The Twilight Parade route for 2025. (Image: City of Healdsburg)

Monday, May 19

  • Healdsburg Garden Club hosts fourth annual “Rose Show & Rose Arrangements Competition” at the Villa Chanticleer (1-3pm)
  • Jumpstart Your Art” working session for artists and creatives at The 222 (weekly, 1-4pm)
  • Dungeons & Dragons Campaign Club” for kids aged 8-18 at Heartizens (3:30-8:30pm)
  • Healdsburg City Council hosts closed meeting at City Hall to speak with labor union reps for electrical workers and firefighters (5-6pm)
  • Healdsburg City Council holds regular meeting at City Hall: Agenda includes design review of Laura Fish Somersal Park plans and discussion about choosing an official city plant/flower/tree (bimonthly, first and third Mon, 6pm)
  • Sonic internet company installing “underground telecommunications infrastructure” at Vine and Mill streets: Overnight work could block traffic (Mon-Tue, May 19-20, 9pm-6am)

Tuesday, May 20

  • Healdsburg Chamber of Commerce hosts social media marketing workshop at the CraftWork co-working space (8:30-10am)
  • Healdsburg Farmers Market on the plaza (9am-12:30pm)
  • “Ben’s Friends” group hosts sober meetup at Lo & Behold for “anyone struggling with addiction in the hospitality industry” (weekly, 10am)
  • Book club meeting at the Healdsburg Senior Center: Discuss “All Her Little Secrets” by Wanda Morris (monthly, third Tue, 10-11am)
  • Aikido class for adults at the Healdsburg Community Center (5:15-6:15pm)
  • Healdsburg Running Company hosts run to Solful weed dispensary for BBQ (6pm)
  • Echo Lens, an indie-rock band from West County, plays the Elephant in the Room pub (7:30pm)

Wednesday, May 21

  • Farm animals start arriving at Rec Park for the Healdsburg Future Farmers Country Fair (6am)
  • Teen hangout at the mini Healdsburg Library with rock painting activity (weekly, 1:30-3pm)
  • Intercambio” grupo de conversación / conversation group at the mini Healdsburg Library: Learn English or Spanish (weekly, 4:30-5:30pm)
  • The Raven Players theater troupe hosts season reveal party at the Raven Theater (5:30pm)
  • Healdsburg Unified School District’s board of trustees holds regular meeting at City Hall (monthly, third Wed, 6pm)

Thursday, May 22

  • Farm to Pantry hosts community garden workday at Mason Street Garden: Weeding, mulching, planting and more (weekly, 10am-noon)
  • Live jazz at Furthermore Wines (weekly, Thu-Sat, 5:30-8:30pm)
  • Healdsburg Future Farmers Country Fair hosts 76th annual Twilight Parade through town, followed by fair kickoff at Rec Park with Swan Brothers Circus (6-9:30pm)
  • Anna Moss, a New Orleans-based singer-songwriter, plays free show at Little Saint (6-9pm)
  • Voces y Pasos: A Cultural Celebration” at the Luther Burbank Center in Santa Rosa: Performances by 170-plus youth in the LBC’s after-school Mexican mariachi and ballet folclórico programs (7pm)
  • Beginning “Lindy Hop Swing” dance class at Dragonfly Farm & Floral (weekly, 7-8pm)

Friday, May 23

  • Healdsburg public schools closed for “FFA Day” (all day)
  • 76th annual Healdsburg Future Farmers Country Fair at Rec Park: Classic fair food, games, shows, contests, animals, exhibits and more (Fri-Sat, May 23-24, 9am-9:30pm)
  • Ribbon-cutting ceremony for JANE Dispensary, Healdsburg’s new cannabis store in the Mill Creek shopping center (noon)
  • Art therapist Erin Partridge hosts “intuitive movement to art” dance session at The 222 (weekly, 1-3pm)
  • The Fargo Brothers, seasoned roots rockers, play Coyote Sonoma (doors 5pm, show 6pm)
  • Friday night dance band at Longboard Vineyards: “A night of wine, classic rock and Mediterranean bites” (5-7pm)
  • Dry Creek Fridays” party at the Dry Creek General Store and Bar: Live music by Peyton Roze, food by Dan Lucia (weekly, 5-8pm)
  • Friday Night Live” concert series kickoff in downtown Cloverdale: Street fair with live music by “blue eyed soul” musician Eric Lindell (weekly, 6-9:30pm)
  • New family dramedy play at The 222: “The Burdens” (Fri-Sat, May 23-24, 7pm)
  • Domestic comedy play at the Raven Theater: “Home, I’m Darling” (Fri-Sat, May 23-24, 7:30pm)
  • Dans of Steele, a Steely Dan tribute band, plays the Elephant in the Room pub (8-11pm)

