Get in the Halloween spirit this weekend with Dragon Days, ‘Little Shop of Horrors’ & more in the Lake Geneva area
Look Ahead is the weekly event listing of The Resorter, suggested happenings to check out in the Lake Geneva area. Note: Information is subject to change. While ticket prices are provided, there are often additional taxes and fees. Email Special Sections Coordinator Steve Targo to have an event appear in a future Look Ahead.
Wednesday, Sept. 30
Terry Byrne — 5:30-9:30 p.m., Pier 290, 1 Liechty Drive, Williams Bay, pier290.com/events. Chicago-based singer-songwriter performs country, folk, rock, Americana, Irish music and more.
Dragon Days returns to downtown Lake Geneva this weekend.
Thursday, Oct. 1
Joseph Ribkoff 2026 Fall Trunk Show — Noon-6 p.m., Cornerstone Shop & Gallery, 214 Broad St., Lake Geneva, cornerstonelakegeneva.com/pages/upcoming-events. Shop the winter/holiday collection and preview the spring 2027 line from Joseph Ribkoff, which was founded in 1957. RSVP in advance for 10% off trunk show orders.
Wise Fest 2026 — Noon, Jennings Holler, W379 S9674 County Road S, Eagle, jenningsholler.com/event/wise-fest. Numerous musical acts are performing at this three-day music festival, including Wise Jennings, Indigo Canyon and Craig Baumann & the Story. As of press time, tickets started around $50. For full artist list and more, see link.
D’Lite Duo — 5-8 p.m., Next Door Pub Lakeside, W4118 Lakeshore Drive, town of Geneva. Expect smooth vocals and feelgood classics from the musical duo, which frequently performs in the Lake Geneva area. Those who cannot make this show can catch D’Lite Oct. 3, 7-10 p.m., at Pier 290.
Friday, Oct. 2
Dragon Days Fall Fantasy Festival — 9 a.m.-9 p.m., various locations in Lake Geneva, dragondays.org. Another three-day festival this weekend, celebrating the city as the “birthplace of fantasy” as it is the home of the role playing game “Dungeons & Dragons” and best-selling author Gary Gygax. Activities are for all ages, include Fantasy Village, a Dungeon Maze, trick-or-treating in the Enchanted Bazaar, a costume contest, movie screenings and more. Passes start at $15.
Jeff Trudell — 5-9 p.m., Geneva Lake Distilling + Winery, 401 Sheridan Springs Road, Lake Geneva, genevalakedistilling.com/music/live-music. Trudell will play classic rock, according to the link.
Dan Patch Stables Haunted Hayride — 6-11 p.m., 2567 Highway 120, Lake Geneva, danpatchstables.com. Lake Geneva-area Halloween event recently announced some changes, including a new location. Now, the hayride is behind Emagine Geneva Lakes, town of Lyons. The more kid-friendly rides are from about 6-7 p.m. Tickets $25 adults, $10 ages 4-10, free ages 3 and younger. Tickets sold night of, starting at 5:45 p.m. Future hayride dates: Oct. 3, 9-11, 16, 17, 23, 24, 30 and 31. See website.
Bob Bero — 6-9 p.m., Topsy Turvy Brewery, 727 Geneva St., Lake Geneva, topsyturvybrewery.com/events. Live music.
Lakeland Players Presents “Little Shop of Horrors” — 7:30 p.m., Sprague Theater, 15 W. Walworth St., Elkhorn, lakeland-players.org. Opening night of this musical based on the film by Roger Corman. Intended for a PG-13 audience, the musical is the latest production from the long-running Elkhorn-based community theater group. Future event dates: Oct. 3, 9 & 10, 7:30 p.m.; and Oct. 4 & 11, 2 p.m. Tickets $20.
Telstar is performing live in Williams Bay this weekend.
Saturday, Oct. 3
Craft Brew Open — 9:30 a.m.-5 p.m., Majestic Oaks Golf Course at Lake Lawn Resort, 2400 E. Geneva St., Delavan, lakelawnresort.com/calendar-of-events. Golf tournament and craft beer sampling event returns for its eighth year, for teams of four. The Oktoberfest-themed, 18-hole scramble starts with a continental breakfast and registration 9:30 a.m. Tee times at 11 a.m. Awards, raffles and more. Two-person teams $250, four-person $450.
Duesterbeck’s Seventh Annual Oktoberfest 2026 — 10 a.m.-10 p.m., Duesterbeck’s Brewing Company, N5543 County Road O, Elkhorn, dbcbrewery.com/oktoberfest. Craft beer, food, live music, children’s activities such as face painting, Batter Up Tee Ball, a bounce house. Instructional German dancing, local vendors and a limited supply of barrel-aged Oktoberfest beer being released at noon. Visit link for schedule and more details.
Hobie & the Leftovers — 5-9 p.m., Geneva Lake Distilling + Winery. Long-running local blues act performs.
Scott Huffman — 6-9 p.m., Topsy Turvy Brewery. Live music.
Telstar — 7-10 p.m., Pier 290. Multi-genre duo of Anthony Calderisi and Michael Whalen, performing music by Stevie Wonder, the Grateful Dead, Coldplay, the Beatles and more, according to micaelwhalenmusician.com/telstar.
Monday, Oct. 5
Boo In the Bay: Scarecrow Walk Begins — Starts today, Williams Bay Lake Path, williamsbayrecreation.checkfront.com/reserve. The village’s Halloween celebration begins with scarecrow-themed displays along the path to boost the festiveness. Displays should be up today, and remain through Oct. 31. Other Boo in the Bay events: Trunk-O-Treat, Pumpkin Races, Murder at the Monster Mash, Monster Walk and the Fall Festival. More at the link.
