Sandwiching the Flavors of Fall in a Whoopie Pie

The pumpkin spice whoopie pie at Jesse Pepper’s Smoke Shack in White Sulphur Springs, Montana. (Ari LeVaux)

Autumn is a time for foliage, crisp temperatures, hunkering down, and of course, pumpkin pie spices. On this trip around the sun, our pie spices come in the form of a fall-flavored whoopie pie.

Whoopie pie consists of two large, soft cookies sandwiched around a creamy filling. With roots in Pennsylvania and New England, whoopie pie is the official state pie of Maine. The chocolate version stuffed with vanilla, sometimes called a Big Fat Oreo, is the most common rendition. Mel Redding of Jesse Pepper’s Smoke Shack in White Sulphur Springs, Montana, hails from Vermont. Accordingly, her pumpkin spice whoopie pie contains a maple cream cheese filling.

Redding owns and operates Jesse Peppers Smoke Shack along with her children Lily, Ollie, and Travis. When her daughter Bailey got married in Bar Harbor, they served whoopie pies at her wedding. Redding’s other son Jesse, aka Jesse Peppers, died in a car crash two years ago. The last time she saw him, he made her promise that the family would start a restaurant together. Jesse Peppers Smoke Shack, perched on a high, windy plateau between the Yellowstone and Missouri rivers, is a green shoot that grew from that promise.

Jesse’s exuberant spirit remains present in the kitchen, where his urn and knives have a have a place of honor, and his favorite dubstep music plays every afternoon. Although the entire family is food-focused, Jesse was the only member to actually graduate from culinary school, and his experience laces the menu. A larger-than-life portrait of this larger-than-life man smiles at you when you enter the dining room. Although Jesse’s story isn’t posted, the locals are learning why Jesse Pepper’s Smoke Shack is here.

“I make sure to tell his story to at least two customers every day,” Mel told me.

After about 10 months in business, this culinary shrine has been embraced by a population that could not be further from BBQ country or Vermont.

Last summer, after I wrote about the show-stealing potato salad at Jesse Peppers, Redding says they received visitors who had also lost children. They made pilgrimages from as far as Nevada, looking to connect with Mel and her family. “There is a bond among people who’ve lost a child,” she told me.

I popped into Jesse Pepper’s a few weeks ago for some Texas Tacos, filled with burnt ends of brisket, cheesy potatoes, and pickled jalapeños. Mel gave me a pumpkin maple whoopie pie to sample, and I had to pass it along to you. Or y’all, as they say in BBQ country. She agreed to share the recipe.

I was living in Vermont when I first heard the expression “frost on the pumpkin.” It comes from a poem by James Whitcomb Riley, and conveys the feeling of sitting by a warm fire on a chilly evening. I will leave you with the opening stanza of Riley’s poem, followed by Redding’s pumpkin maple whoopie pie recipe.

When the frost is on the punkin and the fodder’s in the shock, And you hear the kyouck and gobble of the struttin’ turkey-cock, And the clackin’ of the guineys, and the cluckin’ of the hens, And the rooster’s hallylooyer as he tiptoes on the fence; O, it’s then’s the times a feller is a-feelin’ at his best, With the risin’ sun to greet him from a night of peaceful rest, As he leaves the house, bareheaded, and goes out to feed the stock, When the frost is on the punkin and the fodder’s in the shock.

Happy autumn.

Mel Redding, who is from Vermont, sandwiches her pumpkin spice whoopie pies with a maple cream cheese filling. (Ari LeVaux)

Pumpkin Maple Whoopie Pies

This big, fat, pumpkin spice-flavored treat will make you feel cozy while it tickles your sweet tooth.

Makes 6 whoopie pies

For the Pumpkin Cookies

• 3 cups flour
• 1 teaspoon salt
• 1 teaspoon baking soda
• 1 teaspoon baking powder
• 3 tablespoons pumpkin pie spices
• 1 cup white sugar
• 1 cup brown sugar
• 1 cup vegetable oil
• 3 cups pumpkin puree
• 2 eggs
• 1 teaspoon vanilla

For the Maple Cream Cheese Filling

• 3 cups powdered sugar
• 1/2 cup butter, softened
• 8 ounces soft cream cheese
• 1/2 cup maple syrup
• 1 teaspoon vanilla

Make the cookies: Preheat oven to 350 degrees F.

In one bowl, add the flour, salt, baking soda, baking powder, and pie spices. Whisk together. In another bowl, combine the eggs, oil, both sugars, pumpkin, and vanilla. Add the dry ingredients to the wet ingredients. Don’t over-mix.

Use an ice cream scoop—about 1/4 cup—to dollop the cookies onto an oiled cookie sheet.

Bake cookies for 12 minutes.

Make the filling: Mix all ingredients and stir until light and fluffy.

Make sure the cookies have completely cooled. Make sandwiches with the cream cheese mixture.