About this Event
Holly Dolly Holiday — Ladies Night Out in Woodstock!
Grab your girlfriends and get ready for a festive night of shopping, sipping, and celebrating in Downtown Woodstock! Held annually on the Thursday after Thanksgiving, Ladies Night Out brings holiday magic to our beautifully lit historic Square.
This year, we're adding a little extra sparkle with our Holly Dolly Holiday theme! Break out the sequins, rhinestones, and Dolly-inspired outfits for a fabulous girls' night out!
Your ticket includes:
🍸 A festive welcome cocktail or mocktail to kick off the evening
🛍️ An official Ladies Night Out tote bag
🥤 A souvenir lidded drink cup so you can stroll around the Square with your drink while enjoying the festive holiday lights and Dolly music!
🛒 An Event Guide featuring participating shops and exclusive specials
🎟️ Opportunities to win fabulous raffle prizes
🎄 A Holiday Wish List to drop a few hints about what you really want under the tree!
🎟️ Round up your girls, grab your tickets, and get ready for a Holly Dolly Holiday to remember!
Check-In at Squire on the Square 101 N. Johnson St. (enter the door the left of the Courthouse stairs)
Ladies Night Out 2026: A Jolly Dolly Holiday!
Grab your girlfriends, break out the rhinestones, and get ready for a holiday shopping night that's as fabulous as Dolly herself!
Ladies Night Out is back on Thursday, December 3, from 4:30–9:00 PM, and this year, we're bringing a little sparkle to Downtown Woodstock with a Dolly Parton-inspired holiday celebration!
Think pink, boots, bows, big hair, and plenty of holiday cheer as you sip, shop, and stroll your way through downtown! Enjoy an evening filled with exclusive shopping specials, festive refreshments, raffle prizes, and a whole lot of fun with your favorite ladies.
Your ticket includes:
- A festive welcome cocktail or mocktail to kick off the evening
- An official Ladies Night Out tote bag
- A souvenir lidded drink cup
- An Event Guide featuring participating shops and exclusive specials
- Opportunities to win fabulous raffle prizes
- A Holiday Wish List to help you drop a few hints about what you really want under the tree!
Whether you're checking off your holiday shopping list, treating yourself, or just looking for a fun girls' night out, this is one holiday tradition you won't want to miss!
🎟️ Only 300 tickets available! Grab yours early, round up your favorite ladies, and get ready to celebrate the season with a little extra sparkle!
Because when it comes to the holidays, a little Dolly goes a long way!
🎄 Drop & Shop During Ladies Night Out! 🛍️
Enjoy A Jolly Dolly Holiday – Ladies Night Out while the kids have a fun-filled evening at the Woodstock Recreation Center!
Kids will enjoy festive crafts, group games, 9-square, and a pizza dinner with Playground Program Staff.
You get a few uninterrupted hours to shop, and they get an unforgettable night of play!
📅 Thursday, December 3, 2026
⏰ 4:30–9:00 PM
📍 Dean Street Recreation Center | 1201 Dean St.
👧 Ages: 5–12 | Cost: $40/$60
🎟️ Registration required: Register Here
Check-in for A Jolly Dolly Holiday will take place at Squire on the Square. (Left door entrance from the courthouse stairs).
Event venue & nearby stays
Squire on the Square, 101 North Johnson Street, Woodstock, United States
Concerts, fests, parties, meetups — all the happenings, one place.