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Upcoming Events at Twisted Trail Winery

Twisted Trail Winery October events

MRS. ROPER ROMP - A GIRLS NIGHT OUT! SOLD OUT!

Friday, October 23, 2026 at 6PM - 8:30PM

SORRY. THIS EVENT IS SOLD OUT! 

Come and knock on our door… we’ve been waiting for you! 


Grab your girlfriends, dig out your most fabulous caftan, pile on the big jewelry, tease up that hair and join us for our Mrs. Roper Romp!


Friday, October 23 | 6:00–8:30 PM

Twisted Trail Winery

150 Twisted Trail, Fillmore, IL


In honor of Breast Cancer Awareness Month, all ticket proceeds from our October 23 Mrs. Roper Romp will be donated to the the Montgomery County Breast Cancer Support Group, supporting those in our local community affected by breast cancer. 


We’ll have 70s music and plenty of laughs with:


Mrs. Roper Runway… Strut your stuff!


What’s in Your Purse?… You never know what we’re going to ask you to find.


The Girlfriend Game… How well do you REALLY know your friends?


Mr. Roper Says… Think Simon Says… after a little wine. 😂


And at the end of the night, one fabulous lady will be crowned Mrs. Twisted Trail 2026!


Caftans, wigs, big jewelry and all things 70s are highly encouraged.


And if you’ve got a Stanley Roper brave enough to join you, bring him too! 😂


Our last two ticketed events sold out. Don’t miss this one!


$10 + ticketing/processing fees | 21+ event

SORRY! THIS EVENT IS SOLD OUT!

The Twisted Table: A Wine Pairing Dinner

Monday, November 2, 2026, 6:00 PM

Introducing The Twisted Table, our new dining series held on select Mondays, bringing together local culinary talent, thoughtfully paired wines, and great company!

For our first gathering, we’re partnering with Curbside Cravings for an intimate three-course dinner.

Picture two beautifully arranged long tables, soft candlelight, seasonal touches, and an evening designed to be savored. Each course will be paired with a specially selected Twisted Trail wine.

THE EVENING’S MENU

First Course | Marquette Rosé

Fresh garden salad with balsamic vinaigrette and bread, paired with our semi-sweet Marquette Rosé.

Second Course | Vignoles

Fettuccine topped with your choice of chicken or steak, accompanied by green beans and paired with our crisp, dry white Vignoles.

Third Course | Cayuga

Chocolate ricotta cake paired with the debut of our sweet Cayuga white wine! Be among the first to try our newest wine!

Monday, November 2, 2026

Doors Open: 6:00 PM

Dinner Begins: 6:30 PM

Twisted Trail Winery, 150 Twisted Trail, Fillmore, IL

General Admission: $55 per person

Wine Club Members: $49 per person

Includes three courses and three 3-ounce wine pairings.Ticketing and processing fees are additional. 

LIMITED SEATING | ADVANCE TICKETS REQUIRED

Not a Wine Club member? Join here for exclusive benefits and special pricing:

https://twistedtrailwinery.com/join-the-wine-club

IMPORTANT INFORMATION

Guests must be 21+. Choose chicken or steak when purchasing tickets. Seating is communal at our long tables. Due to limited seating and advance meal preparation, all tickets are non-refundable

Reserve Your Seat Here
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Twisted Trail Winery

150 Twisted Trail, Fillmore, Illinois

Copyright © 2026 Twisted Trail Winery - All Rights Reserved.


A Quick Note About Outside Food & Drinks

We love partnering with local small businesses to bring you delicious food options throughout the season. Because of that, we kindly ask that you do not bring outside food or beverages to the winery.

Every purchase helps support not only Twisted Trail Winery, but also the amazing local vendors we work with. Thank you for helping us build a community that supports local!

Creating Memories, One Glass at a Time.

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