ToquiNotes: Best Long-Time Italian Restaurant in City? Twin Oaks, Oliverio's Too Close, Too Good to Call
By Jeff Toquinto on February 04, 2023 from ToquiNotes
A lot of times I like to get a good debate going on here. The easiest way to do that is to talk about the best types of foods.
This week, it is not really a debate. The reason for that is simple.
There is no wrong answer here. That, of course, lends itself to what is the question.
The question is simple. And it involves what is the best of the old-school, long-time Bridgeport Italian restaurants? The options are two – Twin Oaks and Oliverio’s Ristorante.
I know people have strong opinions based on certain dishes, prices, service, atmosphere, convenience, and likely others. But when you get right down to it, is anyone wrong for saying they like one over the other or saying they are both fantastic?
Count yours truly as part of the mix who falls in line with calling it a draw. I have my reasons for calling it down the middle, and it is not the cowards way out. Far from it.
While there are other places to get an Italian dish in Bridgeport, these are the two standard bearers. And they go back decades.
Twin Oaks started in 1957 and was opened by Joseph and Michael Ielapi, brothers. It started out as a one-room restaurant and has seen multiple expansions over the years that have it as one of the most well-known stops on anyone’s food tour.
The food? As you might suspect, its menu is based heavily on family recipes. Their Web site lists some of the items made fresh daily including pizza dough, ravioli, lasagna, meatballs, Italian sausage, sautéed peppers, their own salad dressing, and all sauces. I am certain there are 
more.
more.
For fans of Twin Oaks, there is certainly a menu item of choice. Mine is the pizza. Always has been, always will be. And as good as it is to take home, it is actually better eating it in house. Maybe that is a mental thing on my part, but my wife as always agreed on that point.
One of my best friends, Andrew Banko, swears by the hoagies. He insists they are the best that can be purchased anywhere. That, my friends, is no small claim in a city, county, and region littered with high end food choices.
Although I am a bit uneasy when it comes to super-hot food items, their “fried hots” on pizza or hoagies is a must for those with good tolerance or even minimal. The whole thing is worth it.
I am betting most reading this have stepped through the doors of Twin Oaks. I am also betting most of you reading this have done so multiple times.
If you have not done so, make it a point. I would bet my reputation, what little remains, you will not be disappointed.
That, of course, brings us to Oliverio’s Ristorante. Twin Oaks is located near the Route 50 West entrance to the city, while Oliverio’s is on the opposite end of Route 50 East of the heart of Bridgeport. And it opened less than a decade after Twin Oaks.
Back in 1966, Sonny and Shirley Oliverio opened up their restaurant. At that time, 57 years ago, it began as Sonny’s, which I have written about from back in the 1980s when they ran the rare “buy one, get one free” special and we ordered a pair with extra cheese. So much cheese, in fact, that the opened box looked like nothing but a box of melted cheese.
To this day, my favorite slice of pizza I ever had was devoured back, probably in 1984. It was just a few years later, in May of 1988, when a kitchen fire stopped operations and a decision was made to reopen with changes.
A few months later, in September, it reopened. And it was under the name that is known today as Oliverio’s Ristorante. And while there have been additional renovations, the one thing has remained the same – high quality food.
How good are things at a restaurant when you sometimes cannot get enough of the all-you-can-eat homemade bread sticks. They are the 
best, and when going with a salad it is an unbeatable combo and often the start of a uniquely homemade menu for many. (A bit of advice, start things off with the Angel Hair Crab Ball appetizer – you can thank me later).
best, and when going with a salad it is an unbeatable combo and often the start of a uniquely homemade menu for many. (A bit of advice, start things off with the Angel Hair Crab Ball appetizer – you can thank me later).
While I occasionally get pasta, I have dabbled into the chicken Caesar salad and seafoods. And yes, I will still get the “Sonny’s Original” pizza that can hold its own with just about anyone’s.
My go to – veal parmigiana with a fallback at times of weakness to chicken parmigiana. The veal parmigiana ranks as one of the best I have had anywhere – and that includes stops in Little Italy in Boston.
So, there you go. The reason I have officially called it a draw.
Not only is the food first class as well as the families, but both have been contributing to the Bridgeport community for a combined 100-years plus. When you have been around that long, you are doing something right.
After thinking about it, there is a winner here. It is the community these two restaurants serve. If you have ate at either or both, you know it is true.
Editor's Note: Top two photos shows a Twin Oaks pizza and hoagies, while the bottom two photos are a parmigiana dish and the angel hair crab ball appetizer from Oliverio's. Photos are from both establishments Facebook pages.
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