What’s Happening on the Trail

From wine-paired dinners to crafting events, farm tours, and vineyard yoga, immerse yourself in the Westside Wine Trail beyond the tasting room! Our member wineries host a vibrant calendar of events throughout the year, offering something for everyone. From live music under the summer sky to educational tastings and workshops, enhance your visit with unique experiences.

Annual Events

  • A man and woman sitting in front of a fireplace, holding glasses of wine and smiling at each other.

    Sip into the Season

    A delightful Christmas event gleaming with sparkling lights and holiday decor. Join us for our annual holiday tasting experience in West Kelowna.

  • Two people holding glasses of pink wine, toasting each other.

    Sip with your Sweetheart

    Enjoy chocolate-paired wine tastings at our eleven member wineries at our annual Valentine’s event.

  • Man and woman enjoying wine and cheese at a cozy setting with a cheese platter and a fireplace in the background.

    Cheers to Cheese

    Celebrate spring and embark on a journey through the picturesque Westside Wine Trail with Cheers to Cheese: an unparalleled wine and cheese paired tasting experience.

  • A ghost model, wearing sunglasses, holding a glass of red wine, superimposed over a landscape of vineyards with mountains in the background.

    Trick or Sip

    Trick or Sip on the Westside Wine Trail is a spooktacular Halloween event. This hauntingly delightful gathering promises a fangtastic time for all attendees.