This Chocolate Cherry Pie became a ritual in my home the first summer I wanted an easy, celebratory dessert that felt both nostalgic and a little decadent. I first assembled it for a backyard gathering when fresh cherries were sparse but my pantry held a can of cherry pie filling, a ready-made chocolate crust, and a tub of Cool Whip. The combination surprised everyone: the tang of cherries cut through the sweet, silky filling, and the mini chocolate chips added a playful crunch. It’s the kind of dessert that disappears fast—guests always reach for seconds and someone inevitably asks for the recipe before the plate is cleared.

What makes this pie special is its simplicity without sacrificing layered textures: a crisp chocolate shell, a velvety cream cheese base, airy whipped topping, pockets of cherry compote, and bursts of chocolate in each bite. I learned early on that a full rest in the refrigerator transforms it from a loose, pretty bowl of filling into neat slices that hold their shape. Over the years I’ve adapted the decoration—sometimes dainty piped swirls of Cool Whip and a single maraschino cherry per slice, sometimes rustic dollops and a snowing of mini chips—and each variation becomes a new favorite at family dinners.

Ingredients

• Chocolate crust: 1 (9-inch) chocolate pie crust—store-bought keeps this fast; look for a sturdy shell that won’t soften when chilled, such as a pre-baked chocolate cookie crust from a reputable brand.
• Cream cheese: 8 ounces cream cheese, softened to room temperature—Philadelphia cream cheese works well for a smooth, reliable texture; beating it until silky prevents lumps in the filling.
• Powdered sugar: 1 cup powdered sugar—adds sweetness and stabilizes the cream cheese; sift if you notice any clumps for a smoother finish.
• Cherry filling: 1 (21-ounce) can cherry pie filling—choose a high-quality brand for bright cherry flavor; the whole cherries and syrup provide an attractive texture contrast.
• Whipped topping: 8 ounces Cool Whip, plus extra for topping—thawed and gently folded in for airy lightness; real whipped cream can be used but may affect shelf life.
• Mini chocolate chips: 1 1/2 cups semi-sweet mini chocolate chips, divided—use 1 cup in the filling and reserve 1/2 cup for garnish; mini chips distribute evenly and soften slightly when chilled.
• Maraschino cherries: Optional, for decoration—choose bright, firm cherries to top each slice for classic presentation and a pop of color.

Instructions

Prepare the cream base: In a medium mixing bowl, beat the softened cream cheese with an electric mixer on medium speed until completely smooth and light, about 2 to 3 minutes. Gradually add the powdered sugar and continue beating until fully incorporated and creamy. Properly softened cream cheese ensures a lump-free base; if it resists, microwave in 5-second bursts and rebeat. Incorporate cherries and Cool Whip: Use a rubber spatula to fold the entire can (all syrup and cherries) of cherry pie filling into the sweetened cream cheese. Fold in the thawed Cool Whip gently to keep the mixture airy—use a cutting-and-folding motion to combine without deflating the whipped topping. The filling should be homogenous yet still light. Add chocolate chips: Fold in 1 cup of the mini semi-sweet chocolate chips so they are evenly distributed. The chips will remain slightly firm and provide textural contrast; stirring them in gently prevents streaking of the cherry color throughout the filling. Assemble the pie: Spread the filling evenly into the 9-inch chocolate pie crust using a spatula, smoothing the top for a neat appearance. Tap the crust gently on the counter to settle the filling and eliminate air pockets. For a decorative edge, leave a slight lip of crust showing. Chill to set: Refrigerate the pie uncovered for at least 3 to 4 hours to fully set. Cover loosely with plastic wrap after the first hour to prevent condensation. Proper chilling allows the filling to firm so slices hold their shape when cut. Decorate and serve: Before serving, add dollops or piped swirls of additional Cool Whip, sprinkle the remaining mini chocolate chips across the top, and place maraschino cherries on each slice or down the center. Slice with a hot, dry knife for clean cuts.

Storage Tips

Store the pie covered in the refrigerator for up to three days. Use an airtight pie container or a pie plate covered with plastic wrap to prevent absorption of other flavors. If you need to transport it, place the pie on a non-slip mat in a rigid container to avoid shifting. For freezing, wrap tightly in plastic wrap and then in foil; label with the date and use within two months. When ready to serve, thaw overnight in the refrigerator and re-fluff a small amount of Cool Whip if the topping has wept slightly.

Ingredient Substitutions

If you need different dietary options, swap the dairy cream cheese for a full-fat, plant-based cream cheese and use a dairy-free whipped topping for a dairy-free variation, though flavor and texture will be slightly different. For a gluten-free option, substitute a ready-made gluten-free chocolate crust or make a crust from crushed gluten-free chocolate cookies bound with melted butter. If you prefer less sweetness, reduce the powdered sugar to 3/4 cup and choose a tart cherry filling to balance the sweetness.

Serving Suggestions

Serve slices chilled with a small cup of strong coffee or an espresso after dinner to balance the sweetness. For an elegant presentation, add a sprig of fresh mint and a dusting of cocoa powder around the plate rim. This pie is great for summer gatherings when you want a cool dessert, but it also fits holiday tables where the chocolate-cherry combination echoes classic flavors like Black Forest. Pair with a scoop of vanilla ice cream for an extra-indulgent treat.

Cultural Background

The chocolate and cherry pairing has roots in European desserts—think Black Forest gateau—but this pie adapts that flavor profile into a faster, no-bake American format. The idea of combining canned fruit fillings and whipped dairy became popular mid-20th century when convenience ingredients entered home kitchens, giving rise to layered, chilled desserts that could be scaled for family celebrations. This version nods to that practical heritage while presenting a slightly more modern textural contrast with mini chocolate chips.

Meal Prep Tips

Make the filling up to one day ahead and store it in an airtight container in the refrigerator; fold in the remaining chips and assemble into the crust on the day of serving to keep a fresh chocolate crunch. If preparing multiple pies for an event, assemble and chill them on sheet pans in the fridge to save space. For portion control, use a serrated knife warmed under hot water and wiped dry between cuts for clean slices.

This Chocolate Cherry Pie blends convenience with celebration: quick to assemble, rich in flavor, and consistently a favorite at gatherings. Try variations and decorations to make it your own and enjoy the smiles it brings around your table.