2024 CT Winter Wine Trail – January 6th to March 30th!

One of the most popular and highly anticipated annual events along The Connecticut Wine Trail is the Winter Passport Program – a wonderful opportunity for wine enthusiasts and newbies to explore the breathtaking countryside, visit our member wineries, and win fabulous prizes – valued at over $5,000!

This year, 13 fabulous farm wineries across the state are in the game. Here’s how it works: 
From January 6th through March 30th, wine lovers can pick up a free passport from any of the participating wineries and begin their quest to visit each one (all are unique, giving visitors the chance to experience the wine-making process firsthand, take tours, and taste award-winning varieties as they enjoy first-class entertainment, great food, and special events). Get your passport stamped at all 13 vineyards and submit it by the March 30th deadline and you’ll be eligible to win a prize.

“Beat the winter blues by sipping some wonderful reds, whites, and pinks!” says Margaret Ruggerio of The CT Wine Trail and co-owner of Paradise Hills Vineyards in Wallingford. “Friends and family will enjoy a unique and delicious social experience as they expand their palates and learn about the history of winemaking in the state.”

Start planning an unbeatable day or weekend adventure – a tasty journey with a big payoff – at these 13 participating wineries:

56 Pole Bridge Rd.

1355 Boston Post Rd.

1339 Whirlwind Hill Rd.


28 Plungis Rd.


25 Hopkins Rd.
New Preston


74 Chester Maine Rd.
North Stonington

113 Pendleton Hill Rd.
North Stonington

15 Windswept Hill Rd.


11 Shailor Hill Rd.

108 Wade Rd.

523 Taugwonk Rd.


599 Old Middle St.

818 Route 171


The 2024 CT Winter Wine Trail Passport Program runs from January 6th to March 30th. You must be 21 years of age to participate and have your passport booklet stamped by all 13 participating wineries to qualify. No purchase is necessary; one entry per person and you must be present to have your booklet stamped. Photocopied booklets or pages will be disqualified. Booklets must be submitted to a participating winery by March 30. Random prize drawings will be held by April 19th. Winners will be notified by email or phone. Prize details, restrictions, and expiration dates are listed here. Prizes are non-transferable. Winners agree to allow their names and images to be used in future advertisements and will provide an affidavit of eligibility and liability waiver.