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  • 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...

    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

  • High Road – Matinee at The Fireside

    The Fireside welcomes High Road for a special country, bluegrass and Gospel concert package in Fort Atkinson. This row represents the matinee arrival.

    $41.95

  • Mukwonago Farmers Market

    Shop the Wednesday afternoon Mukwonago Farmers Market at Field Park for local produce, foods, crafts and small-business vendors.

    Free

  • High Road – Evening at The Fireside

    The Fireside welcomes High Road for a special country, bluegrass and Gospel concert package in Fort Atkinson. This row represents the evening arrival.

    $41.95

  • Live Music: Jeff Trudell

    Enjoy Jeff Trudell at Maxwell Mansion in Lake Geneva. Public programming may move indoors for weather; check Maxwell's current event page before heading out.

  • Royal Oak Farm AppleFest

    AppleFest at Royal Oak Farm Orchard features U-pick apples and fall farm activities. Weekend offerings include wagon rides, the Amaze 'N Apples tree maze, children's rides and orchard tours. Activity...

    Varies

  • Royal Oak Farm AppleFest

    AppleFest at Royal Oak Farm Orchard features U-pick apples and fall farm activities. Weekend offerings include wagon rides, the Amaze 'N Apples tree maze, children's rides and orchard tours. Activity...

    Varies

  • East Troy First Fridays: Fall Fair

    Downtown East Troy's October First Friday brings live music, food trucks, fall flavors, artisan vendors, retail and dining specials, and a kids zone to the Village Square.

    Free

  • Grand Geneva Haunted Hayrides

    Haunted hayrides near Grand Geneva run from early family-friendly rides into scarier later-evening rides. Tickets are sold on-site; younger-child pricing is available and details can change by night.

    Varies

  • Elkhorn Holiday Craft Bash

    A large seasonal craft and vendor show at the Walworth County Fairgrounds with indoor and outdoor booths plus food vendors.

    $5

  • Pearce’s Farm Stand October Fest Weekend

    A fall weekend at Pearce's Farm Stand with seasonal farm activities, pumpkins, corn-maze fun and special October programming. Individual activities and purchases may carry separate fees.

    Varies

  • East Troy Railroad Harvest Fest Trains

    Ride the East Troy Electric Railroad during fall Harvest Fest season between East Troy and The Elegant Farmer. Train schedules and ticket classes vary, so use the official schedule when...

    Varies

  • Dragon Days Fall Fantasy Festival

    Lake Geneva's fall fantasy festival celebrates the area's tabletop-gaming legacy with downtown activities, fantasy programming and family-friendly experiences. Festival access and ticketed activities vary.

    Varies

  • Duesterbeck’s Oktoberfest 2026

    Oktoberfest at Duesterbeck's Brewing Company brings German-style fall celebration and live music, including the Mike Schneider Band and Alpine Blast. Check the organizer for any updated food, beer or activity...

  • The Elegant Farmer Autumn Harvest Fest

    An old-fashioned fall farm weekend with apple picking and seasonal activities at The Elegant Farmer. Admission and parking are free; purchases and selected activities are extra.

    Free

  • Royal Oak Farm AppleFest

    AppleFest at Royal Oak Farm Orchard features U-pick apples and fall farm activities. Weekend offerings include wagon rides, the Amaze 'N Apples tree maze, children's rides and orchard tours. Activity...

    Varies