Stroll week 2025 is shaping up to be a fantastic week of local shopping, dining and festivities for the entire family!  Thank you to Winchester Co-operative Bank for making it all happen!

The very popular Red Ticket Raffle will be happening all week long as well.  Click here for participating businesses.

All week long as well:  a Food Drive to benefit ENKA pantry hosted by Shepherd Financial Partners. Non Perishable Donations can be dropped off at the front door at 1004 Main Street from Monday, December 1 through Friday, December 5 during business hours 9am-5pm.

Schedule of Events for Stroll week 2025 (updated daily!):

• Monday, December 1st, 6:00-10:00 pm:  Midnight Madness!  Join local businesses in downtown Winchester as we 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.  Thank you to Winchester Savings Bank for sponsoring the night!
• Monday, December 1st 6-9pm: The Holiday Edit Midnight Madness shopping event with Kate Maloney Interior Design.   A curated selection of local makers for one night only!
• Monday, December 1st:  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 pm
• Monday, December 1st: 20% off all full price purchases at Runway Couture. Sale merchandise excluded
• Monday, December 1st: 4:00-9:00 pm:  Midnight Madness Stocking Stuffing party at Cosmo Capri $30 includes stocking, 10 stuffers, hot chocolate and cookies.  Information here
• Monday, December 1st: 6:00-10:00 pm: Midnight Madness Raclette and Wine Tasting at Nouvelle Maison
• Monday, December 1st
  6-9 pm:  Bespoke of Winchester’s Midnight Madness, Pop-Up!
  Featuring 10 artisans  Enjoy Cider and Music from the Winchester Community Music School  27 Church Street–Bespoke studio
• Monday December 1st 6-10 pm:  Exclusive Midnight Madness shopping event at The Klinic 618 Main Street. Complementary artisan beverages from Amushe Cafe!  Bespoke gifting, skincare and gift card sale
• Monday, December 1st: 6:00-10:00 pm:  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
• Monday December 1st:  Midnight Madness Movie Night at Preschool Social Academy!  Drop the kids off and enjoy a night of shopping.  PSA will remain open until 7 pm for families.
• Monday December 1st:  6 pm – 9 pm Spa Revenir, 10 Thompson Street: Toy Collection for the Marine Corps Reserves TOYS FOR TOTS.  When you donate a new, unwrapped toy for a child up to 12 y.o. you’ll receive a voucher for savings on a product or service for Mary Connell Skincare
• Monday, December 1st, 6:00-9:00 pm Open House, Orazio Tile & Flooring Boutique showroom
• Tuesday, December 2nd 7:00-9:00: “Setting the Table with Anne”: Holiday Decor at Nouvelle Maison.  Click here for more info and tickets
• Wednesday, December 3rd, 5:30 pm-8:30 pm:  Horse and Carriage Rides at A Tavola.  Make a dinner reservation and experience a magical ride through Winchester Center.  Call for reservations:  781.729.1040.  Due to popular demand, an additional night has been added on December 10th! Thank you to The Town Day Committee for sponsoring this special night!
• Wednesday, December 3rd, 7:00-9:00 pm:  Wine Wednesday featuring sparkling wines at Book Ends, click for details.
• Thursday, December 4th, 12:00-4:00 pm:  Home and Garden Club’s Festival of Wreaths, Lohnes Residence 80 Myopia Road–all are welcome!
• Thursday, December 4th 5:30-6:30 pm:  Annual Polar Express storytime with Matt Tavares at Book Ends. Click here for all the details
• Thursday, December 4th 5:30-9:00pm: Progressive Sips, Snacks, and Paint Night by the Common Collaborative (A Tavola, Bespoke of Winchester, Studio on the Common). Sign up here!
• Friday, December 5th:  4:30-7:00 pm:  Lighting of the Trees Santa returns!  Don’t miss out watching Santa arrive by firetruck at 4:30 pm.  Santa will stay and visit until 6:30 pm.  Hot chocolate and goodies provided by Sogno.  The All School Chorus will perform at 6:30 and the lights will be turned on at 7:00 pm.  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!
• Friday December 5th: Jules at 3 Thompson Street 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.
• Saturday, December 6th (Ages 5-8 from 10am-12pm and ages 9-13 (1-3pm): Studio on the Common Demon Hunters Paint Party. Register here!
• Saturday, December 6th 12:00-4:00 pm:  Holiday Open House at StretchMed. Book a FREE 10 min demo stretch at https://momence.com/StretchMed—Winchester/appointment-reservation/32296?boardId=90096&serviceId=61614&venueId=90656&date=2025-12-06 New Member Promotion: $76/month with a 30-day money-back guarantee. Book a FREE 55 min stretch and assessment at https://stretchmedstudios.com/stretchmed-winchester/#book-now .10% off all Stretch Credit Packs

• Saturday, December 6th 3:00-6:00 pm: Yule Ball at Book Ends.  Save the date for our 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
• Sunday, December 7th 11:00 am:  Story hour with Matt Tavares reading from his new book “Dasher and the Polar Bear.  Click for details!
• Sunday, December 7th, 4:00-6:00 pm:  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!