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I Drove To Cupcake Charlie's in Wareham and Had Some "Dan-Good Pizza"!

I posted a blog a couple of weeks ago about South Shore-style bar pizza and before I did I shot a message to South Shore-style bar pizza maker Dan Lessa, hoping to talk to him and use one of his best pizza pics in my blog. I've long admired his pizza pics on South Shore Bar Pizza Social Club's Facebook page. Over the last year, Dan's had many pop-up events at Cupcake Charlie's in Wareham, Massachusetts and I wanted to talk to him about his pizza and his pop-ups. But, Dan's understandibly a busy guy and I never heard back from him...

This is definitely one of Dan Lessa's South Shore-style bar pizzas. (no mistaking it!)

Not wanting to leave him out of my blog, I used a pic I got off a search I did on the South Shore Bar Pizza Social Club's Facebook page and led off the blog with it. Then a week after the blog published I got a FB message from Dan apologizing for not getting back to me sooner and wondering if the blog already posted. I told him that it had, that I led off the blog with a pic of one of his pies, and then I shared the link with him. After reading the blog he messaged me back and thanked me for the shout-out, but said the pic I used was not one of his pies… I apologized and told him I could change it and Dan sent me a new pic and I immediately corrected it. 


We continued messaging and I asked Dan when his next pop-up event was and he said it was in a couple of days (6/10). I ordered two pies and asked if I could steal a few minutes of his valuable time and do an interview when I drove to Wareham to pick up the pizza (35-minute ride from Norton). Dan agreed to the interview and then gave me a 6:30 pickup time, his last one of the day…

I have a horrible sense of direction, so I printed out MapQuest directions and had my GPS plugged in too, I wasn't taking any chances. Well, my GPS and MapQuest didn't agree with each other and I chose to follow MQ… Bad choice! After some indecision, I decided to go back to my GPS and I was only a few minutes late, which for me is good, I usually run much later…

My wife's favorite cupcake bakery is Cupcake Charlie's where their motto is "Life is Short… Eat a Cupcake". We've been to the Mashpee shop and the one in Newport and I gotta say, it's become my favorite too. Cupcake Charlie's makes gourmet cupcakes fresh daily and has been voted best bakery and best cupcakes several times by Cape Cod Life Publications and by South Shore Living Magazine, and they were first runners-up on the Cupcake Wars in 2010. During my ride to Wareham, I wondered, why Cupcake Charlie's? Did Dan Lessa have an arrangement with the popular cupcake shop?

Cupcake Charlie's Wareham is located at 2421 Cranberry Highway #414 (where the pizza pop-ups are!)

When I pulled into a parking spot in front of the store I was still wondering how "cupcakes and pizza" would work together. Would I walk in and smell cupcakes or pizza? The belly wants what the nose tells it to… I walked in and the first thing I saw was the glass display cases full of delicious-looking cupcakes, but I smelled pizza, which isn't a bad thing. I was definitely in the right place… 

Who in their right mind could resist these gourmet cupcakes?

Dan came out from the back with two pizza boxes and after we shook hands he introduced me to his wife Penny, his partner in crime. After a few minutes, I asked Dan and Penny about themselves, where they grew up, how they met. Dan and Penny grew up in Stoughton, MA, graduated from Stoughton High School and were frequent fliers at Town Spa and Dinnenos, the same two places that got me into the pizza game when I was a kid. Although we're a good eight years apart, I grew up in Sharon (or didn't, depending on who you ask) and the three of us enjoyed similar places and activities in the area, like eating ice cream at Crescent Ridge Dairy


Dan was an art student at the Swain School of Design and after two years he left and became a flooring mechanic, installing all types of flooring for the next 20 years. From there, he and Penny traveled to Florida where they began selling real estate. When the market began to collapse in 2007, they decided to move back home (Cape Cod) and give baking a try. They're self-taught bakers, which is pretty incredible in and of itself, and the founders and owners of Cupcake Charlie's, which explains the pop-up location. Their cupcake bakery has grown since the grand opening in Mashpee in 2008, and currently includes five locations. In addition to Mashpee, there's Wareham, Newport, Foxboro, and Plymouth.

