Chocolate Berry Trifle

Have you ever noticed that trifles are so often made with vanilla pudding and vanilla wafers or shortbread or angel food cake? Where’s the chocolate? I know there are people out there who don’t like chocolate, but they are few and far between. There are, however, LOTS of people who think trifle is weird or old-fashioned or just gross. Maybe that’s because, and I’m just hypothesizing here, there is a serious lack of chocolatey goodness in the trifle world.

I’m here today to change that. It involves Oreos and chocolate pudding, which means you can’t possibly go wrong. Unless you don’t like chocolate–then you’re just plum out of luck.

Now…you can either do this as one big trifle in one big trifle dish, or you can do lots of little trifles. From a logistical perspective, it’s significantly easier to put it in one trifle dish, especially since it has so many layers. But from a beauty and photography perspective, it’s not super easy to take a picture of a large trifle and have it not look disgusting, so for the sake of prettiness, I did it in smaller trifle dishes. You could also use jars, and you guys know how we love jars, but since I just posted a dessert in a jar, I figured I’d live on the edge a little.

For the chocolate pudding layer, you’ll need a 4-serving-size (3.9 ounce) package of INSTANT chocolate pudding, 1 cup of cold water, a can of sweetened condensed milk, and 1 cup of heavy cream.

In a medium bowl, whisk together the water, pudding mix, and sweetened condensed milk. Let it chill out in the fridge for a few minutes while you whip the cream with an electric hand mixer until soft peaks form. Gently fold the whipped cream into the pudding mixture until it’s combined and smooth. Refrigerate the mixture until ready to use.

In another medium bowl, whip together 8 ounces of softened cream cheese and 2 8-ounce containers of thawed Cool Whip (you can also use 16 ounces of heavy cream whipped with 1/2 cup powdered sugar). Refrigerate until you’re ready to use.

Chop 2/3 of a package of Oreo cookies.

Or heck, chop up all of them and then you can snack on the tiny Oreo pieces because the calories fall out when you cut them. Truth.

You’ll also need to wash and slice a pint of strawberries and wash about 2 cups worth of blue-ish berries (I used blueberries and blackberries). If you’re a food blogger, it would be awesome of you to take a picture of said berries that didn’t come out blurry, but alas, life does not always come out the way we want it to.

Now…you can layer this however you want to. In the smaller dishes, I did a layer of chocolate pudding…

Then I added some chopped Oreos…

Then strawberries…

Then the cream cheese/whipped cream mixture mixture…

Then topped it off with a layer of blueberries and blackberries.

If you’re going to make this in a large trifle dish, feel free to layer things however you want and repeat the layers until you run out of ingredients or room; I just recommend ending with the blueberries on top of the COOL WHIP layer because it seems to be the prettiest combination. This a seriously delicious make-ahead red, white, and blue (plus chocolate) dessert for Memorial Day or the 4th of July, but really, when berries are cheap and awesome, it’s perfect all summer.


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Chocolate Berry Trifle

  • Author: Our Best Bites


  • 1 4-serving-size (3.9-ounce) package instant chocolate pudding
  • 1 cup cold water
  • 1 14-ounce can sweetened condensed milk
  • 1 cup heavy cream
  • 2 8-ounce containers COOL WHIP, thawed
  • 8 ounces cream cheese, softened at room temperature
  • 2/3 package of Oreo cookies, roughly chopped
  • 1 pint blueberries, blackberries, or a combination of both, washed
  • 1 pint strawberries, washed, hulled, and sliced


  1. To prepare the chocolate layer, whisk together the pudding, cold water, and sweetened condensed milk. Refrigerate. Using an electric mixer, whip the cream until soft peaks form. Fold into the chocolate pudding mixture until well-combined and then refrigerate until ready to use.
  2. To prepare the cream cheese layer, use an electric mixer to whip the cream cheese until it’s light and fluffy. Add the thawed COOL WHIP and whip until light and fluffy and well-combined.
  3. Layer the ingredients in trifle dishes. If using individual dishes, it’s easiest to do a layer of pudding, cookies, strawberries, COOL WHIP/cream cheese, and end with berries. If using one large trifle dish, repeat the layers until you run out of ingredients (or space).


