When visitors stay in Picton and ask me which wineries they should visit, my advice is always:
Don’t spend half your day driving. Spend it sipping.
As someone who has visited all 41+ wineries in Prince Edward County, I’ve learned that some of the best wine touring happens when you focus on a small area and truly enjoy each stop.
Starting from Picton, there’s a fantastic cluster of wineries on the eastern side of the County that are easy to reach, close together, and offer a wonderfully diverse experience.
Some are off the beaten path on back roads, and others are popular or recognizable.
My recommended route is popular or recognizable:
- Black Prince Winery
- Three Dog Winery
- Waupoos Estates Winery
- Amanda’s Vineyards
Together, they showcase everything from historic County winemaking and vineyard views to Italian-inspired wines and waterfront dining.
Stop #1: Black Prince Winery
Distance from Picton: Approximately 1 km (2-minute drive)
I always recommend starting your day at Black Prince Winery.
Why?
Because it feels wonderfully authentic, and if you’re staying in Picton, it’s the closest.
Black Prince has been part of the Prince Edward County wine scene for years and offers visitors a more intimate, educational tasting experience than many larger wineries. The property is also home to Canadian Vinegar Cellars, which adds another unique dimension to your visit.
What Makes It Special?
- One of the County’s early wineries
- Educational tasting experiences
- Wine and culinary-focused atmosphere
- Balsamic and fruit vinegar tastings available on-site
- Wood-fired pizza
Best Wines to Try
- Cabernet Franc
- Pinot Noir
- Chardonnay
- Seasonal specialty releases
Local Insider Tip
Many visitors rush through Black Prince on their way to Waupoos. Slow down. Some of the most interesting conversations about County winemaking happen here.
Stop #2: Three Dog Winery
Distance from Black Prince: About 10 km (15-minute drive)
Three Dog Winery is one of those places that instantly makes you feel relaxed.
Note: We visit here more than any other winery in PEC.
It’s family-owned, welcoming, and refreshingly unpretentious. The atmosphere feels more like a gathering of friends than a formal wine destination. The winery has built a loyal following thanks to its award-winning wines, seasonal events, live music, and wood-fired pizza.
What Makes It Special?
- Family-owned winery
- Relaxed outdoor setting
- Live music events throughout the season
- Wood-fired pizza and casual atmosphere
Best Wines to Try
- Pinot Grigio- Won awards!
- Rosé
- Chardonnay
- Sparkling wines
Food Options
The wood-fired pizza has become a local favourite and makes this a perfect late-morning or lunch stop.
Local Insider Tip
If there’s live music scheduled, typically on the weekends, stay longer than you planned. It’s worth it.
Stop #3: Waupoos Estates Winery
Distance from Three Dog Winery: About 12 km (15-minute drive)
This is the winery I tell first-time visitors they absolutely cannot miss.
Waupoos Estates was the pioneering vineyard and winery operation in Prince Edward County and remains one of the most beautiful winery properties in Ontario. The views overlooking Prince Edward Bay are simply incredible.
What Makes It Special?
- Stunning waterfront location
- Award-winning wines
- Farm-to-table restaurant
- Estate tours and tastings
- Clafeld Cider House across the road
Best Wines to Try
- Chardonnay
- Pinot Gris
- Gamay
- Estate blends
Food Options
The winery restaurant is arguably one of the best winery dining experiences in Prince Edward County. A leisurely lunch overlooking the vineyards and bay is hard to beat.
Local Insider Tip
Bring your camera. Even longtime locals still stop to admire the view.
Stop #4: Amanda’s Vineyards
Distance from Waupoos Estates: Less than 3 km (4-minute drive)
Here’s the local secret many visitors miss.
While larger wineries often get the headlines, Amanda’s Vineyard delivers the kind of intimate, personal experience that reminds you why Prince Edward County became a wine destination in the first place. The atmosphere is warm, welcoming, and wonderfully unpretentious.
What Makes It Special?
- Boutique winery experience
- Family-run atmosphere
- Less crowded than many major wineries
- Opportunity to chat directly with people involved in the vineyard and wine production
Insider Tip
This is the kind of winery where you should ask questions. Some of the best stories in Prince Edward County wine country come from smaller producers who have built their vineyards from the ground up.
Who Will Love It?
- Visitors looking for hidden gems
- Wine enthusiasts who prefer small producers
- Anyone wanting a more personal tasting experience
Local Insider Tip
Ask questions during your tasting. The stories behind the wines are often just as enjoyable as what’s in the glass.
Why These Four Wineries Work So Well Together
This route gives visitors four completely different winery experiences:
| Winery | Personality |
|---|---|
| Black Prince | Historic and educational |
| Three Dog | Relaxed and fun |
| Waupoos Estates | Scenic and iconic |
| Amanda’s Vineyards | Intimate and less busy |
Best of all, you’re never spending more than a few minutes driving between stops, allowing you to maximize your winery experience rather than stare at road signs all day.
Suggested Picton Winery Tour Schedule
10:30 AM
Black Prince Winery
12:00 PM
Three Dog Winery – Worth the drive.
1:30 PM
Waupoos Estates Winery (Lunch) or Cressey Mustard (Fish & Chips)
3:30 PM
Amanda’s on the way back from Waupoos
5:00 PM
Return to Picton for dinner and a stroll through town
Final Thoughts
If you’re based in Picton and want an easy, enjoyable winery tour that showcases the diversity of Prince Edward County wine country, this four-winery route is one of the best you’ll find.
You’ll experience historic winemaking, family-run charm, waterfront views, award-winning wines, wood-fired pizza, Italian hospitality, and some of the most beautiful scenery in the County.
And if you return to Picton with six bottles when you only planned to buy one?
Don’t worry.
That’s not poor planning.
That’s called a successful day in Prince Edward County wine country.
