Rollingdale Winery

The Vibe

Pull into Rollingdale's long gravel driveway and you might wonder if you've taken a wrong turn — there are no grand archways, no marble floors, no sweeping architectural gestures here. What you'll find instead is something far more valuable: a genuine, unpolished, completely unpretentious family farm that happens to produce some of the most interesting organic wines in the valley. Founded in 2004 on land that spent a century growing apples, peaches, and cherries before the first grapevines were planted in 1999, Rollingdale is a winery that wears its soul on its sleeve. Visitors consistently describe it as the surprise highlight of a five-winery day — the last stop that somehow ends up being the best — and return season after season for the combination of quality, charm, and genuine human connection that no amount of architecture can replicate.

The Experience

Tastings at Rollingdale take place directly on the cellar floor — a detail that sounds modest but actually makes for one of the most authentic and intimate wine experiences on the entire Westside Wine Trail. Hosts here are consistently praised by name in guest reviews, with staff like Kevin and John earning near-legendary status among regulars for their warmth, humour, and genuine knowledge of every bottle on the board. After your tasting, grab a bottle from the shop and head up the hill to the vineyard picnic area — a quiet, sun-drenched perch with sweeping views of Okanagan Lake that is one of the finest spots in wine country for an unhurried afternoon. When timing allows, Rollingdale's own winemaker leads educational tours of the property — a rare and genuinely enriching experience that larger estates simply can't offer.

The Wine

Don't let the farm gate setting set your expectations too low — Rollingdale produces a surprisingly broad and diverse range of certified organic wines that consistently punch well above their boutique weight. All grapes are sourced from the estate's 13 certified organic acres, with carefully selected varieties planted to suit each parcel's microclimate — including a north-facing acre of Chardonnay planted specifically to preserve natural acidity. The flagship Flirty Three — a playful and aromatic blend of Riesling, Gewürztraminer, and Pinot Gris — is a perennial crowd favourite, while the Marechal Foch is one of the finest examples of this underappreciated varietal in the valley. The Blanc de Blancs sparkling and Pinot Blanc Icewine are standout special occasion bottles worth seeking out.

Good to Know

• Best for: Couples, organic wine enthusiasts, visitors seeking a genuine and unhurried farm gate experience, anyone who appreciates character over grandeur

• Don't miss: The Flirty Three blend, the Marechal Foch, and a post-tasting picnic on the hillside with Okanagan Lake views

• Signature wines: Flirty Three, Marechal Foch, Blanc de Blancs Sparkling, Pinot Blanc Icewine, Late Harvest Viognier

• Hours: Open daily 10am to 6pm, all four seasons

• Reservations: Walk-ins welcome — groups of six or more should book ahead

• Heads up: The entrance driveway is unassuming — don't let first impressions mislead you. This is one of the most rewarding stops on the trail for those who appreciate substance over style