The Santa Clara Valley Wine Trail runs from Gilroy north through San Martin and Morgan Hill, with a cluster of family-run wineries along Hecker Pass Highway just west of Gilroy. Twice a year, the Wineries of Santa Clara Valley association makes it easy to visit several in one weekend.
Fall Passport Weekend: October 24 and 25, 2026
- One $55 passport gets you a special tasting at each of ten participating wineries, valid Saturday and Sunday.
- Participating wineries include Sarah's Vineyard, Satori Cellars, Solis Winery, Lion Ranch Vineyards and Winery, Miramar Vineyards, CordeValle Winery, and more.
- Check in at any participating winery with your ticket to get your passport lanyard, then visit the rest in any order.
- Collect each winery's Secret Word along the way for a chance at a prize.
Details and tickets: santaclarawines.com.
Barrel and Bites Weekend: February 20 and 21, 2027
- From noon to 4 p.m. both days, participating wineries pour wines straight from the barrel with small bites at each stop.
- One ticket covers both days. Check in at Fortino Winery in Gilroy or Guglielmo Winery in Morgan Hill.
- Guests must be 21 or over. Designated driver tickets are available, and the event is rain or shine.
Details and tickets: Eventbrite.
Tips for a day on the wine trail
- Plan your route around the Hecker Pass Highway wineries to keep drive times short.
- Bring a designated driver or book a car service, and eat along the way.
- Pick up a Wine Trail Pass deck at the California Welcome Center in Gilroy for tasting discounts on other weekends.
Staying at Gilroy Inn
Gilroy Inn is right off Highway 101 on Leavesley Road, about 12 minutes from the Hecker Pass Highway wineries and a short walk from Gilroy Premium Outlets. Enjoy free Wi-Fi, free on-site parking, and a refrigerator in every room for the bottles you bring home. Book direct at gilroyinn.com.
Photo: Wahn, CC BY-SA 4.0, via Wikimedia Commons.