• TGIF at Twomey

    This is a pretty painless way to slide into the weekend: vineyard views, a glass in hand, and no need to overthink dinner-party-level plans. It’s relaxed, polished, and very Russian River. This is TGIF at Twomey, a monthly third-Friday event at Twomey Russian River Valley on June 19 from 5:00 PM to 7:00 PM. The […]

    $20
  • Summer Garden Party

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

    This is summer wine-country without the stiff collar: music, a picnic feel, flowers, and something fun for all ages. It’s more backyard celebration than formal tasting. This is Summer Garden Party at Rodney Strong Vineyards on Saturday, June 20, 2026, from 2:00 PM to 5:00 PM. The event takes place on the Terrace and The […]

    $30
  • Fathers Day Weekend

    Convene by Dan Kosta 14210 Bacchus Landing Way (Ste 300), Healdsburg, CA, United States

    Father’s Day weekend feels a little better when Dad gets handed Pinot before anyone asks what the plan is. This one is low-pressure, wine-country simple, and easy to fold into a Healdsburg afternoon. This is a Father’s Day weekend wine tasting at Convene by Dan Kosta at Bacchus Landing on June 20 and June 21 […]

    TBD
  • Yappy Hour on The Terrace

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

    This is for people who think happy hour is better when the dog gets invited too. It’s simple: wine for you, treats for them, and a terrace setting that doesn’t over-complicate it. This is Yappy Hour on The Terrace at Rodney Strong Vineyards on Sunday, June 21, 2026, from 2:00 PM to 5:00 PM. Guests […]

    FREE
  • Shawn Jones – Tuesday Plaza Concerts

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

    The Shawn Jones Band delivers a masterclass in independent, soul-stirring musicianship. Fronted by Southern California-based singer, songwriter, and exceptional guitarist Shawn Jones, this powerhouse act seamlessly blends a raw, dynamic mix of Roots, Americana, Blues, and Rock. Whether they are stripping it down for an intimate, soulful acoustic set or blowing the roof off a […]

    FREE
  • Sky Eyes – Tuesday Plaza Concerts

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

    Sky Eyes is an infectious, genre-blending musical project led by a charismatic Caribbean artist hailing from the island of Martinique. Known for injecting a fresh energy into the West Coast live music scene, the band seamlessly bridges the gap between traditional roots reggae, modern hip-hop, and slick jazz improvisations. Backed by a rotating, tight-knit collective […]

    FREE
  • Live Music on the Piazza

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

    This is one of those Bacchus Landing afternoons where you can wander, sip, listen, and decide later if you’re staying for pizza. It’s relaxed in the best wine-country way. This is Live Music on the Piazza at Bacchus Landing, a first-Saturday music series from 12:00 PM to 4:00 PM. Guests can enjoy live music on […]

    FREE
  • Stella Heath Live

    Spicy Vines 441 Healdsburg Ave, Healdsburg, United States

    If you like your wine tasting with a little live-room energy, Spicy Vines is built for exactly that kind of afternoon. It’s cozy, social, and not trying to be a hushed library. This is a Saturday Live Music & Tasting Experience at Spicy Vines featuring Stella Heath live in the tasting room. Guests can reserve […]

    $1
  • Nick Foxer at Breathless

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

    Bubbles and classic pop-rock on a garden patio is a pretty painless way to spend a Sunday. It’s casual, sunny, and low-commitment in the best way. This is Nick Foxer at Breathless Wines as part of the Breathless Bubbles & Music Sunday Summer Music Series, with performances in the series running Sundays from 2:00 PM […]

    $21
  • Aki Kumar – Tuesday Plaza Concerts

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

    Hailed as the "King of Bollywood Blues," Aki Kumar is a dynamic, San Jose-based frontman and masterful harmonica player who has carved out a truly one-of-a-kind niche in the contemporary music scene. Originally leaving Mumbai for Silicon Valley to work as a software engineer, Kumar abandoned the tech path after discovering a deep, life-changing passion […]

    FREE
  • Pizza Night on The Terrace

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

    Wood-fired pizza, live music, and Rodney Strong wines is not a complicated pitch, and thankfully it doesn’t need to be. This is the kind of Friday evening that sells itself. This is Pizza Night on The Terrace at Rodney Strong Vineyards on Friday, July 10, 2026, from 5:30 PM to 7:30 PM. The event includes […]

    $65
  • Back to Where It All Began: A 25-Year Celebration

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

    This is a nostalgia tasting, not a flashy production, and that’s the charm. Rodney Strong is leaning into the old-school Cellar Door feeling for a quarter-century toast. This is Back to Where It All Began: A 25-Year Celebration at Rodney Strong Vineyards on Saturday, July 11, 2026, from 10:30 AM to 5:00 PM. The winery […]

    FREE
  • Bastille Day Brunch

    Jordan Winery 1474 Alexander Valley Rd, Healdsburg, CA, United States

    This is the kind of brunch that turns a holiday nod into a whole polished wine-country afternoon. It’s French-inspired, seated, and definitely more “plan ahead” than “drop by.” This is Bastille Day Brunch at Jordan Winery on Saturday, July 11, 2026, from 11:00 AM to 2:00 PM. The event features a four-course French-inspired brunch on […]

    $175
  • 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 and a genuine, soul-searching lyricism that has earned him comparisons to Chris Stapleton and Johnny Cash, the band has steadily grown from a beloved local […]

    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 casual live set. This is Pepper On The Run live at Spicy Vines on Saturday, July 18, 2026, from 3:00 PM to 6:00 PM. Guests […]

    $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. This is Dancing Queen Disco at Rodney Strong Vineyards on Saturday, July 18, 2026, from 6:00 PM to 9:00 PM. The 21+ outdoor party on […]

    $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. This is Ellie James at Breathless Wines on Sunday, July 19, 2026, from 2:00 PM to 4:00 PM, as part of the Breathless Bubbles & […]

    $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, they are a band that prioritizes raw, unvarnished emotion over studio-polished perfection. ✅  See video below. HiH Hint: You can reserve your spot by setting […]

    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 to play. This is Sparkling Mahjong Social at Breathless Wines on Thursday, July 23, 2026, at 12:30 PM. The event features American-style Mahjong social play […]

    $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. This is Much Ado About Nothing at Bacchus Landing, running July 23 through August 7, 2026, with evening performances at 7:30 PM. The Raven production […]

    $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 than another quiet flight. This is Whiskey Dent Live at Spicy Vines, part of the winery’s Saturday Live Music & Tasting Experience. Guests can reserve […]

    $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 rigid, note-for-note copy of the studio tracks, this talented collective of seasoned musicians leans honestly into the element that made the Grateful Dead a phenomenon: […]

    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 award-winning North Bay super-funk-rock band Frobeck—this duo is a prolific songwriting powerhouse with over 65 original tracks to their credit. They artfully blend soul, funk, […]

    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 up from a trio to an impressive 10-piece lineup—is widely recognized for its vibrant energy and unmatched vocals. Formed originally in 2015, the band has […]

    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 has carved out a unique niche by blending traditional banda sounds, tamborazo, and mariachi with unexpected genres—most notably pioneering a fun, high-energy "Rock-Quebradito" style in […]

    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 band" label by delivering a high-octane, arena-grade rock show. Led by the uncanny vocal styling of Randy Cordeiro (affectionately known as "The Surreal Neil"), the […]

    FREE