Plan afoot to relocate Windsor Diner to alternate Main Street lot


The Windsor Diner sits at 135 Main Street in Windsor, Vt., on Tuesday, Feb. 18, 2025. Due to foundation issues, the diner’s owner is hoping to move it to another location on Main Street. (Valley News-Jennifer Hauck)

The Windsor Diner sits at 135 Main Street in Windsor, Vt., on Tuesday, Feb. 18, 2025. Due to foundation issues, the diner’s owner is hoping to move it to another location on Main Street. (Valley News-Jennifer Hauck) Valley News photographs — Jennifer Hauck

Windsor Diner owner Theresa Taylor is hoping to move the diner to another location on Main Street in Windsor, Vt.  The building’s foundation was recently found to have structural problems. (Valley News-Jennifer Hauck)

Windsor Diner owner Theresa Taylor is hoping to move the diner to another location on Main Street in Windsor, Vt. The building’s foundation was recently found to have structural problems. (Valley News-Jennifer Hauck)

Windsor Diner owner Theresa Taylor, middle, helps Andy Briggs and Kristen Reed move a pastry cooler out of the diner on Tuesday, Feb. 18, 2025, in Windsor, Vt. The cooler is going to Maebelline's, a restaurant in Springfield, Vt. Taylor is hoping to move the diner to another location in Windsor. (Valley News-Jennifer Hauck)

Windsor Diner owner Theresa Taylor, middle, helps Andy Briggs and Kristen Reed move a pastry cooler out of the diner on Tuesday, Feb. 18, 2025, in Windsor, Vt. The cooler is going to Maebelline's, a restaurant in Springfield, Vt. Taylor is hoping to move the diner to another location in Windsor. (Valley News-Jennifer Hauck)

By LIZ SAUCHELLI

Valley News Staff Writer

Published: 02-18-2025 5:00 PM

Modified: 02-18-2025 5:45 PM


WINDSOR — When Theresa Taylor closed the Windsor Diner in mid-January, she knew that the diner’s basement kitchen needed a new concrete floor and a furnace.

“That was three weeks worth of work,” said Taylor, who has owned the diner for more than 15 years.

But after workers found more serious problems with the structure, the diner’s closure is going to extend longer than Taylor hoped.

The historic railroad dining car which is home to the diner sits at 135 Main St. on land owned by the Windsor Improvement Corporation, a nonprofit organization that supports economic development in town.

The diner was built in 1952 and is one of the last ones made by the Worcester Diner Company, in Worcester, Mass., according to information from Historic Windsor, a nonprofit organization committed to promoting Windsor’s history. The foundation was poured in the 1930s, Taylor said. The Windsor Diner, which is built in the Moderne style, is the third such diner to occupy the site.

Now plans are starting to form to move the dining car from its current location, to an empty lot on 161 Main St. a few hundred yards away.

“To me it belongs to Windsor,” Taylor said. “I don’t want to move it out of Windsor.”

Taylor hired Greg Blanchard, of Blanchard Contracting in Windsor, to do the work on the floor.

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“Unfor  tunately, the further we went and the more we opened things up, the mo re damage we discovered,” Blanchard said.

The floor and foundation was in worse shape than they originally thought: Load bearing walls in the basement were cracking.

“Essentially the infrastructure is just slowly caving in,” Blanchard said.

Blanchard and Taylor started discussing ideas. In order to repair the foundation, the diner car itself would have to be moved. The lot size itself is also small, which adds to the challenges.

Luckily, there was another option available: The Guy B Vitagliano Foundation, a nonprofit foundation Blanchard founded to help people in need in Windsor. One of the foundation’s goals, Blanchard said, is to clean up blighted properties in town and return them to the town’s tax roll.

More than a year ago, the foundation’s board of directors decided to purchase 161 Main St. to clean up the property — which included removing buildings that were falling apart.

The property was home to the Reuben Dean House, according to information from Historic Windsor. Dean, a Windsor silversmith, made Vermont’s first state seal — “Freedom and Unity” — on the property. The seal was designed by Ira Allen and Dean created the first version of it in 1798.

About a year ago, Windsor’s Historic Preservation Commission and Design Review Commission approved Blanchard’s request to demolish the house on the property.

Dean’s house had undergone numerous renovations and expansions over the years, leaving very little of the original historic structure, said Judy Hayward, executive director of Historic Windsor.

“It’s always sad when you lose a historic building, but there is a point where they’re beyond a reasonable repair,” said Hayward, who also serves on the preservation commission.

When Blanchard heard about Taylor’s plight, the foundation was in the process of deciding what type of buildings to put on the site and he thought the diner would be a good fit.

“She certainly did not want to leave the town of Windsor and she wanted to remain a part of that downtown community there,” Blanchard said. “When it turns out you have a historic site and historic diner, it just sort of made sense to make the whole thing come together and retain that site for that purpose.”

Blanchard and Taylor emphasized that the plans for the move are still the early stages: The pair have submitted building permits to the town and are awaiting approval.

The idea is to subdivide the property, which is less than an acre, to allow a spot for the diner toward the front of Main Street and use the rest of it for multi-family housing, Blanchard said.

If all goes according to plan, Taylor hopes the diner will be moved — using a crane and flatbed truck — in the summer and be able to reopen in the fall.

The diner and its seating would remain the same. The new space would include a kitchen on the same floor, a feature Taylor said she’d like to have “in the future as I get older,” noting the challenge posed by the flight of stairs she and her staff had to traverse dozens of times of day.

Plans also include a parking lot for the diner instead of customers having to rely on on-street parking. A planned ramp at the front door would help people with mobility challenges to better access it, Blanchard said.

“The need showed up, the opportunity was there and we’re fortunate it all came together the way that it did,” he said.

Taylor said she expects the project will cost about $500,000 to complete, although costs are still being worked out. She is looking at a variety of funding options, including loans. Community members are helping her explore grant opportunities and multiple times a day, people reach out asking how they can help.

In some ways, that’s not surprising: Taylor has a large following in Windsor. She provides meals for older adults through Senior Solutions’ meal voucher program and during the early days of the COVID-19 pandemic, she provided meals for community members through Vermont Everyone Eats program.

“There’s lots of folks who didn’t survive it and Theresa did,” Windsor Town Manager Tom Marsh said.

While Marsh emphasized the project will need to gain all the proper permits and approvals from town officials, “I think the town will be supportive of this plan to keep the diner going for the foreseeable future.”

Liz Sauchelli can be reached at esauchelli@vnews.com or 603-727-3221.