The South Side Pie Challenge!

November 2, 2013 • 12:41 pm

Here are most beautiful postprandial words one can hear:


As we all know, pies are one of America’s greatest contributions to world cuisine (and don’t mention the French tartes, which, although often superb, are not PIES, while the best British pies are the savory ones, like Melton Mowbray pork pie).  Our other great contribution is barbecue.

I’ve been keeping a mental fork all week, ever since I saw the announcement of the Second Annual South Side Pie Challenge held in the Ray School, an elementary school a mere two blocks from my office.  The best pie-makers of Chicago’s South Side bring two exemplars of their finest pie to the Challenge, and enter in one of four categories: fruit, nut, cream, and sweet potato/pumpkin.

The judges taste one of the two pies before the competition, and then the doors open to let the eager public in to sample for themselves.  I, of course, was right on time, hoping to eat as much pie as I could.  For $3 you could purchase one piece, or for $10 four (with one cup of coffee per slice). I, of course, went for four, concentrating on the prizewinners. I managed to down two pieces on the spot, and brought the others home for tomorrow to avoid sugar shock.

A beautiful sight:


The fruit pies:

Fruit pies

Moar fruit pies:

Fruit pies 2

The cream pies:

Cream pies

The nut pies (I forgot to photograph the pumpkin/sweet potato pies, but they weren’t moving fast):

Nut pies

And some fruit pies:


Two blueberry pies, one of which I sampled (the first one below, of course, as it was the prizewinner):



Cherry almond pie. Ain’t that a pretty sight?

Fruit almond

Nut pies (these were all pecan, the best of all nut pies):

Pecan 2


The prizewinner: pecan fudge, which is reposing in my fridge right now:

Pecan fudge

The pies were served by cute schookids:

Nut girl

The creme pies, starting with one of my favorites:

Shaker lemon

Raspberry strawberry cream cheese pie. I much regret passing this one up:

Strawberry rhubarb

“S’Cream” pie: peanut butter cream pie topped with crushed peanut M&Ms.  A prizewinner, so I had to try it:

Penut butter cream

Turtle fudge pie: chocolate cream, and a ribbon of caramel, topped with a hard chocolate topping and then whipped cream and pecans. I had to have it.

Turtle pie

After I polished off the blueberry pie, I had the turtle pie. It was fantastic, one of the best pies I’ve ever had:

My turtle pie

And my pies for the morrow: the peanut butter cream pie and the prize-winning pecan fudge pie:

My creme pies

Oy, am I full!

My favorite pies are sour-cream raisin, cherry, low-bush blueberry (as served by Helen’s Restaurant in Machias, Maine), sour cream/raisin, lemon chess, strawberry, and the Midwestern staple, sugar pie.

What’s yours?

86 thoughts on “The South Side Pie Challenge!

  1. Wow that turtle pie looks awesome. I could feel my mouth watering looking at all the pies. I love pie.

    That gooey pecan one looked very close the the texture of a butter tart (I’ve been eating butter tarts weekly).

    All the cherry pies too! Cheery pies, especially sour cherry pies, are the best fruit pies because the texture of the cherries really puts it over the top.

  2. Well, if I’d been there I wouldda been at the pecan table. The first of those that you have pictured looks best to me.

    For this post they oughtta invite you to be a judge next year. That way you get to sample all and take four slices back for later in the week.

    1. I agree on the pecan, but also love a good pumpkin pie. I actually make pumpkin creme caramel for festive occasions….Now I’m beginning to drool.

  3. PS i have that pie kitty postcard in my hall. My good friend, who is a pi and pie ( and, lately, kitty freak) brought it back to me from a conference in Chicago:-)

  4. Are all the recent photos of you photoshopped? You must weigh about 250 pounds now. Or are you gonna give us that metabolism B.S? You’re gonna go from staunch to paunch. Oh, the horror. :)= Happy Pie Face.

    1. The trick is to eat nothing else BUT pie all day. Save the calories up. It doesn’t do you well for sugar shock though. I often get dizzy & feel like I’m going to black out because I forget to eat then eat a bunch of sugar. Poor pancreas.

    2. It’s pretty clear that Jerry’s regular diet is quite healthy. He enjoys his gastronomic indulgences — as well he should — but those are special treats, not the norm.

