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10 Things to Do in Historic Orangeville

Posted : April 1, 2019

Our blog is chock full of great ideas for fun things to see and do in York Durham and Headwaters. We are always adding new content and updating old posts, but sometimes you might stumble upon something from our vault. If this article has inspired you to hit the road, be sure to double-check that the featured stops in this post are still welcoming visitors.

All year long, downtown Orangeville is an inviting destination in the heart of this vibrant community.  Broadway, the town’s main street, invites you to explore its charming selection of boutiques, specialty shops, studios, and eateries.  Here are 10 things to do in historic downtown Orangeville in spring, summer, winter and fall.

Art Walk of Tree Sculptures

Victorian Lady Web

Stroll the beautiful streets of Orangeville to discover the Art Walk of Tree Sculptures, a collection of more than 50 sculptures created by 19 artists since 2003. The goal of the program is to sustain the life of trees that have reached the end of their life expectancy in a way that allows them to continue adding character to the community. http://data.orangeville.ca/StoryMaps/MapTour/TreeSculptures/

Theatre Orangeville

Couple at Theatre

Whether it’s a matinee or evening performance, Theatre Orangeville is a must-visit while you’re downtown. Since 1993, Theatre Orangeville has celebrated excellence in the performing arts, featuring almost exclusively Canadian-written plays and performances.

Wicked Shortbread

Wicked Shortbread

All Butter, All Day – good luck making it home from Wicked Shortbread with a full dozen cookies intact. Wicked has a well-stocked case of mix-and-match shortbread cookies, as well as a great selection of decadent squares (butter tart squares, anyone!?) and non-shortbread cookies to treat yourself. Pick up a bottle of sparkling local Spirit Tree Cider, and you’ve got yourself a dessert picnic in the making!


Fromage Orangeville

The Big Cheese around town, Fromager Christine Patton owns and operates the perfect store for gourmands. Locally-baked breads, imported oils, exquisite cheeses and pates from the world over are all on offer. Or enjoy a lunch selected from a lovely Bistro menu and then enlist Christine’s expertise in curating the perfect charcuterie board.

Orangeville Farmers’ Market (Winter and Summer)

Orangeville Farmers Market

Town Hall plays host to Orangeville’s Winter Farmers’ Market, running every second Saturday from November to April. Once spring has sprung, the Farmers’ Market claims its weekly space just outside Town Hall every Saturday morning. At both markets, you can find local produce, baked goods, meats, eggs, and many more local goodies.

Maggiolly Art

Maggiolly web

Step into a stunning array of colourful art supplies at this awesome source of creativity. Pick up some fresh new tools or try something new in one of the many art classes and workshops. Maggiolly even offers art camps and lessons for kids!


go yoga

Drop in for a class led by some of the area’s most skilled teachers (you can even borrow a mat), or simply browse the thoughtfully selected pieces of ridiculously comfy yogi clothes and accessories at this bright, airy and welcoming sanctuary.

Dragonfly Arts on Broadway


This beautiful gallery showcases one-of-a-kind pieces by over 200 artists (many of them local); you’ll find anything from glass and wood art, to pottery, to jewelry. Take your time to browse and you’ll find something unique at every turn.

The Barley Vine Rail Company

The Barley Vine Rail Co. Orangeville 1250

One of Orangeville’s most beloved restaurants, the BVR (as it’s fondly called) is located inside Orangeville’s historic former train station. This restaurant prides itself on food celebrating Canada, which includes (no shocker here) an extensive menu of craft brews. Tuck in to a piping hot plate of Newfie Fries (fries and gravy, topped with stuffing), or deep-fried pickle spears – a local favourite.

Island Lake Conservation Area

Island Lake

Not to be missed, this beautiful 400-acre reservoir is nestled at the edge of downtown Orangeville and offers a year-round recreational retreat. Hike, bike or run the 8.2 km of undulating trail during the Spring, Summer and Fall. Rent a canoe or kayak in the Summer sun or try kick-sledding, snowshoeing or ice fishing during those winter months when you’re itching to get outdoors!

For all of these, and SO many more great places to eat, shop, browse and sweat, visit https://www.orangevilletourism.ca/

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