Taste of Madison - Madison, WI - Sep 5 to Sep 6, 2020
The city’s annual Labor Day weekend event, attended by over 250,,000 people each year, with three stages of live music, food from more than 80 restaurants and food trucks, and other activities. Located all around Capitol Square. Free admission! Raises over $60,000 annually for non-profit organization.
Chilimania - Edgerton, WI - Sep 11 to Sep 12, 2020
A chili cooking contest that has been going on for more than 25 years. It features a morning 5k/10k run-walk, various contests and of course great food.
Platteville Dairy Days - Platteville, WI - Sep 11 to Sep 13, 2020
Held at Legion Field with lots of food, music, 4-H and FFA exhibits, a parade and lots more. Since 1947.
Wisconsin Sheep and Wool Festival - Edgerton, WI - Sep 11 to Sep 13, 2020
Wool classes, sheep shearing demos, country store and more. Located at the Jefferson County Fair Park.
Apple Dumpling Days - Elroy, WI - Sep 12 to Sep 12, 2020
Marathon, half marathon, 5K and two kid’s races are held the first Saturday after Labor Day. Event is hosted by the Elroy Lions Club. Since 2007.
Thirsty Troll Brew Fest - Mount Horeb, WI - Sep 12 to Sep 12, 2020
Beer sampling features craft brewers serving over 100 different beers. Use Troll’s Gold to vote for your favorite beer of the festival! Masskrugstemmen (steinholding) competition too!
Wo-Zha-Wa Days Fall Fest - Wisconsin Dells, WI - Sep 18 to Sep 20, 2020
A harvest festival with parade, antique flea market, arts & crafts, and Wisconsin’s oldest long distance race. Activities throughout downtown Wisconsin Dells and Bowman Park. Enjoy live entertainment, a 100 unit parade, and more.
Tyranena Oktoberfest Bike Ride - Lake Mills, WI - Sep 19 to Sep 19, 2020
Ride for a reason among scenic Southern Wisconsin views at this annual ride to raise money for Tomorrow’s Hope, which supports programs at local health care facilities and area clinics. Riders get two drink tickets and dinner after the ride.
Gays Mills Apple Festival - Gays Mills, WI - Sep 25 to Sep 27, 2020
Annual celebration of the apple harvest with parades, carnivals, arts & crafts, flea markets, music, dancing, food & festivities. Activities held at various venues in the Village of Gays Mills, Wisconsin.
Warrens Cranberry Festival - Warrens, WI - Sep 25 to Sep 27, 2020
Cranfest draws around 120,000 and is one of the world’s largest cranberry festivals. Features three days of activities including parade, marching bands, marsh tours, food, contests, and over 1300 booths for shopping. Free admission.
Harvest Fest - Green Lake, WI - Sep 26 to Sep 27, 2020
A two day celebration with thousands attending. Expect over one hundred artist and crafters, local farmers, signature restaurants, classic cars, family activities, parade, and live entertainment.
Fermentation Fest - Reedsburg, WI - Sep 26 to Oct 4, 2020
A live culture convergence with classes, tastings, bike tour, art events and more, held at the Wormfarm Institute.
From the Land Festival - Green Lake, WI - Oct 17 to Oct 18, 2020
A gathering of traditional crafts and skills with demonstrations.
Winter Art Fair off the Square - Madison, WI - Nov 14 to Nov 15, 2020
Features 100+ Wisconsin exhibitors. Saturday silent auction benefits youth scholarship fund. Located at the Monona Terrace Convention Center.
Downtown Baraboo Winter Wine Walk - Baraboo, WI - Nov 20 to Nov 20, 2020
A downtown wine tasting tour with merchants offering two wine samples each to enjoy as you stroll. Pick up your tickets and your glass at Bekah Kate’s.
Labor Fest - Janesville, WI - Jan 1 to Sep 2, 2019
Canceled for 2020, look for their return in 2021. Normally: Enjoy mud volleyball, kids games, parade, raffle, demonstrations and entertainment, beer tent, food and more. Free admission!