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Double Decker Pumpkin- Caramel Pie

Every year around this time, our community has a small Harvest Festival, complete with hay rides, Kettle Corn, potato sack races, bratwurst with sauerkraut, those annoying body tattoos, and a pie bake-off/chili cook-off. My son and I always enter the pie contest. It’s fun to sit around and talk about what we’d each like to bake. Usually I let the kiddo enter into the “other” pies category while I tackle a fruit pie. Competing in the same category as your child is never a good idea. This year, however, I competed. I entered a Double Decker Pumpkin- Caramel Pie.

This pie was made late at night- in anticipation for delivery to the contest the following morning, so I didn’t attempt to take step by step photos. You can imagine an Oreo crust (I used the Oreos with CHOCOLATE filling) baked for a short time and then filled with a simple pumpkin custard and baked some more. Refrigerated overnight, the caramel whipped cream layer is added the next day. Where’s the caramel? It’s melted with cream and then whipped into whipped cream to create the best-tasting whipped cream EVER.

There was of course a pie EATING contest too. Chocolate cream pie. My boy competed as the reigning champ from last year. He wasn’t able to shove the pie into his nose mouth quickly enough this year. Maybe the caramel apple, bratwurst and churro he ate prior to competing had something to do with his inability to perform.

There it is in all its glory. Chocolate shavings on top made it more purdy (since my crust was looking rather rustic-looking). Unfortunately, I did not get to take a photo of the pie when it’s cut. Will you trust me when I tell you that it’s beautiful? A chocolate crust, a pumpkin layer and then that wonderful caramel whipped cream layer too. This will most definitely be my chosen recipe for pumpkin pie this Thanksgiving.

And guess what? It took first place too! I’ve entered this darn pie contest every single year since 2004 and this is the very first time I’ve taken first prize. I’d say it’s about time. But this pie was surely worthy of taking it. I’m just glad the judges liked pumpkin pie. And that there weren’t a zillion entries πŸ˜‰ My boy scored with his pie too, which he will be sharing on his blog this Thursday…

Yield: One 9-inch pie

Prep Time: 35 min + chill time

Cook Time: 45 min

Double Decker Pumpkin- Caramel Pie

This pie took first place in a local Fall Harvest Festival pie contest!


25 Oreos (creme included), crushed into crumbs (about 2 cups)
6 tablespoons unsalted butter, melted
3 large eggs
2 3/4 cups heavy cream, divided
One 15-ounce can unsweetened pumpkin puree
1/2 cup light brown sugar
1 teaspoon pumpkin pie spice
1/2 teaspoon salt
28 caramels, unwrapped
1 ounce bittersweet chocolate, for grating


1. Preheat oven to 350 degrees F. In a small bowl, stir the Oreo crumbs and butter until combined. Press the mixture onto the bottom and up the sides of a 9-inch deep-dish pie pan; freeze until set (15 minutes). Bake for 10 minutes; let cool.

2. Meanwhile in a large bowl, whisk together the 3 eggs, 1 cup cream, pumpkin, brown sugar, spice and salt until just combined. Pour into the cooled pie shell and bake until set, 40 to 45 minutes. When you shake the pan, the filling should no longer be jiggly. Let the pie cool at room temperature slightly, then refrigerate for at least 3 hours, or overnight.

3. In a bowl, microwave the caramels with 1/2 cup cream until melted, 2 to 3 minutes- adding 1 minute increments, if needed, if they are still not completely melted. Stir until smooth, then let cool to room temperature.

4. Using an electric mixer, whip the remaining 1 1/4 cups cream until soft peaks form. Drizzle in the cooled caramel and beat until well blended. Spoon the caramel whipped cream on top of the pumpkin filling and refrigerate until completely chilled. Before serving, coarsely grate the chocolate on top of the pie


*If you don't have access to Oreo's, you can use another type of chocolate sandwich cookie. I used the Oreos with the chocolate filling, but you can use the regular ones if you'd like.
*If your pie cracks on the surface while baking, don't worry about it- you'll be covering that up with the caramel whipped cream!
*Don't have any pumpkin pie spice? Make your own by mixing equal parts of cinnamon, ginger, allspice and nutmeg.
*Stick toothpicks in the top of any leftover pie before you cover with plastic wrap (keep stored in the refrigerator).

Source: (adapted from Everyday with Rachael Ray)

54 Responses to “Double Decker Pumpkin- Caramel Pie”

  1. postedOct 3, 2011 3:05 AM

    The pie looks delicious, I’m not surprised that it scooped first place!

  2. postedOct 3, 2011 3:14 AM
    Lauren at Keep It Sweet

    That pie sounds amazing! I love the kicked up version of pumpkin pie.

  3. postedOct 3, 2011 3:43 AM

    This sounds dreamy. Love this!

