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The following was submitted by the Winchester Chamber of Commerce:
The Winchester Chamber of Commerce is thrilled to present the Fourth Annual Holiday Stroll, taking place the week of Dec. 2 to Dec. 8, 2024.
This beloved tradition invites residents of Winchester and nearby communities to celebrate the holiday season in Winchester Center’s Historic and Cultural District with a week full of festive activities.
Thanks to the generous support of Lead Sponsor, Winchester Co-operative Bank, the 2024 Holiday Stroll promises something for everyone.
A look at one of the Stroll’s most popular events – the Gingerbread Contest! COURTESY VIDEO/BARRETT SOTHEBY’S INTERNATIONAL REALTY
Don’t miss the ever-popular Red Ticket Raffle, running all week long! Simply spend $25 at participating stores and enter for a chance to win exciting cash prizes.
Stroll Week Highlights
● Monday, Dec. 2: Midnight Madness (5–9 p.m.)
Winchester stores will stay open late, offering special deals to kick off the holiday season. Enjoy the sounds of carolers filling the air as you shop and soak in the festive atmosphere.
● Wednesday, Dec. 4: Horse and Carriage Rides (5:30–8:30 p.m.)
Guests with dinner reservations at A Tavola Restaurant can enjoy a charming horse and carriage ride through Winchester Center, making for an unforgettable evening.
● Friday, Dec. 6: Lighting of the Trees (5:45–7 p.m.)
Gather on the Town Common for this heartwarming tradition. Highlights include:
○ A performance by The All School Chorus
○ A visit with Olaf and a festive photo booth
○ Complimentary hot chocolate and treats from Sogno
● Sunday, Dec. 8: Drive-By Santa Event (6 p.m.)
The Stroll wraps up with a visit from Santa himself! Be sure to catch the holiday magic as Santa makes his rounds to greet families. Cars will line up on Mystic Valley Parkway to wait for a greeting – each child will go home with a gift.
Join the celebration
The Winchester Chamber of Commerce is delighted to host this cherished community tradition, bringing the magic of the holidays to Winchester and surrounding areas.
The chamber encourages everyone to shop local, enjoy the festivities, and make memories to last a lifetime.
For more information, log on at www.winchesterchamber.com for a full schedule of events.
