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.

Calendar View
Dome Dining at Frind (Wednesday-Sunday)
Nov
1
to Mar 29

Dome Dining at Frind (Wednesday-Sunday)

Join Us This Winter in Our Lakeside Domes at Frind Estate Winery!

Cozy up in one of our stunning lakeside domes and enjoy our specially crafted Winter Menu by Chef Ryan Lauzon, available Wednesday through Sunday each week until March 29th!

✨ Happy Hour from 2:00 PM to 5:00 PM! ✨

Reserve your spot online, with the last seating at 7:30 PM. Walk-ins are welcome on a first-come, first-serve basis, pending availability. We look forward to welcoming you for a memorable winter dining experience by the lake!!

Book your dome here.

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NYE at 31 CHARKAY
Dec
31

NYE at 31 CHARKAY

Start your night with a three-course Canadian-inspired dining experience, then raise a glass and celebrate the New Year in style! 🥂 Enjoy cocktails, champagne, and a full bar — 31 Charkay is the perfect place to share laughs, love, and good company in a warm and relaxed atmosphere.

Book your seat here!

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Great Gatsby NYE Party
Dec
31
to Jan 1

Great Gatsby NYE Party

Step into the glittering chaos of the 1920s this New Year’s Eve. This is one New Year’s Eve you won’t want to miss. Where scoundrels and royalty alike come together to toast the year ahead.

Crown & Thieves will be transformed into a roaring den of glamour, grit, and grape-fueled revelry. We’re throwing a party Jay Gatsby himself would crash—minus the bathtub gin, plus a whole lot of wine. Live music, dancing, and decadence await as we ring in the new year in true prohibition fashion.

Can’t make it for dinner? No problem—there’s still plenty of Gatsby-style revelry waiting for you. Join us later in the evening and dive straight into the fun with our reception-only experience. It’s a full night of music, dancing, and indulgence in the sultry depths of the Broken Hearts Club.

Choose to come early and have dinner, including a 3-Course wine paired dinner, or come later for the reception and party.

Your ticket includes:

  • 3-Course Wine Paired Dinner

  • Two drink tickets

  • Late-Night Bites & Gatsby Grazing

  • Champagne Toast at midnight (because resolutions taste better with bubbles)

  • Live entertainment and dancing deep in the Broken Hearts Club

Pearls, gloves, and Gatsby glam encouraged - we will be handing out prizes for the snazziest scoundrels and most dazzling dames. Our crew will be pouring, toasting, and stirring up trouble in true prohibition style. Limited tickets - book today!

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Christmas Ornament Painting at Little Straw Winery
Dec
20

Christmas Ornament Painting at Little Straw Winery

Christmas Ornament Painting at Little Straw Winery

Don't miss out on this chance to have fun and make a beautiful ornaments. We look forward to seeing you at the workshop!

Includes:

  • 4 Round or Rectangular wooden Ornaments (approx. 3.5” each)

  • Paint it in colours of your choice

  • Choose your set of designs for the 5 options

  • Glass of wine or organic juice

Cost: $50 per person (Kids 6 & under can share one project with an adult)

Book your spot here!

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Sip & Create Festive Doormats at Little Straw Winery
Dec
20

Sip & Create Festive Doormats at Little Straw Winery

Join us for a creative night out while enjoying some wine or organic juice at our cozy Little Straw Winery in West Kelowna.

You will start the evening with wine tasting and then continue with a Doormat Painting Workshop.

In the 1.5 hour workshop our instructor, Jennifer, will guide you through the process of painting a festive doormat (or year-round design) using vinyl stencils. Choose from variety of designs when you register and will have the opportunity to customize it in colours of your choice.

Cost:

  • 16”x23” - $75

  • 23”x35” - $90

Includes:

  • doormat project

  • wine tasting

  • glass of wine or non alcoholic beverage

Book your spot here!

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Christmas Ornament Painting at Little Straw Winery
Dec
19

Christmas Ornament Painting at Little Straw Winery

Christmas Ornament Painting at Little Straw Winery

Don't miss out on this chance to have fun and make a beautiful ornaments. We look forward to seeing you at the workshop!

Includes:

  • 4 Round or Rectangular wooden Ornaments (approx. 3.5” each)

  • Paint it in colours of your choice

  • Choose your set of designs for the 5 options

  • Glass of wine or organic juice

Cost: $50 per person (Kids 6 & under can share one project with an adult)

Book your spot here!

