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Have you ever wanted to take a peek inside some of Winchester’s historic homes? Well, get ready.
On Saturday, Sept. 20, nonprofit Histoury.org will host “Winchester’s Fabulous First 50: A Tour of 19th Century Home Interiors,” from 1-4 p.m. This unique guided tour showcases some of the town’s earliest residences.
This event is part of Winchester Chamber of Commerce’s annual Spirit Weekend and is being presented with the support of Winchester Historical Society.
Histoury, an organization dedicated to educating communities on architectural histories, aims to connect residents with the story behind their local buildings.
“Understanding the ‘why’ and ‘how’ of historic buildings gives us a fuller understanding of daily life, the development of a community, the evolution of technology and artistic expression, and the touchpoints of our history,” says Allison Casazza, tour research and production manager for Histoury. “Historical buildings are a tangible link to the past and an incomparable way to connect with our cultural heritage.”
The timing of the tour is especially fitting as Winchester celebrates its 175th anniversary. Originally a village center in the 1840s, Winchester officially became a town in 1850.
Winchester’s development reflects the larger creation of suburban towns during the industrial age. The town’s unique architecture invokes an “en vogue” style paired with decorative embellishments.
“The second half of the 19th century showed no signs of stopping, the population continued to grow in great stride and the landscape had increasing numbers of new homes — from modest to mansion — built in the variety of styles popular in the Victorian era: Queen Anne, Mansard, Italiante, and Colonial Revival styles to name a few,” Histoury’s statement of the event reads.
The guided bus tour will take participants inside several of Winchester’s first homes from the 19th century. Highlights include an Italianate home circa 1880 that was home to a prominent local official and a refined 1876 brick home in the historic Rangeley Estates residential park, designed by the architect of Winchester Town Hall.

“This unique, one-time-only tour will take you inside several of these homes built during Winchester’s fabulous first 50 years, with more to see and learn about along the way from the comfort of a charter bus,” Histoury continued.
The tour departs from the Winchester Historical Society, participants are encouraged to arrive early for a tour of their headquarters, the Sanborn House, and refreshments.
Tickets are limited and advance registration is required. Reserve a spot here.