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The Top Things to Do in Orangeville: An Ontario Town with an Incredible Main Street

Orangeville, Ontario is a pretty Ontario town by any standard. Beyond that though, it’s got a main street that most big cities would covet, as there are shops, restaurants, bars, and historical buildings galore.

Things to do in Orangeville
Bri and Chris on a night out at Theatre Orangeville. Photo Credit: York Durham Headwaters

Orangeville is one of those lovely Ontario towns where a lot of the action takes place on one, lengthy charming street. Recognizing this, Orangeville actually doubled down on Broadway in 2005, and resurfaced the street while adding large planters in the downtown section between First and Third Streets.

Well, any visitor can see that that investment showed a lot of foresight, and Orangeville continues to benefit majorly due to this. And, thankfully, so do we!

It’s also worth mentioning that, for a lot of Ontarians, Orangeville is going to be closer than you thought. This applies largely to our Toronto based readership, who might not know that this town is only about an hour away. There’s also no shortage of great spots that surround the town. You’ve got nearby wineries like Adamo Estate Winery, access to fairly close cities like Guelph, and plenty of opportunities for lovers of the Ontario outdoors.

About Orangeville, Ontario

In the present day, Orangeville is a town of roughly 30 thousand people, located in south-central Ontario. It’s the seat of Dufferin County, which covers an area of a little under 1500 square kilometres, and is the highest plateau immediately south of Georgian Bay.

The first patent of land was issued to a land surveyor in the early 1800s, but the modern formations of the town began to take shape when Orange Lawrence, a businessman from Connecticut, began to build mills in the village. A post office was built in 1851, and on January 1st, 1874, Orangeville was given town status (and named after Orange Lawrence).

Fun fact – the beloved Orangeville Public Library (located at Broadway and Mill Street) that was built in 1908 was actually funded by the famous businessman, Andrew Carnegie!

Fans of Canadian literature may know that author Robertson Davies is from Orangeville, and they’ve also had a number of famous athletes come from the town such as basketball player Jamal Murray, skier Laurie Graham, WWE star Edge, and hockey players such as Brett and Nick Ritchie as well as Dan Ellis.

What to Do in Orangeville, Ontario

There are lots of things to do in Orangeville, and we’ll walk you through some of our favourite activities so that you can make the most of your visit there.

Visit Island Lake Conservation Area

Part of what makes Island Lake Conservation Area great is that it’s very much accessible and appreciated throughout all four seasons. The warmer months provide locals and visitors with incredible opportunities for hiking, canoeing, camping, cycling, paddle-boarding and fishing. And the winter months offer the chance for ice-fishing, cross-country skiing, snowshoeing, and more! You can find more information on specific trails etc. here.

The Island Lake Conservation Area is home to over 800 kilometres of lakes, wetlands, forests and meadows in the towns of both Orangeville and Mono. It’s an important habitat for many of our animals, but is known in particular for Osprey sightings.

In the case of a lot of Ontario towns, they have conservation areas nearby, but this is as close as it gets. It’s as accessible as it could be.

See a Show at Theatre Orangeville

Theatre Orangeville
From a 2018 show at Theatre Orangeville. The sets are fantastic! Photo Credit: Christopher Mitchell

Is there anything better than a historic theatre with big, comfy plush red seats?

Since the mid 1990s, Theatre Orangeville has been a trailblazer in showcasing what regional theatre can be. If you’re a fan and supporter of Ontario theatre and the arts in general, then it would be a missed opportunity to not try to see something at Theatre Orangeville during your visit. On that note, you can head to their site to see what’s coming up!

The playbill is really quite diverse, so you’ll find a nice mixture of classic shows and intriguing, original Canadian works.

The last time we visited the town, we had a chance to meet David Nairn, the Artistic Director since 1999. He deserves a lot of credit for dreaming big and making a name of Theatre Orangeville, and for ensuring that a visit to Theatre Orangeville simply has to be on any list of things to do in Orangeville, Ontario.

