This Chocolate Cherry Pie has been a staple at our family get-togethers for years. I first discovered the combination of tangy cherry filling and creamy sweetened cream cheese when I was searching for an easy make-ahead dessert to bring to a summer potluck. The contrast between the dark chocolate crust, the bright cherry interior, and the pillowy whipped topping is what makes this pie unforgettable. It’s the kind of dessert that gets requested repeatedly: bright fruit notes balanced by chocolate, just enough sweetness, and a creamy texture that slices beautifully.

I love this pie because it’s approachable and forgiving. The recipe relies on a ready-made 9-inch chocolate crust to save time, but the filling—softened cream cheese, powdered sugar, cherry pie filling, Cool Whip, and a generous scatter of mini chocolate chips—feels homemade and luxurious. It sets in the refrigerator rather than the oven, which means you can prepare it on a hot day without heating up the kitchen. Serve chilled with extra whipped cream and a maraschino cherry for a nostalgic retro finish that always brings smiles.

Ingredients

• 9-inch chocolate pie crust: Buy a pre-baked crust from any grocery brand for convenience—look for one labeled "chocolate cookie crust" or graham-style chocolate crust. A firm, fully-baked crust gives the best texture contrast to the soft filling.
• 8 ounces cream cheese (softened): Full-fat cream cheese yields the creamiest, most stable filling. Bring to room temperature for 30–60 minutes so it whips smoothly with the powdered sugar—avoid microwaving, which can make it too soft.
• 1 cup powdered sugar: Confectioners’ sugar dissolves into the cream cheese for a silky texture. If you prefer less sweetness, reduce to 3/4 cup and taste before chilling.
• 21-ounce can cherry pie filling: Classic cherry pie filling adds color and a tart-sweet pop. Choose a brand with whole cherries and a glossy, not-too-runny syrup. Drain slightly if your filling seems excessively syrupy to avoid watery pie slices.
• 8 ounces Cool Whip: Folded into the filling for airiness; thaw in the refrigerator and gently fold to preserve volume. You can substitute 1 cup freshly whipped cream if you prefer.
• 1 1/2 cups semi-sweet mini chocolate chips (divided): Use mini chips so they distribute evenly through the filling. Reserve about 1/2 cup for the top to create an attractive sprinkle when serving.
• Maraschino cherries (optional): For a classic garnish, drain cherries well and place on top of each slice or in the center as a finishing touch.

Instructions

Step 1 — Soften and whip the cream cheese: Place the 8 ounces of cream cheese in a medium mixing bowl and beat with an electric mixer on medium speed until smooth and fluffy, about 2–3 minutes. Add 1 cup powdered sugar and continue to beat until fully incorporated and light in color. The mixture should be lump-free and creamy; stop and scrape the bowl with a spatula if needed. Step 2 — Add cherry filling: Use a spatula to gently fold in the 21-ounce can of cherry pie filling. For a neater slice, gently drain a tablespoon of excess syrup from the can first. Fold just until the cherries are evenly mixed; overmixing will break down the cherries and create a runny texture. Step 3 — Fold in Cool Whip and chocolate chips: Fold 8 ounces of thawed Cool Whip into the cherry-cream cheese mixture with a large rubber spatula. Work gently to maintain the airy texture. Once combined, fold in 1 cup of the mini chocolate chips so the chips are evenly distributed but you still see bright cherry pieces throughout. Step 4 — Fill the crust: Transfer the filling into the prepared 9-inch chocolate pie crust, spreading it evenly with the spatula and smoothing the top. Tap the pie gently on the counter to release any large air pockets. Clean the crust edge for a tidy presentation. Step 5 — Chill to set: Cover the pie loosely with plastic wrap and refrigerate for 3 to 4 hours, or until the filling is firm to the touch and slices hold their shape. The chilling time allows the filling to stabilize and the flavors to meld. Step 6 — Decorate and serve: Before serving, top the pie with dollops or piped swirls of extra Cool Whip, sprinkle the remaining 1/2 cup mini chocolate chips across the surface, and add maraschino cherries if desired. Slice with a sharp, warmed knife for clean cuts.

Storage Tips

Store the pie covered in the refrigerator for up to 4 days. Use airtight pie boxes or wrap the pie plate tightly with plastic wrap, pressing lightly against the surface of the Cool Whip to prevent the topping from absorbing fridge odors. Do not freeze assembled pie; the whipped topping can become watery and grainy after thawing. If you need longer storage, freeze the filling in a freezer-safe container before assembling into the crust—thaw overnight in the refrigerator, then assemble and serve within 24 hours.

Ingredient Substitutions

Substitute freshly whipped heavy cream (1 cup, whipped to soft peaks) for the 8 ounces of Cool Whip for a fresher flavor and fewer stabilizers. If you want a dairy-free option, use a non-dairy cream alternative that whips and a dairy-free cream cheese; be mindful that flavor and texture will vary. For a gluten-free version, choose a store-bought gluten-free chocolate crust or make one from crushed gluten-free chocolate cookies combined with melted butter. Reduce powdered sugar by 1/4 cup if you prefer a less sweet finish.

Serving Suggestions

Serve slices with a small scoop of vanilla ice cream or an extra dollop of whipped cream for contrast. Garnish each slice with a maraschino cherry and a few extra mini chocolate chips or shaved dark chocolate for elegance. This pie complements coffee-based drinks and dessert wines; for summer parties, serve with espresso or iced coffee. For a retro presentation, pipe rosettes of Cool Whip around the edge to create a professional-looking finish.

Cultural Background

The chocolate-and-cherry pairing has long been popular in American desserts, often inspired by classic Black Forest flavors which combine dark chocolate and cherries. While this pie is a modern, no-bake American adaptation—friendly to busy cooks—it nods to European traditions of combining fruit and chocolate. Canned pie fillings became popular in mid-20th-century American home baking for convenience, and this recipe follows that time-honored tradition of transforming pantry staples into celebratory desserts.

Seasonal Adaptations

In summer, swap the maraschino cherries for fresh cherries lightly macerated with a teaspoon of sugar and a splash of lemon juice for peak-season brightness. For winter holidays, add a teaspoon of kirsch or cherry liqueur to the cherry layer for depth of flavor and a festive touch. You can also sprinkle toasted chopped pecans or almonds over the top for a holiday crunch. Swap semi-sweet chips for dark chocolate chips in colder months for a richer profile.

Meal Prep Tips

Prepare the filling up to a day in advance and store it in an airtight container in the refrigerator. When ready to serve, spoon into the crust and chill for the final hour before guests arrive for the freshest appearance. Use a sharp, warm knife for clean slices: run the blade under hot water, dry it, and slice; wipe the knife between cuts for neat portions. Portion the pie into 8 to 10 slices depending on how rich you want portions to be.

This pie always invites conversation—its bright cherries and chocolate base are a universal crowd-pleaser. Make it once and you’ll find yourself reaching for it for parties, potlucks, and cozy family evenings alike. Enjoy sharing it as much as eating it.