
These mouthwatering Boston Cream Pie Cookies turn a traditional favorite dessert into handy grab-and-go treats. Every mouthful delivers a soft buttery vanilla cookie topped with creamy vanilla filling and covered in decadent chocolate ganache. They'll vanish quickly at gatherings and give everyone the impression you slaved away in the kitchen (though they're actually pretty simple to put together!).
The first batch I whipped up for a family event had my usually recipe-shy aunt practically stalking me for the instructions. They've become a must-have at all our holiday get-togethers since.
Key Components
- All-Purpose Flour: Spoon into measuring cups then level off for just the right cookie structure
- Cream of Tartar: This ingredient is crucial for creating that wonderfully soft, delicate texture
- Vanilla Extract: Go for the real stuff here, not imitation - your taste buds will thank you
- Cool Whip: Creates a stable yet fluffy filling; make sure it's completely defrosted
- Semi-Sweet Chocolate: Grab a quality brand for your ganache layer; it's what ties everything together

Step-by-Step Baking Guide
- Mix Up Fantastic Cookie Bases
- Whip softened butter until it's extremely airy and light. Slowly add sugar while beating for a full 3 minutes. Add egg and vanilla, mixing just until blended. Gently incorporate dry ingredients until all flour disappears.
- Form Your Cookies
- Grab a cookie scoop for even sizing. Flatten slightly with a glass dipped in sugar. Leave enough room between dough balls since they'll expand during baking. Make a small depression in the middle for your filling.
- Prepare The Creamy Center
- Combine pudding mix with cold milk and whisk until it thickens. Carefully fold Cool Whip into the mixture with broad, gentle strokes. Refrigerate until set enough to pipe. Put into a piping bag fitted with a large round tip.
- Whip Up Silky Ganache
- Warm cream just until it starts to steam. Pour it over your chocolate pieces. Wait 3 minutes before stirring. Let it cool until it thickens slightly but still pours smoothly.
- Put Everything Together
- Let cookies cool completely. Add a big swirl of filling on each. Drizzle ganache over the top. Allow time to set before stacking or storing.
As someone who grew up in New England, I can't remember a bakery that didn't showcase Boston Cream Pie. These cookies bring back fond memories of our Saturday trips to our neighborhood bakery, where beautiful Boston Cream Pies always caught my eye in the display.

After testing many versions (with plenty of willing samplers), I've found these cookies hit that sweet spot between fancy dessert and cozy snack. They'll fit right in at upscale parties but they're easy enough to make just because you're craving something special.
Frequently Asked Questions
- → Is there a specific pan I need?
- Yep! A muffin top pan works perfectly to make cookies with a pocket for the filling.
- → How long will these stay fresh?
- Keep them in the fridge, sealed up tight, for about a week. They’re best eaten in the first couple of days!
- → Can I prepare the layers earlier?
- You can bake the cookies ahead of time, but add the pudding and chocolate no more than a day before serving.
- → Why combine two fats in the dough?
- Using both oil and butter keeps the cookies super soft and fresh, better than just butter alone.
- → Can I freeze them for later?
- Not a great idea—the filling and chocolate don’t handle freezing and thawing very well.