Explore Oakland’s wineries by bike on the East Bay Winery Bike Tours (Fridays, Saturdays, and Sundays, 11:30 a.m.), a group trip that takes cyclists to three to four of over a dozen small wineries that have opened throughout Oakland in the past five years. The $89 cost covers tasting fees and free transportation for any bottles or cases you buy.
Sample soon-to-be-released single-origin coffees for free at Blue Bottle’s headquarters (Saturdays at noon), which opened in this twenties-era warehouse last year. Pair your brew with treats like vanilla-saffron snickerdoodles and absinthe-sesame biscotti.
Skip Art Murmur's boozy First Fridays event—it now draws such large crowds that you can barely see the art. Instead, create your own art crawl among eleven of the area’s galleries, which host Saturday open houses. Start at Vessel, where sculptures, paintings, and handmade jewelry are showcased in a turn-of-the-century horse stable, and end at Flora, a flower depot turned cocktail bar that serves up unusual drinks like the Steps of the Empire: tequila, local citrus juices, and coffee-cinnamon-chipotle syrup.
Mingle with area hipsters at the Fox Theater, a lavish twenties movie palace that now hosts bands like Widespread Panic (October 15-17) and Florence and the Machine (November 5). Just don’t expect PBR: The Den lounge next door offers elderflower and Tuaca-infused cocktails, Pointe Reyes cheeses, and charcuterie from Berkeley's Star Meats.