The Top Things to Do in Orangeville: An Ontario Town with A Cozy 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. Your next visit here will have you feeling like you’re on a movie set!

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Orangeville is one of those lovely Ontario towns where a lot of the action takes place on its charming main street. Over the past 20 years, Orangeville has focused on invigorating its downtown core, which has led to a truly memorable series of places to visit and things to do in Orangeville.

Orangeville is a hop, skip and a jump from neighbouring places like Ontario Honey Creations, the town of Mulmur and the city of Toronto.

No matter the time of year, Orangeville is a wonderful place to visit during any season. If you’re planning on visiting Orangeville during the winter, then I’ve included a special “Holi-Day Trip” itinerary near the end of this post.

It’s worth mentioning that for anyone looking to head to Orangeville from the Greater Toronto Area, it’s going to be closer than you think. 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.

This post contains affiliate links. Simply put, this means we may receive a small commission at no additional cost to you for sharing our honest recommendations.

A Little Bit 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.

Its name comes from the early 1800’s, when a businessman from Connecticut named Orange Lawrence built mills in and around the village. A post office was built in 1851, and on January 1st, 1874, Orangeville was given official town status.

A fun fact about the beloved Orangeville Public Library is that it was built in 1908 and was actually funded by the famous businessman, Andrew Carnegie, the same person who built Carnegie Hall in New York City.

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.

Where to Stay in Orangeville

The best place to stay on any multi-day trip to Orangeville and the surrounding Headwaters Region is at the Best Western Plus in Orangeville. It’s walking distance to all of the attractions on Broadway, and conveniently located right at the entrance to all of the action in town.

If you’re travelling with a family or small group, its suites are a great size, and offer kitchenettes perfect for storing any goodies you might pick up from the farmer’s market or shops during your stay.

Breakfast is included with most of the room offerings, and they have special event and meeting spaces on the main floor, too. If you’re interested in booking a stay at the Best Western Plus during your trip to Orangeville, then you can click here to learn more.

What to Do in Orangeville, Ontario

There are a lot of things to do in Orangeville, so allow me to walk you through some of my favourite activities so that you can make the most of your time during your next visit here.

Visit Island Lake Conservation Area

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.

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.

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

See a Show at Theatre Orangeville

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

For 30 seasons, Theatre Orangeville has been a trailblazer in showcasing what regional theatre can offer. 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.

David Nairn has been the Artistic Director since 1999 at the theatre. 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.

Their playbill is quite diverse, and offers a little bit of something for everyone. Since they’re celebrating their 30th season, they’re throwing a little extra flare into the mix, including their first ever original pantomime show called Cinderella…if the Shoe Fits. They also have guest performances and plenty of other shows lined up, so make sure you head to their website to see what’s on.

Before moving on, I also want to acknowledge the work that the theatre puts into supporting 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 that 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. The Ultimate Ontario Team is a big fan of what you’re doing!

Check Out the Orangeville Farmers’ Market

The Orangeville Farmers’ Market is, a year-round Ontario farmers’ market. They have an excellent setup during the warmer months of the year outside, but during the colder months they set up the Orangeville Winter Market on Saturdays in Orangeville Town Hall.

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. Their winter season is from November to April, and their summer season operates from May-October. 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. They have local vendors selling everything from meats to baked goods, and during the colder months you can expect warm delights like homemade sweet and savoury pies and organic teas.

You can take a look here to see what’s up and running at the time you’re interested in checking it out.

Dine Like a Pro at One of Orangeville’s Delicious Restaurants

Orangeville is full of incredible places to dine, no matter the meal time. The main street, Broadway, is 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.

Bluebird Cafe and Grill is an Italian restaurant owned by the kindest couple who bring local, delicious flavours to each dish they serve. Their menu draws on inspiration from all over, and you can count on their specials including some tasty seasonal fare.

On a recent trip for dinner during winter, I feasted on expertly prepared escargot, a seasonal chicken pot pie and rich homemade pasta for dinner. It’s important to save room for dessert here too, since owner Michelle prepares all of the desserts from scratch. Her white chocolate cheesecake and maple creme brulee were absolutely delicious. It’s well worth sharing two (or more!) desserts when you visit.

If you’re looking for an excellent place to grab a quick snack or a light lunch, Mochaberry Coffee & Co. is a fantastic cafe with delicious baked treats, sandwiches and a variety of freshly brewed coffees and seasonal delights.

I recently visited during the holiday season, and not only were they serving unique festive warm drinks, but they had a variety of flavoured coffee beans for sale, too. I ended up picking up a bag of Spiced Egg Nog beans, and they were absolutely incredible.