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Wine & Paint Night with Monet Meets Merlot
Dec
16

Wine & Paint Night with Monet Meets Merlot

We are beyond excited to announce that Monet Meets Merlot is back, bringing another class of creativity, laughter, and unforgettable memories to our beautiful winery. Treat yourself to a night he won't forget!

Join us for an evening where art and wine flow together effortlessly. Whether you're an experienced artist or picking up a brush for the first time, we've got you covered! Not confident in your artistic skills? No worries – Lynn's team will happily pre-trace your canvas, ensuring you can focus on the fun. After all, this is about FUN Art, not FINE Art! So, grab your friends, sip on some of our finest wines, and let your creativity run wild. Spaces are limited, so be sure to reserve your spot today. We can't wait to see you there!

Reservations Are Necessary. $65.00 per guest This experience includes a complimentary glass of Frind wine (white, red or rose)! *There is an option to add an individual charcuterie board (per guest) to your experience!*

Book your spot here

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The Prohibition Party featuring The Anna Jacyszyn Trio
Dec
11

The Prohibition Party featuring The Anna Jacyszyn Trio

The Anna Jacyszyn Trio will be performing inside the speakeasy Jazz Lounge at Crown & Thieves Winery, 3887 Brown Rd, West Kelowna from 7 – 9 p.m. Creating fresh stylings of Jazz, Latin and Blues peppered with classics you will be humming throughout the rest of your days! Cocktails, Wine, Beer, Cider and snacks will be available for purchase in The Broken Hearts Club Speakeasy.

Doors Open at 6:00pm - Show Starts at 7:00pm.

Seating for events in the speakeasy is preassigned, not first come first served. If you would like to be seated with a group that purchased tickets separately please include their name in the order form.

Book your tickets here.

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Sweet Sips & Clay Creations Pottery Night
Dec
9

Sweet Sips & Clay Creations Pottery Night

  • 3725 Boucherie Road West Kelowna, BC, V4T 0A8 Canada (map)
  • Google Calendar ICS

Treat yourself to an evening of pure indulgence at one of the most exclusive wineries in West Kelowna - Frind Winery. In this intimate workshop, you’ll hand-build your own custom pottery dessert bowl, perfect for your favorite treats at home. While your creativity flows, savor four exquisite sparkling / dessert wine tastings and enjoy a decadent mini dessert from Frind Winery’s kitchen.

What’s included:

  • A guided pottery hand-building workshop where you’ll create a beautiful dessert bowl

  • A tasting flight of 4 Frind wines from their sparkling/dessert collection

  • A delicious Frind chef-crafted dessert to enjoy during your session

Pearl & Fern will glaze and fire your pottery piece, ready within 2 weeks $120 per person. Choose from 2 limited edition dates! Reserve now to sip, savor, and sculpt something sweet this winter.

Book your spot today.

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Sip & Dip Silk Scarf Workshop
Dec
7

Sip & Dip Silk Scarf Workshop

We bring the beautiful, ancient art of water marbling to the 21st century by inviting you to be the artist. Come and make your own water marbled silk scarf, or art canvas. Each artist chooses their colours and floats the paint one drop at a time on the surface of the water, then uses marbling combs, rakes, or stylus to create the design of their liking.

Get your tickets here.

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Sip into the Season
Dec
6

Sip into the Season

We’re hosting our annual holiday event on Saturday, December 6! Complete with festive paired tastings, new releases, and a healthy dose of holiday spirit, Sip into the Season is sure to be a magical time!

🍷 Festive Tastings at 15 Wineries

🗓️ Saturday, December 6th from 12pm-5pm

🎟️ $20 Tickets

Get your tickets here!

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Wine & Paint Night with Monet Meets Merlot
Dec
2

Wine & Paint Night with Monet Meets Merlot

We are beyond excited to announce that Monet Meets Merlot is back, bringing another class of creativity, laughter, and unforgettable memories to our beautiful winery. Treat yourself to a night he won't forget!

Join us for an evening where art and wine flow together effortlessly. Whether you're an experienced artist or picking up a brush for the first time, we've got you covered! Not confident in your artistic skills? No worries – Lynn's team will happily pre-trace your canvas, ensuring you can focus on the fun. After all, this is about FUN Art, not FINE Art! So, grab your friends, sip on some of our finest wines, and let your creativity run wild. Spaces are limited, so be sure to reserve your spot today. We can't wait to see you there!