Before moving on, we also want to acknowledge the work that the theatre puts in to supporting the youth in the community. The Theatre Orangeville Youth Academy has been an inspiring model for what can be accomplished when we support the arts, and the arts provide support right on back.

And, as they also note, “since 2008, Theatre Orangeville in partnership with Community Living Dufferin has been offering the Creative Partners On Stage (C.P.O.S.) program.  This program provides educational and performance opportunities for adults with developmental disabilities. At Theatre Orangeville we are dedicated to the development of this on-going arts-based quality-of-life enrichment programs.”

Good on you, Theatre Orangeville. We’re huge fans.

Take a Self-Guided Walking Tour or Do a Scavenger Hunt

Orangeville knows they’ve got a town that’s worth exploring, and as such, they’ve put together some programming that makes it both fun and easy to explore.

There are 3 historic walking tours. There’s the 2.2 kilometre “Booming Broadway Tour,” which highlights Orangeville businesses that helped the town grow. There’s the 2.5 kilometre “Founders Tour,” which highlights the founders of the town and celebrates some notable landmarks. And there’s the “Prosperous Years Tour,” a 2km tour which focuses on Zina Street and the success of local merchants and business people, while also showcasing landmarks.

If any of those tours sound intriguing and you want to complete them on your visit, you can download the maps and information you’ll need nice and easily from the Orangeville website, and we’ve linked it for you in the preceding words.

On that page, you’ll also find information about a downtown scavenger hunt, where you’ll solve 16 clues during a 30 minute stroll along Broadway. There are also two public art scavenger hunts.

Especially if you have a family, anything we’ve mentioned here could be a lot of fun!

Do Some Shopping on Broadway

Downtown Orangeville has a plethora of locally owned shops that have some unique items that are worth taking a look at. Not to mention, our experience with shop owners on Broadway has always been nothing but pleasant. Orangeville may have some of the kindest shop owners in Ontario!

One thing that’s fun about shopping on Broadway is that when you’re walking up and down the street, you can appreciate the Broadway medians, which are especially gorgeous in the warmer months. If you haven’t been, we’re referring to the way Orangeville has built sections in the middle of the road to grow trees and showcase their history, and just generally beautify the town.

Take your time and pop in and out of shops. Broadway is also known for the window displays that almost act as public art exhibits!

Some well known shops include Dragonfly Arts on Broadway, Healing Moon, Sproule’s Emporium, and Readers’ Choice.

Check Out the Orangeville Farmers’ Market

Firstly, the Orangeville Farmers’ Market is, typically, a year-round Ontario farmers’ market, but at this time, they’re focusing on their outdoor operations taking place in the warmer months of the year. Typically, though, the Orangeville Winter Market takes place in Orangeville Town Hall. You can take a look here to see what’s up and running at the time you’re interested in checking it out.

The Orangeville Farmers’ Market is Dufferin County’s largest farmers’ market, and it’s actually one of the largest markets in the entire Headwaters Region.

In the summer season, the market operates from May-October, and it runs from 8am-1pm. It’s all about local food and supporting local vendors. Speaking of that, they do an excellent job on their Facebook page of highlighting some of those local Ontario vendors and keeping everyone informed. You can just over 5k others in liking their page if you’re keen!

It’s a great market that we’ll be sure to visit again soon, I’m sure!

Keep Tabs on Orangeville Events

There’s a lot going on in Orangeville for a town its size. So much so, they’ve actually got a searchable events calendar, so you can always see what might be going on when you’re hoping to visit Orangeville, or can even plan your visit to Orangeville around a particular event.

Some top events include:

  • Orangeville Blues and Jazz Festival: Running the first week of June, it regularly features almost 100 acts across for stages as well as local restaurants and bars.
  • The Harvest Celebration: The Harvest Celebration usually takes place in Downtown Orangeville around Halloween.
  • Moonlight Magic & The Tractor Parade of Lights: This takes place around the Christmas holidays.
  • The Taste of Orangeville: This usually takes place in August and celebrates the best of Orangeville food, music, and shopping.
  • The Great Taste Fashion Gala: This also typically takes place in August and is a celebration of local fashion and food.

