design of radial semicircular streets embellished with elaborate flower and tree plantings. The failure of the railroad cut short development, perhaps happily. The second half of the century has seen construction of some stunning and palatial hillside gems as well as admirable restoration of authentic, late 19th century weekend cottages.

Princeton's Cape Cod facade, with constant foot traffic exploring the seafood restaurants and quaint shops temporarily obscures the fact that one of the largest fishing fleets in Northern California operates from here. With an annual haul of ten million pounds of fish, one can buy fresh crab, salmon, squid, or whatever is in season right from the fishermen's boats, or sign up for a charter boat day trip to catch one's own. Whale watching is possible from both boats and a resident bi-plane.
Boat building and repair yards support both the 200-vessel fishing fleet the 170 recreational boats that moor in the fine marina protected on three sides by a beautiful rock breakwater. Only ghosts remain of the Portuguese sailors from the Azores who ran a whaling station here from 1860 until the 1890's.
Boat building and repair yards support both the 200-vessel fishing fleet the 170 recreational boats that moor in the fine marina protected on three sides by a beautiful rock breakwater. Only ghosts remain of the Portuguese sailors from the Azores who ran a whaling station here from 1860 until the 1890's.
Boat building and repair yards support both the 200-vessel fishing fleet the 170 recreational boats that moor in the fine marina protected on three sides by a beautiful rock breakwater. Only ghosts remain of the Portuguese sailors from the Azores who ran a whaling station here from 1860 until the 1890's.
Boat building and repair yards support both the 200-vessel fishing fleet the 170 recreational boats that moor in the fine marina protected on three sides by a beautiful rock breakwater. Only ghosts remain of the Portuguese sailors from the Azores who ran a whaling station here from 1860 until the 1890's.
Miramar Beach has nurtured the offbeat since 1964 when Pete Douglas's Sunday afternoon jazz gatherings became known as the Bach Dancing and Dynamite Society. (It's a great story, ask). Today, "The Bach" showcases world-class jazz and classical artists. There's also the New Age Center, built from found objects, and a cluster of architecturally startling cottages.
Site of the old Amesport wharf, built in 1868, and for many years the only consistently reliable link with the outside world, Miramar (Spanish for "behold the sea") Beach remains a sandy stretch popular with surfers and walkers.

San Gregorio & La Honda
Ten miles south of Half Moon Bay is San Gregorio Beach, the first and largest of a series of splendid state beaches. White sand, protecting cliffs, and a warmish lagoon create a pleasant spot for picnicking and beachcombing. One mile east on Highway 84 is the town of San Gregorio (population 150), famous chiefly for its extraordinary store, built in 1889. Kerosene lanterns, saddles, a surprisingly serious book section, home-baked goodies, live music, and a cowboy bar satisfy a wide spectrum of needs. A pottery shop next door showcases local artisans. Of late, the town has become a favorite location for film companies seeking "funky historical" backdrops.

In the 1850's, the San Gregorio House hosted prominent San Franciscans who traveled the long distance by stage to enjoy first class trout fishing, hunting, sea bathing, and boat races. The building still stands, but no longer functions as a hotel.
A drive eight miles deeper into the redwoods on Highway 84 brings one to La Honda (population 600), first settled in 1861. A forest retreat for San Francisco society in the late 1800's, it became a popular summering spot in the first part of this century. By the 1960's, it was discovered by counter-culture gurus such as author Ken Kesey. Today it boasts camps, gardens, several tasty eateries, a craft gallery, and burgeoning small businesses.