11 places to visit on Wisconsin’s Pumpkin Trail

There are a few surefire signs that the season has changed from summer to fall beyond looking at a calendar. The leaves are changing color, there’s a chill in the air, and just about every food and drink option suddenly sprouts a pumpkin spice option.

The beloved flavor was initially popularized with pumpkin pies, but reached a new level with pumpkin spice lattes. It has since expanded to a wide range of food and drinks, from pumpkin-flavored cheese to pumpkin tea drinks. 

While some establishments celebrate pumpkin spice all year, others only have pumpkin-flavored items on seasonal menus. No matter how long they’re available, there’s plenty to choose from throughout Wisconsin. Here are some of the best places to visit on a trip through the state to sample delicious and creative pumpkin and pumpkin-flavored foods and beverages.

Madison Chocolate Company – Pumpkin Spice Latte

729 Glenway St., Madison

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It’s not truly fall until coffee shops start serving pumpkin spice lattes. The iconic autumnal drink can be found all over the state, but it’s been perfected at the Madison Chocolate Company. Served hot or iced, the coffee drink comes with two shots of espresso, homemade pumpkin syrup, milk, and pumpkin spice whipped cream.

The woman-owned cafe and chocolate shop has two locations in the state’s capital city, where they offer a wide range of seasonal treats as well if you want something to accompany your PSL, including apple cider doughnuts and pumpkin bars. Have someone tagging along who’s not a pumpkin fan? There’s also the maple cinnamon latte, which comes topped with whipped cream. 

Norske Nook – Pumpkin Cream Cheese Pie

13804 7th St., Osseo

Photo courtesy of Norske Nook Restaurants and Bakery via Facebook

A staple on every Thanksgiving dessert table, pumpkin pie is an absolute classic—but sometimes classics need to be revamped a bit. Norske Nook, a Norwegian-inspired restaurant that’s famous for its pie, has its own spin on the beloved autumnal dish: the pumpkin cream cheese pie. The restaurant piles a layer of cream cheese on top of a graham cracker crust and covers that with its pumpkin filling and a thick layer of whipped cream for a decadent and filling dessert.

Norske Nook has three locations throughout the state—in Osseo, DeForest, and Rice Lake—and makes all of their pies from scratch at each respective spot.

Henning’s Cheese Store and Museum – Pumpkin Spice Cheddar Cheese

20201 Point Creek Road, Kiel

Everywhere has pumpkin-flavored desserts and beverages, but it wouldn’t be autumn in Wisconsin without some pumpkin-flavored cheese. Yes, even Wisconsin’s staple dairy product isn’t safe from the pumpkin craze during the fall, as Henning’s Cheese, a company based out of Kiel, has crafted a pumpkin spice cheddar cheese. The company recommends adding it to a cheese board, melting it over bread, or using it in a sweet potato recipe.

The seasonal creation is available to sample and purchase at the Henning’s Cheese Store and Museum, or can be purchased from the store’s website.

O&H Danish Bakery – Pumpkin Caramel Kringle

5910 Washington Ave., Racine

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Kringle might be Danish in origin, but few foods are as identifiable with Wisconsin as this flaky pastry is. It’s the state’s official pastry, after all. You can find it all around the state, but especially in Racine, the southeastern city that’s home to a large Danish population, which popularized kringle in the city.

O&H Danish Bakery, which has five locations in and around Racine, serves up a variety of flavors all year long, but also specializes in seasonal favorites. During the fall one of its specialties is the pumpkin caramel kringle, which blends pumpkin, caramel, and autumnal spices like cinnamon and ginger, with pecans on top for added crunch. 

If you’re not up for eating kringle but still want to satisfy your fall fix, try out the bakery’s pumpkin brownies, pumpkin crown cake, or its decadent chocolate pumpkin pie cake roll.

Motor Bar & Restaurant – Pumpkin and Pecan Bread Pudding

401 W. Canal St., Milwaukee

During the fall season, pumpkin flavor dominates all the sweet treats. So it only makes sense that Milwaukee’s Motor Bar & Restaurant has transformed it into a bread pudding as well. The pudding itself is made out of a warm baguette and roasted pumpkin, then filled with pecans. It’s topped with vanilla ice cream and caramel apple sauce for some additional fall flavoring.

