Thousand Islands Winery

Cheri is an Award-winning vocalist with a growing regional following. Her performances are a polished jazz cabaret that blends classic jazz, cabaret charm, and soulful storytelling, creating an elegant and intimate entertainment experience that pairs perfect with a glass of wine.

Comedy Night at Thousand Islands Winery Join us for a fun evening of laugher. Grab your friends, grab your tickets, and get ready to laugh with us. We can’t wait! Cocktail Hour: 6:30pm-7:30pm Show: 7:30-9:00pm Buy your tickets here: July Comedy Show

Join us as we welcome the Orion Art Gallery’s 2026 Plein Air Artist Competition, held here at the Thousand Islands Winery! Organized and hosted by the Orion Art Gallery & Studio. Whether you are an artist looking to compete, or a spectator wanting to grab a glass of wine and view local masterpieces, we want to see you there! Awards will be given to competing artists, and beautiful local art will be available for purchase. If you are an artist looking to sign up

Welcome to the 2026 Pirate Palooza at Thousand Islands Winery ! Get ready to set sail on August 14, 2026 at 5:00 PM for a swashbuckling adventure. Join us for a day filled with treasure hunts, pirate games, and delicious food and drinks. Don’t forget to dress up in your best pirate attire and bring your crew along for a day of fun on the high seas. Arr matey, see you there! 12 & under FREE 13 & up only $5.00 Buy tickets here:

Welcome to the 2026 Pirate Palooza at Thousand Islands Winery ! Get ready to set sail on August 15, 2026 at 2:00 PM for a swashbuckling adventure. Join us for a day filled with treasure hunts, pirate games, and delicious food and drinks. Don’t forget to dress up in your best pirate attire and bring your crew along for a day of fun on the high seas. Arr matey, see you there! 12 & under FREE 13 & up only $5.00 Buy tickets here:

Comedy Night at Thousand Islands Winery Join us for a fun evening of laugher. Grab your friends, grab your tickets, and get ready to laugh with us. We can’t wait! Cocktail Hour: 6:30pm-7:30pm Show: 7:30-9:00pm Buy your tickets here: https://August2026comedyshow.eventbrite.com

Blues at the Winery Come join us for an afternoon filled with soulful blues music at Thousand Islands Winery ! Get ready to sip on some delicious wine while grooving to the tunes on September 5, 2026 at 2:00 PM . It’s the perfect way to unwind and enjoy the company of good friends. Don’t miss out on this fantastic event! 12 & under FREE 13 & up only $5.00 Buy Tickets here:

Comedy Night at Thousand Islands Winery Join us for a fun evening of laugher. Grab your friends, grab your tickets, and get ready to laugh with us. We can’t wait! Cocktail Hour: 6:30pm-7:30pm Show: 7:30-9:00pm Buy your tickets here: https://September2026comedyshow.eventbrite.com

Join us for a fun time at our annual Oktoberfest with great live music, German food and beer and local craft vendors . 12 & under is FREE 13-20 only $6.00 • Military $6.00 • Seniors $6.00 21+ $10.00 Buy Tickets here: Oktoberfest Tickets

Comedy Night at Thousand Islands Winery Join us for a fun evening of laugher. Grab your friends, grab your tickets, and get ready to laugh with us. We can’t wait! Cocktail Hour: 6:30pm-7:30pm Show: 7:30-9:00pm Buy your tickets here: https://October2026comedyshow.eventbrite.com

Comedy Night at Thousand Islands Winery Join us for a fun evening of laugher. Grab your friends, grab your tickets, and get ready to laugh with us. We can’t wait! Cocktail Hour: 6:30pm-7:30pm Show: 7:30-9:00pm Buy your tickets here: https://November2026comedyshow.eventbrite.com

Welcome to the 2026 Kris Kringle Market ! Join us at Thousand Islands Winery on December 5, 2026 at 10:00 AM for a festive day of shopping, food, and holiday cheer. Get ready to browse through unique gifts, sip on delicious wines, and enjoy the merry atmosphere. Don’t miss out on this jolly event!