Posted on October 1, 2025
With Autumn settling in, there is no better time than now to enjoy the many festivities across the Midwest this season. Our selection of festivals has drawn in countless tourists over the years. Come and explore our personal picks for Midwest Fall Festivals in the great states of Minnesota, Wisconsin, Illinois, Indiana, and Michigan. Plan your Fall weekend getaway today!
(906) 847-3783 | Website
The Mackinac Island Halloween Weekend is around the corner with a full lineup of events across Mackinac Island! Earlier in the weekend, the prominent Grand Hotel provides a weekend-long Haunted Trail & Maze as well as live music in the evening! On Halloween, a count of afternoon and evening events offer fun for kids across town! Trial runs, fall crafts, local trick-or-treating, and of course the adult costume parties, all to be enjoyed by visitors! When deciding what to do for the spookiest time of the year, keep the Mackinac Island Halloween Weekend in mind! All proceeds for the Haunted Trails & Maze are dedicated to the Give Kids the World Village as a yearly charitable donation by the Grand Hotel.
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The Milwaukee Oktoberfest celebration is not something to miss! This historical celebration has been a charm of the city since the 60s with every year bringing in endless entertainment, bratwursts, and steins to pair! What is there not to love? Get your tickets on the website today or check out the available packages and reservations if you have friends and family in-mind!
(507) 233-4300 | Website
The town of New Ulm has been known for its brewing and sites over the years, but one of the most revered parts of the town's culture in the New Ulm Oktoberfest. Set across the first two weekends of October, this impressive take on the original Munich Oktoberfest has kept its prominence as one of the best Oktoberfest celebrations in the US! When thinking about enjoying the celebrations, check the schedules throughout your stay as the locations do change from day-to-day.
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For a more quiet, intimate celebration, the Sycamore Pumpkin Festival provides an undeniably impressive creative outlet to the Sycamore community while also supporting the many non-profit organizations in town! The festival's iconic Pumpkin Parade and Pumpkin Displays make for quite the experience. And for more traditional fun, the festival carnival and set of various community events rounds out the week of activities!
(765) 569-5226 | Website
As the largest seasonal festival in Indiana, The Parke County Covered Bridge Festival presents the beautiful impressions of the county's communities with their welcoming historic covered bridges! Delicious meals, sweet treats, tours and sites, and local crafts make the two weeklong celebration an unforgettable assortment of fun and flavor! Be sure to check out the goods markets throughout the various locations to snatch yourself a souvenir.