Kentucky Derby, Taste of Lake Geneva & some local theater this weekend
Look Ahead lists some of the events happening this weekend in the Lake Geneva area. The following information is subject to change. Confirming details with event planners is recommended. Email Special Sections Coordinator Steve Targo at stargo@lakegenevanews.net to have an event appear in this listing.
Friday, May 1
TFI Friday: Free Comedy Series — 7-9:30 p.m., Lake Geneva House of Music, N3241 County Trunk H, town of Geneva. Hosted by Addison O’Neal, featuring Eliza O, headliner Issa Laird and special guest Hector J. Ages 18 and older. Free admission and parking. More at the Lake Geneva House of Music Facebook page.
Simon & Garfunkel Tribute — 7 p.m., Belfry Music Theatre, 3601 Highway 67, Delavan, belfrymusictheatre.com. Forever Simon & Garfunkel perform. Tickets $74-92. Another performance is set for Saturday, May 2, at 7 p.m.
“Into the Woods” — 7:30-10:30 p.m., Sprague Theater, 15 W. Walworth St., Elkhorn, lakeland-players.org. Opening night for the latest production by the community theater group Lakeland Players includes a fairytale costume contest. This musical take on “Little Red Riding Hood” characters is rated PG-13, according to the Players’ website. Tickets $20. “Into the Woods” will also be performed Saturday, May 2, at 7:30 p.m.; and Sunday, May 3, at 2 p.m. More dates: May 8-10 and 15-17. Visit website.
Saturday, May 2
In-Water Demo Days — 10 a.m.-5 p.m., Jerry’s Majestic Marine, 352 Lake St., Fontana, jerrysmajestic.com/event/in-water-demo-days. Want to buy a boat? Here’s the first of three chances this month at Jerry’s to take one on the water and try it out. More In-Water Demo Days are set for Sunday, May 3; and Saturday, May 9, 10 a.m.-4 p.m. Registration required. Visit link to register.
Kentucky Derby Party — 1-6 p.m., Maxwell Mansion, 304 S. Wells St., Lake Geneva, staymaxwell.com. A big race like this will require big hats and bowties. Not only will Maxwell award prizes for Best Hat, Best Dressed and Best Couple, but there will be a meet-and-greet with therapy horse Nugget, of SMILES; a 50/50 raffle, silent auction items, specials and a J Henry rep will be pouring tastings on-site. No tickets or reservations required.

Quick, the Kentucky Derby approaches! Need to find a mint julep? Grab a big hat or bowtie and head to Walworth County this weekend. You could even meet a horse in Lake Geneva and have dinner on a train in East Troy.
Kentucky Derby Party — 2 p.m., Pier 290, 1 Liechty Drive, Williams Bay, pier290.com/event/kentucky-derby-party-2. Bourbon, big hats and Derby-inspired bites with special features from Maker’s Mark. Website ensures there will be plenty of “photo-worthy moments” on Derby Day at Pier 290. Reservations recommended. Visit link for menu and more.
Live Comedy: Natalie Whalen, Mike Maxwell & Jayson Cross — Shows 5 & 7 p.m., The Bottle Shop, 617 W. Main St., Lake Geneva, thebottleshoplakegeneva.com. Tickets $25, plus tax. Ages 21 and older. Strong language. Call 262-348-9463 to reserve. In a recent email, The Bottle Shop stated that this is its last comedy show until October.
Kentucky Derby Dinner Train — 5:30-6:30 p.m., East Troy Electric Railroad Depot, 2002 Church St., East Troy, easttroyrr.org/dinner-trains.html. Among the Kentucky Derby events in Walworth County, this may very well be the only one on an actual train. Menu includes Kentucky Hot Brown Sliders, Shrimp & Smoked Grits and Dirty Derby Bread Pudding. Tickets $135 each. More at link.
A Tribute to the Talking Heads with Big Suit — Doors open 6:30 p.m., show starts 7:30 p.m., Geneva Stage, 244 Broad St., Lake Geneva, genevastage.com. Big Suit was a 2024 Tribute Band of the Year nominee at the Josie Awards. Tickets $40-45, plus fees. See website.
Tuesday, May 5
Taste of Lake Geneva — 5:30 p.m., various Lake Geneva locations, wl.donorperfect.net/weblink/WebLink.aspx?name=E130830&id=27. Various venues will offer unique tastings and experiences to raise funds for the Forbeck Foundation. Oakfire and Queen Bee Artisan Market explore the hot honey pizza trend from 5:30-6:15 p.m. The Bottle Shop has a curated, three-wine tasting flight 6:30-7:15 p.m. At Geneva Tap House, celebrate Cinco de Mayo with a meal by Chef Abel, of Elena Catering. Cost $65 per person, $30 for designated drivers. More at link.