Some other restaurants you’ll want on your radar (in no particular order) on any trip to Orangeville are:

1. Greystone’s Restaurant: This restaurant is owned by the same family as Toronto’s most famous restaurant, Scaramouche. You can expect rich and delectable entrees and inventive cocktails here.
   
2. Pia’s on Broadway: Fresh, vegetarian and vegan friendly, and the ideal spot to get a soup or sandwich for lunch.
   
3. 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.
   
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.
   
6. Rustik Local Bistro: This homey kitchen offers warm and fresh dishes with locally sourced produce. They’re well known for their lunch, brunch and dinner offerings.

Hit the Shops on Broadway

Downtown Orangeville has a plethora of locally owned shops with unique items that are worth taking a look at. So many of the shop owners on Broadway are not only passionate about their stores, but passionate about Downtown Orangeville, too. Orangeville may have some of the kindest shop owners in Ontario, in our humble opinion!

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 both the summer and winter seasons. Orangeville has built sections in the middle of the road to grow trees and showcase their history, and 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 and are changed at various times throughout the year.

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

If you’re keen to pick up some sweets which would make the nicest gift, definitely check out The Chocolate Shop, Wicked Shortbread or Le Finis.

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.

At any given time, there are often three walking tour scavenger hunts that you can participate in. They range from offering ways to check out local art to learning about the history of the town.

Right now, the options for scavenger hunts are:

1. The Pursuit of Public Art Scavenger Hunt, which takes you through town to see all the beautiful displays of public art. As you make your way through the scavenger hunt, you can collect points and earn a free “Love, Orangeville” tote bag once you’ve completed it.
2. The Central West Art Quest Scavenger Hunt takes you on a hunt through the public art located on the west end of the city. There are clues to solve about the art you see along the way.
3. The Downtown Scavenger Hunt focuses primarily on the heart of Orangeville, with many clues you can solve along the way while learning about Orangeville’s history.

You can visit the Love, Orangeville website to learn more!

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 an Orangeville Art Walk

Orangeville is full of fun ways to explore public art in the city. Their Art Walk of Tree Sculptures is a unique experience that needs to make any list of what to do in Orangeville. 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.

There are several other ways to admire public art in Orangeville, like checking out the local artists’ murals that are painted across town, and seeing different sculptures in town, too.

Grab a Pint at Hockley Valley Brewing Company

If you’re keen to try some local beer, Hockley Valley has you covered. They’re located just a little outside of Downtown Orangeville.

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. I 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.

Visiting Orangeville in the Winter: A Cozy “Holi-Day” Trip

Orangeville makes for such a wonderful destination in the winter time, and especially during the holidays. The whole town gets decked out for the holidays, and it makes for an incredible shopping, entertainment and cozy celebration location for the perfect “holi-day” day trip!

This town truly has that special Hallmark movie quality where everything feels warm and cozy, and everyone knows your name. It’s the perfect place to spend some time during the holidays, and do some holiday shopping for your loved ones and yourself!

If you’re planning a holiday visit to Orangeville, or just planning for a little winter escape, then I’d propose this winter itinerary during your trip:

1. Stop by the Orangeville Farmer’s Market, located inside its historic Town Hall during the winter months. You can find gifts and goodies for everyone on your shopping list, especially the specialty food lovers!
2. Go shopping on Broadway. There are too many great stores to count, but some of my favourites are: Suzanne Gardner Flowers, Readers’ Choice Rare Books Store, Dragonfly Arts on Broadway and Pear Home. Whether you’re present shopping or looking for yourself, you’re bound to find something good here.
3. Have a light lunch or coffee break at Mochaberry Coffee & Co. They have all sorts of fun specialty coffees and treats to help you properly celebrate the holiday season.
4. Spend the afternoon popping into some of the best sweet shops around! The Chocolate Shop makes all of their own chocolate on site and feels like you’ve entered a European sweet shop. Other excellent stops are Le Finis for your French patisserie fix, and Wicked Shortbread for your Scottish sweet tooth.
5. Have a delightful, seasonally scrumptious dinner and the cozy and intimate Bluebird Cafe and Grill.
6. Finish off your day in Orangeville by catching a show at Theatre Orangeville! Tickets to one of their shows would make a great holiday gift, too.

That’s a Wrap on Orangeville Things to Do!

As always, I hope that this information serves you well in your adventures exploring this province.

Orangeville is an ideal place to head on a Saturday, or a weekend in general, and visit other nearby towns, cities, wineries or breweries as well.

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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This article was written in partnership with Central Counties Tourism. All opinions are my own.

If you’re looking for more information about York, Durham or Headwaters regions, then you can visit the York Durham Headwaters website. If you appreciated this article, you’ll love our newsletter, as well as our Facebook group! Feel free to join; all are welcome.