Winchester Annual Events

The Chamber’s commitment to town beautification not only enhances the visual appeal of downtown Winchester, but also fosters an inviting ambiance that beckons locals and visitors alike to explore and engage with our local businesses.

Town Beautification includes the Hanging Basket program in the Spring, the Wreaths that adorn the historic lamp posts during the Holiday season and the partnership with Lucille Murray’s Lights of Love that keep the festive lights on all year round in the center.  The Chamber remains steadfast in its commitment to nurturing this vibrancy and fostering an environment where local businesses can thrive, ensuring that Winchester continues to be a beacon of community spirit, beauty, and growth.

Community support is vital to keeping the Town Beautification programs up and running.  Consider a donation of any amount to keep Winchester looking vibrant and festive year round. LINK TO DONATION PAGE HERE

Networking plays a pivotal role in fostering professional growth and community engagement, which is why The Chamber is dedicated to continuously exploring innovative ways to facilitate and enhance networking opportunities for our valued members.  The Chamber partners with 11 other area Chambers in a close working relationship to bring several Multi-Chamber opportunities per year.  Additionally, The Chamber hosts Learning Series Events to spotlight members as well as Women in Winchester events that connect members with each other.  Make sure to subscribe to our newsletter so you never miss an opportunity!

The Chamber organizes an Annual Luncheon in February, hosted by the current President of the Board of Directors and the Executive Director of the Chamber of Commerce to update the membership on plans for the upcoming year.  All are welcome to attend and guest speakers usually include a member of Town Government with pertinent information for the local business community.  Past speakers have included the Town Manager, the Town Planner, the Chief of Police and members of The Select Board.  We look forward to seeing you at the next President’s Luncheon!

In the first quarter of each year, the Chamber of Commerce requests nominations for the Citizen of the Year Award.  

This prestigious award honors individuals of local prominence whom the Chamber and the community recognize as contributors to the betterment of life in Winchester.  There are no specific criteria for the award itself.

The stature of the individuals who have been honored in the past serves as the true benchmark for selection.

To nominate an exemplary citizen, complete this form.

Past Citizen of the Year Recipients:

Harrison Chadwick, “Whip” Saltmarsh, Dr. Robert Nickerson, Dr. Gustave Kaufmann, John J. Sullivan, Clarence Borggaard, John Ciarcia, Harry Chefalo, Dr. Lenor Rich, Dr. Donald McLean, Paul Mahoney, Arthur Griffin, Judie Muggia, Austin Broadhurst, Sandy Thompson, Justin Magee, Ann McGovern, Peter Van Aken, Chad Maurer, and Charles Tseckares, Edward O’Connell, Corie Nichols, Sandy Rogers, Kevin Mawn, Dot Butler, Stephen Parkhurst, Allan Eyden, Alan MacDonald, Carol Kent, Marie Johnson, The Ryan Family, Charles Price and Carl Boerner, Helen Babcock and Tom Howley, Jay Gill, Jan Dolan, Sal Caraviello, Jimmy Johnson, Robert Deering, Peggy and Jack Roll, Sally Quinn, Essential Workers, Sgt. Dan Perenick, Judy Manzo and Cathy Alexander.

Each year the Chamber of Commerce coordinates the Annual Garden Tour with beautiful home gardens that showcase the artistry and creativity of Winchester’s talented residents.  

All proceeds from the event go toward the Town Beautification Fund which supports such projects as the hanging baskets, the holiday lights and and the wreaths adorned on the Winchester Center’s historic lamp posts every Holiday season. The Annual Garden Tour is a great opportunity to make a tangible difference to the beauty and vitality of Winchester! Enjoy this video of the 2023 Annual Garden Tour

The Winchester Chamber of Commerce, in partnership with The Glen Doherty Memorial Foundation, annually organizes Spirit Weekend  for the third weekend of September to coincide with the running of the Glen Doherty Memorial Road Race.  The weekend is a celebration where the community comes together to not only honor Winchester’s hometown hero,  Glen Doherty, but also to celebrate the unique spirit of Winchester’s historic downtown area.  The schedule of events for the weekend includes:    