  4. postedOct 3, 2011 3:54 AM
    Averie @ Love Veggies and Yoga

    Congrats on 1st place and they were clearly blind or without tastebuds in years 2004-2010. Glad they finally came to their senses. It looks incredible!

  5. postedOct 3, 2011 4:00 AM

    Yum on this pie! Pumpkin pie is a favorite of mine and I love the caramel whipped cream. Congrats on your win:-)

  6. postedOct 3, 2011 4:00 AM

    you took first!! woohoo! i can’t wait to see RB’s pie too. this sounds so delicious and unique… i’m definitely wishing i was a pie judge.

  7. postedOct 3, 2011 4:37 AM
    Carrie @Bakeaholic Mama

    I need to make this! Congrats on 1st place! It looks like its a winner I can’t wait to try it.

  8. postedOct 3, 2011 7:17 AM

    Congrats on 1st place!! The pie looks amazing πŸ™‚

  9. postedOct 3, 2011 7:30 AM

    Congratulations! This sounds amazing – especially that whipped cream!

  10. postedOct 3, 2011 7:42 AM

    Love it!

  11. postedOct 3, 2011 8:37 AM

    Congrats on the first place prize! Love the idea of caramel whipped cream…will definitely have to try that πŸ™‚

  12. postedOct 3, 2011 8:42 AM

    Congratulations on your win! It looks decadent and delicious!

  13. postedOct 3, 2011 8:54 AM
    Joanie from CLBB

    Yahoo, congrats! Glad those judges finally came to their senses! A well-deserving family of winners! Will look forward to the winning mystery recipe on your son’s page later this week. Your pie looks amazing, printing if off to add to my special Recipe Girl binder o’successes! (Now that I’ve started hoarding cans of pumpkin in anticipation of the alleged upcoming shortage, I think I can spare a can for this luscious pie). Thanks, Lori

    • postedOct 3, 2011 11:48 AM

      You’re welcome! And so happy to hear that there is a Recipe Girl binder of successes! πŸ™‚

  14. postedOct 3, 2011 9:04 AM

    This looks like it is more than deserving of that first prize ribbon! Yum!

  15. postedOct 3, 2011 9:08 AM
    Heather @ Get Healthy with Heather

    It looks like a first place recipe!!

  16. postedOct 3, 2011 9:18 AM

    Yay!! What a fabulous pie, I can see why it took first place πŸ™‚ Love the fun photos here πŸ™‚

  17. postedOct 3, 2011 9:39 AM

    Oh Lori that is awesome.
    What an amazing pie! Good combo too!

  18. postedOct 3, 2011 9:54 AM

    Congratulations to you both!!
    I’ve never been a pumpkin pie fan, but I’m thinking this may be the way to go this year.
    Thanks, Lori!

  19. postedOct 3, 2011 10:19 AM
    Abigail - MyNappytales

    Wow! I’ve never liked pumpkin as a veggie but with the Oreo crust and caramel whip frosting my oh my it sounds so good. Congratulations!

  20. postedOct 3, 2011 1:15 PM

    Now I know what I’m taking to Thanksgiving dinner. Thanks. Looks delicious!

  21. postedOct 3, 2011 1:29 PM

    This looks like a pumpkin-chocolate combination that cannot disappoint! Congrats on your first place win. Just might try this out this year for Thanksgiving!

  22. postedOct 3, 2011 1:44 PM
    Rikki Rogers

    Just wanted to drop a comment to say that I REALLY enjoy RecipeGirl! The website design is *superb* and you are a very entertaining writer. πŸ™‚ Keep these wonderful recipes coming and great job – my own little recipe blog has a long way to go in becoming as fantastic as yours.

  23. postedOct 3, 2011 2:42 PM

    I just read the ingredients list…no kidding you took 1st place! YUM!

  24. postedOct 3, 2011 3:03 PM

    Sounds so up my type of pie alley…although I know I would have found somewhere for a bit of bourbon; I can’t seem to help myself with pumpkin pie; they are soooo good together.

  25. postedOct 3, 2011 3:09 PM
    Kat connelly

    Wow! Can’t wait to try it!! Thank you as always for sharing your recipes πŸ™‚

  26. postedOct 3, 2011 5:11 PM

    I’ve been craving a caramel *something* lately and this looks totally awesome! And congrats on first place πŸ™‚

  27. postedOct 3, 2011 5:42 PM

    Lovely pie – congrats on winning first place!! πŸ™‚

  28. postedOct 3, 2011 7:18 PM

    Sounds amazing! I love fall!

  29. postedOct 3, 2011 10:53 PM
    Koko @ Koko Likes

    OH MY this looks GOOOOOD! Hello Fall!

  30. postedOct 4, 2011 4:46 AM

    Congrats on you BLUE RIBBON PIE!!!!! yeah!!!! Looks like a fun little festival!

  31. postedOct 4, 2011 7:22 AM

    I will definitely be making this pie soon. So many tasty components to it who wouldn’t crown it first place?!?!

