Fun Outdoor Activities in San Francisco

October in San Francisco has long been locals’ favorite time of year – the sun seems to shine a little brighter, the streets are less hectic, and pumpkin spice everything is back on the menu. There’s so much of outdoor San Francisco to see and do this month, and with the thermometer set to rise into triple digits this week it’s the perfect time to get out there and experience it all for yourself! As always, the best way to navigate the city is by bicycle.

Hardly Strictly Bluegrass has been a Bay Area staple since the first event in 2001, with San Francisco locals and visitors turning out every year in huge numbers to the 100% free and non-commercial music festival in Golden Gate Park. Since its inception, the festival has been funded by local venture capitalist Warren Hellman (Hellman Hollow in the park was re-named in his honor in 2011 to acknowledge his contribution to the arts and public health), and a staggering number of world-class musicians have graced its stages over the last two decades.

Crowds fill Hellman Hollow for the 2010 festival

Crowds fill Hellman Hollow for the 2010 festival

Ryan Adams, Yo La Tengo, Béla Fleck and festival regular Emmylou Harris will headline the event this year, which takes place over Friday 3rd, Saturday 4th, and Sunday 5th October. Thousands are expected to attend each day, so beat the crowds packing out the Muni buses and take advantage of the festival’s awesome valet bike parking program! For more information on the lineup and getting to the event, check out the official website here:

If bluegrass isn’t your thing, why not check out the Castro Street Fair? Started by Harvey Milk in 1974, the first Sunday of October traditionally plays host to this event, bringing out hundreds of local artists, vendors, and organizations. The fair always has and always will be completely non-profit, with all proceeds going directly to charitable organizations and to fund the iconic rainbow flag at the intersection of Castro and Market. DJs, dance competitions, Broadway, and drag performances all feature in the lineup this year, and it’s sure to be a fantastic and fabulous slice of San Francisco life! For more info, visit the fair’s official website:

Harvey Milk at the 1974 Castro Street Fair

Harvey Milk at the 1974 Castro Street Fair

The beautiful weather always makes October a big month in San Francisco, and this weekend will kick everything off in style. Whether it’s any number of street fairs, festivals, or just soaking up the rays in one of the city’s gorgeous urban parks, get out there like the locals do – on your bike!

Photos copyright Castro Street Fair, 2014

Additional Blog Posts

Wharf Fest Stage and Crab Wheel

We had a great time at the 2017 Fleet Week festival, and in just a few weeks we'll have another special event - Wharf Fest! This uniquely San Francisco event celebrates our little corner of the Bay Area, and we hope to see you for the fourth annual Wharf Fest next Saturday, October 21! 

Blue Angels fly over the Golden Gate Bridge

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Bike to Work day is coming up next week on Thursday, May 11, and we want everyone to try out the most fun, healthy, and clean way to get to work - a bicycle commute!