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 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 Vaughan, 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 1800s, 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

If you’re searching for an ideal place to stay in Orangeville, the Hampton Inn & Suites by Hilton is the town’s newest hotel. They’re located a short drive from the hustle and bustle of Broadway in Downtown Orangeville, with comfortable rooms and plenty of parking.

A hot breakfast is included with every night’s stay at this hotel, and their rooms have comfortable beds and ample pillows, which makes relaxing between activities in town extra enjoyable. They even have a pool if you’re looking to take a splash.

If you’re interested in booking a stay at the Hampton Inn & Suites 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.

Make Memories at Pottery Parties Studio

If you’re looking for a memorable experience during your time in Orangeville, this is an exciting activity to enjoy during your visit. Locally owned by Tanya Frew, Pottery Parties has been a beloved community staple in Orangeville for many years. It’s a great place to come for exactly that–a pottery party for all ages. But Tanya and her staff also offer a variety of unique experiences for guests to take part in at her bright and cozy studio.

Tanya prides herself in offering visitors the opportunity to create “fired arts with memories” attached to them. Whether you have a group class, bring a family member or take part in some pottery making on your own, you will surely to leave with memories. On my most recent trip to the studio, my dear friend Allison and I decided to try our hand at making some silver clay jewellery with Tanya.

The Silver Clay Jewellery experience offers visitors the opportunity to select a piece of silver jewellery they’d like to make–either a bracelet or a necklace–and then create a pendant formed with clay that transforms into silver, stamped with a fingerprint. Tanya walks guests through the entire process, and it’s a fun way to commemorate a friendship or partnership with a loved one, since you can both imprint your fingerprints on the same pendant.

Sitting with Tanya and learning about her studio and how the jewellery is made is a very relaxing process. Tanya is warm and welcoming, and clearly a supportive instructor and beloved person by the many families and patrons who have been visiting her studio for years. She patiently walked Allison and I through the process of how the fingerprint pendants are made, and let us take our time making just the right impressions on our pendants.

In less than 24 hours, Tanya completed the firing and polishing of our silver jewellery, so that we could take it home. I opted for a bracelet, and Allison opted for a necklace. This was such a fun experience to have together, and I would highly recommend this as a unique experience gift to give for a holiday or special occasion, or just as a fun afternoon spent out with a loved one!

Whether you are coming to paint pottery, roll out clay to make impressions on for family memories, make silver clay jewellery, or make your own pottery on the wheel in their studio, there is a truly a memorable experience for anyone who visits Pottery Parties Studio.

You can learn more information about all of the studio’s offerings on their website.

See a Show at Theatre Orangeville

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

For more than 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. In the 31st season of the theatre, Nairn is officially in his final year as Artistic Director. The community will welcome Jennifer Stewart as the incoming Artistic Director in 2025.

Their playbill is quite diverse, and offers a little bit of something for everyone. During the holiday season specifically, they typically do a pantomime show. The 2024-2025 season’s panto show is called Sleeping Beauty. 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, and 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.

Sip on Crafted Cocktails at a Speakeasy

If you’re looking for the perfect addition to an evening spent in Orangeville, then I always have a hard time turning down a good speakeasy. Revival 1864 is an excellent place to come for just this.

They’re located under Barley Rail Vine along Broadway, and they serve up delicious cocktails and live entertainment, all tucked behind an unassuming bookcase. A visit here will make for a memorable nightcap with whomever you’re visiting.

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 tasty, seasonal fare.

You can enjoy dishes like 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.

Rustik Local Bistro is another inviting, inventive restaurant on Broadway. They serve up a range of seasonal dishes featuring a wide variety of locally sourced produce. They’re well known for their lunch, brunch and dinner offerings.

During a recent winter time visit, we dined on dishes like Maple Roasted Squash Buffalo Mozzerella Salad with shaved brussels sprouts and pickled red onion, homemade Daily Spätzle with pork, zucchini and fresh corn, and Duck Breast with celery root puree and heirloom vegetables. Each dish was uniquely different from the next, and packed with local flavour. I’d recommend saving room for dessert and trying a slice of their famous Rustik Beer Pie–it’s a rich chocolate pudding and beer pie, with a graham cracker and pretzel crust, topped with a toasted marshmallow meringue. And it might just be even more delicious than it sounds.

If you’re looking for an excellent place to grab breakfast, 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 one of Toronto’s most famous longstanding restaurants, 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.

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 their 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, Moguls in Mocean, Suzanne Gardner Flowers, and Readers’ Choice Books.

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

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 town 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.

Venture Over to Nearby Hockley Valley for a Taste of Small Town Living

If you’re keen to get a taste for small town living just outside of Orangeville, the Hockley Valley area offers some excellent opportunities to do so.

Hockley Valley General Store

One of my favourite places to visit is the Hockley Valley General Store. It feels like the type of place you’d find in a cozy, feel-good TV show, and is a community gathering place. They have a small but mighty cafe serving up delicious coffee and freshly baked bread and sweets, and an incredibly curated boutique grocery, spirits and gift section.

Hockley Valley Brewing Company

Another staple in the area is Hockley Valley Brewing Company. 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.

Hockley Valley Tree Farm

This is a must-visit place if you’re in and around the Orangeville area during the holiday season. From late November to late December, they open as a tree farm and gift market, making for the perfect place to come for a horse and wagon ride as a family, or to find your perfect tree.

Note that they’re only open on Friday afternoons, and 9am to 5pm on weekends during this time of year.

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 and more 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.

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, Moguls in Mocean 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. Another excellent stop is Wicked Shortbread for your Scottish sweet tooth.
5. If you’re looking for another fun day-time activity, Pottery Parties Studio is the perfect place to come and make silver fingerprint jewellery with a loved one, or paint holiday-themed pottery for the perfect gift, Christmas ornament, or to take home. Or maybe you’re interested in some holiday shopping just outside of Orangeville. The Hockley Valley General Store is an excellent shop to come to for gifts, and the Hockley Valley Tree Farm offers all sorts of Christmas trees if you’re looking to bring one home.
6. Have a delightful, seasonally scrumptious dinner at the cozy and intimate Bluebird Cafe and Grill or Rustik Local Bistro.
7. Admire the lights downtown, lit up along Broadway, and Christmas in the Park at Kay Cee Gardens.
8. 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 Orangeville Tourism, or 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.