The 203’s Local Guide to the Best Wineries in Connecticut
Sweater weather is officially here, and we can’t think of a better way to soak it up than with a glass of wine in hand and some classic Connecticut views all around. This season, we’re trading beach days for vineyard hangs and weekend drives along the Connecticut Wine Trail - packed with hidden gems, local favorites, and plenty of fall charm.
We’re all about celebrating local flavors, beautiful views, and time well spent with good company (and a glass of wine), so grab your crew, pull on your coziest layers, and get ready to sip your way through some of the best wineries in our home state!
Hopkins Vineyard: (Warren, CT)
The drive to Hopkins Vineyard winds through the prettiest back roads in Litchfield County- golden trees and lake views. Set on a hill overlooking Lake Waramaug, this tenth-generation family vineyard feels timeless in the best way. The tasting room is cozy and full of character, and the patio is made for lingering. We love the laid-back hospitality that makes you feel like a regular (even when you're not). Grab a bottle of their sparkling wine, snag a seat outside, and stay until the light hits that golden-hour glow. Simple, classic, and effortlessly beautiful.
Stappa Vineyard: (Orange, CT)
At Stappa Vineyard, everything feels intentional. Run by three sisters, this spot is all heart and community. It’s dog-friendly, family-oriented, and exactly the kind of place that reminds you why small, local vineyards always hit different. The wine list isn’t huge, but every bottle has a story (and chances are, you’ll hear it straight from one of the owners). The patio is casual and inviting, dotted with picnic tables and twinkle lights, and the pace is blissfully unhurried.
Hawk Ridge Winery: (Watertown, CT)
Hawk Ridge Winery is the definition of a good-time vineyard… annnnd it checks all the boxes for a perfect fall hangout: great wine, killer views, and food that goes way beyond cheese and crackers. Set on what used to be a horse farm, it still has that rustic countryside charm- big skies, rolling fields, and plenty of space to spread out. The wines are approachable, the staff is friendly, and the whole place just feels easy in the best way.
Aquila’s Nest Vineyard: Newtown, CT
Aquila’s Nest feels more like an experience than a typical vineyard stop. Set on a hilltop in Newtown, it’s got serious creative energy - think fire pits, modern architecture, and art installations scattered through the grounds. It’s female-owned, sustainability-focused, and the type of spot that’s somehow calm and social at the same time. Grab a glass, settle into one of their outdoor lounges, and catch the sunset. It’s an easy place to spend an afternoon without realizing how much time has passed.
Gouveia Vineyards:(Wallingford, CT)
If you’ve ever been to Gouveia, you know the view alone is worth the trip. Perched high above Wallingford, this spot gives you sweeping hills, golden light, and some of the best sunset hangs in Connecticut. The vibe is relaxed… bring your own snacks, grab a bottle, and camp out at one of the picnic tables overlooking the vines. Inside, the rustic stone tasting room feels cozy and inviting, especially once the weather cools down.
Jones Winery: (Shelton, CT)
Tucked into the hills of Shelton, Jones Winery is part of the Jones Family Farm you probably already know and love. The same family that grows your fall pumpkins and strawberries also happens to make some really good wine. The tasting room is warm and casual, and their seasonal flights are always worth exploring. It’s easy to make a day out of it- start with a tasting, stroll through the vines, then stop by the farm stand for whatever’s in season.
Paradise Hills Vineyard: (Wallingford, CT)
Paradise Hills Vineyard is one of those places that just feels good the second you pull up. Set among the rolling hills of Wallingford, it’s family-owned, Italian-inspired, and full of that warm, welcoming energy that makes you want to stay all afternoon. On weekends, there’s always something happening- live music, groups of friends sharing bottles, and that easy, “hang out and take your time” rhythm that makes it the perfect fall escape. You don’t need a reservation or a plan here… just show up, grab a bottle, and find a spot among the vines. It’s relaxed, unpretentious, and always a good time.
Stonington Vineyards: (Stonington, CT)
Set among the coastal hills of Stonington, Stonington Vineyards is the kind of spot that makes you want to slow down and stay awhile. It’s got all the charm of a small New England winery - laid-back vibes, scenic views, and wine that perfectly fits the seaside setting. Their tastings are relaxed and friendly, and on sunny days, the patio is the place to be. Pack a picnic, grab a bottle of your favorite, and let the afternoon roll by. If you visit in summer, check out one of their outdoor concerts - good music, good wine, and a golden-hour glow you won’t want to leave.