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How well do you know Winchester?

PHOTO BY FRANK SITEMAN

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Latest in the series. Photographer Frank Siteman has taken photos of places downtown, and your job is to guess where they were taken.  

If you know the answer, send an email to editor@winchesternews.org and put How well in the subject line.  

Last time there six winners. Mike Arwe, Neil Foley, Carl Hagge, Susan McPhee, Elisabeth Westner, and Marc Wilson guessed that it’s inside the prepaid dropoff area in the post office. See last week’s to refresh your memory. 

Latest

Winchester Planning Board OKs plans for five-story residential project, number of issues still to be resolved

Winchester Planning Board OKs plans for five-story residential project, number of issues still to be resolved

The Planning Board unanimously approved tentative plans for a five-story residential building at 10 Converse Place/33 Mt. Vernon Street — with a number of issues still needing to be resolved. “This seems to be the direction this thing is going,” board member Nicholas Rossettos said in discussion referencing original plans

Sen. Jason Lewis to host Mass. state budget 101 community conversation

Sen. Jason Lewis to host Mass. state budget 101 community conversation

The following was submitted by the Office of Sen. Jason Lewis: Sen. Jason Lewis is pleased to announce he will be convening a Community Conversation to discuss how the $60 billion+ Massachusetts state budget is drafted each year, how funding decisions are made, and how your voice can be heard.

Winchester Historical Society announces spring program series commemorating the 250th anniversary of United States

Winchester Historical Society announces spring program series commemorating the 250th anniversary of United States

The following was submitted by the Winchester Historical Society: The Winchester Historical Society is proud to announce its 2026 Spring Program Series, commemorating the 250th anniversary of the United States. This special season will feature four engaging programs that bring the Revolutionary era to life through firsthand perspectives, historical analysis,

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