Commercial

Each year, the Winchester Chamber of Commerce proudly presents the Annual Holiday House Tour, featuring a curated selection of beautifully decorated homes that will fill you with inspiration and festive cheer. All proceeds from this magical event go directly to the Town Beautification Fund, supporting vital projects that make Winchester shine year-round, like the Hanging Baskets.  Your participation helps keep Winchester as beautiful as ever!

• Explore stunning homes showcasing creative holiday décor.
• Get ideas to make your own home festive and welcoming.
• Be part of a community-driven effort to

The Town Meeting Members Association is holding a State of the Town Briefing on the progress that the group has made and to answer questions. This meeting will also be hybrid and the general public is invited to attend.

FREE to attend! Join us as we wrap up Town Day 2026 with an unforgettable afternoon at the Town Day Beer Garden! Enjoy locally crafted beer poured by Arlington Brewing Company, wine from Marble Ridge Winery, and live music by Scott Damgaard -- all set on the beautiful outdoor terrace of The Griffin Museum of Photography.

Gather with friends, neighbors, and the community for a fun and relaxing celebration to close out an amazing Town Day.

A special thank you to our generous sponsors for making this event possible: Catherine Albiani Real Estate, Conquer Ninja Gyms Woburn, and Kate Maloney

A perfect opportunity to stock up on Winchester themed clothing and other gear. Buy for yourself or as gifts for friends and family!