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Top 5 Wineries Near Chatfield Farms in Southwest Connecticut

If you live in southwest Connecticut, you already know that Autumn is a beautiful time of year. Bursts of colorful foliage that look like painted oil portraits, brisk and invigorating air that’s perfect for long afternoon walks, and miles of charming countryside to explore. 

If you live in Chatfield Farms in Beacon Falls, it’s the perfect time to take a leisurely weekend drive to one of the many wineries and vineyards that dot the landscape. Enjoy tastings al fresco, or if it’s too chilly, warm up in a toasty tasting room with a nice flight of local wines. You can’t go wrong with any of the wineries just up the road in Litchfield or Middlesex Counties, but here are a few of our favorites.


Best Wineries in Southwest Connecticut


Arrigoni Winery & Cider Co. | 50 minutes away

1287 Portland-Cobalt Rd. (Route 66) | Portland, CT

Come enjoy local wine, craft beers, and delicious food in a gorgeous, rustic setting overlooking the vineyards. No matter the season or the weather, there’s always a reason to celebrate wine (and life!) at Arrigoni Winery.


Hawk Ridge Winery | 30 minutes away

28 Plungis Rd. | Watertown, CT 

Come for the wine, stay for the amazing views! Hawk Ridge Winery is located on a 58-acre working farm that dates back decades. There are four acres of beautiful vineyards, which are in full view from the modern tasting room and clubhouse.


Hopkins Vineyard | 1 hour away

25 Hopkins Rd. | New Preston

This heritage farm nestled in the Litchfield County countryside has been in operation for 225 years. Today, you can sample their many wines, then enjoy a glass of your favorite at the historic wine bar, overlooking beautiful Lake Waramaug (which was the inspiration for our Waramaug floorplan!).


Walker Road Vineyards | 35 minutes away

17 Walker Rd. | Woodbury

Drive up to Woodbury to go antiquing for the day, then stop at Walker Road Vineyards for a taste of the local wine. Taste wines by the glass or flight in the renovated, 150-year old, distinctive red barn while sampling local cheese and enjoying the good life. 

DiGrazia Vineyards | 40 minutes away

131 Tower Rd | Brookfield, CT 

If you’ve never had DiGrazia’s famous Wild Blue blueberry wine with brandy, now’s a good time. Enjoy this and a dozen other local wines at this family-owned winery. Pack a picnic lunch and enjoy your tasting outdoors, or have a seat in the wood-clad Barrel Room and appreciate its unique ambiance. 


If weekends at the winery sound like just your speed, schedule a showing to see Chatfield Farms, an award-winning 55+ community from EG Homes, located in the heart of beautiful Connecticut wine country.



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