Windermere Wine & Dine

❄️🍷 Chilly weather, unforgettable night! 🍽️✨

Despite the cold, our community showed up in a BIG way for Windermere Wine & Dine. From incredible food and exceptional wine to even better company, the night was a true celebration of connection, generosity, and purpose.

Proceeds support charitable initiatives through the West Orange Foundation, the philanthropic arm of the West Orange Chamber of Commerce, and the Town of Windermere’s Windermere Legacy Fund.

Thank you to our attendees, sponsors, restaurants, and wine vendors for making such a meaningful impact. 🥂

We can’t wait to see you at Windermere Wine & Dine 2027! ✨

PHOTOS: Windermere Wine & Dine 2026 | West Orange Times & Observer Cold temperatures didn't keep the crowd away from the annual Windermere event.

🍷 Are You Ready Wine & Diners?!?!🍷

We’re popping the cork a little earlier tonight! Doors for Windermere Wine & Dine will now open at 5:30 PM — giving you extra time to sip, stroll, and savor the evening.

✨ Enjoy an unforgettable night of wine, food, and community
🎟️ Ticketed entry only
🔞 21+ event

Come ready to indulge, connect, and toast to a fantastic evening — we can’t wait to welcome you early! 🥂

🍷 A HUGE THANK YOU TO OUR INCREDIBLE RESTAURANT PARTNERS! 🍷

Windermere Wine & Dine would not be the mouthwatering, memory-making, community-loving event it is without these amazing culinary stars! 🌟

From savory bites to sweet treats, craft cocktails to bold brews — they’re bringing the FLAVOR and the FUN.

We are so grateful for the chefs, teams, and owners who are donating their time, talent, and tastiest creations to make this night unforgettable ❤️

Because of YOU, our guests get to sip, savor… and support all at the same time. That’s what community is all about 🙌

👏 Show these restaurants some love
📍 Visit them
🍴 Follow them
💬 Tell them THANK YOU when you see them at the event!

Get ready to eat your way around the room at Windermere Wine & Dine — it’s going to be delicious 😋 T-Minus 4 days!!!

T-minus 5 days until the most delicious, feel-good night of the year — Windermere Wine & Dine!

We’re keeping a close eye on the forecast and doing everything we can to make sure the evening is as comfortable and enjoyable as it is unforgettable. Heaters will be on site, and hand warmers will be available, so you can sip, stroll, and savor with ease.

And honestly… what better excuse for us Floridians to finally break out those “winter” outfits that only see daylight once a year? Dust off the coats, boots, and scarves—it’s their moment to shine!

As a reminder, this event is rain or shine, with a 100% chance of wine, great food, and an incredible community coming together for a great cause.

Please note: unfortunately, given the charitable nature of the event and commitments to our vendors, refunds are not available – the event will go on, rain or shine, cold or hot! If you decide the chill just isn’t for you, Tim’s Wine Market is maintaining a waitlist of guests eager to purchase tickets, so your spot won’t go to waste!

We can’t wait to celebrate, toast, and make an impact with you at Windermere Wine & Dine! 🥂