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San Francisco has a lot of quirky history, and walking is a healthy way to explore a city. What are some good resources for learning about local history? Bonus points for anything free, cheap, or discounted. (Inspired by this other question about Emperor Norton.)
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Walking in San Francisco for Health and History is an active group on meetup.com that addresses this exact question. The group organizer plans walks in historic neighborhoods in SF and sometimes the nearby suburbs (generally Oakland / Berkeley). The events are free, but sometimes will incorporate a talk by a local history expert. If there are costs, they are low, and Howard always gives the members a heads up to chip in $5. (Disclaimer: I can vouch for Howard's prompt online communication, but I've never actually attended an event.)
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Walk San Francisco is an advocacy group that lobbies for pedestrian-friendly streets. They have an email list and an event calendar.
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San Francisco Walking Tours offers free tours of city neighborhoods nearly every day. If you've got a group, you can also reserve a private tour for around $10 per person.
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Thinkwalks.org - I was taking a friend to see Twin Peaks, and met Joel Pomerantz, who runs the show @ Thinkwalks.org. He seemed really cool and knew a lot about old San Francisco. I told him I would post about his site; Hello if you you're reading this!
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I used to download some free podcasts that were very good walking tours for certain neighborhoods! I'd post it as an answer, but I can't remember what they were called...