This Chocolate Cherry Pie is one of those simple pleasures that turned a casual weeknight into a small celebration the first time I made it. I discovered this combination when I wanted a dessert that felt indulgent but did not require an oven. The bright pop of cherry filling paired with a smooth cream cheese and Cool Whip base makes every bite both sweet and refreshing. The chocolate crust holds everything together and the mini chocolate chips add little bursts of texture. It became my go to for potlucks because it travels well and most people love the familiar flavors.

I first made this pie for a family picnic on a rainy afternoon and it ended up being the star. The kids dove in for seconds and my sister asked for the recipe on the spot. Texture is the magic here, creamy filling contrasted with crunchy chips and a firm chocolate crust. It sets in the refrigerator rather than the oven, which makes it a fast assemble and long chill treat perfect for warm days or when you want to avoid turning on the oven.

Ingredients

• 9 inch chocolate crust: Use a store bought chocolate cookie crust for convenience or a homemade pressed cookie crust made with chocolate wafer cookies for extra depth. Look for a sturdy crust that will hold a soft filling without weeping.
• 8 ounces cream cheese: Full fat block style, softened to room temperature. Softening fully is key to a lump free, silky filling and brands like Philadelphia work reliably.
• 1 cup powdered sugar: Also called confectioners sugar, it sweetens without adding grainy texture. Sift if it has clumps.
• 21 ounce can cherry pie filling: Choose a classic bright cherry filling for that jewel like appearance and syrupy texture. If you prefer more real fruit, use a high quality brand or homemade cherry filling.
• 8 ounces Cool Whip: Thawed, from the tub for easiest folding and the airy lift it provides. This keeps the filling light yet stable.
• 1 1/2 cups semi sweet mini chocolate chips, divided: Use mini chips so they disperse evenly. Reserve about 1/2 cup for topping and fold the rest into the filling.
• Maraschino cherries: For optional decoration, choose cherries packed in maraschino syrup for classic color and flair.

Instructions

Prepare the cream cheese base: In a medium mixing bowl, beat 8 ounces of room temperature cream cheese with 1 cup powdered sugar until the mixture is smooth and light. Use an electric mixer on medium speed for 2 to 3 minutes, scraping the bowl once for an even texture. The mixture should be free of lumps and slightly airy which helps the final mouthfeel. Fold in the cherry filling: Use a spatula to gently fold in the entire 21 ounce can of cherry pie filling. Stir until the cherries are evenly distributed but avoid over mixing which will cause the filling to become runny. The syrup from the filling will loosen the cream cheese base which is expected. Add the Cool Whip and chocolate chips: Fold in 8 ounces of thawed Cool Whip until fully incorporated and the mixture looks light and fluffy. Fold in 1 cup of semi sweet mini chocolate chips so they are dispersed through the filling. The mini chips offer texture without sinking to the bottom. Assemble in the crust: Spread the filling evenly into the 9 inch chocolate crust using an offset spatula to smooth the top. Tap the pie gently on the counter to settle the filling and remove air pockets. Clean the edges for a neat presentation. Chill to set: Refrigerate the pie for 3 to 4 hours to allow the filling to firm. The chilling time gives structure so the pie will slice cleanly. For best results chill overnight if you have time. Finish and serve: Before serving, top the pie with dollops or piped swirls of additional Cool Whip, sprinkle the reserved mini chocolate chips and place maraschino cherries for decoration. Keep slices chilled until serving time and use a warmed knife to cut neat slices.

Storage Tips

Store the pie covered in the refrigerator for up to 4 days. Use a cake carrier or wrap the pie plate with plastic wrap to prevent odor transfer. If you need to freeze it, remove the whipped topping and wrap the pie tightly in plastic wrap followed by foil. Freeze up to 3 months. Thaw in the refrigerator overnight and add fresh Cool Whip and cherries just before serving for best texture. To re chill a cut slice, place it on a tray and cover with plastic to keep edges from drying.

Ingredient Substitutions

If you need a dairy free version, use a dairy free cream cheese alternative and a nondairy whipped topping. For a gluten free option use a 9 inch gluten free chocolate cookie crust. Swap cherry pie filling for raspberry or blueberry for a change in flavor. Replace semi sweet chips with dark chocolate chips for deeper chocolate notes or white chocolate chips for a sweeter contrast. Adjust sugar to taste if using a very sweet filling.

Serving Suggestions

Serve chilled with a dollop of Cool Whip and a maraschino cherry for a classic look. For a more grown up presentation add a drizzle of warm dark chocolate and a sprinkle of finely grated orange zest. This pie pairs well with coffee or a small scoop of vanilla ice cream. It makes an attractive addition to summer potlucks and festive holiday dessert tables.

Cultural Background

Combining chocolate and cherry is a classic flavor pairing with roots in both American and European desserts. The idea of layering creamy fillings in a cookie crust is modern and convenient, drawing from no bake traditions where whipped dairy lends lift and lightness. Cherry pie filling in a creamy context recalls classic American diner flavors while the chocolate element adds a dessert bar sensibility.

Seasonal Adaptations

In summer use fresher elements by folding a jar of lightly macerated cherries into the filling instead of canned filling, and lighten the topping with fresh whipped cream. For winter holidays add a splash of cherry liqueur to the filling for warmth and replace maraschino cherries with glacé cherries soaked in brandy. Seasonal spices like a pinch of cinnamon can complement fall menus.

Meal Prep Tips

Make the filling a day ahead and keep it chilled, then assemble into the crust and chill to finish. This divides work and makes hosting easier. Pack slices in individual containers for grab and go desserts. Use an airtight container and include a small chilled gel pack when transporting to keep the topping firm. Label containers with the date to track freshness.

Make this pie your own by adjusting the chips and topping to match your sweetness preference. It is simple to assemble, delightfully familiar, and reliably loved by family and guests.