  • Serving Size: 10

Disclaimer: This post was sponsored by COOL WHIP, but, as always, our opinions, recipes, and ideas are completely our own.


  1. This looks perfect for this weekend and I have a plethora (yes, a true plethora)of chocolate pudding we need to use up. I have never made any trifle because although I think it looks pretty in the bowl once you take a scoop it is visually disturbing to me (weird, I know!) So now I will have to go hunt down these little trifle bowls since they are adorable! Keep up the great work ladies, you’re amazing!

  2. People still make trifle with vanilla pudding (I’m thinking ‘dream topping’ or ‘angel delight’ from the UK)?? No wonder they think it’s old fashioned and icky. Trifles are ever popular over here but nowadays are made with fresh custard and whipped cream, plus fresh fruit- usually with strawberries at this time of year.

  3. My friends and I do a “death by chocolate trifle” that includes oreos, broken chocolate cake, chocolate pudding, and heath bar bits with the cool whip. People fight over it! 🙂 This looks great with the berries.

  4. It’s funny how putting it in the small trifle bowl makes the berries look enormous. which makes them look delicious. Also, I’m not usually a huge fan of instant chocolate pudding but I can get on board with anything that has sweetened condensed milk and whipped cream in it! We are having company for dinner on Sunday and I’m pretty sure I’ll have to make this for dessert. Does it work to make this the day before or would I be better off to make the pudding (mousse?) and the cream ahead of time but assemble the trifle the day of?

    1. You could definitely make it the day before–in fact, you’d probably be better off that way (rather than trying to assemble it later) because the pudding/cool whip mixtures will still be workable.

  5. when i think of trifle (i have eaten several different kinds and loved them) I can’t help think of the episode of ‘Friends’ when Rachel tries to make a trifle and mixes up a trifle recipe and shepherd’s pie recipe. One of my favorite TV kitchen blunders of all time.

  6. The thing I love about my English mother is the fact that the only trifle we ever had in our house growing up consisted of chocolate cake, chocolate pudding, Cool Whip and Skor bits. I never had a fruit laden, vanilla pudding trifle until I was in my early 20s! Bless her for loving me enough to only make the really good stuff! This one looks good too, maybe we’ll have to switch things up one of these days and surprise the family with a trifle that has fruit in it! Haha

  7. Hi, I love the thought of chocolate in trifles! I have a trifle I made this week and am posting this Friday with pound cake, lemon curd and gingersnap crumbs, it was delicious! My husband is English and grew up with the more traditional English trifle which has a layer of fruit and jello on the bottom with ladyfingers too. Not quite as appetizing as I’d like, especially after the first few bites, it just looks messy. We’ll have to give your chocolate creation a try.

  8. One of our family’s favorite trifles is a prepared chocolate cake mix, crumbled, layered with chocolate pudding, cool whip and heath toffee pieces. Wonderful!

  9. I’m going to have to stop reading your blog. I used to come here for trusted recipes, but now everything you post is “sponsored by.” Sure, you need to make money to support you family and make this endeavor worth the time you spend away from your kids. BUT, I feel like the recipes you are throwing at us are only intended to make money…so much for tried and trusted. I wouldn’t mind if the sponsored recipes were few and far between, but lately, it seems like every post is being forced on us.

    And Cool whip, really? That stuff is nasty anyway and I refuse to cook with it. I like recipes with REAL ingredients that I can feel good about feeding my family. Pudding + Cool Whip…yuck!

    1. Or you could say to yourself, “hmm. I’m not really a fan of cool whip, but the concept looks good. I think I’ll do it with real whipped cream instead.” and then keep your mouth shut.

    2. I just want to echo Ellie’s comment. We have to remember how much time it takes for these girls to come up with recipes, perfect them, photograph them and get posts up 3x a week. Reply to comments, questions, pay for the blog and so on and so forth. It IS a full time job. So while you want everything for free, realize they have to get some income to keep this blog up and running and worth their time too. And I don’t care who sponsors what as long it is their opinion and they are honest. I may not like cool whip, but you better believe I will be using this idea – so cute!

