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Make your list, check it twice and mark your calendar for Dec. 1 through Dec. 7 because the Winchester Chamber of Commerce is hosting its 5th Annual Holiday Stroll!
“The Winchester Chamber of Commerce is thrilled to welcome the community to Stroll Week 2025 beginning on Dec. 1st with the kick off of Midnight Madness,” said Executive Director Dana Garmey, of the chamber event. “Stroll week is an amazing reminder of how vital our local businesses are — they bring energy, creativity, and connection to our town every single day and the schedule for the week proves that--there is something for everyone! We can’t wait to join residents and visitors in supporting the shops, restaurants, and entrepreneurs who make Winchester such a vibrant and special place to live.”
The idea for the Stroll and Spirit weekends came about in 2020 when the chamber’s board envisioned events that would bring people to Winchester the way both Town Day and the En Ka weekends do. While both have grown the past five years, the Stroll has grown every year and it always seems there’s something new.
For example, last year A Tavola joined the fun with horse and carriage rides. Because of its popularity last year, an extra night will be added on Dec. 10. But only with reservations.
What else is new?
“All of the Midnight Madness happenings!” Garmey said. “The local businesses are going all out this year to make it a memorable night for shoppers to kick off the week.”
Garmey added Santa Claus will also be coming back to the Tree Lighting on Dec. 5, an activity he hasn’t been see at since before COVID-19. Garmey said Santa is scheduled to arrive by fire truck at 4:30 p.m. and stay until 6:30 p.m.
And don’t forget the always popular Red Ticket Raffle will be happening all week long as well. Click here for participating businesses.
Plus, the chamber, in partnership with the Winchester Cultural District & The Gingerbread Construction Co., is excited to bring back to the community the Annual Gingerbread House Decorating Contest, sponsored by Barrett Sotheby.s International Realty.
Registration is now open and is limited to the first 20 registrants with one house kit per household. Click here for more information.
Don’t forget to vote in 3rd Annual Gingerbread House Decorating Contest.
With all the excitement, Garmey added none of it would happen without sponsors, including the lead sponsor of the week: Winchester Co-operative Bank.
Additionally, there are the following sponsors:
Midnight Madness sponsor: Winchester Savings Bank.
Horse and Carriage Ride sponsors: The Town Day Committee and Julie Wile Fish and Peter Pirani of Gibson Sotheby’s.
Tree Lighting: Shepherd Financial Partners and PDA Dental is sponsoring Santa’s return.
A look at the 2024 winners of the Gingerbread House Contest. COURTESY PHOTOS/WINCHESTER CHAMBER OF COMMERCE
Gingerbread House Contest: Barrett Sotheby's International.
Other corporate sponsors: ServPro, Sogno, A Sweet SurpriZe, Distinctive Pergolas and Eastern Bank.
The following is a schedule of events for Stroll week 2025. Don’t forget the chamber updates the information daily!
Schedule of Events
Dec. 1
6-10 p.m.: Midnight Madness!
Join local businesses in downtown Winchester to kick off the holiday season and Stroll week with a beloved tradition of shopping, festive cheer and holiday magic. Shop local. Stay late. Celebrate Winchester.
Check out the following specials and events:
4-9 p.m.: Midnight Madness Stocking Stuffing party at Cosmo Capri, $30 includes stocking, 10 stuffers, hot chocolate and cookies. Information here.
6-9 p.m.: The Holiday Edit Midnight Madness shopping event with Kate Maloney Interior Design. A curated selection of local makers for one night only!
6–9 p.m.: Spa Revenir, 10 Thompson St.: Toy Collection for the Marine Corps Reserves TOYS FOR TOTS. When you donate a new, unwrapped toy for a child up to 12 years old. You’ll receive a voucher for savings on a product or service for Mary Connell Skincare.
6-9 p.m.: Bespoke of Winchester’s Midnight Madness, Pop-Up!
Featuring 10 artisans, including the following: Kanch by Kolika - art glass; Rebecca Scott – Shepherd’s Run, jewelry; Ariel Kessler – ceramics; Helen Frances Ray - HFR soaps; Bob Marcellino - fine art; Mud Dove Pottery; Yeiou paper objects; alooDesign - ceramics & graphic design; Banyan & Birch - Luxury Home Linens and Studio on the Common - Simon Pearce.
Also, enjoy cider and music from the Winchester Community Music School, 27 Church St., at Bespoke of Winchester.
