• Autumn Harvest Fest at The Elegant Farmer

    Spend a fall weekend at The Elegant Farmer in Mukwonago with orchard activities, a corn maze, farm food, hayrides and seasonal family fun. Admission and parking are free; individual activities may have fees.

    Free admission and parking; activity fees vary
  • East Troy Bluegrass Festival – Saturday

    Spend Saturday on the historic East Troy Village Square for Wisconsin bluegrass, food and a full day of roots music. The festival is scheduled rain or shine.

  • Live Music with Scott Huffman

    Hear live music at Topsy Turvy Brewery in downtown Lake Geneva. Check the brewery event page for any same-day schedule changes.

    Free
  • Yerkes Cosmic Construction Fall Fundraiser

    Support the restoration and future of Yerkes Observatory at its ticketed fall fundraiser in Williams Bay. Parking is offsite at Williams Bay School with shuttle transportation to the observatory.

    $300
  • Duran Decade – Duran Duran Tribute

    Plan an evening at Geneva Stage in downtown Lake Geneva for a live tribute concert. Tickets and final show details are available from the official venue/event listing.

    $30 – $35
  • Pitbull with Lil Jon at Alpine Valley

    Pitbull brings the I'm Back tour to Alpine Valley Music Theatre in East Troy with special guest Lil Jon. Confirm gate time, parking and ticket details with the venue before the show.

  • Lake Lawn Queen Fall Colors Tour

    See Delavan Lake from the water as fall colors begin to arrive around the shoreline. Confirm boarding time and seasonal conditions with Lake Lawn Resort.

    $15 – $25
  • Come From Away at The Fireside

    The Fireside Dinner Theatre presents the Tony Award-winning musical Come From Away in Fort Atkinson. Multiple meal-and-show times may be available on this performance date; verify the exact arrival and curtain time when booking.

    $100
  • Geneva Outdoor Market

    Spend Sunday at the Geneva Outdoor Market near Lake Como and Lake Geneva, with local vendors and an easy weekend stop for visitors exploring the Southern Lakes region.

    Free
  • Fall Harvest Fest Trains

    Ride a historic electric train between East Troy and The Elegant Farmer during fall harvest season. Day-pass tickets are valid for scheduled trains; advance reservations are recommended.

    Free – $18
  • Grandparents Day at East Troy Railroad

    Celebrate Grandparents Day with a historic train ride from East Troy; participating grandparents ride free under the museum's promotional rules. Check the official schedule and reservation details.

    Grandparents promotional fare; regular fares otherwise
  • Autumn Harvest Fest at The Elegant Farmer

    Spend a fall weekend at The Elegant Farmer in Mukwonago with orchard activities, a corn maze, farm food, hayrides and seasonal family fun. Admission and parking are free; individual activities may have fees.

    Free admission and parking; activity fees vary
  • East Troy Bluegrass Festival – Sunday

    Return Sunday for the second day of the East Troy Bluegrass Festival on the Village Square, with bluegrass music and community festival activity.

  • Sunday Brunch Train

    Pair a meal with a ride aboard the East Troy Railroad for a ticketed fall dining experience. Reservations are strongly recommended; confirm current menu and departure details before attending.

    $125
  • Burnin’ Down the Docks

    Spend Sunday afternoon on the harbor at The Abbey Resort in Fontana with live music, food and drinks along the Waterfront patio.

  • 2026 Cars & Company

    See classic and exotic cars at Lake City Social in Lake Geneva while supporting Curing Kids Cancer. The fundraiser includes food, an open bar, live music and a silent auction.

    Ticketed fundraiser
  • Live Music with J Henry

    Hear live music at Topsy Turvy Brewery in downtown Lake Geneva. Check the brewery event page for any same-day schedule changes.

  • Fun & Food on First

    Monday evenings bring food trucks, kids activities, vendors and entertainment to Ten Club Park in Waterford. The official program excludes Labor Day, so only the remaining September Mondays are included here.

    Free
  • Whitewater City Market

    Visit Whitewater's Tuesday evening City Market at the historic depot for farmers, artisans, food vendors, live music and a community-focused local shopping experience.

    Free