Two Books to Read Before Visiting San Francisco | Scott Benbow’s City Guide

San Francisco rewards curiosity. You can explore its neighborhoods, admire its architecture, celebrate its perfect weather, and run its Marathon. However, understanding the city requires a little more than a good map. Through many boom and bust cycles, San Francisco has reinvented itself repeatedly, and its history helps explain the city you encounter today. If you want to learn more about San Francisco before you visit, check out these two books that tell different parts of that story. Both are engaging histories, full of memorable characters, political battles, and the competing visions that have shaped San Francisco.

Written by Scott Benbow
Edited by Pavlína Marek

Season of the Witch: Enchantment, Terror, and Deliverance in the City of Love, by David Talbot (May 8, 2012).

If you want to understand the San Francisco that emerged from the Summer of Love, This book is the perfect start.

Talbot chronicles the tumultuous years from the late 1960s through the early 1980s, when counterculture, political activism, violence and social change collided.

The story brings together figures including Harvey Milk, Janis Joplin, Jim Jones and Dianne Feinstein, tracing the city’s struggles over its identity and its eventual emergence as a symbol of progressive politics and cultural experimentation.

This book about San Francisco is a sweeping, sometimes unsettling account of a city that has never been conventional. I’ve read the book and listened to the audiobook, the latter of which is an excellent companion for a long run. Put on your headphones, head out for a long run, and let Talbot take you through the city’s tumultuous past.

City on the Edge: Technology, Politics and the Fight for the Soul of San Francisco, by Jonathan Weber (June 9, 2026).

Weber picks up the story in the decades that followed, examining how San Francisco became the global center of the technology industry and how that transformation reshaped the city.

Drawing on his experience as a journalist covering Silicon Valley and San Francisco, he explores the rise of the internet economy, the arrival of tech workers and corporate buses, and the political and social tensions surrounding the city’s changing identity.

Along the way, Weber examines the competing interests that have made housing, economic inequality, and the future of San Francisco such contentious subjects. If you’ve ever wondered how a city associated with counterculture and progressive politics became the home of some of the world’s most powerful technology companies, Weber offers a useful guide to the forces behind that transformation.

This book is a timely read for visitors who want to understand the debates unfolding around them as they walk through the San Francisco’s neighborhoods. As of this writing, City on the Edge has not been recorded as an audiobook.

San Francisco’s history is too complicated to fit neatly into a single narrative. These two books approach it from different angles. Read them together, and you’ll gain a better appreciation for the people, conflicts and ambitions that have made the city what it is today. You might even find yourself looking at a familiar street or neighborhood a little.

About Scott

Scott Benbow is a San Francisco Marathon Ambassador, attorney, nonprofit specialist, and passionate SFM runner. He lives in San Francisco and runs the hills of our incredibly beautiful city with us every year.