Oak Tree Winery

10/13/2026

09/27/2026

We had such a great time at the Windsor Day Parade. Huge thanks to everyone who came out, cheered us on, and brought that classic Windsor spirit. And a special thank you to the Windsor Kiwanis Club for organizing such a fun and community‑filled event.

09/19/2026

Come join us today!!

Windsor Locals, today’s your day! Join us at Locals Day & Sidewalk Sale on the Town Green from 12–6 PM and make the most of downtown.

Tasting Notes is celebrating with Complimentary 3‑Flight W**e Pours and 20% off all w**es. Come sip, stroll, and support the businesses that make Windsor feel like home.

Pick up your FREE Locals Passport (with proof you live or work in Windsor) at the Windsor Chamber of Commerce, collect stamps as you shop and dine, and enter to win a Downtown Windsor Gift Basket.

Support Local • Shop Downtown • Save More
See you at Windsor Town Green and stop by Tasting Notes for your pour.

09/15/2026

Comedy next Friday, 7pm! Tickets available!

Join us for a hilarious evening of stand-up comedy at Tasting Notes!

09/13/2026

Oak Tree W**ery showed up big at the Windsor Chili Cook‑off, three full cases poured, countless great conversations, and a whole lot of “Wait… you have a tasting room downtown?” moments.

We loved sharing our award‑winning w**es with Windsor residents, meeting new neighbors, and telling the story of our cozy downtown tasting room that’s been part of this community for over two years. Events like this are the perfect chance to connect, hand out our 2‑for‑1 tasting cards, and invite folks into our local family business.

Here’s to new faces, returning friends, and seeing everyone again soon at Oak Tree W**ery. Cheers to Windsor.

09/06/2026

Sundays are for slowing down, sipping well, and soaking up the long weekend energy.

We’re pouring 2‑for‑1 tastings all day, plus the perfect duo of Mimosa Sunday and Game Day from 12–5 PM. If you’re looking for a laid‑back spot to wrap up Labor Day Weekend, you just found it.

Bring your people, grab a table, and let Windsor’s favorite w**e lounge take it from there.