      He also doesn’t seem to be a couch potato. The more you exercise, the more lean body mass you build up, and the more forgiving your metabolism is of indulgences.

      There are exceptions, of course, but fewer than you might think. I suspect that most Americans, including most obese Americans (but not the ones in the “morbid” and above categories), are actually under their ideal weight; if they built up their lean body mass to where it should be, they’d shed the excess fat and wind up tipping the scales at or above their current weights…but far, far healthier and much more attractive.

      It doesn’t take a lot of time, either…just a half an hour or so a few days a week of intensive exercise will do the trick, and you don’t need any equipment more exotic than a chair or a towel, if even that much. See Mark Lauren’s You Are Your Own Gym for everything you need to know.



      1. No, I am not talking about pot pies.

        From wikipedia: “The pot pie does differ from the Australian meat pie and many British regional variants on pie recipes, which may have a top of flaky pastry, but whose body is usually made from heavier, more mechanically stable shortcrust, hot water crust or similar pastry.” (

  5. I do love pies! As in most things I can’t decide on a favorite. If you force me to I’ll probably blow a gasket and melt several fuses.

    My wife makes a superb cherry pie that is definitely on my list of favorites. One of the best pies I ever had was at a potluck kind of party.

    Nobody could figure out what it was and everybody loved it. There were only two of them and they were gone within minutes. As we were all arguing about what kind of pie it must have been the person, a young woman, who made them finally showed up and we learned that they were pistachio cream pies. I have tried pistachio pies everywhere I find them since then, but have never found one that was even in the same solar system as that one.

    I have a pear pie that I make that is one of my favorites, but it might be an aquired taste. Fresh pears, honey, pecans and a small amount of top shelf blue cheese. Yum!

    I’ve got to give a shout out for meat pies though too. Used to know a place that made fabulous steak & kidney pies. I’d bring a good book, order a pie, a wedge of some nice sharp cheese and a good ale. That was especially nice on a dreary rainy day.

    1. I’ve always disliked meat pies. I think it’s because the adults around me had not appropriately set my expectations when I was a child & figured pie was going to be something sweet then meat in a pastry. Also, meat pies seem extra shitty in north america. I do like other things like sausage rolls which I get when I go to New Zealand.

        1. Yuck. The only one I like is pizza but it isn’t covered in with pastry. Quiche is tolerable but I don’t eat pigs so not the Lorraine.

              1. Don’t think I’ve heard of it before your post, but I’ll be sure to keep my eye out for some next time I’m in Canada. Or I just might make some, myself….


      1. Oh, I feel so bad for you. A Canadian who doesn’t like meat pies? 🙂

        Maybe it is confined to Quebec, but my wifes side of the family, Quebecois, always serve meat pies as part of any special meal (like when company is over for dinner). Salmon pie, trout pie, beef pie, pork pie. Yummy!

        One of the best I had was a smoked trout pie at a cousins place on a beautiful lake near the little town of Armagh. The trout were from the stream about 10 meters out the back door.

        1. The first time I ate fish and actually liked it, it was a trout that had been swimming in the stream we were camped next to. It’s long enough ago I don’t really remember any particulars, but I’m pretty sure it was just fried with some butter and instant bouillon powder in a cast-iron skillet over a campfire. And I’m sure it was under an hour from stream to plate.

          If somebody offers me a pie of trout they caught and smoked themselves from a stream a stone’s throw away, and I turn it down…well, assuming that hygiene isn’t a problem, it’s a sure sign I’m dead.


        2. Yeah, I don’t know. I don’t see people eat them much in Ontario. My dad never liked meat pies either & he is from the east coast.

          One of my favourite pies is banana cream pies. I always request them for Xmas.

        3. My mother fed us tourtiere from as far back as I can remember. (She’s an Ottawan.) Pretty traditional, simple ingredients list but the result makes a pastie look like fast food. And I love pasties too! (British people, attack not.)

    2. Not quite the same thing as a pie, but on this side of the pond there is nothing quite as comforting on a cold winter’s night as a steaming hot Cornish Pastie!

      1. There’s actually a Cornish Pasty Co. restaurant several miles north of me. Damned good food! They not only serve traditional pasties but some regional variations on the theme…they have a chicken vindaloo pasty, I think, as well as a carnitas one. And an apple pie pasty for dessert!


