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On a cold Monday night, residents came together to celebrate the 5th Annual Holiday Stroll week, a festive tradition that combines the small-town charm of Winchester with holiday excitement. The colored lights flickered in the trees while people of all ages came together to celebrate and shop local.
This year, the Stroll runs from Dec. 1st to 7 with events, shopping specials, family activities and seasonal cheer provided and hosted by local businesses and community organizations. From Midnight Madness to gingerbread house decorations, Stroll week accentuates everything that makes Winchester special: community, local pride and coming together to welcome the holiday joys.
The week began on Monday, with the beloved Midnight Madness. Businesses stayed open late, offering festive deals, holiday treats, and special pop-ups, all while the holiday spirit is everywhere you look.
Studio on the Common offered 10% off on purchases, giveaways, and complimentary bubbly, while Runway Couture featureed 20% off full-price items. Families visited Cosmo Capri’s Stocking Stuffing Party, enjoyed raclette and wine tasting at Nouvelle Maison, browsed artisan pop-ups at Bespoke and The Klinic, sipped and shopped at Revel, or dropped off kids for a special movie night at Preschool Social Academy.
Spa Revenir and Katana Spa hosted holiday-themed events, and Orazio Tile & Flooring welcomed visitors to an evening open house. Many shops in town, including The Holiday Edit, Bespoke of Winchester, and The Klinic featured curated local makers, pop-ups, drinks, and exclusive promotions to kick off the holiday season.
The goal of the holiday week events are to encourage residents to stay local, shop local and love local.
The week will include a host of other events, including the following:
On Tuesday, Dec. 2, Nouvelle Maison hosts Setting the Table with Anne, a hands-on holiday décor workshop from 7 to 9 p.m.
On Wednesday, Dec. 3, the magical Horse & Carriage Rides at A Tavola comes to town from 5:30–8:30 p.m., along with a Wine Wednesday featuring Sparkling Wine at Book Ends.
Stroll Week continues on Thursday, Dec. 4 with the Home and Garden Club’s Festival of Wreaths from 12 to 4 p.m. the annual Polar Express Storytime with author Matt Tavares at Book Ends from 5:30 to 6:30 p.m., bringing fun for the whole family. Progressive Sips, Snacks, and Paint Night hosted collaboratively by A Tavola, Bespoke, and Studio on the Common.
One of the most anticipated and beloved Stroll traditions takes place on Friday, Dec. 5: the Lighting of the Trees from 4:30 to 7 p.m. in the town center. Santa arrives by fire truck at 4:30 and stays for visits until 6:30.
From inside and outside, Winchester businesses are ready to celebrate the holidays during the annual Holiday Stroll. WINCHESTER NEWS STAFF PHOTOS/XIYUE ERIC HAN
Families can enjoy hot chocolate and treats from Sogno, and the All-School Chorus performs at 6:30 before the trees officially light up at 7 p.m. Bring the whole family for a night of holiday cheer. Jules also hosts a special Happy Camp3r pop-up featuring uplifting apparel that supports mental health awareness.
The weekend rounds out the celebration. On Saturday, Dec. 6, Studio on the Common offers Demon Hunters Paint Party sessions for kids, ages 5 to 8 and 9 to 13, StretchMed holds a festive Holiday Open House with free demo sessions and special promotions, Jules continues the Happy Camp3r pop-up, and Book Ends hosts its 4th annual Yule Ball from 3 to 6 p.m. with author signings, beer and wine tastings, and bookish merriment.
Stroll Week concludes on Sunday, Dec. 7, with a morning story hour featuring Matt Tavares reading from “Dasher and the Polar Bear,” followed by an afternoon of community caroling and hot chocolate with the Family Action Network from 4–6 p.m.
From shopping to festive traditions, Winchester Stroll Week 2025 offers something for everyone of all ages, all coming together to celebrate the vibrant local businesses and community connections that make Winchester feel like Winchester during the holiday season.
For a full list of activities, check out the Chamber of Commerce schedule here.
Xiyue Eric Han is a sophomore at Winchester High School. He has been interning at Winchester News since 2025.
