Light Up & Sip the Square

Nov 6 – Dec 31, 2026

New for the 2026 Holiday Season: A beverage tour and a downtown holiday lights display!

If you’ve landed here because you’re looking for details on the drinks that are part of the Sip the Square promotion, please keep scrolling down to see them.

Light Up the Square

New for 2026, Downtown Baraboo proudly introduces Light Up the Square, an incredible holiday lighting display surrounding the Sauk County Courthouse 7 days a week Nov 6th to New Year’s Eve 5pm to 10pm. 

The celebration officially begins at 5:00 PM on Friday, November 6, as thousands of lights illuminate the courthouse lawn for the first time. Created through a public-private partnership between Downtown Baraboo, the BID, Ho-Chunk Gaming, Festival Foods, WCCU, and local artisans, the display will shine nightly and provide the perfect backdrop for holiday photos all season long.

Lights will be illuminated 5-10PM every night.

Plan an evening shopping trip, walk the lights on the courthouse square, and grab dinner or a cocktail for Sip the Square.

THANK YOU TO OUR PRESENTING SPONSOR, HO-CHUNK GAMING WISCONSIN DELLS.

And to our additional sponsors, Festival Foods, WCCU Credit Union, and Fairfield Inn & Suites, Baraboo.

Thank you to MC Plumbing and Bachrodt Baraboo Motors for their sponsorship as well!

Sip the Square

Sip the Square | Coffee, Cocoa, & Cocktail Tour in Downtown Baraboo

Be one of the first to experience Downtown Baraboo’s inaugural Sip the Square Beverage Tour, starting on Nov 6 through Dec 31. Visit eleven participating coffee shops, lounges, and bars around the historic Courthouse Square, each serving an exclusive seasonal drink created just for the holidays.

Pick up your Sip the Square Passport at your first stop and collect stamps throughout the weekend or anytime during the holiday season. Complete every stop and receive an exclusive commemorative sticker and be entered to win $350+ in prizes.

Whether you’re craving peppermint mochas, festive cocktails, hot cider, or cozy winter creations, there’s something new waiting at every stop as you shop your favorite shops around the courthouse square.

Detailed List of Sip the Square Locations, Hours, & Drinks

Balanced Rock Winery
1065 Walnut St, Baraboo, WI 53913
Decorations: Christmas
Hours: Daily, 11am to 7pm
Holiday drinks: Holiday Mulled Wine & Cranberry Apple Slush

Baraboo Burger Company
116 4th Ave, Baraboo, WI 53913
Decorations: Santa Presents Burgers
Hours:
Monday, Tuesday, Thursday: 11am to 11pm
Friday and Saturday: 11am to 12am
Sunday: 11am to 10pm
Closed Wednesdays
Holiday drinks: Chocolate Covered Cherry, Holly Jolly Juice, Santa’s Midnight Snack, Santa’s Night Cap
Holiday burgers: Jolly Ol’ Double Bacon, Santa’s Belly Buster

Brother’s On Oak
412 Oak St, Baraboo, WI 53913
Decorations: Christmas
Hours:
Monday: 5pm to 2am
Tuesday through Thursday: 11am to 2am
Friday through Sunday: 11am to 2:30am
Holiday drinks: Santa’s Nightcap (alcoholic and mocktail versions)

Gina Jenny’s
126 3rd St, Baraboo, WI 53913
Decorations: Jingle Jennys
Hours:
Monday through Thursday: 4pm to 9pm
Friday: 4pm to 11pm
Saturday: 3pm to 11pm
Holiday drinks: Coming soon

Little Village Cafe
146 4th Ave, Baraboo, WI 53913
Decorations: Winter wonderland / Snow globe
Hours:
Monday through Thursday: 11am to 8pm
Friday & Saturday: 11am to 9pm
Sunday: Closed
Holiday drinks: Holiday Aperol Spritz, Keoke Coffee, Blood Orange Ginger Mocktail Spritz