      2. I kid you not, I just had a Cornish Pastie today! My son and I were out and about, and we happened to go by a place called “British Bakery & Tea Room” that I had been meaning to check out. It was a small pleasant place that smelled wonderful. We got one Cornish Pastie and one Steak, Potatoe & Gravy Pastie and shared. They where both great! I will be back to that place to try more, including some of the sweet stuff.

      3. Yes, Cornish pasties are hard to beat. And apricot pie for dessert.

        I was surprised at PCC’s restraint. I would have had four slices at the venue and taken eight home.

  6. Here in UK we have the ‘Great British Bake Off’. The judges are constantly looking for soggy bottoms which apparently is a no no.

    1. With the brilliant, gay presenter Sue Perkins admitting that “I have never eaten a nun before”

      (A “Nun” in this context is a choux pastry treat!)

  7. Since I’m 2,000 miles from Chicago this quibble means nothing, but wouldn’t it have been more appropriate to hold this event on Pi Day?

  8. A cousin of mine got married recently in his home town of San Francisco. Our shared grandparents lived on the south side of Albany Hill (across the Bay, bordering on Berkeley). On the north side of the hill runs a creek lined with blackberries. Growing up, we would pick them, of course. Us kids generally managed to eat many more berries than wound up in our pails, but the adults harvested more than enough for pies and jams and what-not.

    Instead of buying a cake, they enlisted all the family who lives in the Bay Area to bake blackberry pies, some with berries from those same bushes.

    Best damned wedding desert ever served at any ceremony ever, period, full stop.

    I’m sure all the pies at the Challenge were fantastic. But give me a choice between any of them and Albany Hill blackberry pie made by one of Mom’s clan — ideally mom herself, of course, though they all know what needs be done — and there’s simply no competition. Nothing else is truly pie.



    1. As a kid I picked the local wild blackberries in OR (an introduced species, actually) and my Mom made pie–absolutely my all-time favorite!

  9. Your photos brought back memories of childhood summers going to community dinners in the small towns near my grandparents cottage near Sault Ste. Marie, Ontario. Community Nights were great festivities that included parades, carnival games, and the big communal dinner at which there would be an enormous table covered with pieces of pie of every description made by the local ladies. The meals have long been forgotten, but the sight of those amazing tables full of pies are forever embedded in my mind. I was always partial to lemon meringue…mmm, pie…

  10. I’m a sucker for anything chocolate. French Silk might not count as a “real” pie, but it is damn amazing!

  11. I still make a lot of sweet pies, though we switched to a lower-carb diet a few years ago and I gave up most things that I used to bake. We like blackberry, cherry, rhubarb, pineapple coconut custard, cream cheese with a crust of homemade graham crackers….
    This buttermilk pie is one of our favorites, especially when made with homegrown lemons:

    As a child I learned to make meat and potato pie, steak and kidney pie, and Cornish pasties (called empanadas in the U.S.; my current version uses green chiles instead of potatoes).

    These are all treats for special occasions. It’s a good thing I can still get out for a (nearly) daily walk!

    1. Oh my. I don’t suppose you’d be willing to share the recipe for that buttermilk pie, would you?

      Looks great, and I’ve never heard of such a thing. Those two things make it a must try for me.

      Just out of curiosity, have you ever tried using agave nectar in place of regular sugar for any baking?

  12. Ok, that wasn’t fair. That many shots of delicious pies? And you actually got to sample them? Not fair at all.

    I’ll have to haul out that frozen apple pie from my freezer now.

  13. Mmmmm mmmmm good…

    For me, the best sweet potato ‘puddings’ (because they’re very moist and succulent) are the ones made from deep red/burgundy-ish or purple sweet potatoes that come from the Caribbean or South America. There’d have been a run on *that* table!

    1. In a similar vein…the best “pumpkin” pies I’ve had have been ones that Mom has made from kabocha squash. Though dessert last Sunday was pumpkin pie from a garden pumpkin and her hens’s eggs…and, I gotta say, she nailed the filling. It practically evaporated instantly in your mouth as it exploded with flavor. The crust was tasty, but it was a bit crumbly and didn’t hold together ideally. She blamed the lard : butter ratio, though Dad wasn’t sure that was it.


