Events

The Fireside Theatre presents A Christmas Story: The Musical as a dinner-theatre holiday production. Calendar time is the published showtime; dining and arrival begin earlier.

Weekly Thursday live music at Harpoon Willies in Williams Bay.

Whitewater's annual Holiday Parade of Lights is held on the first Friday in December, followed by the lighting of Christmas at Cravath. The 2026 date is December 4; exact parade time should be rechecked before event week.

East Troy Railroad's 2026 Santa's Special Evening Christmas Trains depart the East Troy Depot in the early evening. Advance reservations are required; exact departure is selected through ticketing.

Whitewater's Christmas at Cravath display is illuminated after the Holiday Parade of Lights and remains a seasonal attraction into early January. December entry is listed as a planning window; verify nightly display details locally.

The Fireside Theatre presents A Christmas Story: The Musical as a dinner-theatre holiday production. Calendar time is the published showtime; dining and arrival begin earlier.

The 531 Fund Christmas Festival transforms the PIER 290 Boat Showroom into a holiday experience with decorated themed booths and charity raffle packages. Admission is free. Santa Cruise guests also begin their holiday experience in this area; Santa Cruise departure times are tracked separately until the 2026 schedule is posted.

Downtown Elkhorn's annual Christmas tree lighting begins at 5 PM, followed by caroling and Santa activities.

December live music in the Geneva Lake Distilling tasting room. The venue lists Jeff Trudell for this date.

Downtown Delavan holiday kickoff with the tree lighting, DDHS Comet caroling, Santa and the parade around Tower Park.

Indoor Friday live music at the Mars Resort piano bar.

Jacqi Michaels and Friends performs a holiday concert at Belfry Music Theatre. Belfry evening events begin at 7 PM.

The Fireside Theatre presents A Christmas Story: The Musical as a dinner-theatre holiday production. Calendar time is the published showtime; dining and arrival begin earlier.

Friday night live music at Bar West at The Abbey Resort. Holiday-week programming should be rechecked before December 25.

East Troy Railroad's 2026 Santa's Special Evening Christmas Trains depart the East Troy Depot in the early evening. Advance reservations are required; exact departure is selected through ticketing.

A heated Christmas train ride from the East Troy Depot to Santa's Workshop, with a visit to Santa and a gift for child and toddler ticket holders. Multiple departures are offered; the railroad currently lists departure time as to be determined, so verify the ticket calendar before publication.

Choose-and-cut and pre-cut Christmas trees, wreaths, garland, hot chocolate and cookies at Conifera Tree Farm near the Southern Lakes/Illinois border.