Your wine country summer bucket list

Five things worth putting on your calendar before the season slips away

Healdsburg summers have a way of filling up fast. One weekend it's the Fourth of July on the Plaza, the next it's harvest season and somehow three months went by. If you're trying to make the most of it — whether you're visiting for the first time or you've been coming here for years — here's what we'd put on the calendar.

Kids' Parade & Duck Dash · July 4

There's something about the Healdsburg Fourth of July that never gets old. Kids show up on bikes and wagons decked out in red, white, and blue, the Plaza fills up, and for a few hours it feels exactly like a small town should. Sign-up starts at 10:00 AM; the parade kicks off at 11:00 AM.

After the parade, stick around for the Duck Dash — organized by the Healdsburg Sunrise Rotary. Adopt a duck, watch it race, and know the donations go toward local scholarships, the Choices Program, Wonder League, and more. One of the best mornings of the summer.

Songwriters in Paradise · July 15–18, 2026

Four evenings, four wineries, and rotating songwriters performing intimate sets you don't get at bigger festivals. You’re close to the stage, the wine is good, and the views are incredible. Venues include The Ranch at Calegari Vineyards, Bricoleur Vineyards, Verité Winery, and Robert Young Estate.

Single-night tickets are available.

John Legend · July 31, 2026

“All of Me. Ordinary People. Tonight.”

John Legend brings his “An Evening of Songs & Stories” tour to Graton Resort & Casino, just a short drive from Healdsburg. It’s an intimate format, so tickets will go fast.

Location: The Event at Graton Resort & Casino

Gravenstein Apple Fair · August 8–9, 2026

Sebastopol’s annual celebration of the Gravenstein apple turns 53 this year with the theme “Where Joy Takes Root.” Two days of live music, apple tastings, cider, food vendors, artisan booths, and an Apple Pie Baking Contest.

Location: Ragle Ranch Regional Park, Sebastopol
Hours: 10 AM – 6 PM

While you're here

A few things worth doing:

• Rent a kayak and float the Russian River (Burke’s Canoe Trips in Forestville)

• Drive Dry Creek Valley on a weekday when it’s quiet

• Walk the Healdsburg Plaza early in the morning

• Visit the Saturday Farmers Market

• Drive out to Bodega Bay for the coastal views

And if you need a place to land, we've got you covered.

We might be biased, but we think we've got the best seat in the house. Wander Alexander Valley sits on 44 private acres in the hills above Alexander Valley — and it's about as far from a typical wine country rental as you can get. Think working ranch meets full resort: a pool and hot tub, a chef's kitchen built for long dinner parties, a Game Barn with bocce and pickleball, a Playbarn for the kids, horses to visit, private trails to explore, and a fire pit under more stars than you're used to seeing.

It sleeps up to 8 guests across four bedrooms, with enough space that a group can actually spread out. Most people show up with a packed itinerary of wineries and restaurants. Most end up spending more time on the property than they planned.

Healdsburg, Geyserville, and every event on this list are just minutes away — when you're ready to leave.

Book Wander Alexander Valley →