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The Sweet Story of Cupcake Charlie's

How this local small business started from scratch to quickly become the best cupcakes destination in Massachusetts and Rhode Island

Chocolate raspberry cupcake from Cupcake Charlie's in Falmouth, Mass. (Cape Cod)
Chocolate Raspberry Surprise cupcake from Cupcake Charlie's in Falmouth.

Article and photos, unless otherwise noted, by Eric Hurwitz. Article updated on 7/25/2018.

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On a hot mid-June day in Falmouth, Mass., tourists start to gather in crowds on Main St. as a preview to the Cape Cod summer vacation season. The big storefront windows at one of New England's nicest Main Streets reveal a healthy number of restaurant customers and retail shoppers inside, but none as busy, at the moment, as Cupcake Charlie's.

The small shop with the happy Cupcake Charlie's cartoon mascot store sign, pink, white and blue awning, sweet aromas, old-fashioned tiles floors, pink chairs, retro hanging lights, colorful cupcake display case and sunny, open kitchen looks like something out of a happy 1940s movie scene portraying the classic small town American Main Street USA mom and pop business.

Cupcake Charlie's store in Falmouth, Mass. (Cape Cod)
Lining up for cupcakes and other baked goods at Cupcake Charlie's in Falmouth.

It's a place where little kids eyes' automatically widen at the sight of yummy sweets and mouths get covered with frosting. Adults go against the "No dessert unless you eat your dinner" warning and instead take on the "When in Rome..." mantra by unhesitatingly following the eating habits of their children.

4th of July cupcake at Cupcake Charlies' in Falmouth, Mass. (Cape Cod)
Enjoying a Fourth of July cupcake at Cupcake Charlie's. Photo credit; Cupcake Charlie's.

Beyond the counter, a sign that states "Life is Short...Eat a Cupcake" appears to reflect real life, as customers order these tasty small cakes as if there was no tomorrow. The thing is, there was supposed to be "no tomorrow" a few years back as the cupcake craze found the icing coming off the cake with many businesses closing -- similar to the once popular frozen yogurt trend. The cupcake, dating back to 1796, and given a new life courtesy of Carrie and Miranda devouring vanilla cupcakes with pink frosting outside Magnolia's Bakery in New York City on the classic Sex and The City episode, somehow lost its way in the business world. Part of the problem: Business owners took on a one-note mission to sell just cupcakes in locations that couldn't support such stores in small downtowns and cities with high rents exceeding the cost of operations.

Fortunately, someone forgot to send Cupcake Charlie's the "cupcake craze is over" memo. Penny and Dan Lessa, husband and wife and owners of Cupcake Charlie's, got off to a spectacular small business start not too long after first opening their business. The Food Network's Cupcake Wars recruited Cupcake Charlie's in 2010 to team up against other cupcake shops across the country. Penny and nephew Mike Centamore (who runs the Plymouth Cupcake Charlie's) appeared on the show. Although they didn't win, Cupcake Charlie's made it to the end of the competition with, along the way, celebrity host Duff Goodman "bowled over by Charlie's Samoa Chocolate Cupcake with caramel and coconut."

Reality check: Cupcakes never really went away. They just returned to mom, grandma and auntie's kitchen, at elementary school birthday parties and family outings. Penny and Dan, however, knew that they could make a go at their new found passion in the form of a business by making high quality cupcakes in a warm and inviting place that cupcake lovers could call a second home. The Lessas, Stoughton, Mass., natives with backgrounds in Florida real estate, intuitively realized the value of "location, location, location," and expanded beyond the success of its first shop that started in 2008 at the Mashpee Commons in Mashpee (Cape Cod). Within a few years, Cupcake Charlie's also opened by the Plymouth waterfront in Plymouth, Mass., in the heart of famous Newport, R.I., known for its mansions and ocean, at the world-class Patriot Place dining, shopping and entertainment complex at Gillette Stadium in Foxborough, Mass. (home to the New England Patriots), and popular Main Street in Falmouth. Interesting side note: Rob Ninkovich, the former New England Patriots outside linebacker star, is a big Cupcake Charlie's fan -- the Lessas created a "Twixovich" cupcake (with Twix candy) for him and customers.  The Lessas even made a "TB12" cupcake for Tom Brady with avocado, zucchini and spices, knowing his healthful ways (for the record, it is not known whether Mr. Brady tried the cupcake).

Cupcakes Charlie's in Falmouth, MA (Cpae Cod)
Out front at Cupcake Charlie's in Falmouth.

"We are trying to evolve without losing the main interest in cupcakes," said Penny. "Cupcakes are not the 'thing' right now, so it is important to figure out how to stay in business. We have done well. The cupcake is just one product. We needed to do more. We needed to be where people are. If you rely just on a residential area, it is often not going to work. Look at how many stores like that had to close."

Initially, the then-troubled real estate market forced the Lessas to rethink careers, but they had no fear delving into an unfamiliar career field. The couple found out, fortunately, that locals couldn't get enough of the cupcake recipes they created, so they took that formerly untapped talent to opening the Mashpee location. Dan, who also possesses a background in art and laying out floors, designed the colorful, well laid-out upbeat stores that are as welcoming as the presence of cupcakes.  "People thought we were crazy wanting to open a cupcake shop, but we ran with it from the beginning," said Penny. "It is more than a mom and pop shop. We have the Cupcake Charlie character that made us more identifiable. We have great customer service and amazing products. That combination is not always common."

Display case at Cupcake Charlie's in Falmouth, Mass. (Cape Cod)
Display case with Vanilla luvs Chocolate and Lemon Drop cupcakes.