Make Time for the Orangeville Art Walk of Tree Sculptures

Orangeville art walk of tree sculptures from
A map of the Orangeville Walk of Tree Sculptures from a 2016 brochure. Credit: The Town of Orangeville

Orangville’s Art Walk of Tree Sculptures is so utterly unique that it needs to make any list of what to do in Orangeville. Not to mention, by following the trail of tree sculptures, you’re going to also learn a ton about the town.

In all, there are over 50 tree sculptures on public property made by about 20 different artists from the Headwaters Carving Club. The first tree was carved back in 2003, and since then this project has taken on a life of its own.

The program came about as a way to take trees that were dying or reaching the end of their life cycle and repurpose them to add character back into community. As the notes notes in their brochure about the program, “the sculptures are about art, heart, and community. They have stories to tell.”

We’ve taken a screenshot of the map and included it up above so that you can use it to guide your walking around the town, and keep your eye out for them!

Grab a Pint at Hockley Valley Brewing Company

If you’re keen for a wobbly pop, Hockley Valley has you covered, Monday to Friday 9am-5pm. They’re located in Orangeville, more or less, and not well outside the town, so it should be relatively easy access.

Their most popular beer is the Hockley Dark. The brewmaster at Hockley combined two styles of ales that he loved while studying in the UK, and the result is this beer. It’s likely a little on the lighter side of dark beers you’ve had in the past, but it’s a hit with customers. We wouldn’t be surprised if this was their best seller by a hefty margin.

Their Amber Ale and Classic would be the other two beers that are filed in the “popular” category. The Amber is apparently inspired by the warmth and colour of autumn in Ontario, and there’s a nice caramel finish. The Classic is, as it sounds, a fairly easy drinking blonde beer.

Taste What Orangeville Has to Offer

The main strip that we’ve mentioned a good thousand times, Broadway, is also packed with excellent spots to eat. If you’re looking for a quick bite or sip, keep your eyes peeled for a coffee shop that looks inviting.

If you’re looking to properly sit down, then here’s a few restaurants you’ll want on your radar.

  1. Pia’s on Broadway: Fresh, vegetarian and vegan friendly, and the ideal spot to get a soup or sandwich for lunch.
  2. Forage: This is regularly in the conversation for the best restaurant in Orangeville. They personally describe themselves as the “top casual dining restaurant in Orangeville.” Seasonal fare in a stylish space.
  3. Bluebird Cafe & Grill: Located on Broadway (surprise, surprise), this spot is all about pastas, pizzas, and contemporary Italian cuisine.
  4. Coriander Kitchen: A fantastic Indian restaurant that had ended up offerings some of the best vegetarian food in the town (though they do serve meat as well).
  5. Mill Creek Pub: If you’re looking for the local watering hole with pub fare, this is it.

If Rustik is opened up again, that should also be near the top of your list as well.

That’s a Wrap on Orangeville Things to Do!

Orangeville Town Hall
Orangeville Town Hall. Photo Credit: Christopher Mitchell

As always, we hope that this information serves you well in your adventures exploring this province. Orangeville is an ideal place to head on a Saturday (or weekend in general) and to visit other nearby towns, cities, wineries or breweries as well. You can also make a weekend of it, and stay somewhere like Hockley Valley Resort, grab a glass of wine or bottle at Adamo, and then head into town for some walking around and a meal, and perhaps a show at Theatre Orangeville.

How you choose to explore is up to you. There are no wrong answers, but, to us, it’s clear that Orangeville is an Ontario town worth appreciating.

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Sharon Spittachine

Sunday 7th of August 2022

Is there a current map of the walk of tree sculptures available and how could I get a copy?

Christopher Mitchell

Monday 8th of August 2022

This may work!

Larry Duwyn

Thursday 13th of January 2022

Orangeville, Ontario has so much to offer. If you haven't visited there yet then it is time to plan a visit and take in a show at Theatre Orangeville.

Christopher Mitchell

Friday 14th of January 2022

We agree, Larry!