CT Pizza Trail: Tipsy Tomato in Derby- The Unexpected Stop That Won Me Over

I’ve added another satisfying notch to my pizza belt and one more stop checked off the CT Pizza Trail.

Tipsy Tomato sits tucked in the corner of a strip mall along Route 34, halfway between Routes 8 and 15. I know that sounds a bit vague, but once you find the right plaza (think Big Y), the next challenge is locating the entrance, which is slightly hidden from view, two nondescript doors next to the pet store. When you approach, you might wonder if the interior is too small to seat adventurous pizza addicts, but step inside and your worries will immediately vanish. There’s an “S” shaped bar immediately to the left with a dozen stools, tables for another two dozen guests, and in the rear is a spacious dining room that seats dozens more. Anchoring it all is “pizza central,” an open kitchen where you can watch the stretch-top-bake ballet unfold right before your eyes.

Tipsy Tomato isn’t a one-trick pony, focused exclusively on pizza. The menu is generous, featuring both hot and cold appetizers, classic chicken, eggplant, and meatball entrées, a full lineup of pastas, and the three S’s, soups, salads, and sandwiches. Their pizza section proclaims it serves “New Haven Apizza” as the style of choice (I’ll share my thoughts on that claim a bit later), with pies offered in two sizes, plus gluten-free and cauliflower crust options available. Beyond the basics of sauce and cheese, there are thirty different toppings ready to be mixed and matched to satisfy every desire.

For my order, I kept things classic, a small pie, half plain for tradition’s sake, and the other half adorned with sausage and pepperoni.

I grabbed a seat at one of the bar’s high-top tables and caught a bit of mid-day TV. When the pizza arrived, my first impression was that it leaned more toward a New Jersey bar-style pie than a traditional New Haven apizza. The crust was minimal and less airy than what you’d enjoy down on Wooster Street. The sauce and cheese stretched nearly to the edge, reminiscent of that classic Jersey bar pie. The toppings were generous, a good layer of sauce, a large amount of melted cheese, hearty chunks of sausage, and crisp rounds of pepperoni. It looked ladened, but well balanced. A quick glance underneath revealed a firm, golden-brown base, crisp and sturdy enough to support the generous toppings without sag or flop.

 As the pizza cooled, I started with the meats. The sausage came in large chunks, which was my preference and offered a nice balance of flavor, with a touch of fennel notes and a moderate spiciness. Each chunk delivered a satisfying bite. The pepperoni slices followed suit, bringing a slightly bolder level of heat, which played well with the cheese and sauce.

I pulled the first slice from the plain side, and strands of cheese stretched and clung to the pie, a promising start. The slice held firm with no flop, and that first bite included a generous amount of cheese approaching, but not crossing, the line of “too much.” The sauce was bright and rich in tomato goodness, and the crispy crust was a perfect counterpart. The plain slice was delicious.

Then onto the meat-laden side. My first bite was a large chunk of sausage, soft in texture, rich in flavor, with a pleasant little after-burn of spice. The next bite caught some pepperoni, equally satisfying with its sharper heat. And finally, the grand finale, crust, sauce, cheese, sausage, and pepperoni all came together in harmony. The balance was spot-on, sweet, savory, spicy, and crunchy, an excellent turbo-combo slice.

I walked in skeptical and walked out converted. I left Tipsy Tomato with a smile and a reminder that great pizza doesn’t always come from the places everyone talks about. Tipsy Tomato isn’t loud or flashy, but it delivers the kind of honest, satisfying pizza that makes the search worthwhile. Each stop on my ongoing journey to find great pizza in CT has a story, and this one reminded me of the adage, “don’t judge a book by its cover.”

Tipsy Tomato Bar and Pizzeria

656 New Haven Ave.

Derby, CT 06418

203.732.7931

https://tipsytomatopizzeria.com