A few weeks ago, I was on a cruise and chatting with another couple when I mentioned that I own a vineyard tour business in Connecticut. The wife looked at me and said, "Connecticut has vineyards?"
I laughed. They were from California, so I'll give them a pass.

But then, just a few weeks later, I was attending a Small Business Summit right here in Connecticut. I mentioned my vineyard tour business to the person sitting next to me and she said "Connecticut has vineyards?"
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And that, my friends, is not acceptable.

How do you live in a state with 55 farm wineries, 35 tasting rooms, an official Wine Trail, a Passport Program, wine festivals, vineyard concerts, and thousands of acres of vineyards and not know they exist? At that moment, I realized something: the problem isn't that Connecticut vineyards aren't worth visiting. The problem is that we're doing a terrible job telling people they exist.

Connecticut's Wine Industry Isn't New
One of the biggest misconceptions people have is that Connecticut is somehow new to wine. We're not.
Grapes have been grown in Connecticut almost as long as Europeans have been living here. More importantly, Connecticut vineyards have been welcoming visitors into tasting rooms since 1978. That's nearly 50 years of people gathering with friends, enjoying local wine, and supporting Connecticut agriculture.

These aren't brand-new wineries trying to figure things out. Many Connecticut vineyards have spent decades refining their craft, expanding their offerings, and creating beautiful destinations that attract visitors from all over New England. Yet somehow, people still act surprised when they find out we have vineyards at all.

I have a friend who LOVES Negronis.
Now, if you’ve never had a Negroni before, imagine somebody took orange peel, bitterness, sadness and rubbing alcohol and stirred it together over ice. Apparently this is sophisticated. She’s Italian, drinks espresso like water, and I’m pretty sure they permanently damaged her taste buds as a child.
One day on a cruise, she convinced me to try one. The second it touched my tongue, I looked at her in horror while she stared at me waiting for my reaction and I said: “It tastes like my mouth will never be happy again.”

She was genuinely confused. “What? What is wrong?” THAT was the moment I started realizing people’s taste buds are wildly different and what one person considers “smooth with herbal complexity,” another person considers “burning tire fire with notes of regret.”

Which got me thinking…

 There’s a moment at the end of almost every tour where someone hugs me or says, “Thank you. That was SO much easier than trying to do this ourselves.”

And honestly? That’s kind of the whole point.

People imagine a DIY vineyard day being simple. You pick a few wineries, throw together some snacks, maybe rent a limo, and spend the day sipping wine with your friends. Easy, right?

Except… after working in the vineyard tour world, I can tell you that there are about 500 tiny details people don’t think about until they’re already in the middle of them. One of the biggest surprises is simply knowing whether vineyards are actually open. A lot of people assume wineries are just open every day for whoever wants to stop by, but that’s not always how it works. Each vineyard in Southeastern CT has different hours and different days off. (open at 11 on Thursday but 2 on Friday? Open every day, or only open weekends? I know all these schedules) Some have private events. Others have opening weekend celebrations where you need tickets just to get in. Some vineyards close early for weddings and some don't open at all if there is a wedding. One local vineyard, for example, is closed almost every Saturday in May because of weddings, and there are special June and September events coming up where people are going to be very disappointed if they show up without tickets.

That’s the kind of thing that can completely derail a carefully planned day.

You spend all this time coordinating people, mapping routes, packing food, figuring out timing… and suddenly one or two of your planned stops aren’t even an option anymore.

That’s one of the biggest advantages of a guided vineyard tour: we already know what’s happening. We’re constantly keeping up with closures, events, availability, and changes so our guests don’t have to spend hours researching and double-checking every stop.

If you’re looking for the best wineries near Mystic, Connecticut, you’re probably picturing a perfect day—beautiful views, great wine, maybe a little buzz, and absolutely no stress.

And honestly? That does exist here.

But what most people don’t realize when they start searching for things to do in Mystic or nearby is that a winery day can go one of two ways: either it’s relaxed, fun, and memorable… or it turns into a rushed, confusing blur where someone ends up playing designated driver and missing half the experience.
I know this because I’ve done it both ways.

How It All Started (aka “The Lost Summer”)
Back in July of 2018, the Fourth of July fell on a Wednesday. Everything was closed, the big parties weren’t happening until the weekend, and someone posted in a local Facebook group listing a few vineyards that were open. One of them was Stonington Vineyard, and I already knew Susan, the tasting room manager, so we decided to go. That one decision turned into what we now call “The Lost Summer.”

We discovered the Connecticut Wine Trail Passport that day and spent the rest of the summer driving all over the state, visiting wineries and vineyards, collecting stamps, and chasing that last stop like it was a prize. We didn’t win anything… but we absolutely won. 

That summer is when we realized vineyards aren’t just places to drink wine—they’re places to spend time. To relax. To connect. To make a whole day out of it. Fast forward to now, and let’s just say I’ve spent enough time at Stonington Vineyard that during big events, I’m allowed to use the staff bathroom. If you know, you know. 😂

Short answer? Usually, yes—but it depends. 
Long answer? Let me save you from a soggy charcuterie board and a whole lot of unnecessary stress.
As someone who runs vineyard tours and has personally lived through the “Pinterest picnic gone wrong” experience, here’s what you actually need to know.

The General Rule: Most Vineyards Do Allow Outside Food
​If you’re visiting vineyards in Connecticut (and most places, honestly), bringing your own food is typically allowed.
There are a few exceptions:

• Vineyards that have on-site restaurants usually do not allow outside food
• Special events may have different rules

But overall? Packing a picnic or charcuterie board is pretty common—and honestly, part of the vibe.