      1. Had to look up Kobacha, Ben. What a coincidence! I made roasted squash today. The squash looked exactly like the one in the wiki photo, but I don’t remember what the store label said. I found whatever I cooked to be sweeter and more toothsome than the squashes I’ve cooked in the past. I see that kobacha can be used for tempura too… must try that!

        You must have had Chinese eggplant before, haven’t you? So delicious compared to regular garden variety eggplant.

        1. From your description of the taste and texture, combined with the outward appearance, sound quite likely that that was, indeed, a kabocha.

          When the garden goes in, I’ll be doing various variations on the “three sisters” — corn, beans, and squash. In at least one of those variations, the squash will be kabocha….


          1. Sounds lovely, Ben. When will you start the garden?

            This year, I hadn’t much time and grew tomatoes in planters, as there’s no room left in my garden (all ornamentals). But in a previous bigger garden and at various times, I used to grow cherry tomatoes, lettuce, cucumbers, hot peppers, eggplants, pumpkins, Chinese winter melon, asparagus, and cantaloupe (not much success with the cantaloupes, as I started them too late, our growing season being too short; the couple of small ones I got were very delicious though).

            1. With luck, not that much longer. I’ve got a couple other projects left ahead of it it in line, but I could conceivably be breaking ground before the end of the year if the gods smile upon me.

              I’m not worried about seasonal timing. The hard part will be getting all the infrastructure in place — the terracing, the irrigation, the pathways, the trellis / fencing, all that sort of stuff. After that, the first round of crops will be green manure / cover crops, and those can go in almost any time. Once that foundation is laid, the rest should mostly take care of itself; all I should have to do is plant, weed, and harvest. And judicious use of mulch should do a lot to cut down on the time needed for weeding, as well.

              That’s for the vegetable “Victory” garden in the front. The back is almost certainly at this point going to wind up mostly being a replica of a native Sonoran desert wash, such as you might find just a few miles away in South Mountain Park. That will likely take even more work initially, but even less work over time. Ideally, once it’s established, I shouldn’t have to do much more than maintain the pathways and let the rest take care of itself. If I really get it right, the natives will even crowd out invasive species, meaning no weeding.



  14. Buckhorn Inn Peanut Butter Pie! It’s actually a vanilla custard pie with a layer of peanut butter crumbles on the bottom, so the flavor is really well balanced. Needs to be served with a big mound of whipped cream on top, of course.

    Besides that, Lemon Chess, Lime Chess, and Apple Crumb, served warm with vanilla ice cream. My kids said Key Lime should be in there too.

    1. The key lime pies served seasonally at some Houston’s or Bandera or Hillstone restaurants (all owned by the same parent company) are basically the Platonic ideal of the form. There’s nothing exotic about them — no special ingredients, nothing unusual. But the execution is superlative. The texture, the balance of flavors, the intensity of the lime and the sweetness and sourness, the ratio of filling to crust, the size of the crumb in the crust, the amount of cream (fresh-whipped) on top — every aspect is exactly as it should be. If you wish to master the citrus pie art form, you would do well to first duplicate that pie — and it’ll take you quite a while to do so — before attempting anything more adventurous.



      1. Your comment inspired a pie idea for me. I don’t know why I never thought of this before, but I am going to have to experiment with adding tequila to a key lime pie to make a margarita pie. Getting tequila flavor into the filling, balanced properly with the lime as in a good margarita, and maintaining a proper consistency, could be tricky. I’ve never come across it before, but I’m sure it must have been done already though.

        1. That sounds like a good idea!

          I saw a Martha Stewart baking show today, all about cheesecakes. And she made this crustless one with ricotta cheese, with liqueur of one’s choice. I forget what she chose but I’d go for Amaretto. I made a different kind of Xmas cake years ago using the usual ‘mincemeat’ and Amaretto, and the folks at work scarfed it down in no time!

          I’m partial to barely sweet, crustless pies, as I eschew the crust unless it’s mostly dark chocolate. 😛 Don’t like overly sweet things.

            1. Thank you very much, Kurt! I think I’ll make this for Xmas dinner, using a tad of honey or agave instead of sugar. That’s way too much sugar for me. I love the addition of the mascarpone cheese!

        2. Well, the original key lime pies weren’t baked, and instead relied on the reaction between the acid in the lime and the egg for thickening. I imagine you should have good success with an unbaked tequila pie, though I would, of course, urge caution in your selection of eggs….


