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Lonely Chicago Pie.

I’ve become completely obsessed by pie baking. I blame it on the fact I was a pie judge for the Cville Pie Fest back in October. I bought a bright red deep dish ceramic pie plate and am on goal to wear it out by the end of the year. I found a pie crust protector even though I’m still too scared to make actual handmade pie crust, and I’ve been perusing websites galore looking for ultimate pie recipes.

I’ve perfected the Yard Sale Quiche, debated the pros and cons of using lard in a crust (many of the former, none of the latter), and watched my favorite food movie, Waitress, for like the 16th time. It’s about a pie diner, and this waitress named Jenna who invents unique pies in her head. I watched it once before the contest to get me in the mood, and once again after when I was still on a pie sugar high.

Still on that high, I realized my first task as a newly-ordained pie minister would be to perfect Jenna’s Lonely Chicago Pie. A cinnamon custard pie with smashed blackberries and a top layer of melted chocolate. Dreamy, decadent, and worthy of being the first pie to live in my brand new cherry red ceramic deep dish pie plate. Did I tell you I got one? Did I tell you how I danced around the room when I got it in the mail? I did. With glee.

Much credit and pie kudos to A Dash of Nutmeg for the recipe. I must say my first attempt at custard pie was pretty dismal….it turned out a runny, watery mess. Anybody know what I did wrong? The cinnamon, blackberry, and chocolate somehow made up for the custard FAIL. The combination of tastes sent me to pie heaven. I will perfect this custard pie, I will. Only then will I attempt the lofty goal of homemade crust. With lard of course. Straight from Leni Sorensen’s freezer..

Lonely Chicago Pie


  • 1/2 cup sugar
  • 1/2 cup brown sugar
  • 1 tbsp cornstarch
  • 1 tbsp ground cinnamon
  • 1 dash of nutmeg
  • 1 egg, beaten
  • 2 tbsp butter, melted
  • 1 tsp vanilla extract
  • 1 1/2 cups milk
  • 1 unbaked 9-inch deep-dish pie crust
  • 1/2 cup fresh blackberries, lightly crushed
  • 3/4 cup semisweet chocolate chips
  • 1 tsp butter


  • Preheat oven to 400F.
  • In a large bowl, combine the sugar, cornstarch, cinnamon, nutmeg, and salt. Add the beaten egg, butter, and vanilla. Mix well and add the milk.
  • Pour mixture into crust.
  • Bake for 15 minutes, then reduce heat to 350F and bake 40 minutes.
  • Top pie evenly with crushed berries, return to oven and bake 10 minutes longer.
  • Let cool completely on rack.
  • Melt together chocolate chips and 1 tsp butter, pour thoroughly over baked pie. Allow to chill in fridge before serving.
5 Comments Post a comment
  1. Yours looks even yummier than mine did! I would suggest more cornstarch next time – maybe an extra 1/2 tsp, or more if you want it even firmer. Is it possible that you left it out altogether? That would certainly make a runny custard.When I make homemade pie crust I use crisco. I really miss using my mom's food processor to make pie crust–I think that's part of the secret.

    November 10, 2010
  2. Whoops. I just made it my personal mission to get you comfortable making from-scratch pie crust. When do you want to get together? :)

    November 10, 2010
  3. I'm sure it still tasted delicious! If you like pies, this site might interest you or at least entertain you for a few minutes:

    November 10, 2010
  4. @Nutmeg, wow thanks! :) Thank YOU for the recipe! Where do you find tapioca flour anyway? I'll try adding more cornstarch next time. This is my first attempt with custard pie…it was bubbling a lot when I took it out to add the blackberries, is this normal? Did the whole thing curdle?@StLmom…anytime! Would make a great blog post!@Food – great site, thank you so much! :) :)

    November 11, 2010
  5. Ok, so I'm a little late to the party, but I usually take a day every few monthes to sit and read up on all of your posts -anyway, yes, pie crust is the scariest thing to me – My mom, aunt and gram got together for our annual apple pie making session – we made nearly 50 apple pies – with crust from scratch. Let me tell you – those pies wouldn't be half as good without my gram's crust. It took much longer to do those 50 pies because I had never rolled out dough before but they were patient and I can now roll the perfect dough. Just don't ask me to make it without my gram's supervision. I'm happy to send you her flaky crust recipe though. Good luck.Penny

    December 28, 2010

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