Ah, Brimfield. Home of strip plazas that appear to be born out of cornfields, like a little oasis of retail and restaurants.

Also what’s the plural of oasis? Oasises sounds weird. Oasi? Also strange. Can you not have more than one and so no one ever made up a word for it?

These are the things that keep me up at night, kids.

This plaza is so new that the Verizon has apparently moved with the times and changed its name to RIZ.

So Gen Z.

Anyway, here we are inside Jack’s, a very tiny establishment with a handful of tables next to and in front of the exposed pizza ovens and kitchen. You’ll find the tables thanks to the bright spotlights above each of them. Because apparently if the staff has to stand next to a giant oven then dammit you’ll eat under a sunlamp too.

They have a bar but beware that options are quite limited. It’s mainly canned or bottled beer and seltzers, and no actual bartender on duty most nights – so don’t come here expecting to get a Long Island or anything fancy you have to list the ingredients of. It was canned High Noons for me and Shane, and a Sam Adams for Ted.

Ted pointed out they have a Stromboli challenge. You have 30 min to eat a xxx lb Stromboli with no breaks. If you do it you get it for free ($45 value) along with your name on the wall and a tumbler. 

A true bargain for the carb overload and inability to poop for a week from cheese overdose, no?

Needless to say, we passed.

I mean, I did order a Stromboli. But like the size normal people eat. Along with a side salad, because let’s try to at least have some balance here.

Although that salad is mainly cheese – and some weird not-seeming-to-be-actually-cooked pieces of bacon – so maybe missed the mark on that whole trying to get some vegetables with my carbs thing. Oh well.

We asked our server which pizzas are the best and we were told the Tiffany’s Choice and the Big Mac. Which – spoiler alert – the Big Mac pizza is not actually on the menu. When we all asked what her to repeat herself as we scrambled to search the menu for this mysterious amazing pizza she mentioned she was like oh yeah it’s like a secret menu.

Silly us for leaving our decoder rings at home! Lesson learned.

But she did sell Ted on the Tiffany’s choice pizza from that recommendation. It’s basically a chicken bacon ranch sandwich on a pizza with a drizzle of buffalo sauce.

Then Ted asked about the wings and she said that’s actually what they’re known for.

Probably should’ve led with that, no? Like maybe in the name of the restaurant? Just a thought.

In any case, that became a game changer at our table.

Ted added six of the regular buffalo wings to his order, and Shane – who had already put in his pizza order – decided now he needed wings to go with it, but his original order felt gluttonous if he added them on. Not sure why this is stopping him now after 10+ years of these outings, but remember 2025 is also the year of Healthy Shane’s return, so bear that in mind.

In any case, he switched from the Jack’s Choice pizza – which has a lot of meats on it – to the Cody’s choice – which only has two kinds of pepperoni – so that he could add six boneless wings.

And jojos. Because, well, who knows.

Unfortunately for Ted, he spent most of his time peeling the cheese off of his pizza than he did actually eating the slices. We all remember Ted is president of the local cheese haters club, and while he knows pizza typically is known for having much of that topping he usually is able to disguise it with the other toppings (read, lots of meats). This pizza has chicken and buffalo sauce, but the words “ranch dressing base” led him to believe he might be in the clear of and overwhelming amount of shredded cheese along with that.

Welcome to the Midwest, where those two things are what we seem least inclined to have any sense of moderation on when it comes to food.

He said the wings were good though.

Shane and I swapped a piece of my Stromboli and his pizza – I think mainly just because Shane’s pizza was way too hot to eat when it arrived and he was just super hungry. But honestly I thought the Stromboli was the better option of the two, so I was happy with my pick.

And Shane did like his pizza. He did say it wasn’t in his top (insert whatever number he thinks most cool to rattle off this week) list, but it was still good and he would order it again.

Word of warning, Jack’s closes at 8pm on Wednesday nights, which is far earlier than most places we visit. We didn’t even get there until close to 7, and while we did have time to eat and have a few rounds of beverages, we also kind of had to make a quick exit and early night. I’m assuming just from the setup of the place and the few other tables that were occupied during our time that most of their business comes from takeout orders – which is a solid choice. We all left with leftovers, although Ted’s came home with us given his lack of desire to work for his meal on the next round. Which, fair.

Picked by: Shane