          1. Thanks. I’ll have to do some research, and experimenting. Find out if alcohol interferes with the emulsification reaction. Maybe gently cooking down the tequila before adding to the rest of the filling ingredients. Remove some of the alcohol and concentrate the flavor.

            1. Another possibility: somewhere, perhaps even in this thread, somebody suggested using vodka instead of water for the crust, as the alcohol evaporates more completely than water. A Tequila crust might or might not be sufficient unto itself for what you have in mind, but I’m sure it’s worth an experiment….



  15. Do you have any idea how much weight I gained just READING your post!? I’m gonna have to jog from now to Thanksgiving (which is when I’ll see my family again.) And I DON’T JOG! I guess I could jog to Chicago, but the weather is a little iffy between Houston and Chicago this time of year.

    By the way, just how old do we have to be before we can stop worrying about our looks and weight and not care what people are comparing to the size of our bottom?

    1. How old do we have to be before we stop caring about our looks? I’d say 3-10. At that age I just got out of bed & ran out to play & never thought about what I looked like. Unfortunately, that time has passed.

    2. You’re never to young to stop giving a damn about what others think of you. But…your body is your home. As Tim Minchin would put it, it’s where you spend the vast majority of your time. And strong, healthy bodies make for much nicer homes to live in than weak, sick ones with lots of needless junk to haul around with you wherever you go.

      You’d be amazed at what just a half an hour or so of intensive exercise a few times a week can do — and you don’t need any special equipment or tools or anything, just the body you already have, wherever you happen to be. See Mark Lauren‘s works for all you need to know.



  16. Oh, where to start? 1. My grandmother’s cherry pie, still made by my 92-year old mother. 2. Mom also makes a rhubarb pie, no strawberries, thank you, that is to die for. 3. For my birthday Mom makes banana cream pie, or chocolate cream with a layer of bananas on the bottom. And 4. Mom makes mince meat pie during the winetr holidays, a sweet and sour delight. Mom’s secret for a flaky crust is to use vodka instead of water. It evaporates during baking, of course, leaving a wonderful, not soggy, crust.

  17. Lemon pie. My mom used to make it for me when I was a kid. In fact, I had a slice today. Delayed birthday treat. I’m 81 in the shade and just as ornery as ever.

  18. My all time favorite pie from 60 plus years ago was my Aunt Velma’s green tomato pie. I’ve never seen it replicated, but I can still taste it, light, heavenly and completely unlike anything else I’ve ever tasted.

    Another Midwestern pie from my youth that I have never seen since is mince meat pie, made with real meat, probably beef, not ground, just very well cooked until it was falling apart. It was a sweet pie, much like today’s mince pie, but with, you know, meat.

  19. Sweet! Hey, I’m an alumnus of the illustrious William H. Ray school. They never had anything like this when I was there, though.

  20. Oh, “world cuisine”. So no Tex-Mex, or fast food, I take it?

    I remember the frozen yogurt of California, but now when it has gotten over here my taste has changed. :-/ :-/ :-/

    Not generic pies, though, still don’t like them overly much, basically too much sugar (and often too much fat). Some are delicious though, especially if I’m tired so sugar demand override my regular tastes. At a guess it would work better for me with some habituation.

    Maybe I have to wait for barbecue season. =D

    cute schookids

    Ha! As in “S[c]hoo kids, get off my lawn!”!?

  21. Peach cobbler, not actually a pie in the round with crust sense, is very popular here in Texas. Even the Chinese buffets have peach cobbler.

  22. Barbecue actually comes from the West Indies (the word itself comes from Haiti, “barbacoa”), where the practice of drying, smoking, and spicing meat on wooden racks was developed by the French, English, etc. from the Taino Indians. The most famous of these European students of Taino meat preparation called their meat racks “boucan” (apparently from a South American Indian word), and they themselves were called “boucaniers”. (For various reasons, the boucaniers later took up maritime piracy as a way of life.)

    There have of course been many elaborations and variations on barbacoa over the centuries, with many contributions by Americans, but the origin is West Indian. Modern Jamaican jerk-style cooking is close to the original, and you can still see there spiced meat being jerked over fragrant, smoky, wood fires in the traditional way in certain places.

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