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The kickoff to the Christmas shopping season

A Christmas Welcome

Three festive days of shopping, sipping and holiday magic in downtown Waupun.

November 5 to 7, 2026Thursday to Saturday
Peek in the windowsHow the passport works

Your holiday story starts here

A shopping adventure in three parts.

Call your sister, your mom and your best friends. This is the weekend the Christmas season begins in Waupun.

Holiday shoppers browsing a boutique decorated with a Christmas tree.
Part OnePick up your passportGrab your Playbill Passport at any participating business and start your adventure.
Two friends strolling a downtown Waupun sidewalk.
Part TwoFollow the big red bowsStroll downtown and look for the big red bows marking every participating business.
A holiday coffee flight in black and white plaid cups on a Happy Holidays board.
Part ThreeWrap it up SaturdaySip a drink while your gifts are wrapped at our Saturday gift-wrap stations. Locations coming soon!

Peek inside to see what’s in store

Stroll the holiday windows.

Tap any window to peek inside for holiday specials, hours and more. New shops are joining every day, so check back soon!

Shop small · Downtown Waupun
  • The Graceful Nest | Holiday sales, Gift with purchase, refreshments, giveaway and festive photo opportunities. | Hours coming soon | www.thegracefulnestwaupun.com | 11 N. Madison St.
  • Werner Harmsen | Holiday retail specials all weekend. | Thu to Sat: 8 to 7 | www.wernerharmsen.com | 116 E. Main St.
  • My Property Shoppe LLC | Free Nutcracker cookie (one per person while they last), Sign up to win a hand-painted 6-foot nutcracker! | Thu and Fri: 9 to 3 (subject to change) | www.mypropertyshoppe.com | 6 E. Franklin St.
  • C.VERHAGE.PHOTO | Christmas Traditions with Santa on Saturday, Nov. 7, plus Holiday Simple Sessions on Friday, Nov. 6 and Sunday, Nov. 8. | Fri 8:30 to 6 · Sat 8 to 5 · Sun 9 to 2 | www.cverhagephoto.com | 426 E. Main St.
  • Chic Tique | Holiday retail specials. | Hours coming soon | www.chictiquegirls.com | 301 E. Main St.
  • The Clothing Pallet | A gift with purchase, a giveaway and festive holiday decor. | Hours coming soon | | 18 N. Madison St.
  • Blue Heron Antiques/ Bh Home | Holiday sales, Gift with purchase, refreshments, giveaway and photo opportunities. Mrs. Claus may even stop by! | Thur 9 to 7 · Fri 9 to 7 · Sat 9 to 4 | | 309 E. Main St.
  • Firefly Giftshop and Reiki Essentials | Thur: Buy two Reiki sessions, get one free. Fri: Free holiday tarot readings, Free 15-minute Reiki sessions and free samples of the Don’t Scrooge Yourself oil blend. Sat: In-store specials and Hot Chocolate. | Thur: Noon to 7 · Fri: Noon to 7 · Sat: 9 to 5 | www.facebook.com/TyraReiki | 314 E. Main St.
  • Charming Reads | Store specials, activity TBD. | Hours coming soon | www.charmingreadswaupun.com | 20 S. Madison St.
  • Madeline Clothing Company | Sales or giveaway in the works. | Hours coming soon | www.madelineclothingcompany.com | 300 E. Main St.
  • Revived Roots Studio | Holiday discounts and giveaways, details coming soon. Thur and Fri only. | Hours coming soon | | 102 Washington Ave.
  • Gysbers Jewelry | 20% off anything over $100 (some exclusions apply). | Thur 9 to 6 · Fri 9 to 5 · Sat 9 to 3 | www.gysbersjewelry.com | 305 E. Main St.
  • Glamour Shop | Gift with purchase and a Giveaway. | Thur 9 to 8 · Fri 9 to 5 · Sat 8 to 12 | www.glamourshopwaupun.com |
  • Kartechner & Girls Flower Co. | Make Your Own Simmer Pot Mix! | Thu to Sat: 9 to 2 | | 18 S. Madison St.
  • Bargains Galore Thrift Store | 20% off on Saturday, + drawing for a gift basket. | Thu 10 to 8 · Fri 10 to 2 · Sat 10 to 2 | www.bargainsgalorethriftstore.com | 810 W. Main St.
  • Wind & Unwined, Coffee & Wine House | Drink specials all weekend. Other specials coming soon!

    Dear Santa,




    The festivities

    What’s in store.

    • Playbill PassportPick one up at any participating business and complete your stops for chances to win gift baskets and cash prizes.
    • Gift-wrap stationsSaturday only. Sip a drink while your gifts are wrapped. Locations coming soon!
    • Roaming Christmas musicHoliday tunes around downtown all weekend.
    • Nutcracker photo stopGrab your crew for the perfect holiday photo.
    • Surprise Prize PatrolKeep an eye out for surprise moments while you shop.
    • Red bow holiday displaysFestive displays at every participating business.
    • Mouse King HuntCan you find the mischievous Mouse King?
    A downtown shop decorated for the holidays with gifts and garland.A cozy shop with a Christmas tree and holiday gifts.Silver tinsel trees sparkling in a holiday display.
    A holiday gift basket wrapped with a festive ribbon.
    Win gift baskets and cash prizesComplete your Playbill Passport stops for chances to win.

    Downtown Waupun presents

    The Playbill Passport

    A Christmas Welcome · November 5 to 7, 2026

    1. IPick one upGrab your Playbill Passport at any participating business during the event.
    2. IIShop the red bowsVisit participating businesses and complete your passport stops.
    3. IIIWin something merryComplete your passport for chances to win gift baskets and cash prizes.

    Drawing details coming soon.

    Make it a girls’ weekend

    Shop all day. Cozy up all night.

    Turn the kickoff into a getaway. Linger over dinner, toast the season and wake up ready for one more day of shopping.

    Sip and savor →Places to stay →Downtown map →
    The Mouse King holding a sword and wearing a golden crown.

    The Mouse King scavenger hunt

    The Mouse King is loose!

    Tap the button to set the Mouse Kings loose. Seven of them will sneak onto pages all around this website. Find each one and tap him to send him scurrying back to his castle.

    See you downtown

    Save the date and bring your crew.

    November 5 to 7, 2026 in downtown Waupun. Hours coming soon, and more participating businesses are joining every day.

    Events calendarPlan your visit
    A nutcracker rising from a red gift box.