Something Old, Something New - Exploring Historic Downtown Half Moon Bay

By Old World standards, Half Moon Bay is young. But in California history, the town dates back to the Spanish land grants issued in 1841 - and before that, the native Ohlone populated the area since around 320 AD. Half Moon Bay, called "Spanishtown" by the Anglo settlers who came with the great California Gold Rush of 1849, is blessed to have so many 19th century buildings around and near historic downtown Main Street.

One of my favorite tours is a stroll through downtown to see Half Moon Bay through the lens of its 19th century buildings. Along the way, I point out architectural highlights and what I consider some of the gems of this community - notably the Zaballa House (1855), the Pablo Vasquez House (1869), the Sperling House (1892), and the Community United Methodist Church chapel (1872). There are fascinating Old West and seafaring stories - including a few ghost stories - to share along the way. It’s a great introduction to a town where most people come just to eat and shop.


Don’t get me wrong: I love shopping at Posh Moon for wonderful and unique clothing and accessories from France and California, buying pumpkin caps at P. Cottontail for baby gifts, and completing my outfits with amazing jewelry from Personal FX. Food and drink abound as well. I love tiny Café Capistrano for its authentic Mayan cuisine and the best fish tacos around, Barterra Winery for its award winning wines and Tuscan villa courtyard, Pasta Moon for its wood-fired pizzas, and It’s Italia for its outdoor patio and Eggs benedict perched atop polenta cakes.


Some of our guests love to immerse themselves in the history of the town and we often book them into the Zaballa House, which is not only Half Moon Bay’s oldest building but now doubles as a bed & breakfast and home to a tiny Half Moon Bay history museum. There we meet them to orient them to the town and show them the highlights.

California history buff or just looking for a Bay Area getaway? Give us a call at 650-720-7050 or This email address is being protected from spambots. You need JavaScript enabled to view it. for more information. We lead groups from a single individual to 50, but we like to keep this particular hike intimate so I recommend a group size no bigger than 10 for this particular experience. See you in the woods!

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