Cannondale School: Schoolhouse to restaurant

Students standing outside the Cannondale School circa 1912. — Wilton Historical Society/Wilton Library History Room photo
Students stand outside the Cannondale School circa 1912. — Wilton Historical Society/Wilton Library History Room photo

Before it was home to the award-winning Schoolhouse at Cannondale restaurant, the Victorian-style building at 34 Cannon Road served as a one-room schoolhouse for children of Wilton’s seventh district from the the early-1870s until the late-1920s.

Over its years of operation, Cannondale School “progressed from being a poorly attended, ramshackle institution to being named the winner of a highly selective state award,” according to a chapter written by Deborah Hutfilz in Wilton Historical Society’s 1987 book Cannondale: A Connecticut Neighborhood.

Although it is unknown where or when the neighborhood’s first school was built, according to Hutfilz, “tradition places the first school in the Wilton Parish on Sharp Hill Road in 1728.”

In 1729, the Wilton Parish was divided into three separate school districts — one of which was Pimpewaug, which included present-day Cannondale and comprised a large area on both sides of the Norwalk River.

According to Hutfilz, the Pimpewaug district received one-third of the parish’s yearly “country money,” and held school — most likely in a private home — during August and September.

According to a timeline found in the Wilton Library History Room, there was a school at or near the home of Jacob Patchen on Cannon Road between 1750 and 1760. According to Wilton Village: A History by G. Evans Hubbard, Pimpewaug held school “near Jacob Patchen’s on the north end of Buckingham Ridge” in 1751.

In 1760, part of Pimpewaug’s school money was paid to the widow of Capt. Thaddeus Mead, who lived on Chicken Street, to keep a school, according to the timeline.

According to both the timeline and Hubbard, there was a “schoolhouse at Pimpewaug” in 1766.

In 1792, Wilton’s three school districts were replaced by nine smaller ones. Pimpewaug became the parish’s seventh district.

The first meeting of the new Episcopal Society in 1802 was held in “the little Pimpewaug District School on the triangle where the road to Olmstead Hill branches west from the Danbury Road,” according to a history room document.

The document states that the school “adjoined the ‘Old Red Store’ of Matthew Marvin and his late partner ‘Dr.’ John Cannon.”

The district’s old schoolhouse burned down around 1862 and the district spent several years looking for a new site to build a new one.

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Wilton Historical Society/Wilton Library History Room photos

Wilton resident Lyman Keeler reported in 1869 that no public schooling had been held in the seventh school district for several years due to a lack of schoolhouse and an inability to procure a room for public school. As a result, residents of the district established a private school, which they supported for a few months.

New schoolhouse

Although Hutfilz states that Cannondale’s new schoolhouse was built on the corner of Olmstead Hill Road and Danbury Road in 1872, Wilton land records show that Charles Cannon sold that piece of land to the town for $150 in March 1873.

A state law amended in 1819 required each town to tax all its property owners, which made educating children the responsibility of not just the parents of a given district, but all the town’s residents.

With the whole town forced to contribute funds, Cannondale built its new schoolhouse at one-ninth the cost to the people of its district. The new schoolhouse was painted yellow, had a bell in it, and was built with many windows.

The town of Wilton got its first superintendent, Hugh Alder, in 1911. Under his guidance, Cannondale School replaced its old benches with brand new single seats, bought a dictionary for every seventh and eighth grader, and received new geography books.

According to a Wilton Library History Room document written by Stowell Rounds in 1955, the school’s sanitary facilities were “doubtless primitive,” and the schoolhouse didn’t have a “modern sanitary drinking fountain” until 1916.

Cannondale School had “remarkably high attendance,” according to Hutfilz.

The school, which received a state commendation for having 90% attendance in 1914, had a number of interesting teachers over the years.

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Wilton Historical Society/Wilton Library History Room photos

“Former students at the schoolhouse recall with glee deaf David Hurlbutt, who used an old-fashioned hearing trumpet and disciplined cut-ups by spitting tobacco in their faces with astonishing accuracy,” according to Hutfilz.

According to Wilton Library History Room documents, Hurlbutt taught at the school various years, including 1889.

“There was also lame Mrs. Carter,” according to Hutfilz, “who reportedly cleaned her ears with a hairpin but was still nice enough to take the entire class to her house for a taffy pull.”

Before being appointed Wilton’s postmaster in 1889, Richard H. Fitch taught at the Cannondale School in 1891 and 1892.

According to Hutfilz, Lottie Behn was a frequently mentioned teacher, “who apparently intrigued students by meeting and marrying a certain Mr. Brundage while she was teaching at Cannondale in 1914.” Behn taught at Cannondale School from 1912 to 1915.

