Winsted Diner Exterior
The Winsted Diner, located at 496 Main Street in Winsted, Connecticut, was a historic train car-style eatery known for its classic American fare and community role. Manufactured in 1931 by PJ “Pap” Tierney’s diner factory in New Rochelle, New York, as part of a series of 38 railroad-car-inspired diners, it measured 30 feet long by 10.5 feet wide and featured 15 counter stools, original marble tiles, and fixtures.
Brothers Louis and Edward Venezia purchased it that year and had it shipped via flatbed rail car to its Winsted location, where it became one of the longest continuously operating diners in the U.S. It survived major events like the devastating 1955 flood and remained remarkably preserved compared to other Tierney diners, with only two others still in Connecticut by the 2010s (Grandma Rosie’s in Waterbury and the Quaker Diner in West Hartford).
Over the decades, ownership passed through several local hands, including Hoppy DeGuzman, Art Peck, and Andy Tabak. In 1973, Carol and Robert “Bob” Radocchio acquired the diner and ran it as a 24/7 operation (six or seven days a week) for 32 years, turning it into a town fixture affectionately called the “Carol & Bob Show.” The family, including their five children like daughter Trudy Gillette, worked long hours—Bob on nights from 2 p.m. to 3:30 a.m., Carol on days—with additional staff.
It drew crowds after bar closings, enforced a no-swearing rule, and was known for generous portions and free meals for those in need. Bob invented the signature “Ra-Doc-A-Doodle” sandwich (scrambled egg, sausage, and cheese on an English muffin), which predated similar fast-food items and remained a menu staple. In 2005, an electrical fire damaged the diner, prompting the Radocchios to sell it to Jean Renkowsky after renovations supported by community fundraising.
Renkowsky reopened it but faced challenges from the economic downturn, declining breakfast traffic, increased competition from nearby eateries, and rising costs, leading to its closure in February 2011 after over 80 years of operation. The building’s age and size made compliance with modern codes (like handicapped-accessible restrooms) difficult if closed too long, adding urgency to finding a new operator. The town’s Economic Development Commission explored options like converting it to a tavern to attract a different crowd.
Community advocacy and the Friends of Main Street group helped revive it, and it reopened on December 11, 2012, with a ribbon-cutting ceremony attended by local officials like Mayor Maryann Welcome and Town Manager Dale Martin. Salisbury resident and chef Asa Flint took over operations (leasing from Renkowsky), expanding the menu with items like natural-casing brats, hand-cut fries, and homemade chili, while adding an outdoor patio for evening barbecues and catering services. Hours shifted to 5 a.m. to 3 p.m. daily, with extended evenings on weekends.
Bob Radocchio passed away on July 15, 2013, at age 82, leaving a lasting legacy; Flint kept the Ra-Doc-A-Doodle on the menu in his honor.
The diner operated successfully for several more years but closed permanently in late 2021, reportedly due to the building’s condition. As of 2023, it was listed as closed or missing, marking the end of an era for this piece of local history.
