SOLD OUT! Paint Your Partner: Sip, Paint & Laugh! SOLD OUT!
Friday, September 4, 5-7 PM
Grab your partner, bestie, sister, or anyone brave enough to let you paint them!
Join us at Twisted Trail Winery for Paint Your Partner, a fun evening of wine, painting, and plenty of laughs with local artist Vicki White.
No artistic talent required…in fact, that might make it even more fun!
Your ticket includes:
- Guided Paint Your Partner experience with Vicki White
- All painting supplies
- One bottle of Twisted Trail wine per couple
📅 Friday, September 4
⏰ 5:00 - 7:00PM
📍 Twisted Trail Winery, 150 Twisted Trail, Fillmore, Illinois
$70 per couple ($35 per person)*
Come with a partner or friend and leave with two portraits, some great memories, and quite possibly a new appreciation for professional artists. 😂
Space is limited and advance tickets are required.
*By purchasing tickets, I understand that all ticket sales are final and non-refundable. Ticket price does not include applicable service/processing fees, which will be added at checkout. Guests must be 21 or older to consume alcohol and agree to drink responsibly.
First Responder Appreciation Night
Friday, September 11, 4-8:30 PM
FIRST RESPONDER APPRECIATION NIGHT
Friday, September 11 | 4:00–8:30 PM
September 11 is a day we will never forget.
A day to remember those we lost, honor those who answered the call, and show our appreciation for the men and women who continue to serve and protect our communities every day.
This night is especially meaningful to us. Both Cindi and Bobby are retired law enforcement, and we wanted to set aside an evening at Twisted Trail Winery to say a simple but heartfelt THANK YOU to our fellow first responders.
Law Enforcement
Firefighters
EMS
Dispatchers
First responders, your hot dogs and chips are on us!!
And because we know a little friendly competition is inevitable…
FIRE gets RED
POLICE gets BLUE
We’ll have special red and blue wine slushies available for purchase and keep track of which side orders the most. Will Fire or Law Enforcement take the win???
Not a first responder? Please come out too! Grab a glass of wine, enjoy the evening and help us show some love to the people who serve our communities.
No tickets. No big production. Just an evening to remember, honor, appreciate and spend some time together.
Friday, September 11, 2026
4:00–8:30 PM
Twisted Trail Winery | 150 Twisted Trail, Fillmore, Illinois
We remember. We honor. We appreciate.
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. 🍷🎲
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. 💗