• A Friday night festival/block party with live music and performances and retail shops stay open later for local shopping and dining
• Saturday includes a Beer Garden at the scenic Griffin Museum’s outdoor patio with fireworks lighting up Winchester later that night
• Sunday is the annual running of the Glen Doherty Race–Create a team with neighbors and friends and enjoy this wonderful event.  Over ten years of friends, family, neighbors, runners, walkers, ruckers, locals and visitors honoring Winchester’s  local legend Glen Doherty! Register for the race early to be guaranteed a race day T shirt! 

Be sure to sign up for The Chamber’s newsletter and follow our socials to keep up to date with this year’s schedule of events for Spirit Weekend!

Each year the Chamber of Commerce coordinates the Annual Holiday House Tour with beautiful homes that showcase the artistry and creativity of Winchester’s talented residents and get everyone in the mood and inspired for the upcoming Holidays!

All proceeds from the event go toward the Town Beautification Fund which supports such projects as the hanging baskets, the holiday lights and and the wreaths adorned on the Winchester Center’s historic lamp posts every Holiday season. The Annual Holiday House Tour is a great opportunity to make a tangible difference to the beauty and vitality of Winchester! 

The Winchester Chamber of Commerce organizes the Annual Holiday Stroll weekend every year during the first weekend of December. The weekend has now become an annual event where the residents of Winchester and surrounding communities can enjoy four days of holiday festivities in Winchester Center’s Historic and Cultural District.  The very popular Red Ticket Raffle promotion runs all during the Stroll weekend as well:  simply spend $25 at a participating store and win cash prizes!  The Chamber would like to thank our Lead Sponsor, Winchester Co-Operative Bank, for making the Stroll weekends possible.  The weekend’s events typically include:

• Midnight Madness “Shop and Stroll Event which features a  line-up of independently owned shops, boutiques,  pop-ups, food, drink and entertaining festivities that will kick off your holiday season in style! Get ready to shop, stroll, sip and snack as you enjoy exclusive holiday cheer in Winchester Center’s Historic District. 
• Winchester’s  Holiday Tree Lighting Celebration.  Holiday music, performances from the All School Chorus, hot chocolate, popcorn and a visit from a favorite holiday character await this family friendly event. 
• “Best in Stroll” Dog Contest.  Bring the kids and your fur babies to this fun event where the star of the show are the furry ones!  Dress up in costumes, practice those tricks and meet us on The Town Common to see who will be crowned this year’s “Best in Stroll”. 
• Gingerbread House Decorating Contest, see the entries in stores throughout the town center and vote for your favorite while shopping!
• Santa!  Put the kids in the car and head out to meet Santa!  Cars will line up on Mystic Valley Parkway and enter behind McCall Middle School.  Decorate your car, dress up or stay in your pajamas.  All kids will receive a personal gift from Santa himself.

The Winchester Chamber of Commerce is proud to bring Winchester and surrounding communities,a full weekend of events to support the local economy and celebrate the holiday season.

To encourage shopping locally for the holiday season and promote the sustainability of Winchester,  the Chamber continues to organize and promote the Annual Red Ticket Raffle Promotion.

Red Ticket Raffle Promotion Rules

When? End of November-the third week of December.  For every $25 spent by a shopper in a participating Chamber of Commerce business, the shopper will receive a “Red Raffle Ticket” that enters them into a drawing to win cash prizes:  $3,000, $1,000 and $500.  Multiple drawings so plenty of opportunities to win!  The promotion is for retailers, restaurants, food stores, nail salons, gyms, stretch studios and any business that distributes gift certificates and/or sells products.  In 2022 over 25,000 Red Tickets were distributed by Chamber Member merchants to their customers. With each ticket representing a value $25, that approximates to over $600,000 in sales generated through the program.