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🍇 My Sweet Sips & Bites Trail – Windsor Essex Edition
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items Explore the best wineries, tastiest bites, and dreamy wedding spots in Windsor-Essex County, Ontario. This is my personal take after road-tripping through the region with a camera in one hand and a glass in the other.
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Sections
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🍷 Wines Worth the Drive
🧀 Tasty Bites & Wine Pairing Delights
💍 Wineries That Make Dreamy Wedding Venues
☀️ Hidden Gems & Chill Day-Trip Spots
🍷 Wines Worth the Drive
Where every sip feels like summer and no one judges how many tastings you’ve had.
My go-to for casual vibes and a super friendly tasting bar. Try the LOLA wines — fruity, light, perfect for picnics. The rosé is dangerously easy to drink. 🍓🍷
Kingsville Winery | Pelee Island Winery and Vineyards
Loved the lavender fields out front — feels like you’re in a Hallmark movie. Their Gewürztraminer surprised me — floral, crisp, almost too pretty to drink (almost).
North 42 Degrees Estate Winery
Name’s fun and so is the tasting flight! The Cabernet Franc here has a deep, smoky finish. I walked out with two bottles and zero regrets.
Colchester Ridge Estate Winery
Cute little patio, killer Riesling. Staff were super chatty and down-to-earth. Try the Fire Roasted Red with cheese — chef’s kiss.
Oxley Estate Winery
🧀 Tasty Bites & Wine Pairing Delights
Because good wine needs great food — and Windsor-Essex doesn’t disappoint.
Their wood-fired pizza is what I think about when I can’t sleep. Paired it with their Merlot and sat under the trees. Magical.
Paglione Estate Winery
Massive lakefront view, and their kitchen surprised me. The whitefish sandwich? 10/10. Wine slushies are a must in summer.
Viewpointe Estate Winery
Yes, again! Their menu changes with the season. I had a peach and prosciutto salad in July and cried a little. It paired SO well with their Pinot Grigio.
Oxley Estate Winery
💍 Wineries That Make Dreamy Wedding Venues
If I ever get married in a vineyard, it’ll be at one of these.
Saw a wedding set-up while I was sipping — white chairs, grapes in the background, and a cute little rustic barn. The whole vibe is romantic and laid-back.
Cooper's Hawk Vineyards and The Vines Restaurant Canada
This one’s right on the lake and has an almost Mediterranean feel. Imagine golden hour photos on the beach with a glass of bubbly in hand. Swoon.
Sprucewood Shores
Very elegant interiors, kind of Tuscan-inspired. I met a couple celebrating their anniversary here and they said the wedding coordinator was amazing.
Mastronardi Estate Winery
☀️ Hidden Gems & Chill Day-Trip Spots
For when you just want to drink wine and feel cute.
Smaller, quieter, but sooo charming. I felt like I found a secret. Their Riesling Icewine is sweet but not syrupy. Definitely gift-worthy
Vivace Estate Winery
Good place to grab a few bottles to take home. They’ve got value picks and sparkling wines that taste way fancier than the price.
Colio Estate Winery