Quick editorial note before we go any further. Let’s talk doughnut vs. donut, shall we? The word is doughnut. According to Merriam-Webster, the variation donut has been present in published, edited text since the mid-20th century. There’s some excuse-giving about spelling reform led by Benjamin Franklin and Noah Webster that justifies the adoption of the more phonetic spelling of donut but that’s not for me. Where specific to a business’ name, I’ve kept it. Everywhere else it’s a doughnut, you doughnut.

Well, friends. It’s happened. We knew it wouldn’t last forever. We had to lose the alliteration some day, I just never imagined that it would be death by doughnut.

Actually, that’s a lie. I’ve been planning this crawl for over a year, possibly even two, and the naming thing has remained my biggest stressor. But in the spirit of a new year, we’re going to acknowledge our loss, process it, and move on. Consider it a fresh(ly baked) era.

You know as much as I do that a new Cass Crawls installment has been long overdue. The original, our Skibbereen Café Cake Crawl, happened back in 2016 and its follow-up, the Queen City Caffeine Crawl, in 2018. It was always going to be doughnuts up next.

Before we get into it, allow me to set the scene for you.

The day, New Year’s Eve. The time, uncomfortably early in the morning. Sure, some people spend their last day of the year with loved ones or setting resolutions or reflecting back on fond memories and impactful moments. Others try to make themselves as sick as possible on the overconsumption of sugar. Hi, hello, present and accounted for.

As you may remember from other crawls, I don’t do this for enjoyment. This is a test of stamina. What kind of stamina? Hell if I know. All participating establishments are visited on the same day, back to back. Local and regional chains are permitted but nothing bigger. Unlike the caffeine crawl where all parameters were kept as constant as possible, cakes and other baked goods allow for some variability. I didn’t want to constrain myself to eating six glazed doughnuts, so any flavor and any type—cake or yeast—goes. Despite the breakdown below, I feel like it has to be disclosed that I’m typically more of a yeast gal, but it is what it is. My selections were based almost exclusively on trying different flavors.

There were two specific complications this year that resulted in a significantly modified format for the Windy City Doughnut Crawl: 1) the ongoing Covid-19 pandemic and 2) winter in the midwest. Of the six doughnut purveyors selected for this crawl, only two were equipped for indoor dining, though it wasn’t exactly encouraged thanks to current surges. Maybe in the spring or summer, where you can comfortably find a spot to sit outside and enjoy your treats, this wouldn’t be a problem, but in the winter that is absolutely not an option. You get in, get your doughnuts, and get out.

Yes, I could have sat and ate them in my car but that’s no way to preserve the vibes and spirit of the crawl! My usual approach is to pack up a sack full of books and leisurely make my way from one place to another, spending about an hour in each, absorbing the atmosphere and trying not to visibly show the chaos that happens to my body about half way through the day (nausea for cakes, visible shaking for caffeine). I was also on a tight timeline to pick up the doughnuts from each of these spots so I could guarantee getting the flavors I wanted to try. Even if I did eat them in my car, it would have been a remarkably condensed format compared to other crawls, which takes all of the fun out of it.

Long story short, scarfing six doughnuts from the driver’s seat of a 2008 Volkswagen Beetle in under an hour was neither the vibe nor the spirit of this endeavor.

So I did the best I could. I picked up my six doughnuts, brought them all home, and ate them gradually throughout the day as I read books and watched TV and genuinely wondered how on earth my body was going to survive. But more on that in the end notes.

One last thing I have to address is this year’s rating scale. In the past, I’ve attempted a joke or a pun when giving my crawl ratings but I regret to inform you that I’ve lost my touch. I’m just not as witty as I once was, and that’s as hard for me to admit as it is for you to read. Instead, the idea came to me to rate each of these doughnuts as a song from my longest running Spotify playlist called Liked @ One Point or Another. There are no rules for what gets added to that list and it’s almost 18 hours long, meaning I had plenty to choose from. Right, shall we crack on with it?

In the words of the brilliant Ali Smith, “it was the worst of times, it was the worst of times.”

Allons-y.

---

Dinkel’s Bakery

Okay, you may not be thinking it but I have to say it. It was a last minute decision to allow bakeries into the crawl. At first I was staunchly opposed, but upon researching doughnut spots in and around the city, Dinkel’s was heralded for its commitment to the cause. Plus it’s a local, one shop, family institution (that also happens to ship nationwide but that’s neither here nor there and good for them). It was my first time in this place and it showed when I started mildly panicking because I couldn’t see any doughnuts. As the woman behind the counter asked how she could help me, I bumbled and mumbled total nonsense to stall until I realized that all of the doughnuts were shelved on racks behind the bakery cases.

