Stroll Week 2026!
Stroll week 2026 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.
Schedule of Events for Stroll week 2026 (updated daily!):
Monday, November 30th, 5:00-10:00 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, November 30th: 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, November 30th: 5:00-10:00 pm: Midnight Madness Raclette and Wine Tasting AND Curio Mulled Spiced Bar at Nouvelle Maison
- Monday, November 30th: 4:30-8:30 pm: Join The Shanahan Group as they host Jules and their Happy Camp3r pop up! 30 % off!
- Tuesday, December 1st 7:00-9:00pm: “Setting the Table Holiday Edition with Chestnut Grove Design at Nouvelle Maison. Click here for more info and tickets
- Tuesday, December 1st 7:00 pm: Winchester Community Music School and The Griffin Museum Present Common Time Concert Series. The concert will feature Miles Blackwood & Friends and is a tribute to all the songwriters that have inspired his approach to Americana, alternative, and jazz-laced alt-pop-rock: Paul Simon, Stevie Wonder, Jeff Tweedy, Brittany Howard, John Linnell & John Flansburgh (TMBG), Warren Zevon, Roland Orzabal (Tears for Fears), Bill Withers and more. Miles is joined by guest vocalist Prophet PM and members of The Oddlot and The New Limits
- Wednesday, December 2nd, 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 9th! Thank you to The Town Day Committee & Julie Wile Fish/Peter Pirani or Gibson Sotheby’s International for sponsoring this special night!
- Wednesday, December 2nd , 7:00-9:00 pm: Wine Wednesday featuring sparkling wines at Book Ends, click for details.
- Wednesday, December 2nd 12:00-4:00 pm: Home and Garden Club’s Festival of Wreaths, Lohnes Residence 80 Myopia Road–all are welcome!
- Friday, December 4th 4:30-5:00 pm: Annual Polar Express story time at Book Ends. Click here for all the details
- Friday, December 4th: 5:00-7:00 pm: Lighting of the Trees Santa returns! Don’t miss out watching Santa arrive by firetruck at 5:00 pm. Santa will stay and visit until 7:00 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. At 7:15, the lighting of the Menorah will take place as well with a blessing. 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 4th, 7:00-8:30 pm: Join Studio on the Common after the lighting of the trees for food, fun and Jellycats! Registration includes pizza drinks and a Jellycat Yankee Swap. Register here
- Saturday, December 5th 2:00-6:00 pm: Yule Ball at Book Ends. Save the date for the 6th annual Yule Ball! Join Book Ends for an afternoon of merriment and bookish joy as they kick off the holiday season–featuring Joanne Chang of Flour Bakery as the featured author! Click here for all the details and to RSVP
- Sunday, December 6th, 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!
