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If you’re looking to get into the holiday spirit, there’s no better way than the annual Winchester Chamber of Commerce Holiday Stroll, which is being held Dec. 2 to Dec. 8.
For Executive Director Dana Garmey, the week-long event is the perfect way to not only kick off the holiday season, but draw people to the downtown business district. And in its fourth year, the event adds a bit here and there to keep things exciting.
“At first, it was just the weekend,” Garmey said, of the event. “Then last year, we did it for the full week and it was a hit. We have a lot of events so it’s just turned into the full week.”
Garmey said the idea for the Stroll and Spirit weekends came up in 2020 when Rich Mucci, a member of the chamber’s board, envisioned events that would bring people to Winchester the way both Town Day or En Ka weekends do.
Garmey said both have grown in the past four years, but only the Stroll has moved beyond the weekend. And it requires all of her attention once Spirit Weekend takes place in late September.
“It’s an exhausting week for me,” Garmey said, with a laugh. “But that’s OK, it’s all good!”
And, she added, every year seems to feature something new. For example, this year, A Tavola on Church Street will be hosting horse and carriage rides on Wednesday night with a reservation.
“Joe [Carli, owner] texted me and said, ‘I think I’d like to do a horse and carriage ride’ and because our office is right next door, I ran right over there,” Garmey said. “I helped him find someone to sponsor it.”
The rides take place from 5:30-8:30 p.m. on Dec. 4 and are only available with a reservation to A Tavola.
Midnight-ish Madness on Monday
If you missed Black Friday or Small Business Saturday, don’t panic. The Holiday Stroll offers Midnight-ish Madness on Monday, Dec. 2, when businesses downtown stay open later than normal.
“About 20 years ago, businesses used to stay open until midnight,” Garmey said. “But then they balked so now the event goes on from about 5 o’clock to 9 or 10 p.m.”
And to make the event even merrier, Garmey said the high school carolers will be out.
“It’s supposed to be a gorgeous night,” she said, of the weather forecast. “And a lot of the businesses are running specials.”
There will also be a Stocking Stuffing Party at Cosmo Capri and a Gift Wrapping Fundraiser by Friends of Winchester Recreation at Shanahan BHG Real Estate, both from 5-9 p.m. There will be a Dean Davidson Trunk Show, from 10 a.m. to 10 p.m. at Revel Boutique.
Tuesday and Wednesday nights
Cosmo Capri will be hosting a second event Tuesday, Dec. 3 with a Momhood Events Floral Night, beginning at 6:30 p.m.
Winchester Hospital will be hosting the Winton Club Gift Shop’s “Holiday Fair” on Wednesday, Dec. 4, from 12-4 p.m.
And don’t forget to make your reservation for the A Tavola horse and carriage rides!
‘Festival of Wreaths’ on Thursday
If you don’t get the chance to drop by the hospital on Wednesday, you’ll have another chance on Thursday, Dec. 5, from 10 a.m. to 4 p.m.
Then you can try to figure out when to fit in the Home & Garden Club’s “Festival of Wreaths, Trees & Tablescapes” at the Lohnes residence, 80 Myopia Road. The event runs from 12-2 p.m. and again from 6-8 p.m.
“They open up the first floor,” said Garmey, of the Lohnes family. “You can buy a raffle ticket and put it into the wreath you like most. It’s very cool!”
And, she added, the chamber will also be hosting its own Holiday Networking event at Sanctuary West, 3 Wainwright Road, from 5-7 p.m.
Friday Tree Lighting
OK, if you’ve missed the fair at Winchester Hospital again, today is the last day to check it out — because the upcoming weekend is going to be full of holiday activities.
Head downtown on Dec. 6 for the Polar Express Storytime at Book Ends, beginning at 5 p.m. before the big event — the “Lighting of the Trees” celebration at the Town Common, from 5:45 to 7 p.m.