Saturday, May 24

  • Second annual Edge Esmeralda “popup village” at hotels and other venues across Healdsburg: “A monthlong gathering for people building a brighter future” (May 24-June 21)
  • Opening reception for new “Journeys” multimedia exhibit at the Healdsburg Center for the Arts (time TBA)
  • Healdsburg Farmers Market in the west plaza parking lot (weekly, 8:30am-noon)
  • Democracy rally on the plaza, at the corner of Healdsburg Avenue and Matheson Street (weekly, 11am-noon)
  • Read to a dog at the mini Healdsburg Library (weekly, 11am-noon)
  • Live music on the piazza at Bacchus Landing (weekly, noon-4pm)
  • Susan Sutton Trio plays live jazz at Hotel Healdsburg (weekly, 6-9pm)
  • Sol Horizon, a popular roots-reggae band, plays the Elephant in the Room pub (8-11pm)

Sunday, May 25

  • Alexander Valley Vineyards hosts first-ever summer marketplace series at the winery: “A farmers market-style shopping experience” (monthly through Aug 17, fourth Sun, 10am-2pm)
  • Avelo Airlines protest outside the Sonoma County Airport in Santa Rosa (weekly, 11am-2pm)
  • Dog-friendly joint birthday party at Smith Story Wine Cellars inside Bacchus Landing for winery co-founder Ali Story and her dog, Lord Sandwich: “Cold water bowls, Wagster treats, sauvignon blanc and buttery snacks” (11am-2pm)
  • Matinee performance of new family dramedy play at The 222: “The Burdens” (2pm)
  • Final matinee performance of domestic comedy play at the Raven Theater: “Home, I’m Darling” (2pm)
  • Vinyl Sundays” at Furthermore Wines: Listen to “great voices” records with jazz musician Stella Heath (weekly, 4-7pm)
  • Nick Otis Orchestra, an R&B band helmed by Johnny Otis’ son, plays the Elephant in the Room pub (6-9pm)
  • LOUIS: A Silent Film” screening at the Luther Burbank Center in Santa Rosa, with live backing concert by two famous jazz and classical musicians: “Pays homage to Louis Armstrong, Charlie Chaplin, beautiful women and the birth of jazz” (7pm)

Monday, May 26 🇺🇸🌙

  • City offices, libraries and schools closed for Memorial Day (all day)
  • Memorial Day garage sale at 230 Clear Ridge Dr. (8:30-11:30am)
  • Memorial Day Weekend celebration at Bacchus Landing, with wood-fired pizza and live music by the BoHoss Boogie Boys (11am-5pm)
  • Banshee Tree, an indie folk-pop band from Colorado, plays the Elephant in the Room pub (6-9pm)
  • Canadian alt-country singer Goldie Boutilier plays Little Saint, fresh off the BottleRock stage (6-10pm)
  • Bellydance basics class at Dragonfly Farm & Floral (weekly, 7-8pm)

Tuesday, May 27

  • Healdsburg Farmers Market on the plaza (9am-12:30pm)
  • “Ben’s Friends” group hosts sober meetup at Lo & Behold for “anyone struggling with addiction in the hospitality industry” (weekly, 10am)
  • Pizza & Posies” workshop at Dragonfly Farm & Floral: Combination pizza-making and floral-arranging class (10am-2pm)
  • City of Healdsburg’s Planning Commission holds regular meeting at City Hall (bimonthly, second and fourth Tue, 6pm)
  • First “Tuesdays in the Plaza” concert of the season in the Healdsburg plaza: Live music by Norteño band Los Cadetes de Memo Cavada (6-8pm)
  • Sparky Mark & The Funky Bunch, a funk-rock party band, plays the Elephant in the Room pub (7:30pm)
Note from Simone: These event listings originally appeared in the weekly email newsletter I write for the Healdsburg Tribune, called Healdsburg Today. Subscribe here!
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Simone Wilson is a former senior product manager and staff writer for the Healdsburg Tribune.