Connecticut Wiffleball League
"Pushing The Next Generation of Wiffleball Forward" 
Where Did We Begin?

Wiffleball came WAY before the start of the CTWL known today. Back in 2016-2017, current commissioner Benjamin Fiore along with several friends began to play wiffleball frequently in the summer when they had free time from their AAU baseball schedules. It did not happen often, but when it did it was quite  fun every time they met up. Over time the games got more and more skilled, and eventually it was not just having a good time but trying to take home the win and up one another each day. While the play on the field was slowly evolving many players in the league were intrigued by the interest of other competitive leagues found on YouTube. They saw all the glory: the beautiful fields, the cool jerseys the players wore, pitches that moved like they were possessed with magic --all of it blew them out of the water. It did not take long for one of Ben's friends to ask, "Hmmm Ben, what if we made our own league, for us to play just like them?" It sounded like a distant possibility at first, but the more he was asked by more and more of his "wiffle" friends Ben could no longer resist. If they made the move, it would be a monumental leap forward from what they had experienced in the past; nothing beforehand involved all of this time and work. They were skeptical at first, but in light of his friends becoming more and more intrigued with the sport and the will to make it a regular part of their summers the move was made almost instantly.

Between the winter and spring of 2019, current Commissioner Benjamin Fiore announced the formation of his own wiffleball league. At the time, the league was called "Project Wiffle". During this time much of the earliest recruiting and planning took place. During this time Ben formed the main executive board of the league, which consisted of the eventual first managers. Through these managers the league recruited its first wave of players, which initially totaled over 30 players. The numbers eventually lessened down to around 20, and a fair number of these initial players have stuck around, many from the "prehistoric" days of backyard wiffle.  These players formed the backbone of the league, and where and how the league has grown since.

What Do We Stand For?

The Connecticut Wiffleball League looks to be a league that pushes the bounds of amateur athletes in the world of wiffleball. We try to make our league the most connected, the most fun, and the most intense wiffleball in all of New England, no matter the skill level being played.

Most Fun

The Connecticut Wiffleball League strives to generate the most enjoyable form of wiffleball possible. Whether you are a Division-1 scholarship baseball stud or have not picked up a bat since your last summer family barbecue, the Connecticut Wiffleball league works to find the best level for you to compete and the best chance for you to excel and enjoy your time here. 

Most Intense

The Connecticut Wiffleball League prides itself in providing one of the most competitive formats in all of semi-professional wiffleball. With a rigorous season schedule, players will constantly be challenging themselves against the best in their division in the hopes of bringing home the finest prizes and titles a young wiffler can be bestowed. In the top flights, only the best of the best compete, creating exciting matchups and tension beyond what any other recreational league can bring.

Most Connected

Wiffleball, no matter the skill level or formality, is a sport meant to bring people together and for others to enjoy themselves. Though we take great pride in the traditions and competition on the field, we love our interactions off of it. Through our constant interaction on our social media pages and our website we make sure to keep everyone in the league up-to-date on everything going on. Beyond the screen players and fans can get to know one another and spend time with one another at public events throughout the year. 

About The Commissioner

Benjamin Fiore (AKA: Ben) is the commissioner of the Connectiuct Wiffleball League and owner of the CTWL Pro Series organization Augervile Defenders.

Ben, a North Haven resident, has attended Xavier High School (Middletown) and is interested in studying computer science in college with a concentration in cyber-security. Ben has a twin brother, Will who also plays in the league. 

Ben has played wiffleball as long as he has played baseball, familiar with the sport since a young age and always wanting to play it at summertime parties with friends and family.

Ben has played baseball since the age of four and played competitively for several years through AAU and high school baseball.

During Ben's time playing baseball Ben discovered competitve wiffleball on YouTube, and suddenly became hooked on the newfound avenue the sub-sport provided. 

With his findings, Ben shared it with some of his closest friends, with several of those that he showed became the original members of the Connecticut Wiffleball League.

As Commissioner Ben has outlined and planned all of the functions of the Connecticut Wiffleball League, from scheduling and recruiting new players to setting up the fields and running the social media and website: everything runs through him, one way or another. Ben is without a doubt the hardest working member of the executive staff, and the league would not exist if it was not for him and his intense passion for obth baseball and wiffleball. 

In his current tenure Ben has looked to push the sport as far-widening as possible, bringing together as much of the State as possible for players, and across both New England the entire country for fans and spectators. Ben has innovated the league by introducing Friday Night Wiffleball for prime-time games and building fields all over the state. 

It will be interesting to see just what Ben has in store in the future, in his effort to put wiffleball into the mainstream and respected as a proper sport. It is a near sure thing that what does come will be surely remarkable. 


North Haven, CT, 06473

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The Connecticut Wiffleball League is a fastpitch wiffleball league based in southern Connecticut founded in 2019. The league holds no legal trademarks, and the names, nicknames, logos, uniform designs, color combinations, and all other team related content are the property/responsibility of the respective CTWL club. World Series, American League, National League, Division Series, League Championship Series, and All-Star Game are trademarks of Major League Baseball.

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