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What to Do in San Francisco This October: Castro Street Fair & Fleet Week

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The best of what to do in and around San Francisco this month.

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Halloween is on the brain in San Francisco this month, with a zombie prom, a boat party, and a tea party all celebrating the holiday. But the star of the month is the Fleet Week Air Show, where you’ll see death-defying stunts courtesy of the Navy’s Blue Angels.

AFAR Local is our monthly insider guide to the best of what’s happening in cities around the U.S.

October 1 | Culture
Castro Street Fair
Join 50,000 new friends as you explore the food and vendor options at the Castro Street Fair, which benefits 20 different nonprofit organizations that provide positive community services to the neighborhood. Check out the Rainbow Walk of Fame along Castro Street while you’re there—it pays tribute to LGBT icons from the Bay Area and beyond with commemorative plaques.
11:00 AM - 6:00 PM | Castro and Market Sts., San Francisco | Free | website

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October 6 - 8 | Festival
Fleet Week Air Show
In honor of Fleet Week in San Francisco (October 2-9), catch a zooming, acrobatic airshow from the U.S. Navy’s Blue Angels and the Canadian Snowbirds. You can hear them zip around all over the city (to some people’s consternation), but you’ll have to head down to the Marina Green for prime viewing boxes to see all the action and what the fuss is really about with a beloved annual tradition.
Marina Green, San Francisco | From $55 | website

October 6 - 8 | Music
Hardly Strictly Bluegrass
San Francisco’s massive annual free music festival, which attracts about 800,000 revelers over three days, has grown so far outside its already open-minded moniker to go well beyond Hardly Strictly Bluegrass. For instance, this year’s lineup includes Nigerian funk bandleader Seun Kuti (son of Fela Kuti) and his band Egypt 80, New Orleans bounce queen Big Freedia, local punk legend and one-time San Francisco mayoral candidate Jello Biafra, and even a silent disco propelled by local DJs, including disco veteran Steve Fabus and funk phenomenon Tom Thump. HSB is a chance to experience a world-class festival without experiencing ticket sticker shock.
Golden Gate Park, Hellman Hollow, 851 John F. Kennedy Dr., San Francisco | Free | website

October 6 - 14 | Literature
Surely no literary scene parties as hard as it does in San Francisco, where the annual Litquake Festival is a celebration of breadth, diversity, activism, and raucous fun. Check out readings and talks with both international and hyper-local subjects, such as the Fillmore’s jazz history and the East Bay’s Black Panther legacy. The festival concludes with Lit Crawl, where you can hop to different bars and venues and sample wildly different works, including action fiction, noir mystery, and drag queen reading.
Times and venues vary, San Francisco | Free | website

October 15 | Food
San Francisco Street Food Festival
Originally established in the Mission District by food business incubator La Cocina, the San Francisco Street Food Festival returns after a year break to cook up an even bigger and better event. This year it’s explicitly billed as a celebration of American food in its truest definition, with mobile vendors and restaurants offering affordable and portable bites and drinks that collectively represent the United States as one great melting pot made tastier with contributions from across the globe.
11:00 AM - 8:00 PM | Potrero Power Station, 420 23rd St., San Francisco | From $5 | website

October 19 | Holiday
Halloween Tea Party
If you’re ready to get in the Halloween spirit a little early and in an extra strange way, this Halloween Tea Party should do the trick. Patrons are encouraged to dress like a deceased loved one to ward off the spirits in the supposedly haunted Gregangelo Museum, a remodeled 1920s house in the tawny St. Francis Wood neighborhood, which you’ll tour after enjoying sips and light bites. With its weird and twisted retro circus vibes, it’s an odd artifact of old San Francisco.
7:00 PM - 9:30 PM | Gregangelo Museum, 225 San Leandro Way, San Francisco | From $85 | website

Hardly Strictly Bluegrass

October 21 - 22 | Dance
San Francisco Trolley Dances
Muni rides from SoMa to the Sunset will be a lot more cultured than usual this weekend, thanks to the annual San Francisco Trolley Dances. If you take the entire route from the California Institute of Integral Studies to Kezar Stadium on both days, you can enjoy live dance performances from host Epiphany Dance Theater, Chaksam-Pa Tibetan Dance & Opera Company, Embodiment Project, little seismic dance company, Maze Taiko, Texas Holly, and Oscar Velarde. You can also hop on and off to sample a wide variety of styles and movements.
Begins at California Institute of Integral Studies, 1453 Mission St., San Francisco | Free | website

October 27 - 28 | Holiday
LoveBoat Halloween
DJ and event promoter Motion Potion’s multi-genre Halloween dance parties—now known as LoveBoat Halloween—have been a popular San Francisco tradition for the past 10 years. This year’s two-day celebration features DJ sets from Moby and Fatboy Slim as well as a solid and broad lineup of local specialists like the Golden State Warriors’ DJ Umami, and Mysterious D from the popular mash-up party Bootie. A Burning Man contingent brings out art cars and ingenious costumery that add to the eclectic mix.
9:00 PM | Pier 70, 420 22nd St., San Francisco | From $90 | website

October 31 | Holiday
Halloween Zombie Prom
Just when you thought San Francisco had jumped the shark on adult proms, the Halloween Zombie Prom ambles along to shake up the now-traditional convention with some bloody good and scary fun (and scares that have prompted a warning not to indulge in psychedelics while there). Costume contests, dancing, Monster Mashing, pizza, and cake are activities and foods worth building an evening around, but if you don’t have enough confidence in your zombie makeup abilities, someone can do it for you on-site.
8:00 PM - 3:00 AM | The Great Northern, 119 Utah St., San Francisco | From $15 | website

November 23 | Plan ahead: Outdoor event
San Francisco Turkey Trot
Since 2003, the San Francisco Turkey Trot has gotten friends and families to exercise a little  around Thanksgiving. There’s still time to prepare yourself physically for either the five-mile Turkey Trail Trot run, the three-mile Pilgrim Promenade walk, or the 100-meter Kids’ Gobbler Chase, which all start and finish at the Polo Field in Golden Gate Park. No matter which pace you choose, everything benefits the track and field team at nearby Lowell High School.
Golden Gate Park Polo Fields, 1232 John F. Kennedy Dr., San Francisco | From $40 | website

Tamara Palmer is a daily news writer, rapper confidante, DJ, and celebrity chef ghostwriter from San Francisco.

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