6-10 p.m.: Midnight Madness Raclette and Wine Tasting at Nouvelle Maison
6-10 p.m.: Exclusive Midnight Madness shopping event at The Klinic, 618 Main St. Complementary artisan beverages from Amushe Cafe! Bespoke gifting, skincare and gift card sale.
6-10 p.m.: Midnight Madness Holiday Sip & Shop at Revel.
*20% off of 1-Full Price Item of Women’s Clothing
*10% off on Scarlett Chase Boots and Booties
*Dean Davidson Trunk Show Event- Spend $300, receive a free gift with purchase ethos bracelet valued at $125 (while supplies last)
*Mini bespoke cupcakes by Baked by Georgia.
Midnight Madness specials at Studio on the Common: (10% off all purchases (excluding Simon Pearce), complimentary bubbly and bites, giveaways every 15 mins starting at 6 p.m.
Midnight Madness Movie Night at Preschool Social Academy! Drop the kids off and enjoy a night of shopping. PSA will remain open until 7 p.m. for families.
Dec. 2
7-9 p.m.: “Setting the Table with Anne”: Holiday Decor at Nouvelle Maison. Click here for more info and tickets
In 2024, A Tavola offered carriage rides with a reservation for dinner. The popular attraction will host two different nights of carriage rides. COURTESY PHOTOS/WINCHESTER CHAMBER OF COMMERCE
Dec. 3
5:30-8:30 p.m.: Horse and Carriage Rides at A Tavola.
Make a dinner reservation and experience a magical ride through Winchester Center. Call for reservations at 781-729-1040. Due to popular demand, an additional night has been added on Dec. 10. Thank you to The Town Day Committee for sponsoring this special night!
7-9 p.m.: Wine Wednesday featuring sparkling wines at Book Ends, click for details.
Dec. 4
12-4 p.m.: Home and Garden Club’s Festival of Wreaths, Lohnes Residence, 80 Myopia Road. All are welcome!
5:30-6:30 p.m.: Annual Polar Express storytime with Matt Tavares at Book Ends. Click here for all the details.
5:30-9 p.m.: Progressive Sips, Snacks, and Paint Night by the Common Collaborative (A Tavola, Bespoke of Winchester, Studio on the Common). Sign up here!
Dec. 5
4:30-7 p.m.: Lighting of the Trees and Santa returns!
Don’t miss out watching Santa arrive by firetruck at 4:30 p.m. Santa will stay and visit until 6:30 p.m. Hot chocolate and goodies provided by Sogno.
The All School Chorus will perform at 6:30 p.m. and the lights will be turned on at 7 p.m.
Other special guests and fun events planned for this special night.Thank you to PDA Dental Group for sponsoring Santa’s return and to Shepherd Financial Partners for sponsoring the night!
· Jules at 3 Thompson St. is completely transformed into a Happy Camp3r pop-up store, featuring high-quality, uplifting apparel that supports mental health awareness. Explore the newest Happy Camp3r styles, including their most current hoodies and sweats designed for comfort and positivity.
With every Happy Camp3r purchase, you’ll be entered into a raffle to win Happy Camp3r merchandise. Come shop, connect, and experience a brand making a positive impact.
Dec. 6
Ages 5-8 from 10 a.m.-12 p.m. and ages 9-13 (1-3 p.m.): Studio on the Common Demon Hunters Paint Party. Register here!
12-4 p.m.: Holiday Open House at StretchMed. Book a FREE 10 minute demo stretch.
New Member Promotion: $76/month with a 30-day money-back guarantee. Book a FREE 55 minute stretch and assessment here.
10% off all Stretch Credit Packs
Happy Cap3r Pop up at Jules, 3 Thompson St.
3-6 p.m.: Yule Ball at Book Ends. Save the date for the 4th annual Yule Ball! Join Book Ends for an afternoon of merriment and bookish joy as they kick off the holiday season — they will have signings with local authors, beer tasting, and a wine tasting led by Book Ends’ co-owner Lauren. Click here for all the details and to RSVP
Dec. 7
11 a.m: Story hour with Matt Tavares reading from his new book “Dasher and the Polar Bear. Click for details!
4-6 p.m.: Join The Family Action Network for an afternoon of caroling and hot chocolate. Song sheets will be available and all are welcome! Exact meeting location will be shared once registered. Click here to register!
Nell Escobar Coakley has been a journalist for more than 30 years. She is co-founder and editor-in-chief of Gotta Know Medford and editor of Winchester News. She can be reached at editor@winchesternews.org.
