• Dustin Saylor – Tuesday Plaza Concerts

    Healdsburg Plaza 100 Matheson Street, Healdsburg, CA, United States

    Dustin Saylor & The Stowaways are a powerhouse of the Northern California music scene, delivering an authentic blend of Americana, folk, and modern country. Driven by Saylor’s rich, gritty vocals […]

    FREE
  • Pepper On The Run Live

    Spicy Vines 441 Healdsburg Ave, Healdsburg, United States

    This sounds like an easy Saturday wine-and-music stop, with just enough groove to stretch the tasting into a real afternoon. Spicy Vines is a good fit for that kind of […]

    $15
  • Dancing Queen Disco

    Rodney Strong Vineyard 11455 Old Redwood Highway, Healdsburg, United States

    This is your permission slip to wear sequins in wine country and mean it. If ABBA, sunset, food trucks, and dancing sound like the plan, you’ve found the right party. […]

    $55
  • Ellie James at Breathless

    Breathless Wines 499 Moore Lane, Healdsburg, CA, United States

    A sparkling wine garden is a nice fit for an indie-pop afternoon, especially when you don’t want the day to feel too planned. This one has an easy Sunday shape. […]

    $21
  • Máxima Frecuencia – Tuesday Plaza Concerts

    Healdsburg Plaza 100 Matheson Street, Healdsburg, CA, United States

    Máxima Frecuencia is a rising, high-energy ensemble that brings a gritty, authentic passion to the modern Latin and Regional Mexican music scene. Specializing in hard-hitting Norteño rhythms and gripping Corridos, […]

    FREE
  • Sparkling Mahjong Social

    Breathless Wines 499 Moore Lane, Healdsburg, CA, United States

    This is basically bubbles, tiles, and friendly table energy, which is a very civilized way to make a weekday feel special. You don’t need a tournament face, just a willingness […]

    $26
  • Much Ado About Nothing

    Bacchus Landing 14210 Bacchus Landing Way, Healdsburg, CA, United States

    Shakespeare outdoors with wine nearby is a very Healdsburg way to spend a summer evening. Just bring a layer, because the charm does not cancel out Sonoma County’s after-sunset chill. […]

    $25
  • Whiskey Dent Live

    Spicy Vines 441 Healdsburg Ave, Healdsburg, United States

    If you like tasting rooms that actually feel alive during live music, this is the lane Whiskey Dent fits into. It’s a Saturday afternoon plan with a little more edge […]

    $1
  • Playing The Dead – Tuesday Plaza Concerts

    Healdsburg Plaza 100 Matheson Street, Healdsburg, CA, United States

    Rooted in a deep, authentic reverence for the Grateful Dead catalog, Playing The Dead captures the true, living spirit of the ultimate jam band experience. Rather than just offering a […]

    FREE
  • Burrows & Dilbeck – Tuesday Plaza Concerts

    Healdsburg Plaza 100 Matheson Street, Healdsburg, CA, United States

    If you are looking for a masterclass in seasoned, localized musicianship, Burrows & Dilbeck deliver the goods. Formed by Spencer Burrows (vocals/keyboards) and Kris Dilbeck (guitar/vocals)—the creative forces behind the […]

    FREE
  • Cassie B – Tuesday Plaza Concerts

    Healdsburg Plaza 100 Matheson Street, Healdsburg, CA, United States

    Cassie B is a powerhouse Top 40, Pop, and R&B band based out of San Diego, California. Fronted by the exceptionally talented singer-dancer Cassie B, this versatile group—which can scale […]

    FREE
  • Banda Potrero – Tuesday Plaza Concerts

    Healdsburg Plaza 100 Matheson Street, Healdsburg, CA, United States

    With a career spanning over three decades, Banda Potrero is a enduring staple in the Regional Mexican music scene. Splitting their time between Mexico and Los Angeles, this versatile group […]

    FREE
  • Super Diamond – Tuesday Plaza Concerts

    Healdsburg Plaza 100 Matheson Street, Healdsburg, CA, United States

    Super Diamond is here to completely shatter the stereotype Neil Diamond tribute bands. Formed in San Francisco in 1993, this powerhouse group has spent over three decades transcending the "cover […]

    FREE