Closing and relocation

As the population grew and transportation became easier, Cannondale’s one-room schoolhouse closed with the opening of Wilton’s new four-room Center School in 1929.

Photo of the schoolhouse taken at an unknown date. — Wilton Historical Society/Wilton Library History Room photo
Photo of the schoolhouse taken at an unknown date. — Wilton Historical Society/Wilton Library History Room photo

In the 1950s, the Wilton Homemakers Organization leased the schoolhouse from the town, made repairs, painted it inside and out, and used it as a meeting place during warm months.

In 1974, the schoolhouse — which had an assessed land and building value of $13,000 — was abandoned and remained unused for about five years.

In 1978, Canadian-born American actress and owner of Cannondale’s Cannon Crossing June Havoc purchased the then-red schoolhouse from the town for $1 with the intent of turning it into a restaurant.

In October of that year, she sought permission to move it to her Cannondale property between the railroad tracks and the Norwalk River at Cannon Crossing and got the go-ahead by 1979.

In December 1979, the schoolhouse was moved a quarter-mile due east to its new home, where Havoc had restored a group of pre-Civil War barns, outbuilding, and the former Ralph Gregory residence that once tripled as a general store and post office. Today, the historically designated part of town is known as Cannondale Village, or simply Cannondale.

An afternoon ice cream social and parade led by Wilton High School’s marching band were held on the schoolhouse’s moving day.

The Wilton High school marching band led the procession as the Cannondale schoolhouse moved from Route 7 to Cannon Crossing on Dec. 4, 1979. — Wilton Historical Society/Wilton Library History Room photo
The Wilton High school marching band led the procession as the Cannondale schoolhouse moved from Route 7 to Cannon Crossing on Dec. 4, 1979. — Wilton Historical Society/Wilton Library History Room photo

More than 100 people, including former Cannondale School students, turned out to watch the schoolhouse inch slowly toward its new home on the west bank of the Norwalk River with the help of a Norwalk-based moving company.

Schoolhouse to restaurant

Not long after the move, the schoolhouse was transformed into the Old Schoolhouse Café and Riverside Gardens. The café seated 32, according to a 1981 New York Times article, and Redding resident Jane Decker became its head chef in 1983.

Eve Raymond and Penny Gerstein, owners of the British food and gifts store Penny Ha’Penny in Cannondale, once operated a shop and eatery out of the former schoolhouse.

Raymond, who came to Cannondale around 1985, said the schoolhouse has “changed a lot of owners” over the years, but never closed.

In 1989, Havoc sold Cannondale Village to James C. Sutherland and Brian A. Opert, according to land records. Not long after that, the village was purchased by its current owner Marc Gueron.

Shortly after acquiring the village, Gueron said, he rented out the schoolhouse to Wilton resident Tom King, who turned it into The Olde Schoolhouse Grill in 1991.

According to a 2005 Wilton Bulletin article, some of Fairfield County’s most famous residents dined at the Olde Schoolhouse Grill before its closing on Dec. 31, 2005, including Academy Award-winning actors Paul Newman and Eileen Heckart and Rolling Stones founding member Keith Richards.

After The Old Schoolhouse Grill, the restaurant became The Schoolhouse at Cannondale — owned and operated by Wilton resident and chef Tim LaBant for the past 10 years.

Schoolhouse at Cannondale Restaurant, 34 Cannon Road. — Kendra Baker photo
Present-day Schoolhouse at Cannondale at 34 Cannon Road. — Kendra Baker photo

LaBant said operating a restaurant in a former one-room schoolhouse “has its challenges.”

“Being efficient [and] making sure there’s a spot for everything is top priority,” he said.

“Other restaurants have an employee locker room and an office, but we don’t have those, and we only have one bathroom.”

Since its relocation, some alterations have been made to the building at 34 Cannon Road, said LaBant, including the installation of extra windows so that patrons could see the Norwalk River and the building of a kitchen.

“The bar area and dining room are the original area, and it’s easy to tell,” said LaBant.

“When you walk in and look up, there’s a big thing hanging from ceiling — that’s where the chimney was.”

From the outside, it’s easy to tell that the restaurant had once been a schoolhouse, but there are also indicators inside the building.

Hanging up on the walls inside the restaurant are old photos of the schoolhouse and its students. What some Schoolhouse at Cannondale patrons may not know, said LaBant, is that on the back of the photos are the names of the children in the photos.

Overall, LaBant said, working in a former one-room schoolhouse is “pretty cool.”


Click here to learn about Wilton’s other district schoolhouses.

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