Mid-May is one of my favorite weekends in Silicon Valley. The wine country an hour north is in full spring bloom, the local concert calendars are loaded, and the brunch reservations from Mother’s Day weekend have finally let up — you can actually get a Saturday-morning table without a 90-minute wait. Whether you want to drive up to Sonoma for a four-day food festival or stay local for a Saratoga foothill concert, here’s the curated list of what’s actually worth your time May 15–17, 2026.

Friday May 15 — Comedy, Concerts & Sommelier Battles

Mountain Winery, Saratoga — Chelsea Handler, 8:00 PM

14831 Pierce Rd, Saratoga. Chelsea Handler kicks off her Mountain Winery date Friday night. The hilltop venue itself is the real attraction — sunset over the Saratoga foothill vineyards, dinner-and-show packages, the historic Paul Masson stone winery as backdrop. Tickets via mountainwinery.com.

Healdsburg Wine & Food Experience opens (May 14–17)

The fifth annual Healdsburg Wine & Food Experience runs four days across Sonoma County, with nearly 20 events. Friday’s anchor: the Sommelier Showdown Dinner at Dry Creek Kitchen — domestic and international sommeliers compete pairing wines with a chef-crafted menu, guests vote for the winning pairing. Friday also features an outdoor concert at Rodney Strong Vineyards with guitarist Grace Bowers and singer-songwriter Hannah Ellis. Healdsburg is a 90-minute drive from Palo Alto — doable for a Friday night, ideal as a 2-night stay.

Analog Reunion Festival — opens at Wildhaven Sonoma

2411 Alexander Valley Rd, Healdsburg. Three-day immersive festival of music, arts, food, and wine beneath the redwoods along the Russian River. Runs May 15–17. If you wanted a full long-weekend escape with single-venue logistics, this is it.

Willie Wonka Jr opens — Playful People, San Jose

Family-friendly stage production runs May 15–24 in San Jose. Tickets via Playful People Productions. A solid Friday-night family option if you’re staying local.

Mountain Winery’s hilltop terrace at sunset is the real draw — the act on stage is the bonus. Spring vineyard views are at peak this weekend.

Outdoor concert silhouette at golden hour — Mountain Winery in Saratoga, Rodney Strong in Sonoma, and Wildhaven all bring this energy this weekend.

Saturday May 16 — Wine Country in Full, Plus Local Festivals

Healdsburg Wine & Food Experience continues

Saturday’s anchor event in Healdsburg: “150 Years of Beringer Vineyards”, a seminar moderated by Ray Isle, executive wine editor at Food & Wine magazine, pairing rare Beringer wines with food from chefs Charlie and Reed Palmer. Plus tastings, masterclasses, and lunch-and-pour events across nearly 20 Sonoma venues.

South Bay AANHPI Festival — San Jose

Local Asian American, Native Hawaiian and Pacific Islander cultural festival in San Jose. Cuisine, dance, music, vendors. Free family-friendly day event — check official AANHPI Heritage Month calendars for exact location and program (typically downtown San Jose civic plazas).

Saturday morning hikes (still peaking)

Mid-May wildflowers are still at peak across the Bay foothills. Best Saturday-morning options:

Wildflowers across the Bay foothills are still at peak through mid-May. Russian Ridge is the standout this weekend.

Hilltop sunset with red wine — the Healdsburg Wine and Food Experience wraps Sunday with exactly this kind of view.

Sunday May 17 — Pizza & Pinot, Candlelight Concert

Hammer Theatre — Candlelight: Tribute to ABBA, 8:45 PM

101 Paseo De San Antonio, San Jose. The Candlelight Concert series returns to Hammer Theatre with a string quartet playing ABBA’s greatest hits surrounded by hundreds of candles. Intimate venue, beautiful setup, broad appeal — works equally well as a date night or a low-key Sunday outing. Tickets via hammertheatre.com or feverup.com.

Pizza & Pinot Party at Copain Winery (Healdsburg)

Sunday’s standout Healdsburg event: handmade pizzas by chefs Ari Weiswasser (Glen Ellen Star) and Joe Sasto paired with Copain’s Pinot Noir program. Casual outdoor format, beautiful Anderson Valley setting. If you stayed up Friday and Saturday, this is the perfect Sunday closer before the drive home.

“Don’t Bust My Chops — Red Wine Loves Lamb” (Healdsburg)

Lunch-and-learn pairing event at Arandas in Healdsburg. The science behind why specific reds elevate lamb. Smaller, more educational format — ideal for the wine-curious who want to come home actually knowing something useful.

Castle Rock State Park trail — the moss-covered oak corridor wildflower hikers find at the start of the 5.6-mile loop this weekend.

Where to Eat & Stay if You’re Going North

Saturday Farmers Markets (Stay Local)

If you’re staying local for the weekend and want a slow Saturday morning, the Bay Area farmers market scene is at its best in mid-May. Strawberries, asparagus, peas, the first stone fruit. Top picks:

Mountain View Farmers Market (Sundays 9 AM–1 PM, Caltrain station). One of the largest in Silicon Valley.

Palo Alto Farmers Market (Saturdays 8 AM–noon, downtown California Avenue). Mid-sized, walkable to brunch after.

Saratoga Farmers Market (Saturdays 9 AM–1 PM, West Valley College). Smaller, more boutique.

Los Altos Farmers Market (Thursdays late afternoon). Weekday market — mention here as a heads-up for next Thursday.

Frequently Asked Questions