Your Guide to the Virginia Wine Gold Medal Trail Experience

I said I wasn’t going to set wine goals this year—life usually has a way of interfering with my best-laid plans. But here I am, eyeing a wine goal once again: getting the big swag from the Virginia Wine Gold Medal Trail.

If you follow the Virginia wine industry, you know we just wrapped up the annual Governor’s Cup Competition. Each year, the Virginia Wine Board (along with the Virginia Vineyards Association and the Virginia Wineries Association) curates the “Gold Medal Trail.” By using the Virginia Wine app, you can check in at gold medal winning wineries to earn points towards some seriously cool swag.

I get excited about this every year, but I usually forget to actually check in once I have a glass in my hand. This year is different. I have a strategy, and I’m determined to get that gear. Think I can do it?

Getting Started

First, download the Virginia Wine app (also available on Apple and Google Play). Once you’ve logged in with your email or phone number, select the Gold Medal Trail experience and hit “View.”

How to Score Points

When you’re at a winery, just search for the name or browse the list. Aside from earning points, keep an eye out for “extras.” For example, Afton Mountain Vineyards often offers a coupon for a tasting upgrade right in the app. Not every winery does this, but it’s a fantastic bonus when they do!

Simply tap the big blue “Check In” button. You’ll need to allow the app to access your location, and—voilà—points added. It’s free to join, and you know you’re going to the wineries anyway, so hop in and earn yourself some swag!

Pro-Tips for the Trail:

  • Location Issues: If the app can’t find you (cell signals can be spotty where vines grow!), try checking in near the property entrance.
  • The “Manual” Save: If it still won’t work, use the “Support” function under the “More” button. Send them a quick message with the date, time, and winery name. They are usually very quick to help and will often check you in manually.
  • Timing: You can only check in at the same winery once per month. I learned this the hard way after visiting Pollak back-to-back weekends! Generally, a user may check in once per month and the next month the check in button resets and you may use it again. Plan your visits wisely!

The Finish Line

I’m currently 400 points in, with my sights set on the 10,000-point pullover. That requires roughly 100 visits, so I have 96 to go. It’s a marathon, not a sprint, but I’m feeling good about it!

Remember that you have until December 31, 2026 to earn your points and redeem for swag. Be sure you have the momentum you need to get to the wineries you love and get points!

Are you traveling the Gold Medal Trail this year? I’d love to hear about your progress, the wines you’ve loved, and what swag you’re chasing. Whether it’s a gold-medal winner or a hidden gem that wasn’t entered this year, there is a Virginia wine for everyone.

Get out there, explore, and let me know: What’s in your glass today?

And while you’re out there, maybe I’ll run into you. If you’re wearing one of these shirts, your glass is on me. Check them out – you’re ready for a winery wardrobe refresh.

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