      Also, I just want to say that I am glad I am not the only one who believes calories don’t count when things are broken – like cookies – or when I cut the brownie in half, then eat both halfs. Totally doesn’t count 😉

    3. So then stop reading, and keep the sour grapes to yourself. In the last few days, they’ve posted a recipe for a refreshing carribean chicken salad, homemade soft pretzels, and a delicious steak-and-brie sandwich, none of which were sponsored in any way. They all contained real ingredients that are fine to feed a growing family. These ladies are doing their best to produce recipes that appeal to a wide audience while supporting their own growing families, not just appeal to YOU.

      You might think Cool Whip and Jello Pudding are nasty but they’ve been around since the 1960s and plenty of folks might like to use them once in a while so why don’t you get off your sassy horse or at least take it somewhere else.

    4. Then stop reading! If you see the title of the post, and you’re not interested, or it’s not up to your “trusted” standards…..don’t keep reading! I had a conversation with my friend the other day about this exact thing. My love for OBB runs deep. She loves the website, just not as much as I do. So, she told me if she isn’t interested in the post for the day, she just moves on. If it’s a recipe that draws her in, she clicks and reads. Easy as pie. I’m just trying to figure out why so many individuals have made it their business to be unkind on these comment boards lately and try to pass it off as being helpful. And I’m with everyone else. If ya don’t like an ingredient, figure something else out.

      Keep it coming, Kate and Sara. (I just admire due-any-minute-Kate for posting anything at this point of her pregnancy! Best wishes, Kate!)

    5. “Every post is being forced on us…” Really? I can’t believe you said that. Who is forcing you? I don’t make every recipe I see here, some look wonderful and fit my lifestyle, others look good but I don’t try them. No one is forcing me to love or try every recipe. No one is forcing you either. If you can’t make necessary substitutions or adjustments to a recipe you see here, then it is your fault, not these talented ladies. Thanks Kate and Sara for all you time in efforts and sharing your delicious ideas with all of us.

    6. I don’t want to be nasty but if you don’t have anything nice to say, please don’t say it. Amy, I think that you might want to think about what you posted. I almost cry whenever I see a post like that.

  10. The only trifle I make is called “Death by Chocolate” and involves devil’s food cake, Kahlua, chocolate mousse, Heath Bars, and Cool Whip. Not a single shortcake/banana/vanilla bland bit in it. Of course, the Kahlua could probably be substituted with a nice strong espresso too. It’s always the first dessert gone at a carry-in. :o)

    I love the idea of using berries, tho. Will have to try this. And I love, love, LOVE your individual trifle bowls. Totally needing some of those now!

  11. Trifle literally means “a bother”. In otherwords they are a bother (worth it though) to make but oh so tasty! I make trifles of all sorts all the time, the commonality being berries and angel food cake, the pudding flavors change depending on what I want and occasionally I make a “tropical” style one, adding in tropical fruits such as pineapple, mango, papya, etc …

  12. If only it wasn’t made with Cool Whip… I am trying to phase out anything that can be considered ‘plastic’ food. I totally agree w/ Amy’s sentiments in post #12. Bring on real food, please!

    1. Just substitute real whipped cream for Cool Whip. Easy peasy. You just take 1 cup Heavy/whipping Cream, 1 teaspoon vanilla and 1 Tablespoon confectioners/powdered sugar. Whip cream in a mixing bowl until stiff peaks are about to form. Then add in vanilla and confectioners sugar (make sure the peaks are already formed). Be careful not to whip too much or it can turn to butter type mush. Warning real cream doesn’t last like the cool whip and needs to be used up or goes all runny and icky.

  13. If you don’t have individual trifle dishes, I’ve used before clear plastic cups. You know, the wide short ones. They work great for something like this, especially if you’re bringing them to a party and don’t want to mess with dishes to take home.

  14. By the way, my new favorite Cool Whip is the container with a brownie picture on it. I believe it’s “thick and rich”. WOW! It’s made with cream and is very tasty!