In the original plan, I had my eye on an Oreo Chocolate Cake doughnut, but for some reason when I got there I thought it was filled and I’m not much of a filled doughnut kind of lady (foreshadowing) so I went for my second choice, the Sour Cream Old Fashioned (also not much of an old fashioned doughnut kind of lady, I’m difficult, I know, you don’t understand what it’s like for me to live with me). Yours truly came around to sour cream in general pretty late in the game but now I’ll put it on almost anything, so I was intrigued to find out what this was going to taste like.

In all honesty, this was probably one of the best doughnuts I’ve ever had. The outside was perfectly crispy and crunchy, which I didn’t realize I even wanted in a doughnut, and the inside was soft and moist and rich thanks to what I’m assuming is the sour cream. You’d never know there was sour cream in it aside from the slightest tiniest hint of a tang in the aftertaste, otherwise it was all sweet.

I give this doughnut a Stompa by Serena Ryder out of 10.

Beacon Donuts

Small-batch. Artisanal. Vegan. And their address literally begins with “in the alley.” What more could you possibly want? Beacon brought all the right vibes to my morning. It really is a wonderland of a walk-up window (see above), with vibrant artwork and beautiful hanging lamps, not to mention all of the plants and bundles of winter greenery. Incredibly earnest, cheerful wishes for a happy new year were exchanged and then on my way I went, bagged doughnut in hand.

Related aside: I went through a whole journey with the vegan doughnut thing back in Charlotte. Pepperbox Doughnuts was my neighborhood spot (and to this day I still dream of that strawberry frosting). The majority of their doughnuts are vegan, which was surprising to me when I first learned this because they tasted no different from any non-vegan doughnut I had ever had. If anything, they tasted better, which then caused this whole confusion for me with thinking well, doughnuts are made from dough, which is just flour and yeast and water, isn’t it? So shouldn’t that make all doughnuts vegan? Is the non-vegan part coming from the way you top the doughnuts? And, reader, let me tell you. I still to this day can’t wrap my head around what makes a doughnut vegan or not.

Back to Beacon. I opted for their blue lavender-infused cake doughnut with vanilla bean icing and candied lavender and then proceeded to completely forget about the whole blue lavender thing, which caused a dramatic gasp when I took my first bite. A blue doughnut is a stunning thing to behold and I’m sorry I didn’t capture it on film for your posterity.

I give this doughnut an Eyes by Rogue Wave out of 10.

Doughnut Vault

Doughnut Vault is another literal hole in the wall with a very Parisian aesthetic. We’re talking black and white tiled floors, blue paint chipping off the front door, gold lettered mirrors, warm lit chandelier. Exposed brick walls! It’s a good thing this place is standing room only otherwise I’d never leave. Big future home kitchen inspiration here.

This was, without any shadow of a doubt, the biggest doughnut I have ever eaten. You can’t tell from the aerial shot, but it was huge. I’ve gone back and forth all week about whether or not it was brioche, because I had to essentially unhinge my jaw to get a full top to bottom bite on this sucker and, let me tell you, that dough was layered up inside.

2021 was apparently the year I got big into chestnut. And by that I mean I had a chestnut tea in my advent calendar (that I became obsessed with) and then I discovered this doughnut. Chestnut glazed, of the yeast variety (again… brioche?). Had I not been a few doughnuts in by this point and definitely starting to feel sick, I might have enjoyed this more. That’s entirely on me and has no bearing on Doughnut Vault, but still this one was my second place selection for the day. Thankfully I live a comfortable walk away from DV and will absolutely be going back to try this again (when I’m no longer shuddering at the thought of doughnuts).

I give this doughnut a One Headlight by The Wallflowers out of 10.

Firecakes Donuts

Foreshadowing has arrived. Filled doughnuts suck. I’m not a filling person, I’m not a spread person, I’m not a sauce person. I refuse to order pasta at untested restaurants for fear of marinara soup. Cream cheese on a bagel? More like bagel on cream cheese. Filled doughnuts are always packed with too much filling so you take a bite and the insides explode out the other side, dripping down the edge of your hand and falling into your sleeve, and then everything’s a mess and am I taking this description too far?

That being said, it’s completely unfair of me to hold that against Firecakes because I knew this about myself and I’ve been completely secure in this personality trait for a long long time, yet I still ordered this filled doughnut. Mostly because it was only being offered for NYE and NYD, but also because it had the word “champagne” in it and I went through a very big champagne phase at the end of 2019. Apologies to my neighbors for Thanksgiving of that year, where I sat in our backyard in a camping chair, cackling to myself and drinking a bottle of champagne for two hours while our turkey burned under a metal trash can heaped with lit charcoal.

Anyways, turns out I’m not a lychee fan. I’d never had lychee before and for some reason I always envisioned it to be sour (mostly because I’m at times culturally ignorant and partly because I’m generally stupid… I definitely drew some kind of mental relationship between lychee and kiwi). One bite of this doughnut and it was an immediate no. In case you were wondering, yes, it did explode down my hand.

