Best Fall Festivals in Door County

With fall on the horizon, get ready for weekends packed full of fall festivals all over Door County! With so many festivities to partake in, which festival should you plan your getaway around?

Sister Bay's Fall Fest is the most popular fall festival in Door County. Photo Credit: Sister Bay Advancement Association

As the weather starts to cool and the leaves begin to change, you’ll start noticing bright orange pumpkins, maple wreaths, spooky decorations, and fall-flavored dishes popping up all over Door County, sometimes even as early as the beginning of September! Fall is unlike any other season in the peninsula; visitors and locals alike cannot wait to lace on their hiking boots and bundle up in a cozy sweater, all while sipping on a pumpkin spice latte or mulled cider from a local shop. Door County residents in particular are going to be rushing to and fro to prepare for the upcoming festivals celebrating the fall season.

October is one of the most popular times of the year to visit Door County, and not just for the changing fall colors. This month is packed full of festivals all over the county, from the northern tip of Washington Island all the way down to Sturgeon Bay. In fact, there’s a festival nearly every weekend starting in September and culminating in October! With so many festivities to partake in, food to eat, and drinks to try, which festival should you plan your vacation around?

1. Sturgeon Bay’s Harvest Fest

Test your strength with Starboard Brewing Company’s Stein Holding Contest for a chance to win $100 and a “Tapping of the Firkin”!

The first festival to kick off the fall season is Sturgeon Bay’s Harvest Fest & Street Art Auction. This event typically takes place in mid-September, just as the leaves are starting to change and the Wisconsin weather fluctuates between chilly wind or sunny skies. That doesn’t stop the fall spirit from flooding in, though!

The festival begins with the “Cruise by the Bay” Classic Car Parade that rumbles down Egg Harbor Avenue. After the parade, the cars will be parked outside the vendors on Third Avenue and even fill up the park by the bay! The classic car show grows every year, and new registrations are always welcome.

Then the official festivities begin, with food trucks and vendors, artisans and crafters, live music, and crowds of people filling the streets. Several stores will be offering in-store specials, and restaurants with booths outside will have samples of their fall menu for you to try. For those feeling brave, you can participate in the Stein Holding Contest hosted by Starboard Brewing Company for a chance to win $100 and a “Tapping of the Firkin” of their limited-edition Oktoberfest brew.

Near the end of the festival, visit Martin Park to admire the several incredible street art projects that are normally placed all over Sturgeon Bay. Artists will share the inspiration and craftsmanship behind their piece before the online auction for their works closes at the end of the night.

2. Autumnfest in Baileys Harbor

The Hey Hey 5K is the staple event of Autumnfest in Baileys Harbor, but there’s still plenty to do if you’re not a runner! Photo Credit: Mike Roemer

Taking place in late September, usually the week after Harvest Fest, Baileys Harbor puts on Autumnfest, quite aptly named for the coming season. It also has an antique car and motorcycle show, but people are encouraged to dress in their favorite ‘50s outfits and pose for a pin-up photoshoot!

Autumnfest begins early in the morning with the Hey Hey 5K run at Door County Brewing Co. Each participant in the run will receive a special Door County Brewing Co. Hey Hey 5K pint glass, which comes with a first pouring free at the taproom!

Shortly after the start of the marathon, the classic car and motorcycle show will begin near the Town Hall, with vehicles parked all up and down the street. As you walk through the show, make sure to stop for some delicious food and drinks, visit the local arts and crafts vendors, and listen to live music at the park.

3. Egg Harbor’s Pumpkin Patch

Egg Harbor’s Pumpkin Patch is the best family-friendly fall festival in Door County.

Now that we’re in October, the fall festivities are just ramping up! On the first weekend of October, Egg Harbor celebrates Pumpkin Patch, which is the perfect start to the following fall festivals. This fun-filled weekend is packed with activities for young ones and the young at heart to enjoy, like live music, carnival rides, arts & crafts vendors, face painting, pumpkin & scarecrow displays, a bucket raffle, and so much more!

Since Pumpkin Patch is so popular, we recommend that you make resort reservations early and drive down to the festival in the morning so you can find parking. Otherwise, the Landmark Resort offers trolley rides down to the festival all day, at no cost to guests!

Once you’re at the festival, peruse the book sale at the Kress Pavilion, or have fun with the kids’ activities and the magician on the lawn. Food vendors, drink tents, and local artisans and crafters will crowd the streets with their seasonal goodies, and you won’t want to miss out on any of the flavors of fall!

4. Sister Bay’s Fall Fest

One of the derby racers gears up to go flying down the highway with his friends cheering him on! Photo Credit: Sister Bay Advancement Association

Quickly following Egg Harbor’s Pumpkin Patch, Sister Bay celebrates Fall Fest on the second weekend of October. This is by far the most popular fall festival in the entire county! Taking place from Friday night through Sunday afternoon, join both visitors and locals for three days of family fun, great food, and the massive arts & crafts fair.

The festivities begin with the Saturday Pancake Breakfast provided by the Lion’s Club, followed by the annual Fall Fest Parade. As you make your way downtown, each store and restaurant will be offering specials both inside and outside their establishments, with fun fall concoctions that you simply must try (the Pumpkin Pie in a Cup is a certified classic!). At the arts & crafts fair, nearly 100 different artists and creators will be showcasing their handmade crafts and artistic works, such as mixed media, fine photography, wood carvings, unique jewelry, essential oils & soaps, and even furniture! Pick up hand-knit mittens or sweaters if the weather doesn’t cooperate, because Sister Bay’s Fall Fest parties on rain or shine!

The fun doesn’t slow on Sunday—in fact, it speeds up! For children ages 7 through 13, they can participate in the Derby Race, where they will race down the highway through the middle of Sister Bay’s downtown in their own hand-built gravity powered cars. It’s an exciting event that’s fun for all ages! Afterward, keep your eyes to the sky, because the annual Ping Pong Drop will shower down ping pong balls featuring discounts and specials at local businesses.

Since this is the most popular fall festival in Door County, make sure to book your resort reservations early! Most lodging will be sold out far in advance of this fun-filled weekend, so you’ll want to secure your spot as soon as you can.

5. Jack O’ Lantern Days in Fish Creek

Fish Creek’s Jack O’ Lantern Days rounds out the fall festivities with town-wide trick-or-treating, a costume contest, and the Haunted Trail. Photo Credit: Len Villano

Finally, rounding out the end of the fall fun, visit Fish Creek for Jack O’Lantern Days and the Haunted Trail. Taking place on the last weekend of October, this small town captures all of the fall charm with a hometown Halloween festival. Dress up in your favorite costume and join the parade through Fish Creek’s main street, and see if your costume stands out in the late-night costume contest! Young children can play carnival games, craft their own masks and other costume pieces, and trick-or-treat throughout the town. As the sun begins to set on a cool fall night, take a test of courage on Fish Creek’s Haunted Trail, a bone-chilling 1/8-mile hike through the trails and bridges of Fish Creek Park at dusk! As the locals say, Jack O’ Lantern Days puts the “Eek!” in Fish Creek!

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