GAME NIGHT AT TWISTED TRAIL
Friday, September 18 | 4:00–8:30 PM
GAME NIGHT AT TWISTED TRAIL
Friday, September 18 | 4:00–8:30 PM
Grab your friends, bring your favorite game and join us for a relaxed Friday night of wine, games and good company!
🀄 Mahjong players… bring your group and your set!
🎲 Bunco groups… round up your crew!
♠️ Cards, dominoes, board games or whatever you love to play… bring a few friends and make a night of it.
No tournament. No complicated rules. Just gather your group, claim a table, grab some wine and play!
And if your group gets a little competitive…even better. 😂
🍷 Wine
🎲 Games
👯 Friends
😂 A little friendly competition
📅 Friday, September 18
⏰ 4:00–8:30 PM
📍 Twisted Trail Winery | 150 Twisted Trail, Fillmore, Illinois
Bring your game. Bring your people. We’ll provide the wine. 🍷🎲
SOLD OUT! A Night for Dolly: Workin’ 5 to 9
Friday, September 25, 5-9 PM
Come celebrate the life, music, style and incredible legacy of Dolly with us at Twisted Trail Winery! 💗
On Friday, September 25, we’re Workin’ 5 to 9 — Dolly style.
Break out the rhinestones, big hair, cowboy hats and all things fabulous for a fun night featuring:
💕 Dolly Bingo with prizes
💕 Dolly Trivia Showdown
💕 Dress in Your Dolly Best — with prizes!
💕 Dolly Photo Booth
💕 Fun Dolly-themed wine slushies & Twisted Trail wines available for purchase
💕 Lolli & Pops Food Truck with food available for purchase
📚 HONOR DOLLY’S LEGACY
Dolly’s love of reading has put millions of books into the hands of children, so we’re adding a little heart to our celebration.
Please bring a NEW or GENTLY USED book to donate to the Hillsboro Library and help inspire the next generation of readers.
🎟️ TICKETS
$10 per person + applicable service fee
Tickets are limited, so we strongly recommend purchasing yours in advance.
Food and beverages are sold separately. Tickets and service fees are nonrefundable.
Friday, September 25 | 5–9 PM
📍 Twisted Trail Winery
150 Twisted Trail • Fillmore, IL
Come for Dolly. Stay for the wine. Leave inspired. 💗
MRS. ROPER ROMP - A GIRLS NIGHT OUT! (Limited Availability)
Friday, October 23, 2026 at 6PM - 8:30PM
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
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