These Banana Oatmeal Cream Pies are one of those treats that feel like a warm hug: soft, chewy cookies with a pronounced banana aroma sandwiched around a silky cream cheese filling. I first developed this version on a rainy afternoon when my overly ripe bananas were staring back at me from the counter. I wanted something that felt nostalgic but tasted a little elevated, so I paired the familiar oatmeal cookie texture with a whipped cream cheese center. The result is a cookie that is tender at the edges, slightly chewy in the middle, and layered with a filling that is sweet, tangy, and utterly smooth.

What makes these especially memorable is how the banana flavor deepens after a day in an airtight container and how the oats and bread flour create a wholesome crumb that still stays soft. I perfected the balance between brown sugar and corn syrup to maintain chew without making the cookie greasy, and the cornstarch gives just enough structure for sandwiching. These cream pies have become my go-to for potlucks, school lunches, and unwinding with a cup of tea. My family will often ask me to bake them a day ahead because, honestly, they taste best after a little rest.

Ingredients

• Oats: Use 3 cups of quick 1-minute oats for tender chew and a light texture. Avoid old-fashioned rolled oats, which are chewier; quick oats integrate more uniformly into the dough.
• Bread flour: 3 cups gives structure without heaviness. Bread flour builds a slightly chewier crumb than all-purpose, which helps the cookies hold together when sandwiched.
• Brown sugar: 1 1/2 cups packed provides moisture and caramel notes that complement the banana. Light brown sugar is preferred for a softer, sweeter profile.
• Fat: 1 cup vegetable shortening or unsalted butter. Shortening yields a tender, soft cookie while butter offers richer flavor. Choose based on desired texture.
• Banana: 1 cup mashed ripe banana, about 2 1/2 medium bananas. The ripest bananas deliver the most banana flavor and natural sweetness.
• Binder and lift: 1 tablespoon cornstarch and 2 teaspoons baking powder stabilize the cookie and add a soft, cake-like crumb. A pinch of salt rounds flavors.
• For the filling: 4 ounces softened cream cheese and 1/4 cup softened unsalted butter whipped with powdered sugar, heavy cream, and vanilla for a silky, spreadable center.

Instructions

Preheat and prepare: Preheat the oven to 375 degrees Fahrenheit and line a baking sheet with parchment paper. Using parchment prevents sticking and promotes even browning. Allow butter or shortening to come to room temperature for easier creaming. Combine dry ingredients: Whisk together 3 cups quick oats, 3 cups bread flour, 1 tablespoon ground cinnamon, 1 tablespoon cornstarch, 2 teaspoons baking powder, and 3/4 teaspoon salt in a medium bowl. This ensures even distribution of leavening and spices so each cookie rises uniformly. Cream sugar and fat: In a stand mixer fitted with a paddle attachment, cream 1 1/2 cups packed light brown sugar with 1 cup vegetable shortening or butter for about 2 minutes until light. Proper creaming traps air which contributes to a lighter cookie; scrape the bowl as needed. Add banana and flavor: Mix in 1 cup mashed banana, 1/4 cup light corn syrup, and 1 tablespoon vanilla extract on high speed until light and fluffy. Corn syrup helps retain chew and shine while banana provides moisture and natural sweetness. Incorporate dry ingredients: Add the dry mix to the banana mixture a cup at a time, mixing just until combined. Overmixing develops gluten and can create a tougher texture; stop as soon as there are no streaks of flour. Portion and shape: Use a medium cookie scoop (1 1/2 tablespoons or roughly 1 ounce) to portion dough about 3 inches apart on the prepared sheet. Gently press each mound to about 1/2 inch thickness using your fingers or the bottom of a glass for even baking. Bake and cool: Bake 6 to 7 minutes for small cookies; the centers should still appear slightly soft. For large cookies bake 8 to 10 minutes. Let cool on the sheet for 1 to 2 minutes, then transfer to a wire rack to cool completely before filling to avoid melting the filling. Make the filling and assemble: While cookies cool, beat 4 ounces softened cream cheese with 1/4 cup softened unsalted butter until smooth. Add 2 1/2 cups powdered sugar, 1 teaspoon vanilla, and 1 to 2 tablespoons heavy cream until light and pipeable. Pipe about 1 1/2 tablespoons onto half the cookies and sandwich with the remaining halves. For best flavor let them rest a day in an airtight container.

Storage Tips

Store unfilled baked cookies in a single layer separated by parchment at room temperature for up to two days, or freeze in a single layer, then transfer to a freezer-safe bag for up to three months. For filled sandwiches, use an airtight container and keep them at room temperature for up to three days; refrigeration will firm the filling but can slightly dry the cookies. To reheat, bring to room temperature or microwave a single sandwich for 8 to 10 seconds to soften the filling. Use airtight, rigid containers to avoid crushing and place a small piece of parchment between layers to prevent sticking.

Ingredient Substitutions

If you prefer butter flavor, substitute equal parts unsalted butter for shortening, but chill the dough for 15 minutes to reduce spreading. For a gluten-free version use a 1-to-1 gluten-free flour blend and certified gluten-free oats; texture will be slightly different but still delicious. To make them dairy-free, replace cream cheese with a dairy-free cream cheese alternative and use vegan butter, noting the filling flavor will vary slightly. If you want less sweetness, reduce powdered sugar in the filling by 1/2 cup and add a touch more cream for spreadability.

Serving Suggestions

Serve these warm with a cup of black tea or cold milk for a classic pairing, or plate them alongside vanilla ice cream for a more indulgent dessert. Garnish sandwiches with a light dusting of powdered sugar or a few banana chips for crunch. For a brunch table, arrange on a tiered stand with lemon bars and cinnamon rolls; their soft texture contrasts nicely with crisp pastries. They also travel well for picnics and potlucks — place them in a shallow box lined with parchment for safe transport.

Cultural Background

Oatmeal sandwich cookies have roots in American home baking traditions where simple pantry ingredients were transformed into portable treats. The classic commercial oatmeal cream pie inspired countless homemade versions; this banana variation borrows the sandwich format but leans into home economics by using ripe fruit to sweeten and flavor. In different regions you might find similar assembled cookies using apples, pumpkin, or molasses, each reflecting available produce and family preferences. This version marries midwestern comfort baking with a modern preference for fresh fruit flavors.

Seasonal Adaptations

In summer, add 1/2 cup finely chopped toasted pecans to the dough for nutty contrast or fold in 1/3 cup chopped dried pineapple for a tropical twist. For fall, increase cinnamon to 1 1/2 teaspoons and add a pinch of ground nutmeg, or swap banana for pumpkin puree with adjusted spices. During winter holidays add a teaspoon of espresso powder to the filling to balance sweetness, or dip half the sandwiches in melted dark chocolate and let them set for a festive finish.

Meal Prep Tips

To prep ahead for a week of snacks, bake and cool the cookies, freeze them unfilled in a single layer, and assemble from frozen when needed; filling from slightly frozen cookies prevents sogginess. Portion the filling into a piping bag and freeze in a tube to thaw quickly. Label containers with dates and plan for up to three months in the freezer for best quality. If preparing for a party, make the filling the day before and refrigerate; bring to room temperature and whisk briefly before piping for the best texture.

These Banana Oatmeal Cream Pies have become a small ritual in my kitchen — a way to celebrate bananas that are past their prime and to share something that tastes homemade and thoughtful. I hope you enjoy making them as much as our family does, and that they become a favorite sweet bite at your table.