An Epic Autumn Grilled Cheese Recipe: Add Cranberries, Winter Squash and Apples

Reader Contribution by Lisa Kivirist and Inn Serendipity
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Being from Wisconsin, my husband-photographer John Ivanko and I love our cheese served all kinds of ways. There is nothing better on these increasingly colder days than a warm and gooey grilled cheese sandwich. Comfort food perfectly timed for the arrival of cooler temperatures.

But it took a trip up north and a visit to Great Expectations in Wisconsin Rapids to open our minds to what an epic grilled cheese experience can be. Thanks to owner Amy Scheide sharing her recipe below, you can discover this magic in your homestead kitchen with a seasonal ingredient mash-up unlike any other, with cranberries, butternut squash, apples and a dash of jalapeno pepper heat.

With our farm, Inn Serendipity, located in the heart of Green County, Wisconsin, the highest cheese-producing county in our nation, we thought we knew grilled cheese: butter bread, add cheese, grill. Maybe get a little crazy and add a tomato or fresh spinach. But after biting into the Grilled Cheese at Great Expectations located in the middle of Wisconsin’s cranberry country, we realized a grilled cheese is really a palette for blending seasonal autumn flavors. 

“Our Great Expectations philosophy is to take what’s locally grown and produced and combine it in a unique and tasty way on your plate,” explains Scheide, whose love and respect for her farm community runs so deep she prints custom coasters listing her sourcing. Supporting cranberry farmers is high on her local priority list. You’ll see cranberries throughout the menu, including the Crustless Cranberry Pie recipe Scheide also shared with us.

“I’m on a mission to get folks to think beyond the traditional Thanksgiving sauce when it comes to cranberries,” Scheide enthusiastically adds. “The tartness of cranberries alone adds a distinct flavor along with all of their health properties. Plus, they can be readily frozen and used throughout the year.”

This recipe involves a couple of steps, including making a batch of Cran-Pepper Jam and her House Apple Salsa, both of which can readily be used in other ways. This recipe is totally worth the effort. Great Expectations uses Dairy State cheddar cheese made locally in Rudolph, Wisconsin and, of course, Wisconsin beer in the batter!

Great Expectation’s Grilled Cheese Recipe

Courtesy of Amy Scheide, Great Expectations, Wisconsin Rapids, Wisconsin

Yield:  One sandwich


• 2 slices of cheddar cheese, approximately ¼ inch thick
Flour and beer batter. (Try Mother Earth’s News’ batter from their Beer-Fried Trout Recipe.)
2 slices butternut squash, sliced ¼ inch thick
1/8 cup balsamic vinegar
2 slices hearty white bread
1 tbsp butter
1/4 cup grated parmesan cheese
1 tbsp cream cheese, softened
Cran-Pepper jam (see recipe below)
House apple salsa (see recipe below)


1. Flour the cheese slices and dip in beer batter. Fry until brown and crispy. Set aside. 

2. Grill butternut squash on flattop and drizzle both sides with balsamic vinegar. Cook until softened and set side. 

3. Butter each slice with ½ T. butter. Add a parmesan crust to the bread by pressing the extra grated parmesan cheese to each side. Place cheese side down on the griddle.

4. To create the sandwich, spread cream cheese on the non-cheese crusted side of the bread. Top in this order: 1 tablespoon Cran-Pepper jam, fried cheese slice, approximately 2 tablespoons House Apple Salsa and grilled squash. 

5. Top with remaining crusted bread and grill over medium-low heat until mixture melts nicely and bread is toasted.  Serve immediately.

Cran-Pepper Jam Recipe and Directions

1. Combine 1 and 1/2 c. chopped fresh cranberry with 2 large minced jalapeno peppers, 2 minced serrano peppers, 1 minced habanero pepper, 1 diced red pepper and 2 c. white vinegar and bring to a boil over high heat.

2. Create thickener by combining 1 T pectin and 4 t water. Add thickener to 1 c. sugar.

3. Stir thickener into cranberry pepper mixture and return to a boil. 

4. Once boiling add another 5 c. sugar and boil for one more minute.

5. Store in jar in refrigerator.

House Apple Salsa Recipe and Directions:

1. Grill 2 sliced sour apples (Great Expectations uses Granny Smith) until soft and readily seared.

2. Combine apples with 4 c. chopped Roma tomatoes and add the zest of one lime, chopped clove of garlic, 1 chopped fresh garden banana peppers and 1 chopped habanero pepper and a pinch of sugar. 

Store in jar in refrigerator.

Lisa Kivirist, with her husband, John D. Ivanko, a photographer and drone pilot, have co-authored Rural Renaissance, Homemade for Sale, the award-winning ECOpreneuring and Farmstead Chef cookbook along with operating Inn Serendipity B&B and Farm, completely powered by renewable energy. Kivirist also authored Soil Sisters. As a writer, Kivirist contributes to MOTHER EARTH NEWS, most recently, Living with Renewable Energy Systems: Wind and Solar and 9 Strategies for Self-Sufficient Living. They live on a farm in southwestern Wisconsin with their son, Liam, and millions of ladybugs.

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