Garmey said the event will feature the All School Chorus sing-a-longs, a photo booth, hot chocolate and pastries from Sogno and of course, the ever popular Olaf.
“There are new twists to the tree lighting every year!” Garmey said, laughing.
A busy Saturday
Saturday kicks off a full day of events for Winchester, beginning with an Open House with Crystal Bowl Meditations, Massages & Demos, from 12-5 p.m., at Ten Wellness.
Then choose between the Ballet Arts Centre’s “Nutcracker to Go” at the Jenks Center at 3 p.m. or the Yule Ball at Book Ends, from 3-6 p.m.
Adults can enjoy the Sip & Paint at Bagels & Brew at 5:30 p.m. and the Annual Holiday Party with a visit from Santa at Rubini Arts, from 5-8 p.m.
Wrapping it up on Sunday
Dec. 8 will wrap up the week-long holiday extravaganza, kicking off with a Story Hour with Matt Tavares & Aaron Becker at Book Ends at 11 a.m.
From 4-6 p.m., Family Action Network will have holiday caroling. And at 4 o’clock, the chamber will announce the “Troll on the Stroll” Scavenger Hunt winner.
And of course, saving the best for last, the Drive-By Santa visit will take place, starting at 6 p.m., behind the McCall Middle School.
“We used to have Santa at the tree lighting,” Garmey said, of the finale to the Stroll. “For me, I had three small boys and I had to chase them around. It was a nightmare!”
Then COVID hit.
Garmey said the chamber decided it had to do something for families. Thus, the new event was born.
Garmey said people start lining up on the Mystic Valley Parkway in their cars and many are in their pajamas and make it a real family event. Then Santa makes his way from car to car, speaking to the kids.
“It’s very popular,” she said. “Last year, it was pouring rain, but people came out.”
Garmey said Santa usually rides in on a fire engine before the event.
“It turned out that this was a nice result of COVID,” she said. “And now, we have Olaf at the tree lighting.”
Weeklong events
If you’re not exhausted enough by all the scheduled events, you can always tackle the ongoing events, like the Red Ticket Raffle, “Trolls on the Stroll” Scavenger Hunt or the Gingerbread House Contest.
Garmey said all the houses for the gingerbread contest are built and will be in store windows from Dec. 2 to Dec. 8. Residents can vote for their favorite by scanning in the QR code by the house sign. Or they can vote online at the chamber website.
This is the third year for the event, which Garmey said sold out immediately, and there will be 20 houses on display throughout downtown.
For kids, there’s the “Trolls on the Stroll” Scavenger Hunt. That’s right, take a stroll through the downtown area and peek inside the local stores to find the eight hidden trolls.
Garmey, who came up with the idea, said residents can take photos of the trolls and send them to the chamber email. The winner of the hunt will be the first in line to meet Santa on Sunday night.
“It’s really great,” she said. “The kids sometimes cry on the phone when I call. I really look forward to this part of the weekend.”
And of course, there’s the Red Ticket Raffle for the adults. Garmey credited Mucci once again for the concept, after he saw something similar on Nantucket.
The idea is that for every $25 spent in a business downtown, you get a red raffle ticket. And on Dec. 19, winners will be drawn for prizes up to $3,000.
The event, which started three years ago, said Garmey, is incredibly popular.
“Last year, we sold about 15,000 tickets,” Garmey said. “About 90% of the businesses downtown participated.”
Garmey credited Winchester Co-operative Bank for the lead sponsorship of the week-long event. She said the bank has been doing it since the event began. And, she added, there are other sponsors who change out from year to year.
“It really gets people downtown,” Garmey said, of the Holiday Stroll event. “The gingerbread contest, for example, gets people walking around. I would say, yes, 100%, it draws people downtown.
“Take Midnight Madness, most shops are closed on Monday nights,” she continued. “A Tavola is a prime example. They had 90 reservations for Wednesday night right away. Then there’s the troll hunt. The [Stroll] gets people into stores they didn’t even know existed!”
