Madison Fall Festivals – Fall 2021 WI Events

Taste of Madison - Madison, WI - Sep 4 to Sep 5, 2021
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 10 to Sep 11, 2021
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 10 to Sep 12, 2021
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 10 to Sep 12, 2021
Wool classes, sheep shearing demos, country store and more. Located at the Jefferson County Fair Park.

Apple Dumpling Days - Elroy, WI - Sep 11 to Sep 11, 2021
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 11 to Sep 11, 2021
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 17 to Sep 19, 2021
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.

Willy Street Fair - Madison, WI - Sep 18 to Sep 19, 2021
Parade and fair with 8 stages, 35 performances and 150+ vendors. It covers 3 community blocks starting on the 900 block of Williamson Street, Madison, Wisconsin.

Gays Mills Apple Festival - Gays Mills, WI - Sep 24 to Sep 26, 2021
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 24 to Sep 26, 2021
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 25 to Sep 26, 2021
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 25 to Sep 26, 2021
A live culture convergence with classes, tastings, bike tour, art events and more, held at the Wormfarm Institute.

Oddtoberfest - Columbus, WI - Sep 25 to Sep 25, 2021
2-10pm. Meet local artists and authors, check out cool cars at the Oddto (auto) show, kids area, live polka music and more. Free admission

From the Land Festival - Green Lake, WI - Oct 16 to Oct 17, 2021
A gathering of traditional crafts and skills with demonstrations.

Winter Art Fair off the Square - Madison, WI - Nov 13 to Nov 14, 2021
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 19 to Nov 19, 2021
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.

Zoo Lights at Henry Vilas Zoo - Madison, WI - Nov 26 to Dec 30, 2021
Experience the Zoo after hours under the glow of almost one million lights! Tickets are $10 for ages 3 plus (free ticket required for 3 and under) – Henry Vilas is one of the few fee-free zoos in the country