Munay Pastry Shop & Cafe
138 1st St, Baraboo, WI 53913
Decorations: Pink Christmas
Hours:
Open in the evening for Light Up the Square (Nov 6)
Monday: 7am to 2pm
Tuesday: Closed
Wednesday through Saturday: 7am to 2pm
Sunday: 8am to 1pm
Holiday drinks: Peppermint Mocha, Hot Chocolate, Caramel Vanilla Latte, Toasted Marshmallow Mocha Latte

Powerline Coffee Co
108 3rd St, Baraboo, WI 53913
Hours:
Monday through Friday: 7am to 4pm
Saturday and Sunday: 7am to 2pm
Event hours:
Holiday Wine Walk (Nov 20): 7am to 9pm
Christmas Light Parade (Nov 21): 7am to 6:30pm
Holiday drinks: Classic Christmas Coffees

Press Coffeehouse
133 3rd Ave, Baraboo, WI 53913
Decorations: Christmas tree
Hours:
Monday, Tuesday, Friday, Saturday, Sunday: 7am to 4pm
Wednesday and Thursday: 7am to 6pm
Event hours:
Light Up the Square (Nov 6): open until 8pm
Christmas Light Parade (Nov 21): open through the end of the parade
Holiday drinks: Candy Cane Latte, Eggnog Latte, Peppermint Mocha, Sugar Cookie Latte

The Relish Tray
106 4th Ave, Baraboo, WI 53913
Decorations: Santa’s Sweet Shoppe
Hours:
Wednesday: 9am to 2pm
Thursday: 9am to 8pm
Saturday: 11am to 9pm
Closed Monday, Tuesday, Friday, & Sunday
Holiday drinks: Cinnamon Maple Whiskey Sour, Butterbeer Bourbon Old Fashion, Peanut Butter White Russian, Rudolph’s Cranberry Margarita, White Christmas Mojito, Mulled Wine, Mrs. Claus’s Eggnog, Peppermint White Mocha, Toasted Marshmallow Mocha, Red Velvet Latte, Christmas Chai, Christmas Circus Cookie Latte, Matcha Turmeric Ginger Latte, Santa’s Strawberry Sparkler, Sugar Plum Fairy Fizz, Salted Caramel Hot Chocolate, Dragonfruit Cream Fizz, Virgin Yule Mule, Heartbeat Juice, Stop, Drop & Kale Juice, Shine Juice, Pineapple Dragon Juice, Celery Juice, Heart Health Tea, Immunity Blend Tea, Anti-Stress Tea

Sweets on Third
119 3rd Ave, Baraboo, WI 53913
Decorations: Have a Sweet Christmas
Hours:
Wednesday through Sunday: 11am to 6pm
Monday and Tuesday: Closed
Special hours:
Nov 6: 11am to 8pm
Nov 20: 11am to 9pm
Nov 21: 10am to 6pm
Nov 27 and 28: 10am to 6pm
Dec 5 and 12: 10am to 6pm
Dec 23: 10am to 7pm
Holiday drinks: Espresso Float, Mochaccino (hot chocolate with a shot of espresso), Peppermint Mochaccino, Pineapple Mango Lemonade (with or without boba), Strawberry Rose Lemonade (with or without boba), Apple Cider Float

Wiscocktail
132 3rd St, Baraboo, WI 53913
Decorations: Brandy Land
Hours:
Tuesday through Thursday: 4pm to 10pm
Friday: 4pm to 12am
Saturday: 1pm to 12am
Sunday & Monday: Closed
Holiday drinks: World Famous Wiscocktail Eggnog, Rum Rum Rudolph, Christmas Cosmo, Mistletoe Manhattan, Mexican Hot Chocolate, Jingle Juice, N/A Mexican Hot Chocolate, Maple Leaf

Make it a Weekend Getaway

Reimagine your holiday getaway in Downtown Baraboo. Baraboo offers a variety of lodging options for every style and budget. Click on a photo below to learn more about each lodging option. Baraboo has everything from cabins to historic bed & breakfasts to modern hotel facilities.