Lenny’s Indian Head Inn, a Branford landmark sitting right beside Sybil Creek, will celebrate its 57th anniversary this year. The restaurant continues a tradition of fresh seafood and an atmosphere very few shoreline restaurants can emulate. 

Since its opening in 1939, consistency has kept Lenny’s doors open. The restaurant’s consistent menu and loyal regulars over the decades have cemented it as a cornerstone of the community. With a rich history to complement its diverse menu, Lenny’s has become the go-to spot for families looking for anything from a formal seafood dinner to casual burgers, appealing to both Branford natives and tourists alike. 

“I remember a few years ago when Lenny’s was receiving a food service industry award, owner Chris Conlin was being interviewed on TV,” Ken B., a veteran bartender at Lenny’s, wrote to the News“When asked what’s the key ingredient to making Lenny’s what it is, he said ‘Love.’” 

So what makes Lenny’s so special – and regularly fills up booths on Monday nights? Some point to overall consistency, others say the quality food. With a long and storied history, some point to Lenny’s Branford legacy as reason enough. 

According to a paper by Branford HistorianJane Bouley and Lenny’s website, Thomas and Katherine Fitzgerald originally purchased a building across the street from the current location in 1939, naming it “Fitzgerald’s.” After Thomas died in 1959, Katherine continued to operate the tavern until finally retiring in 1966, per Bouley’s paper.

The tavern was then bought by Leonard and Theresa Conlin, better known as Lenny and Tee, in 1968 – when the restaurant title changed to its current name today. 

The 70s saw surprisingly slow business as the couple shifted the tavern into a bar with some basic menu items. In this era, the restaurant became known for frequent fights, catering to a high volume of bikers rather than the family diners it sees today. 

In the mid 80s, however, the restaurant transformed again as the state raised the drinking age, prompting Lenny’s to become more dining oriented. Renovations and outdoor seating added in [year TKTK] have changed Lenny’s look into its recognizable form today. The restaurant’s operations have stayed in the Conlin’s hands ever since. 

According to Ken B., Lenny’s has continued to scale up by adding a dairy bar with various ice cream flavors. Along with the dairy bar, Lenny’s has developed its own private-label alcohol – ‘Lenny’s Lemonade’ – a signature lemonade and vodka drink offered both at the restaurant and surrounding establishments. 

Lenny’s continues to be home to warm memories for its patrons

“My favorite memory was when we went there as a family to celebrate one of the birthdays, my son’s or my daughter-in-law’s,” John Thompson, a Branford resident, told the News. “Those are the things I remember most about it.” 

Thompson, who has lived in Branford since 1983, said that the atmosphere of Lenny’s comes from the restaurant’s live music and the presence of locals, along with some signature dishes . 

 Boasting a large outdoor bar and patio facing the Branford marshlands, Lenny’s often hosts live music as well as other events like trivia and the annual ‘Tip-a-Cop’ fundraiser. 

“Branford Police Officers work side-by-side with the wait staff, interacting with patrons and serving the best seafood on the Connecticut Shoreline. They raffle off prizes [and] have a huge silent auction with proceeds benefiting [the] Special Olympics,” Ken followed up. Some of the food served both at the Tip-a-Cop event and year round include a variety of clams, oysters, lobster, along with a variety of steaks and meats ranging from sandwiches to dinner entrees, according to the menu.

“They’re known for certain things [like] their Lobster Bisque,” Thompson claimed. The Lobster Bisque is French-style, creamy soup with lobster stock along with cream and chunks of lobster. Another fan favorite includes “Uncle Lloyd’s Famous Baby Back Ribs” – Lenny’s take on oven roasted ribs accompanied by coleslaw and french fries. The restaurant has also been the winner of Five Star Diamond Award from the Academy of Hospitality Sciences in 2018. 

An extensive history, welcoming atmosphere, and quality food all come together to make Lenny’s the Branford icon it is today.

Lenny’s Indian Head Inn is located at 205 South Montowese Street in Branford.

This article was written for the Yale Daily News’ 2025 Summer Journalism Program for high school students.