Farmers Market with music on Friday evenings (free).
Ruth McGowan's Pub for music
Broadway Under the Stars from the Transcendence Theatre Company has various weekend shows (plus some weekday performances) from mid-June through mid-September. These Broadway productions usually take place in the Jack London State Park.
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First Friday Sunsets at Gary Farrell Winery. On the first Friday of May-October you can sip on wine and watch the sun go down.
Summer music concerts at Rodney Strong Winery. About once a month headliners visit their outside music venue.
Tuesday night concerts in the town square from late May through August. Pack a bottle of wine and a blanket to sit on (free).
The town has a good music scene with Cinnabar, McNears/Mystic, and Zodiacs.
Graton Resort and Casino is a Vegas-style casino with lots of restaurants and entertainment.
Green Music Center on the Sonoma State campus, home to the Santa Rosa symphony with many other guests on the calendar.
Spreckels Performing Arts Center with live theater and musical shows.
D'Argenzio Wine Down Thursday.
Wines and Sunsets at Paradise Ridge Winery on Wednesday evenings. Music, wine, food (or BYO dinner), and get the second best sunset in the county (the best is at the coast if it's not fogged in).
Downtown Market on Wednesday nights. Flea market, music and food vendors (free).
Concerts Under the Stars, Montgomery Village Shopping Center every other Thursday beginning June 11th (free).
Live at Julliard Park. Music on Sunday evenings (free).
Wells Fargo Center for the Arts for live theater and concerts. This summer you'll find everything from Whitesnake to Diana Krall.
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Hopmonk Tavern has live music, sometimes nationally known acts.
There are many tasting rooms on or near the town square; many are open into the evening.
Farmers Market on Tuesday evening (free)
Sebastiani Winery Summer Music Series on Friday evenings. Live music and food available.
(Very) minor league professional baseball played by the Sonoma Stompers.
Thursday Night Market. Much more than a farmers market, it's more of a town celebration with food trucks, music, and lots of people (free).
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For a full listing of summer 2015 events see this earlier blog post.