  32. postedOct 4, 2011 10:31 AM

    CONGRATS!!! i can definitely see why it took first place.

  33. postedOct 4, 2011 5:26 PM

    YUM!!! can’t wait to try

  34. postedOct 5, 2011 7:53 AM

    Thanks for sharing the recipe with us! I will definitely be making this instead of regular pumpkin pie this year for Thanksgiving and I’m sure my family will love it.

  35. postedOct 6, 2011 6:39 AM

    I made this pie last night (at 3am), as soon as I saw the recipe. I used ReddiWhip instead of making my own whipped cream because I don’t have a blender of any sort. It came out kind of wet, like soupy. Still tasted amazing!

    • postedOct 6, 2011 6:50 AM

      Sounds like you may have added *all* of the cream in the filling? Only one cup goes into the filling. No soup!

  36. postedOct 7, 2011 12:45 AM

    First place! Woot! My Smudge can’t wait til Thanksgiving for a pumpkin pie so its on the list for the weekend. Thank you for ending her incessant pleas. No really, thank you.

  37. postedOct 11, 2011 6:35 AM

    I made this pie last night and whipped the cream to finish this morning. When I added the cooled caramel/cream to the whipped cream – it fell! The “whipped cream” was more like soup! I had another carton of whipped cream, whipped it and folded into the first mixture. Still very runny! Suggestions?

    • postedOct 11, 2011 6:50 AM

      Yikes! I followed the original directions from Rachael Ray for that one… whipped the cream to soft peaks- the caramel mixture should be cooled and quite thick (I really had to use a rubber spatula to scoop it out of the bowl) and then it mixed with the whipped cream perfectly. Did you get the caramel mixture mixed very well so that part wasn’t soupy when added to the whipped cream? It should end up… like caramel. Good luck!!

  38. postedOct 11, 2011 6:37 AM

    I also used the vanilla oreos instead of chocolate. The pie seems to have done okay – haven’t cut it yet. It’s for an office party this afternoon.

  39. postedOct 12, 2011 5:38 PM

    Made this on Sunday during football. Good- was interesting w/the chocolate crust and pumpkin pie filling. No caramels to be had at the store so I had to improvise (used bullseyes I had on hand)….which added an interesting taste… Neighbors son, 6, LOVED THIS PIE!!!

  40. postedOct 14, 2011 6:52 AM

    this sounds just divine – congrats on the big wins to both you + your son!

  41. postedOct 19, 2011 10:30 AM

    *drools* This is on my Thanksgiving menu already!

    I always scrape the oreos clean from the creme, afraid that it will stick, burn, or make the crust fall apart. I guess I will try them whole next time.

  42. postedNov 3, 2011 6:10 PM

    How Great! First place and you get to eat such a mouth watering treat!

  43. postedNov 22, 2011 2:28 PM

    I also could not get the cream to whip properly. I looked on rachael ray’s site and they didn’t even have the recipe. I’m chilling the whole thing and hopefully that will work.

  44. postedFeb 24, 2012 5:57 AM

    This pie was AMAZING!!!! Thanks for the recipe, it will be a tradition to make at Thanksgiving every year at my house!

  45. postedMar 9, 2012 7:50 AM

    This was the first pie I’ve ever made. I made it for thanksgiving and everyone who disdains my veggie cooking ate it all up. Sooooo good.

  46. postedNov 23, 2012 12:08 PM

    I just made the pie as apart of my thanksgiving day desserts. It came out great!!!!! Sadly, I’m the only one in my family that eats pumpkin pie. I loved every piece the crust, pie, and whipping. My mom really like the crust and caramel whip cream. The only thing I would change is for a little extra sugar in the pie…since I have a sweet tooth. The whip cream came out wonderfully. I know some people mentioned problems with the cream being runny, but mine came out nice and fluffy. I have the hand held mixer, but I melted the caramel whisked it together with the heavy cream…added in a little sugar and vanilla extract. After I mixed together, I placed the bowl in the freezer for about 5 mintues or so then took it out. I turned my mixer on to the whip setting and after a couple mintues the whip cream came out great. Will do the recipe again.

  47. postedOct 7, 2013 6:14 PM

    Hi, I’m wondering if you might know what the approximate amount is once the caramels are melted down? I had to make caramel sauce for another dessert and wanted to use the leftover for this pie. Any idea – 1/2 C? 1C? This is an amazing pie, by the way! Made it last year…my favorite pumpkin pie ever!

  48. postedNov 18, 2013 10:01 AM

    “In a bowl, microwave the caramels with 1/2 cup cream until melted, 2 to 3 minutes- adding 1 minute increments, if needed, if they are still not completely melted. Stir until smooth, then let cool to room temperature.”

    how many and what kind caramels ? they are not listed in the ingredients.

    • postedNov 18, 2013 10:04 AM

      yes, they are listed there… 28 caramels. Just buy the KRAFT brand of caramels and unwrap them.

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