There has never been a better time to discover, or rediscover, what is Downtown Collingwood.

Article and photos by Heather Goldsworthy.

These days it seems that every time you wander along the streets of downtown Collingwood there is something new to discover. A new flower shop or fashion boutique, an organic eatery tucked down a side street, or a pop-up event. Over the past couple of years, Collingwood’s historic shopping district has evolved to include a diverse mix of iconic established shops and restaurants alongside new cafes, galleries, artist studios, and businesses offering well-curated collections of fashion, decor, and health & wellness products. Along with the retail and fine art sectors, the live entertainment venues, special events and festivals continue to grow along with them. There are too many to mention them all but here are a few downtown Collingwood experiences, winter happenings, and hidden gems to get you started.

Something we are seeing more and more of are businesses who are finding creative ways to elevate your shopping or dining experience. Tucked inside Leuk No.2, the bright, European feel of Lëuk Cafe makes it a beautiful space to enjoy a coffee and bite to eat either on your own or with a group of friends.

If a glass of wine is more your style check out the newly opened Posh Shoppe which, at the time of writing, is in the process of getting their liquor license so you can enjoy a bevie while you try on outfits. Metra Fashion House hosts regular fashion brunches and events giving you the chance to learn about seasonal trends and styles, while one of the newest kids on the block, Homme Femme, plans to host events at least once a month—partnering with the fashion and lifestyle brands they carry in store, or collaborating with other local business-owners. Another shop that consistenly works with fellow retailers to showcase local artisans is Cora Couture. You’ll be introduced to one-of-a-kind jewellery by Kate Knox and trendy eyewear from Blink along with original paintings by Zela.

Gibson & Company is also a fan of collaborations and often has something interesting in the works from tap-takeovers with micro-breweries to pop-up food events featuring local chefs. If you want to stay in the know about who is doing what and when make sure to follow these folks on social media or get on their mailing lists.

While you are wandering down Hurontario don’t neglect the block south of 3rd. Right on the corner, 1858 Caesar Bar has over 20 Caesar cocktails to try, from classic to outrageous (the garnish on some of them constitutes a meal) and all feature their own locally-produced Walkers OneShot caesar additive. Down the block in the old Crow’s Nest building, Mad Dog’s Coffee & Vinyl Cafe, with three-floors of new and vintage vinyl and collectables, is one place you can spend hours exploring. This block also houses a couple of hidden-gem eateries favoured by locals– Cabin Bistro, Fish & Sips, and the newest addition to the lunch crowd, Fig & Feta, a tiny little Greek joint that is a must-try.

There are many tasty reasons to venture off the main drag too. Head down Schoolhouse Lane (behind the CIBC and TD Banks) over to Pine Street to find Tesoro Mercato, and popular lunch spots Bent Taco, Azzurra Trattoria and The Curly Willow—which started as a little cafe in the back of a decor boutique on Hurontario but quickly gained such a loyal lunch crowd they moved into a larger space dedicated just to the cafe. One block further west, the Collingwood Winter Market is held on select Saturdays at the Trinity United Church so you can stock up on fresh produce, bread, meat and goods from local farmers and producers. If you’re looking for a bit of help planning your next Collingwood gourmet adventure check out the Good Food Stroll map at

While you are exploring, make sure to meander over to Simcoe Street. We wrote about this growing cultural district in our summer issue and in the short time since then it has continued to expand. Joining the Tremont Artist Studios, Simcoe St. Theatre and Blue Mountain Foundation Arts (BMFA) are Heather Cook Art and Honour Bright studio who share a space with Simcoe Street Books, and local artist Jason Alexander who has relocated his art supply store and Collingwood Art School to the old Enterprise Bulletin building.

The fun doesn’t only happen during the day – the Downtown Collingwood after-dark scene offers live music, theatre, and great dining. The Simcoe St. Theatre is home to the Be The Change Documentary Film Series—a selection of thoughtfully curated films that look at environmental, health and social change. Also on the billet is ‘Get Happy, That’s Amore’a Dean Martin, Frank Sinatra tribute on March 30th hosted by the Olde Town Terrace.

Theatre Collingwood has an exciting line-up at the Historic Gayety Theatre including The Love Cabaret, February 11 and Girls Nite Out, a comedy show hosted by Canadian comic Elvira Kurt in celebration of International Women’s Day, March 8. The Gayety Theatre also has a full docket of tribute shows in a wide range of music styles from Hotel California, an Eagles Tribute to Simply Queen and The Best of American Graffiti.

If you’re interested in hearing local talent, and live and original music The Huron Club features local musicians Thursday-Saturday and CROW Bar & Variety has a solid music program filling the stage Wednesday- Saturday with local artists, open mic nights, and fabulous acts from across Canada and the US. Both places promote their shows on their social media and you can also find an online calendar of live music events happening in Collingwood and surrounding area at

When you’re scheduling your winter adventures make sure to bookmark the Collingwood Family Jam. Held Monday, February 18 (Family Day) at Central Park Arena – this is a free event chock-full of activities for all ages from skating, swimming, and street hockey to crafts and curling so there truly is something for everyone.

You decide… a solo exploration, an afternoon excursion with friends or an evening out, there has never been a better time to discover, or rediscover, what is downtown Collingwood.

Heather Goldsworthy is a freelance photographer based in the Georgian Bay Area. Her work explores our food + beverage culture.