There is always something going on at The Planted Arrow, and this year, for Shop Crawl Whisk and Willow, a Chesterville Bakery was invited to set-up on their lawn to help sweeten up the shoppers. Tinkess Photo

WINCHESTER – Shop local has become an even more important theme in 2026 as small businesses work hard to deal with increased costs, logistics issues, and the other negative effects that tariffs and the economy in general have imposed on them. On Sat., Nov. 7, merchants in Winchester kicked off the extremely important holiday shopping season with the annual Winchester Shop Crawl, an event designed to show to current and prospective customers that if you are looking for something special, you don’t have to look very far from home to find it.

The event, which ran from 10:00 a.m. until 3:00 p.m., featured several local businesses such as:

  • Main St. Clothing Company
  • Rue Bridal House
  • Heritage House Health Spa
  • Simply Baked
  • The Makers Hub
  • The Planted Arrow Flowers and Gifts
  • Samantha’s Emporium
  • Trixie’s Trinkets
  • The Odd Stop
  • Winchester Pharmasave
  • Harvest Coffee
  • The Lions Thrift Shop

There was one important change this year: In the past, participants were entered to win one big prize. This year, every shop offered its own prize draw, which created more chances to win! There was also no need to collect a stamp at every location; simply pop in and out of the shops you choose.

Customers could enjoy exclusive discounts, special promotions, and giveaways at each location, and in order to make the visit as efficient as possible, a map showing the location of participating shops was posted on Facebook.

With near perfect weather conditions, there was nothing to stop an influx of interested shoppers and judging by how quickly on-street parking filled up, many shoppers made the effort to get there early. Carolyn, a Barrhaven resident, said she discovered Winchester a few years ago and is now a regular visitor.

“it’s nice to walk along a main street in a small community and stop in at the different shops,” she said. “In Barrhaven, it is all shopping malls and big box stores. You could go into Ottawa, but then you have to deal with lots of traffic, and parking, which can get very expensive. This is just so much more welcoming.”

With just over six weeks until Christmas, many merchants are reporting that many customers started their holiday shopping weeks, or even months ago, looking carefully for unique gifts and perhaps watching the amount they spend a little more closely than in previous years. Being able to provide something that you won’t find elsewhere definitely gives you a bit of an advantage.

Kelly Windle is the organizer of many local events but is quick to redirect the credit for the Shop Crawl.  “The Shop Crawl is a group effort organized by Main St Clothing,  and Lisa Williams, to promote the downtown and surrounding Winchester businesses and North Dundas.

“The recipe has changed over the years as businesses have come and gone, but it is always a welcomed event to kick off the holiday season.  We have many Shop Crawl die-hards that make their rounds to each store for the deals and giveaways, sharing laughter and conversations.  I love the supportive community here in North Dundas.”

Windle says it’s also a great way to keep the small businesses connected and to support one another. There are always small changes and additions (Harvest Coffee, for example is a new participant this year.)

“This year The Planted Arrow welcomed Whisk and Willow, a Chesterville Bakery to our lawn to sweeten up the shoppers,” added Windle.” Lindsay’s cookies were super yummy; I may have over indulged.”

The Shop Crawl is just the first of several events (three over the next three weekends) which will hopefully make this a memorable season not only for the customers, but for the small businesses who rely so much on the final quarter of the year.