One of their most popular cupcakes is the "Hostess with the Mostess". (they're unbelievable!)

Dan and Penny are longtime fans of pizza and more specifically, South Shore-style bar pizza and so they decided to start experimenting with making bar pies while they carefully navigated their way through the pandemic like the rest of us. According to Dan, he tried no fewer than 42 variations of their own recipe before arriving at the one he and Penny thought was best. They wanted a sweet sauce, but not too sweet, and a crispy, tasty crust with perfectly burnt edges.

South Shore-style bar pizza aficionados are quick to judge pizzas based on the edge. This is a perfect-looking burnt edge on a Roni! (some pizza makers refer to it as a "laced edge")

Dan and Penny started their pizza careers by providing their neighbors with pies and after getting repeated compliments, they decided to try a "Pizza Night" at their Cupcake Charlie's in Plymouth. Their first "Pizza Night" did not go as planned. There were problems with the dough and the oven and despite a smoke-filled storefront, and a disappointing first night, Dan and Penny stayed the course and remained determined to get it right…


Getting ready to spread the sauce and add the toppings!

Dan and Penny continued their pizza journey using their proprietary recipe along with an improved cooking technique. Bingo! It worked. Now, when they announce a pop-up event at Cupcake Charlie's in Wareham they're taking orders and making pies, sometimes to the tune of 65 in a 3.5-hour window.

It all starts with the dough and there's enough there for close to 60 pies…

During the interview, Dan urged me to try his pizza while it was still hot. I started with the hamburg, onion, and green pepper, my go-to, and it was phenomenal. Dan said that three-topping pizzas are challenging because they can create moisture problems which can ruin the crust if they're not watched closely… Not only was it cooked to perfection, but the sauce was incredible, the dough crispy without being hard-core cracker crust, and the cheddar cheese was unbelievably tasty. Dan did his research and believes a traditional South Shore-style bar pizza should be made using only cheddar and not a cheddar/mozzarella blend. The toppings were fresh, evenly spread, stayed put (no sliding off), and there was no flop. It was an incredible pizza! Dan, however, was more interested in what I thought about his plain cheese pizza, after all, it's the basic cheese pizza that is most telling… His cheese pizza was absolute perfection! 

Another fine example of a South Shore-style bar pizza by Dan Lessa

I asked Dan and Penny if they were considering putting South Shore-style bar pizza on the menus of all their Cupcake Charlie's and to my surprise, they said, "No". Dan said the most important thing to him, whether it's pizza or cupcakes, is "consistency" and at this point in time, he wants to be the only one manning the pizza oven. After glancing at each other momentarily, Dan shook his head and looked at Penny and said, "Okay tell him…" Penny said they're considering opening a dedicated pizza shop down the Cape and calling it "Spannenos", a tribute to their two favorite pizza places growing up, Town Spa and Dinnenos.


Dan, Penny, and the staff enjoying some of Dan's South Shore-style bar pizza

With five Cupcake Charlie locations and pizza pop-ups, you'd think Dan has little time for much else, but something he enjoys during his time off is yard work. When I told him it's my passion as well we started discussing lawnmowers and when I proudly boasted that I still use a 21" walk-behind, he turned his phone towards me and showed me a pic of his two, well-maintained Troybuilts, which are 33" walk-behinds and very impressive looking machines… 

Dan and Penny Lessa are both creative, meticulous, and hard-working and it's no surprise that they've been able to reinvent themselves in different industries and then compete at the highest level in each. It appears that the sky's the limit for these two. Dan's pizzas are truly exceptional works of art, not too unlike their gourmet cupcakes.

By the time I left Cupcake Charlie's not only had I found another great place to get South Shore-style bar pizza, but I also made a couple of new friends…

My wife's pretty fussy except of course with who she married, and that one lapse in judgment may have cost her, but when I got home with the pizza that night, she and I agreed that the pizza we were eating was "Dan-Good Pizza"