They hired well. The Lessas have painstakingly found top performing employees at each store who believe in the Cupcake Charlie's concept and can work consistently at a highly efficient level.  Centamore and his wife Katie moved from South Carolina to manage the Plymouth location. At the Falmouth store, Molly Henderson -- a 2017 Upper Cape Cod Vocational Tech School graduate -- serves as the assistant manager.  She works at a professional level well beyond her years exhibiting superb customer relations skills, the ability to take on multiple tasks at the same time and carry on a pleasant, happy personality through the busier times. When customers walk into the store, Molly instantly and sincerely greets them in a way that makes them want to stay.

"Penny and I went out to eat one night at a restaurant and Molly was working there," said Dan. "We were thinking 'She needs to work for us.' We were so impressed with the way she was working. We are really glad to have her working for us instead!"

Added Molly, "I love working at a place that makes people happy. I love it here. Everyone comes in here happy. It is very uplifting."

Molly Henderson prepares a shake at Cupcake Charlie's in Falmouth, Mass.
Molly Henderson makes a shake at Cupcake Charlie's.

While the Lessas have made shrewd real estate location decisions, used clever marketing campaigns (like the memorable mascot and impressive social media outreach) and benefitted from the Cupcake Wars exposure, the bottom line remains that they couldn't have succeeded without quality products and the vision to expand beyond just cupcakes (more on that shortly).  Penny said that while all locations enjoy seeing many customers, the Falmouth location allows her a "little bit more time" to envision, create and produce cupcakes clearly made with love. Penny can be seen in the kitchen intensely making cupcakes, yet she finds the time to authentically mingle with the regular and new customers.

Penny Lessa creating cupcakes at her store, Cupcake Charlie's in Falmouth, Mass. (Cape Cod)
Penny Lessa creates cupcakes at Cupcake Charlie's.

"We bake fresh every morning at all locations," said Penny. "The bigger bakeries, they just make things and then freeze. We make things in small batches. I think the customers appreciate the fresh products and the consistency."

Mint chocolate cupcakes from Cupcake Charlie's in Falmouth, Mass. (Cape Cod)
Chocolate mint madness cupcake from Cupcake Charlie's.

More than 100 different flavors can be found, at any time of the year, at Cupcake Charlie's (many seasonal flavors), but you'll always see 16 fresh-baked, handmade cupcake flavors in the display case on a daily basis. These "dailies" include Grammy's Carrot Cup, Chocolate luvs Vanilla, Lemon Drop, Hostess with the Mostess (Cupcake Charlie's delicious version of the Hostress Cupcake), Vanilla luvs Chocolate, Oreo Delight, Rockin' Red Velvet, Peanut Butter Pleasure, Orange Dreamsicle, Chocolate Overload, Funfetti, Vanilla luvs Vanilla, Charlie's Chocolate Chip, Chocolate Mint Madness and Chocolate Raspberry Surprise.

Hostess With The Mostest Cupcake from Cupcake Charlie's in Falmouth, Mass. (Cape Cod)
Hostess with the Mostess cupcakes from Cupcake Charlie's.

The sweet fun doesn't end there, however. Cookies, trifle cups, push and cake pops, cake cups and jars, cookies, whoopie pies, shakes and soft serve ice cream (including "Cupcake Whirlies" that combine a cupcake flavor with the ice cream) and more baked goods and frozen treats create more tempting options that make it more difficult to choose amongst the many masterpieces.

Soft serve ice cream with red velvet cupcake mix-in from Cupcake Charlie's in Falmouth, Mass. (Cape Cod)
Whirlies soft serve ice cream with red velvet cupcake pieces from Cupcake Charlies. Photo credit: Cupcake Charlie's.

Whoopie pies from Cupcake Charlie's in Falmouth, MA (Cape Cod)
Homemade whoopie pies from Cupcake Charlie's.

Cupcake Charlie's also makes full-sized cakes -- perfect for weddings and other special events and ceremonies -- as well as gluten free items that Penny said taste like the "real thing."

Gluten free carrot cake from Cupcake Charlie's in Falmouth, Mass.
Gluten free carrot cake from Cupcake Charlie's.

"We are definitely foodies," said Penny. "We appreciate anything that tastes good. We just don't want to make cupcakes. We make them until we can't make them any better. It's all about the flavor combinations and the thought that is put into making each cupcake."

Web site for Cupcake Charlie's:
Facebook fan page:
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Cupcake Charlie's Locations

Historic Downtown Falmouth
153 Main Street
Falmouth, MA 02540
Phone: 508-540-2253
Sunday 11:00am - 9:00pm
Monday 11:00am - 9:00pm
Friday & Saturday 11:00am - 10:00pm

6 Town Wharf, Plymouth Waterfront
Plymouth, MA 02360
Phone: 508-747-9225
Sunday 11:00am - 9:00pm
Monday - Thursday 11:00am - 9:00pm
Friday & Saturday 11:00am - 10:00pm

10 Central Square, Mashpee Commons
Mashpee, MA 02649
Phone: 508-477-2253
Sunday 11:00am - 9:00pm
Monday - Thursday 11:00am - 9:00pm
Friday & Saturday 11:00am - 10:00pm

262 Patriot Place
Foxborough, MA 02035
Phone: 508-698-2253
Sunday 11:00am - 9:00pm
Monday - Thursday 11:00am - 9:00pm
Friday & Saturday 11:00am - 10:00pm

Located on Thames Street in the Brick Market Place
135 Swinburne Row, Brick Market Place
Newport, RI 02840
Phone: 401-848-2253
Sunday 11:00am - 9:00pm
Monday - Thursday 11:00am - 9:00pm
Friday & Saturday 11:00am - 10:00pm

Cupcake Charlie's sign, Falmouth, MA
Cupcake Charlie's sign in Falmouth.

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