September
SUP race
Red Bull Heavy Water Race | Brian Bielmann/Red Bull Content Pool

September

Thursday - Wednesday
Sep 1-28
Ocean Beach to Golden Gate Bridge
Thought stand-up paddleboarding was a leisurely activity? Think again. Forty of the world’s best stand up paddleboard (SUP) athletes will race a 12km open course from Ocean Beach to the Golden Gate, battling huge waves the entire time. This event is ongoing through September, so you’ll need to check the site to find out when it all goes down.
Saturday
Sep 10
Charles Krug Winery, St. Helena
Celebrate 65 years of drinking and dining at Tastings on the Lawn. Host Charles Krug Winery is throwing an Americana-themed party featuring BBQ, live music, and, of course, new release wines. Bring a lawn chair and a picnic blanket.
Saturday - Sunday
Sep 10-11
Ghirardelli Square
The 21st Ghirardelli Chocolate Festival is your opportunity to eat tons of chocolate from noon to 5pm. You’ll want to buy a “Lounge” ticket if you’re 21+ as that’s the place to sip samples from local wineries and breweries, while tasting yummy desserts.
Saturday
Sep 17
Social Hall SF
SF Cheese Fest is back for a second year with samples of dozens of cheeses, alongside cured meats, pickles, jams, craft beer, and wine. So basically: heaven.
Saturday - Sunday
Sep 17-18
Lake Merritt, Oakland
Watch a fleet of colorful 40ft dragon boats race through the waters of Lake Merritt during the free two-day International Dragon Boat Festival. Also on tap are live music, a traditional Chinese ceremony, and lots of food.
Sunday
Sep 18
Sharon Meadow, Golden Gate Park
See more than 40 comedians on one stage for five hours at Comedy Day, a free performance in the park. And yes, since it’s free, that means you can boo if someone bombs. (But no one will.)
Friday
Sep 23
San Francisco Marriott Marquis
WhiskyFest is one of the most popular whiskey festivals in the world because you get to taste more than 300 whiskeys and indulge in a never-ending buffet. Plus, there are seminars and stuff, but mostly: whiskey!
Friday - Sunday
Sep 23-25
Pier 48
Oktoberfest by the Bay is back with tasty food, a 21-piece Bavarian band, dancing, and, last but not least, lots and lots of beer. Lederhosen not required, but... you should wear lederhosen.
Saturday
Sep 24
Marin County Fairgrounds
CLIF Bar CykelScramble is a totally free event where you get to watch teams relay race around a crazy bike track, all while enjoying food and beer trucks, and listening to Portugal. The Man. Did we mention it’s free?
Sunday
Sep 25
Folsom Street between 8th and 13th Streets
Folsom Street Fair, the city’s huge outdoor fetish festival, brings more than 400,000 fetish enthusiasts to SoMa for something other than brunch. Stroll 13 SF blocks to check out booths with fetish gear and toys, dance to EDM, and show off your leather, rubber, latex, or steel. Or, you know, just walk around buck naked.
Thursday
Sep 29
California Academy of Sciences
Sharktoberfest NightLife is you chance to check out the California Academy of Sciences for just $15. Enjoy a 21+ crowd and a pop-up beer garden with dozens of local breweries and a shark-tastic theme.
Friday - Sunday
Sep 30-Oct 2
Golden Gate Park
Hardly Strictly Bluegrass is possibly SF’s best festival not only because it’s free, but because you can BYO beer and wine and BYO canine companion. Oh, and also because there are more than 100 musicians performing more than just bluegrass music (confirmed acts include Cake, Dropkick Murphys, and Cyndi Lauper) on seven stages.
October
The San Francisco BBQ Festival
Ribs from The San Francisco BBQ Festival | Courtesy of The San Francisco BBQ Festival

