Chocolate Chip Cookie Whoopie Pies

Have you ever had a cookie whoopie pie?!  It’s life changing.  (I may be being a bit dramatic, but I’m kinda right.  😉 )

First of all, let’s address the elephant in the room.  I took a little break from blogging because my husband and I went on vacation. We took a 9 day road trip from home to Maine, and then on to New Brunswick, Canada and finally to Prince Edward Island, Canada.  (And then obviously all those things backwards as we made our way home.)  We had a wonderful time and of course I’ll share all the details here on the blog as soon as I go through my pictures.

To make up for my absence, I have one fant-abulous recipe for you.  Chocolate chip cookie whoopie pies.  This recipe was inspired by this cookie whoopie pie.  We stopped by a random truck stop in between our overnight in Maine and New Brunswick, Canada for a pit stop.  The truck stop had a restaurant and a bakery section and they sold giant whoopie pies.  While I’ve seen classic whoopies before (you know, two chocolate cake like things stuffed with sugary filling), I’ve never seen one this big before, or where the cakes were replaced with cookies.  I suspect that makes me relatively sheltered in the whoopie pie department, but it was new to me.  We looked at the nutritional information on the giant whoopie pie and it had almost 1,000 calories!  Why did I even look?  What was I expecting?  They actually said on the side that the whole thing was one serving!

They also sold giant chocolate chip M&M candie whoopie pies.  What the what?!  When we tried to compare it to the normal chocolate kind, we discovered that the nutritional information on the giant cookie whoopie pie was missing most of the information.  We figure it was calorie free so we bought that one.  😉  That cookie whoopie pie was uh-mazing.  Words cannot describe how good it was.

I’m still dreaming of that monster cookie whoopie pie so I knew that I had to make a version of it at home.  I used my trusty chocolate chip cookie recipe (well, it’s really my husband’s recipe so let’s give credit where credit is due).  We honestly make these cookies all the time because they are so delicious.  If you wanted to stop at just the cookie then I would not blame you one bit.  However, if you want to take it up a notch and go crazy with whoopie pie filling and turn these cookies into one of the best cookies sandwiches you’ll ever have, well then I sure wouldn’t blame you for that either.

This cream filling is super delicious (and also super sugary).  Word to the wise, the marshmallow fluff is epically sticky so be careful when you mix it with the rest of the ingredients.  If you manage to slop some out of the bowl you may just need to remodel your kitchen to fix it.  If you’re careful, the cream filling is very quick and easy to make.

Making the whoopie pie is like making an ice cream sandwich.  Scoop some of the creamy filling on to one cookie (with it upside down) and then top it with another cookie.

Easy peezie.  You’ve got a chocolate chip whoopie pie.  It’s impressive looking, isn’t it?

In case you can’t tell from the photos, these cookies are regular sized cookies.  Although my husband says that these are small cookies because anything other than the giant size he recommends in his recipe is too small.  He’s not wrong, especially when it comes to cookies because we do love cookies.  That giant cookie whoopie pie that we had on vacation took the two of us two days to eat it (since we were trying to pace ourselves to avoid feeling sick).

Feel free to make giant cookies instead, and in turn to make giant cookie whoopie pies.  They will certainly be a show stopper.  (And possibly a heart stopper, you’ve been warned.)  The recipe I linked for the chocolate chip cookies gives you instructions on how to make both size of cookies.  If you do make giant ones, then obviously you’ll have fewer cookie whoopie pies and you’ll need more cream on each one.

If you’re wondering, I’ve never made a classic whoopie pie but they are definitely on my list now!

Chocolate Chip Cookie Whoopie Pies
(makes 17 to 18 sandwiches)

Ingredients for the chocolate chip cookies:

Ingredients for the filling:

  • 1/2 cup butter, softened (equivalent to 1 stick)
  • 1 and 1/4 cups powdered sugar
  • 2 cups marshmallow cream (I used 1 whole 7.5 ounce jar of Marshmallow Fluff, even though it’s a little more.)
  • 1 teaspoon vanilla extract

Direction for the chocolate chip cookies:

  1. Make the chocolate chip cookies by following the recipe.
  2. Let the cookies cool completely.

Directions for the filling:

  1. In a large bowl, beat together the butter, powdered sugar, marshmallow cream and vanilla extract until it’s smooth.

Assemble the pies:

  1. Spread about 2 teaspoons of filling on the flat side of one cookie.  (I used my Oxo Small Cookie Scoop for this.)
  2. Place a second cookie on top of the filling and gently press down until the filling comes to the edges of the cookies.

Filling source: Epicurious

Chocolate chip whoopie pie source:  Tina’s Chic Corner





  1. These look amazing! I make a oatmeal cookie sandwich with a similar middle but this sounds so good with the chocolate chip cookies! Can’t wait to try this out!

  2. Christina says:

    Do the Whoopie pies need to be refrigerated?
    If so, how long can they stay out at room temperature. I have read they taste best at room temperature. My daughter at college has requested these for her birthday. Just wondering if I can make them ahead without refrigerating them.🤔
    Thank you!

    1. Tina says:

      Christina, the filling contains uncooked butter & I’ve read conflicting articles on whether butter should stay in refrigerator or not. I will leave it up to you, but I will say that I have done it both ways, chilled & left out on counter. I hope that helps.

  3. Marjorie Davis says:

    I’ve made the cookies so far but not the filling yet. I don’t need them til 3 days from now for a trip. Should I wait to make filling, or can I freeze them with filling in them already?

    1. Tina says:

      I’ve done it both ways. I think it’s easier to fill them on the day you serve. If you freeze them with the filling, you have to place a few on a cookie sheet & freeze them first, before you store them altogether in a container because otherwise the pressure from sandwiches that are on top will squeeze the filling out.

  4. JS says:

    Do I suppose to let the filling sit for a minute because mine isn’t thick.

    1. Tina says:

      The filling does stiffen after a little bit of time, but I think that I would add a little more powdered sugar because I think that is a quicker way to thicken it up.

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