Reservations Are Necessary. $65.00 per guest This experience includes a complimentary glass of Frind wine (white, red or rose)! *There is an option to add an individual charcuterie board (per guest) to your experience!*

Book your spot here

View Event →
JPC Holiday Light Up - Santa's Cellar at Crown & Thieves
Nov
29

JPC Holiday Light Up - Santa's Cellar at Crown & Thieves

Join us for our 5th annual Family Fun Holiday Light Up on Saturday, November 29th — across all Jason Parkes Customs properties. Join us in your most outrageous festive gear as we light up our beautifully tacky JPC trees!

This year, Crown & Thieves is hosting Santa's Cellar.

Here's what is happening at Crown & Thieves:

  • Special tastings from back vintages

  • Speakeasy open for cocktails

  • Tasting fees donated to Central Okanagan Food Bank

  • New this year! JPC Socks and Scarves will be available for purchase at the light up!

Come dressed in your ugly socks or scarves and we will give you 15% off at all JPC locations until the end of March 2026!

Learn more here.

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JPC Holiday Light Up - Jingle Juice Jamboree at the hatch
Nov
29

JPC Holiday Light Up - Jingle Juice Jamboree at the hatch

Join us for our 5th annual Family Fun Holiday Light Up on Saturday, November 29th — across all Jason Parkes Customs properties. Join us in your most outrageous festive gear as we light up our beautifully tacky JPC trees!

This year, the hatch is hosting the Jingle Juice Jamboree.

Here's what is happening at the hatch:

  • Karaoke (4–6pm)

  • Mulled wine available

  • Tasting fees donated to Central Okanagan Food Bank

  • New this year! JPC Socks and Scarves will be available for purchase at the light up!

Come dressed in your ugly socks or scarves and we will give you 15% off at all JPC locations until the end of March 2026!

Learn more here.

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JPC Holiday Light Up - Chocolate & Cheers at Black Swift Vineyards
Nov
29

JPC Holiday Light Up - Chocolate & Cheers at Black Swift Vineyards

Join us for our 5th annual Family Fun Holiday Light Up on Saturday, November 29th — across all Jason Parkes Customs properties. Join us in your most outrageous festive gear as we light up our beautifully tacky JPC trees!

This year, Black Swift is bringing Chocolate and Cheers.

Here's what is happening at Black Swift Vineyards:

  • $15 wine and chocolate tasting. 3-4 chocolate bites paired with wine and welcome bubbles.

  • Kids hot cocoa station by donation

  • Live music by Ayla Buckberry

  • Tasting fees donated to Central Okanagan Food Bank

  • New this year! JPC Socks and Scarves will be available for purchase at the light up!

Come dressed in your ugly socks or scarves and we will give you 15% off at all JPC locations until the end of March 2026!

Learn more here.

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Swift Loves Cheese: Tasting Event
Nov
24

Swift Loves Cheese: Tasting Event

We’re bringing together two of life’s greatest pleasures: wine and cheese. Join us for a guided tasting featuring four Black Swift wines, each perfectly paired with artisan cheeses from Perseval & Young, Kelowna’s beloved cheesemongers known for sourcing some of the finest cheeses around. 4 tasting times available - reserve your spot now!

Your ticket include:

  • 4 Black Swift vineyard wines

  • 4 samples of Parseval & Young cheese

Tickets: $50, plus gratuity & taxes - book your spot here.

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hatch Loves Cheese: Tasting Event
Nov
24

hatch Loves Cheese: Tasting Event

We’re bringing together two of life’s greatest pleasures: wine and cheese. Join us for a guided tasting featuring four Hatch wines, each perfectly paired with artisan cheeses from Perseval & Young, Kelowna’s beloved cheesemongers known for sourcing some of the finest cheeses around. 4 tasting times available - reserve your spot now!

Your ticket include:

  • 4 Samples of Hatch Wines

  • 4 samples of Parseval & Young cheese

Tickets: $50, plus gratuity & taxes - book your spot here.

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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.

    Learn More
  • 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.

    Learn More
  • 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.

    Learn More
  • 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.

    Learn More