I give this doughnut a She’s Not There – (The Zombies cover) by Owlle out of 10.

Do-Rite Donuts & Chicken

This was the most underwhelming doughnut of the day. It was pitched to me, by the menu, as Pistachio-Meyer Lemon. Now, I’m new to the pistachio world, and they’re fine, I have some friends who make them their entire personality but that’s not me. Lemon, on the other hand, I’ll put on and in pretty much everything. I saved this doughnut for later in the day and I was glad I did because it tasted like nothing. The pistachios somehow lost all of their flavor (does “Sicilian” make a difference?) and there was not a single wisp of lemon to be had in the frosting, which it where it was allegedly supposed to be (does “Meyer” make a difference?). Ultimately, it ended up tasting like a plain cake doughnut with weird flavorless frosting and some dust on top!

Do-Rite is a local chain that I hold pretty similarly to Stans, except where Stans is known for its doughnuts, Do-Rite is known for putting its doughnuts around a friend chicken sandwich. If I wasn’t a vegetarian, I’d give it a whirl, I’m not going to lie to you. It sounds horrific, but I’d do it. I came so close to picking the Spiced Maple Chai doughnut over this one, and it’s a decision I will regret until I work up the courage up to go back. Do-Rite did wrong. (There she is.)

I give this doughnut a Keeping Me Under by Two Another out of 10 (though I so wanted it to be a Lady (You Bring Me Up) by Commodores).

Liberation Donuts

Last but definitely not least, the most anticipated doughnut of the day, the Sanctuary from Liberation Donuts. These doughnuts aren’t just vegan, they’re radically vegan. What more would you expect from the folks over at Upton’s Naturals?

Liberation was the spot I was most stressed about because I got a very “pre-order or die” vibe from what I was reading online, but I honestly don’t think that’s too much of the case after going there. Then again, I was in a little bit of a sugar daze when I went in to pick up my order so who knows. They also opened the latest out of the six shops (11am) so I was most of the way done in my crawl by the time I had to drive over for the last melon. Or, should I say pineapple?

This happened to be a pleasant surprise order because I forgot what I submitted the night before and totally thought I ordered the strawberry one which, by the time I had to go get it (4 doughnuts down), felt disturbingly excessive. Take a peek at the pics online, you’ll know what I mean. When I got home I discovered that I had actually ordered a plain cake doughnut with vanilla frosting, bruleed sugar, and… pineapples? There was a little bit of a pineapple on pizza syndrome going on, and it felt like a weird move. I was hesitant.

But, I couldn’t have been more wrong. The charred pineapples absolutely made this doughnut. I can confirm that because I tried a bite without it and it was a totally lame-o experience. In fact, there should have been more pineapples! I’ll even go so far as to admit to you that I left some doughnut behind because the pineapple bits were all gone. I’m not going to attempt to pretend I’m a food critic here, but trust me on this. Pineapples belong on doughnuts.

I give this doughnut a 1000 Words by 0171 out of 10.

---

There you have it. Part One of the Windy City Doughnut Crawl is complete. That’s right, there were so many options in Chicago that I had to create a second list of places to eventually try… some day that may or may not be 2-3 years in the future.

How did I feel at the end of all this, you ask? Not great but not as bad as I thought I would. One wrench that I didn’t think about, and that ultimately served as my biggest hang-up, is how I’m not a sweets person anymore. I used to live and die by my sweet tooth but in the past couple of years I’ve switched over to the savory side. I’m still an absolute fiend for chocolate, however I now prefer sweets as meal caps to send a signal to my brain that eating time is done. I don’t like them as the meal itself. Difficult way to be for a doughnut binge fest, I know.

Other than that, I went into this expecting to get wrecked and I somehow came out of it totally fine, which says more about me than I really think it needed to. I didn’t notice any energy spikes, maybe because the sugar was so heavily balanced with the carbs in the dough, and tea was my best friend to cleanse the palate between courses. I expected to be nauseous like the cake crawl, and it did get a little tough to stomach the first two back to back but I think that was because they were literally had one after the other. Everything else was spaced out by about an hour and we were rocking and rolling. I also expected to be completely full for the day, considering I was basically eating a big loaf of bread, but by late afternoon I was starving.

Do I recommend for anyone else to do this? As with both of my other crawls, absolutely not. There are reasons I don’t bring friends along with me on these things, as much as I might like to. Because they’re weird and ridiculous ideas and because I do not take responsibility for any negative repercussions outside of my own.

Here’s wishing you and yours a marvelously happy new year.

See you next time, friends.

Chicago crawl doughnuts food Illinois local business music weekend