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The Westside Wine Trail certainly has some of the most iconic wineries to boast about, such as Quails’ Gate and Mission Hill. However, when it comes to wine touring along the Okanagan’s oldest wine trail, sometimes it’s the unique, smaller hidden gem wineries where the experiences come alive! 


Rollingdale Winery

Rollingdale is known for its relaxing atmosphere and award-winning wines. A plain and unassuming farm gate certified organic winery where the tasting room doubles as their wine cellar, and the focus is more on their amazing selection of wine, rather than the esthetics.

Specializing in ice wines and fortified wine, Rollingdale has won numerous awards and was given a perfect score by reviewers at the Vinoble 2008 Dessert Wine Festival in Spain. 

Bring a picnic basket, grab a bottle of wine from the shop and enjoy views of the vineyard and Okanagan Lake from the picnic area, nestled at the top of the hill.


Ciao Bella Winery


Proudly producing Okanagan wines with an Italian flair, the family owned and operated 2.5 acres vineyard, recently won two national gold medals at the National Wine Awards of Canada and the National Wine Align Competition. 

The boutique wineshop carries a variety of Italian products along with their award-winning wine. Have a seat in their beautiful backyard picnic area, where you can enjoy some Spuntini (charcuterie the Italian way), with a cappuccino, an Italian soda, or of course, a glass of vino!

Indigenous World Winery

Modern culture meets indigenous history, combining the unique terroir of the valley and the indigenous people’s stewardship of the lands. Every effort has been made to produce world class wines in a respectful way to the environment and its people. 

Opened in 2016 by Robert and Bernice Louie, as the second Indigenous winery owned in BC, the facility features a wine tasting room that overlooks the ravine and vineyard below, a native themed gift shop and picnic area. It is the first of many operations being developed and are set to include a craft distillery, entertainment facility and possibly guest accommodations in the future.

Off The Grid Winery

If looking for a unique, off the beaten path, funky boutique winery, Off The Grid should most certainly be on your list. 

Boasting over 100 years and five generations of farming, a selection of high-quality organic wines, a spectacular view of West Kelowna and Okanagan Lake, along with their own little hobby farm which includes goats, rabbits and more, you’ll be sure to have an amazing experience! 

Frind Estate Winery

Ok, so Frind really isn’t that small, however, as one of the trail’s newest additions, we had to sneak this one in! 

Flaunting an awe-inspiring view, situated right on Okanagan Lake on the historic Bennet property – where owner Markus Frind renovated the former BC Premier’s home and office space into the tasting room – Frind has become the first ‘beach winery’ on the trail, and has quickly risen to almost iconic status in only a couple of years!

The tasting room is casual and inviting with white granite counters, and plenty of room to host multiple groups for tastings. It sports a temperature controlled automatic serving dispenser for the wine – a system you would see more in the Bordeaux region than in the Okanagan. 

Frind also opened Annie’s Café + Lounge, where you can sit, relax, have a glass of wine and grab a bite – or grab a bottle of vino, something from the bakery, and sit on the beach at one of their picnic tables.