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!

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 6:00 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.

PRESENTED BY:

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 7 through Dec 31. Visit seven 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 to earn your official Downtown Baraboo Sip the Square Badge of Honor.

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.