The restaurant serves as the official restaurant of the Harley-Davidson Museum, which celebrates the iconic motorcycle’s history and Milwaukee roots. While you don’t have to visit the museum to grab a bite at the restaurant, it’s an added perk for interested visitors.

Gilles Frozen Custard – Pumpkin Shake

7515 W. Bluemound Road, Milwaukee

Frozen custard is a storied tradition in Wisconsin, especially at Gilles Frozen Custard, a fast food joint in Milwaukee that’s been in operation for 85 years and the first place to serve the frozen treat in the state. While the restaurant has an extensive menu of quickly made favorites, it specializes in frozen custard, and customers can have it served in scoops, sundaes, and shakes. 

Throughout October, Gilles Frozen Custard is offering up a pumpkin shake, which blends frozen custard with real pumpkin and pumpkin pie spices, then tops it with whipped cream and a dusting of cinnamon.

Gilles Frozen Custard has even more autumnal options on its monthly menu, including the caramel apple crunch sundae, which features vanilla frozen custard topped with warm caramel, warm apples, and mixed chopped nuts. Like any good sundae, there’s a cherry on top, of course.

Egg Harbor Cafe – Pumpkin Creme Brulee Waffle

827 W. Main St., Lake Geneva

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Breakfast is said to be the most important meal of the day, and for pumpkin lovers, it’s another opportunity to incorporate even more pumpkin-flavored foods into their diet. At Egg Harbor Cafe, in southeastern Lake Geneva, pumpkin fanatics can order the pumpkin creme brulee waffle—a decadent breakfast dish that features two stacked Belgian waffle halves covered in white chocolate sauce, topped with pumpkin custard and a layer of caramelized sugar. If that’s not enough, the plate is finished with a pile of whipped cream.

Egg Harbor Cafe has 21 locations in Illinois, Wisconsin, and Georgia, and has been family-operated since its founding in 1984. The restaurant also serves up pumpkin pancakes, which come topped with whipped cream and sugared pecans.

Lakefront Brewery – Pumpkin Lager

1872 N. Commerce St., Milwaukee

There are few places in the world that love beer as much as Wisconsin does. Why is it so beloved throughout the state? Well, a lot of it’s made here. There are more than 200 breweries based in the Badger State, and with all of those options, it’s easy to find some pretty interesting flavors—including Lakefront Brewery’s pumpkin lager.

The seasonal drink contains real pumpkin and pumpkin pie spice, which are thrown into the mix of Munich and caramel malts. The resulting brew is sold at liquor stores and available on tap at a lot of different restaurants, but it can also be sampled at the brewery’s riverfront location in Milwaukee.

J’s Cafe – Pumpkin Pie Chai

444 Main St., Suite 103, La Crosse

The pumpkin spice latte might be the most famous pumpkin-inspired beverage, but if you feel like mixing it up, try the pumpkin pie chai at J’s Cafe. The La Crosse cafe has been open for a year, serving up coffee, tea, and food like its breakfast bagel or avocado toast.

The cafe is more than a place to get your favorite fall beverage—on Thursday afternoons it hosts Creative Thursdays, where attendees can take part in a paint-and-sip with tutorial videos.

Hill Top Bakery – Pumpkin Tarts

100 E. 7th St., Kaukauna

The Hill Top Bakery in Kaukauna is best known for its wide array of doughnuts, but it also specializes in other baked goods like tarts and hand pies. The miniature, hand-held pies come in an assortment of flavors, including its cherry and apple tarts, which are made fresh every day.

But the bakery also serves up seasonal flavors like key lime and peach during the summer and pumpkin during the fall. Not only are the tarts pumpkin-flavored, they’re also adorably pumpkin-shaped and come in large and small sizes.

Sunday Dough – Pumpkin Cheesecake Doughnut

1402 S. 8th St., Sheboygan

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Sheboygan’s Sunday Dough is known for the bakery’s fun and creative doughnut flavors, so it comes as no surprise that they’ve also hopped on the pumpkin spice bandwagon, unveiling a pumpkin cheesecake doughnut. The doughnut is made out of a homemade brioche dough that’s fried then covered in pumpkin spice-flavored sugar. The doughnut is filled with a pumpkin cheesecake filling, then topped with a dollop of cream cheese frosting and a decorative candy pumpkin.

Sunday Dough is open Friday through Sunday for walk-ins and order pickups, but preorders on the bakery’s website open on Wednesdays at 5 p.m.