October

Saturday
Oct 1
The Armory
Sake Day is your chance to taste and buy over 200 sakes and test your sake knowledge at sake challenge stations. Yes, that’s a lot of sake, and yes, it’s worth it.
Sunday
Oct 2
Market and Castro Streets
The Castro Street Fair, a community celebration that was founded by Harvey Milk in 1974, will be going off from 11am to 6pm with live entertainment, dance stages, tons of good food, and lots of exhibits from local artists.
Friday - Monday
Oct 7-10
Various locations
San Franciscans love to bitch about the Fleet Week, but you can’t deny that watching the ships come in and the Blue Angels fly through the air is always a mesmerizing display. Plus, who doesn’t love a sailor? Find a seat with a view of the Bay and look to the sky.
Friday - Saturday
Oct 7-15
Various locations
Litquake is a nine-day literary festival for book lovers, complete with panels, readings, and even a literary bar crawl at various locales in the city. Because even the smart people in SF still love a bar crawl.
Monday
Oct 10
City View at Metreon
Wine & Spirits Top 100 Tasting gives you the opportunity to taste wine from this year's top wineries, meet the winemakers, and snack on delicious bites from notable Bay Area restaurants. Can you taste all 100? (We bet you can.)
Friday - Saturday
Oct 14-22
The Cow Palace
Throw on your oversized belt buckle and your boots because the Grand National Rodeo is back for two weekends of classic rodeo horse shows, a livestock exposition (cows, pigs, sheep, goats, and rabbits!), plenty of BBQ, and lots of shopping.
Saturday
Oct 15
20th St between Wisconsin and Missouri streets
The Potrero Hill Festival, a neighborhood street fair, brings together good food, local artists and musicians, and lots of entertainment for the kiddos (and their adults, too).  
Saturday - Sunday
Oct 15-16
Treasure Island
Sigur Rós, Ice Cube, Purity Ring, Glass Animals, and a ton of other acts are performing at this year’s Treasure Island Music Festival, so get your tix now.
Saturday
Oct 22
The Yard at Mission Rock
The second annual SF BBQ Festival promises to be even bigger and tastier than last year with more than 40 competition teams serving up grilled and sauced meat, as well as 15 local breweries, live music, and a cornhole tournament.
Saturday
Oct 22
Fisherman’s Wharf
Wharf Fest is the perfect time to hang out on the waterfront. The tourists are (sorta) gone, the sun is still shining, and there’s a battle of the bands and a chowder cook-off competition!
November
Taste San Francisco
The James Beard Foundation's Taste San Francisco | Marc Fiorito, Gamma Nine

November

Friday
Nov 4
The InterContinental San Francisco
The James Beard Foundation’s Taste San Francisco is an exclusive dining event with a cocktail and tasting reception followed by dinner and featuring chefs from ICHI Sushi + Ni Bar, The Slanted Door, Luce, Mister Jiu’s, and more.
Saturday - Sunday
Nov 5-6
Fort Mason
SnowBomb’s annual ski and snowboarding festival is the place to go if you need new gear or just want a bunch of free lift tickets. If you get the VIP pass ($50), you’ll also get unlimited beer and wine tastings and even more cool stuff.
Friday - Sunday
Nov 11-13
Pier 35
It’s easy being green thanks to the Green Festival Expo, an event that’s all about sustainability and green living where you can check out green products and services and learn how to live a healthier and more sustainable life.
Sunday
Nov 13
The Regency Ballroom
Over 50 barbacks from San Francisco's top spots, like LihoLiho, Trick Dog, and Comstock Saloon, will compete in Fernet's 10th annual Barback Games. You’ll have a much better appreciation for your favorite bar’s staff after watching them go head-to-head in competitions like spill clean-up -- how quickly can they navigate an obstacle course to clean up that  spilled beer and Fernet shot? -- and a keg changing relay. 
Saturday - Sunday
Nov 19-27
Moscone Center
The theme of this year’s 59th annual SF International Car Show is “technology and future of personal transportation” -- but we just want to go because there’s sure to be tons of automobile porn.
Saturday - Sunday
Nov 19-Dec 18
Cow Palace Exhibition Halls
If you love Christmas, you’ll love The Great Dickens Christmas Fair. Exhibition halls are transformed into Christmas Even in old London, complete with pubs, music halls, tearooms, costumed characters, and plenty of places to shop for gifts.
Thursday
Nov 24
Golden Gate Park
Do a quick five-mile Turkey Trot before you feast on Thanksgiving dinner and earn a third piece of pie.