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.

Filtering by: “Holiday”

Traditional Christmas Culinary Class
Dec
15

Traditional Christmas Culinary Class

Indulge in classic comforts with our twist on a traditional holiday feast. Paired with our best vintages, our culinary team will guide you through the preparation of seasonal dishes that promise to enrich your holiday table with nostalgic flavors.

Book your seat here!

$185 Per Person / $169 Club Member Price

Please note - arrive by 5:30PM for Friday & Saturday Classes and 4:30PM for Sunday Classes

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Traditional Christmas Culinary Class
Dec
13

Traditional Christmas Culinary Class

Indulge in classic comforts with our twist on a traditional holiday feast. Paired with our best vintages, our culinary team will guide you through the preparation of seasonal dishes that promise to enrich your holiday table with nostalgic flavors.

Book your seat here!

$185 Per Person / $169 Club Member Price

Please note - arrive by 5:30PM for Friday & Saturday Classes and 4:30PM for Sunday Classes

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Holiday Wreath Making at The Gallery Winery
Dec
7

Holiday Wreath Making at The Gallery Winery

Join us on Saturday, December 7 from 2-4 pm, for a holiday wreath making class in our wine shop. Sarah from Simply Floral will help lead you in creating a beautiful and unique holiday wreath. Make the perfect accent piece to compliment your own personal style. Cost is $100 and includes all supplies and a glass of our Inspiration Sparkling Wine.

Sign Up Link for December 7, 2024 Holiday Wreath Making Class:

https://www.thegallerywinery.com/product/holiday-wreath-making-december-7-2024

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Sip into the Season 2024
Dec
7

Sip into the Season 2024

Click for Tickets

Sip into the Season is back again, inviting you on a festive wine journey through the Westside Wine Trail!

This annual holiday event offers a delightful Christmas tasting of two wines and a festive treat at the wineries of West Kelowna's Westside Wine Trail - all gleaming with sparkling lights and holiday decor, creating a perfect blend of Christmas cheer and renowned wine culture for everyone to enjoy. Tickets are limited - be sure to get yours before they sell out! Get your tickets here.

View the interactive Google Map here.

Everyone is welcome - only those partaking in wine tastings require a ticket.

* Attendees must be 19+ to partake in wine tasting offerings *

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Italian Christmas Culinary Class
Dec
6
to Dec 8

Italian Christmas Culinary Class

Experience the magic of an Italian Christmas through a four-course dinner prepared by our culinary team. Elevate your holiday celebrations with authentic Italian flavors and timeless wines to pair.

Book your seat here!

$185 Per Person / $169 Club Member Price

Please note - arrive by 5:30PM for Friday & Saturday Classes and 4:30PM for Sunday Classes

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Traditional Christmas Culinary Class
Nov
30

Traditional Christmas Culinary Class

Indulge in classic comforts with our twist on a traditional holiday feast. Paired with our best vintages, our culinary team will guide you through the preparation of seasonal dishes that promise to enrich your holiday table with nostalgic flavors.

Book your seat here!

$185 Per Person / $169 Club Member Price

Please note - arrive by 5:30PM for Friday & Saturday Classes and 4:30PM for Sunday Classes

View Event →
Traditional Christmas Culinary Class
Nov
29

Traditional Christmas Culinary Class

Indulge in classic comforts with our twist on a traditional holiday feast. Paired with our best vintages, our culinary team will guide you through the preparation of seasonal dishes that promise to enrich your holiday table with nostalgic flavors.

Book your seat here!

$185 Per Person / $169 Club Member Price

Please note - arrive by 5:30PM for Friday & Saturday Classes and 4:30PM for Sunday Classes

View Event →
Holiday Wreath Making at The Gallery Winery
Nov
23

Holiday Wreath Making at The Gallery Winery

Join us on Saturday, November 23 from 2-4 pm, for a holiday wreath making class in our wine shop. Sarah from Simply Floral will help lead you in creating a beautiful and unique holiday wreath. Make the perfect accent piece to compliment your own personal style. Cost is $100 and includes all supplies and a glass of our Inspiration Sparkling Wine.

Sign Up Link for November 23, 2024 Holiday Wreath Making Class:

https://www.thegallerywinery.com/product/holiday-wreath-making-november-23-2024

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Winter Wanderland at Quails' Gate
Nov
23

Winter Wanderland at Quails' Gate

Join us on Saturday, November 23 & Sunday, November 24 from 11:00 AM – 5:00 PM for our annual Winter Wanderland. Guests are invited to wander the estate and immerse themselves in all kinds of holiday wonder!

The Market will be brimming with delicious food and treats to enjoy day of or to take home. Gourmet coffee, cookies, sandwiches, soups and wood-fired pizza.

Mulled wine, spiked lattés, wine by the bottle and the glass will be available for purchase and fire pits will be dispersed throughout the market area for those looking for a place to visit and mingle.

We will also have a handful of local artisans setup in the parking lot next to The Market selling their products. Inside The Market you’ll find a permanent bracelet booth from JK Schmidt on Saturday!

Some fun for kids too, there will be a special table set up with free hot chocolate, cookies and colouring.

Market Hours: 9:30 AM – 5:00 PM

Wood-Fired Pizza: 12:00 PM – 4:00 PM

Inside the wine shop we will be offering our classic tasting with a twist! A splash of Fortified Vintage Foch and a chocolate from Karat Chocolate.

Holiday gifting has never been easier! The wine shop shelves will be filled with wine and other goodies to gift this holiday season. As a special treat we will be offering a 15% discount on all purchases, 20% off on glassware, and $25 gift cards to Old Vines Restaurant for anyone spending $250 or more.

Wine Shop Hours: 11:00 AM – 6:00 PM

Step into a cozy winter retreat at Old Vines Restaurant! Enjoy an Outdoor Happy Hour Lounge with cozy firepits and blankets to keep warm as you sip on festive cocktails and indulge from a featured menu all while soaking in the festive Winter Wonderland atmosphere.

For those looking to dine in the restaurant, we’ll be offering our brunch menu on Saturday, Jazz Brunch & Happy Hour on Sunday as well as our evening dinner service on both days.

Old Vines Restaurant Hours: 11:00 AM – 9:00 PM

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Festival of Trees Celebration
Nov
22

Festival of Trees Celebration

Celebrate our 8th annual Festival of Trees at Mission Hill Family Estate. Revel in the holiday spirit at our 8th annual Festival of Trees opening with live music, mulled wine, and other holiday treats prepared by our culinary team, along with special photo opportunity with Santa Tom. This year, we're also introducing our first holiday market, showcasing a variety of local artisans with jewelry, pottery, candles, and more. The perfect way to complete your holiday gifting in one stop.

$20 per person - a percentage of proceeds go to BC Children’s Hospital Foundation.

Learn more

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Annual Events

  • 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.

  • Sip with your Sweetheart

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

  • 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.

  • 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.