  15. Love the recipe and also love the huge variety of recipes you guys are always posting. No matter if I end up making it or not, I enjoy every new blog entry you post, and rarely read one where I don’t smile to myself and laugh out loud about something you’ve written. I’m tired of all the complaining some people have chosen to do lately as far as a recipe using this or that ingredient. Seriously, people? If you’ve got the whole try to balance life and cook/bake for your family, too, figured out so perfectly, then why are you even reading this blog??? I love OBB! Reading the new posts is a highlight to my day. 🙂 Keep up the great work, ladies! It’s appreciated!

  16. Thanks for another fun recipe! Just in time for Memorial Day! I even love making mini-trifles in clear plastic punch cups – they actually turn out cute! We are a try-our-best-to-eat-whole-foods kind of family, that happens to also be a “thank you Jesus for Cool-Whip from a plastic bucket” family. 🙂 Keep ’em coming friend!

  17. My favorite trifle is actually a deconstructed version of your chocolate mousse crunch cake. Layer cake, mousse, and heath bits and top it off with some whipped cream. Super chocolatey and decedent. 🙂

  18. Whoa! Halt cool whip haters! Running a website is tough enough– a few sponsers are greatly appreciated! Lay off these ladies! Also, umm, yummy and yes, trifles always remind me of that friends episode–I’m thinking if I make this some nutella might sneak it’s way in there somehow.

  19. How interesting!I’ve never tried making trifle with pudding mix, but it does look tempting, and, a lot easier! For chocolate trifle, I make my own chocolate pudding & the layer of chocolate sponge that’s needed. I’ve never thought of using chocolate cookies instead of the sponge, but I’m sure that idea would go over quite well with my 8 grandchildren!

    Being Brit born, trifle has always been a family favorite. Be it, traditional trifle layered with fresh custard, white sponge, sherry, berries, fresh whipped cream, & toasted nuts & angelica for decor served at Christmas & one of my grandchildrens BDs, as it’s her favorite dessert.

    Or.. Chocolate trifle with layers of chocolate pudding, chocolate sponge, chocolate liquor, chocolate syrup, berries, fresh whipped cream & a sprinkle of shaved chocolate,served on most any other occassions.

    In my world, whatever way it is made, Trifle is a wonderful dessert!

  20. I’m with you, Joycelyn, I like tifle any way it comes. (And no, I’m not British!)

    As for replacing Cool Whip, I’ve read on the web that adding a stabilizer like unflavored gelatin to whipped cream is a good idea. (Especially if you’re making it ahead.) Just Google “Cool Whip substitute.”

  21. This was a HUGE hit today! I work at a machine shop and held a BBQ for the boys and a couple of them actually asked for the recipe.

    Shame on you Amy for being so grumpy. Without these pictures, I would have had a tough time finding things like sweetened condensed milk which is an ingredient that is not in my vocabulary. And coolwhip for us young folks is a win-win.

  22. This was amazing. I didn’t have any cool whip on hand, and aren’t a big fan of it, but I just substituted heavy whipping cream whipped up with some powdered sugar and it worked perfectly. Might be a new favorite recipe actually. LOVE IT!

  23. I was on the hunt for something with fresh summer berries and chocolate (couldnt agree more with all the berry, white cake and cream trifles out there- not that they atent delicious but uou need to mix it up a little and my husband specifically asked for chocolaye. I just couldn’t deny him ). Made this yesterday for the fourth and it was a HUGE hit, with both men and women. And the cool whip ( extra creamy) was specifically mentioned as really tasty! I did substitute ghiardelli brownies for the Oreos just for something different. Will definitely make again!

  24. I had to post and say I made this today for our Christmas dessert and everyone loved it! The only thing I changed was using whipping cream instead of cool whip. It was fantastic and I am sure I will be asked to bring it again.

  25. I served these at a large gathering yesterday and they were a huge hit! Made them in little punch cups, using the chocolate mixture (oh my Yum!), strawberries, cool whip and instead of Oreos I used cut up brownies . They turned out so flavorful with lots of texture. Wonderful!!

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