Commercial

Business-related activities: promotions, sales, Chamber of Commerce events, tourist attractions, etc.

Rise and Shine Marketplace

Rise + Shine Marketplace is a unique shopping showcase featuring the finest makers in the New England area. The experience will include passed hors d'oeuvres, local samples from our food vendors, beverages, and live music. Our goal is to build a community that you will be able to connect with long after you experience our Rise + Shine Marketplace gathering. Tickets are $25 for adults, $15 for age 12 and under. Your ticket price will support our effort to shine a light on these small businesses while celebrating the craft community as a whole. 

Founders are Sarah Motzkin of Busy Bostonians &

Rubini Art Holiday Party

A holiday reception in Lucia Rubini's art studio and school. Refreshments served, all are welcome! 15% of all sales will benefit children of Ukraine.

Spirit Weekend 2025

On Friday

  • Streets are closed 4 - 9 pm, but businesses are open!
  • WHS football game at Knowlton Stadium @ McCall Middle School

On Saturday

  • Farmer's Market on the  Town Common
  • Beer Garden with Live Music on the Griffin Museum Patio

On Sunday

  • Annual Glen Doherty 5K/10K Road Race, at Town Hall

Events may change as the date approaches!

Spring into Wellness Health Fair!

Join us for the Winchester Chamber’s first-ever Health & Wellness Fair, a dynamic event dedicated to promoting healthier lifestyles and well-being in our community!

Discover local businesses and professionals specializing in mental health, physical wellness, fitness, stress management, financial health, coaching, physical therapy, and more. Whether you’re looking for expert advice, wellness products, or new ways to improve your overall health, this event has something for everyone!