Orillia is an awesome Ontario weekend getaway destination

If you’re looking for a new place for a fantastic day trip or weekend getaway in Ontario, take a close look at Orillia. This city with a true small-town feel is less than two hours north of the Greater Toronto Area. Orillia is rich in arts and cultural experiences, plus it offers a wonderfully eclectic downtown shopping district. Mix in some excellent restaurants and cafés, and you’ll find Orillia provides a cozy and fun escape you’ll want to return to again and again.

Here’s a look at some of the best things to do in Orillia, Ontario. Build an itinerary around these great options and you can enjoy a romantic getaway, a girls’ weekend, or a road trip for family and friends.

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Fill a weekend in Orillia with fabulous cultural experiences

Orillia has a long and storied history with the arts. It’s well-known as the birthplace of legendary Canadian folk singer and songwriter Gordon Lightfoot. Stephen Leacock, one of the world’s most famous humorists in the early 20th century, called Orillia home later in his life. Thanks to these connections and many others, Orillia’s arts and culture scene is a delight to explore. Here are some ways to discover it for yourself.

A Night at the Museum is a unique way to visit the Orillia Museum of Art and History

The Orillia Museum of Art and History tells the city’s stories through a series of ever-changing exhibits featuring local archival content and visual arts. Visitors can explore the exhibits during the day for a nominal fee. It’s a great way to get to know the city.

Now, there’s a unique way to enjoy a visit. Through the new program A Night at the Museum, you can book exclusive after-hours access to the Orillia Museum of Art and History for a group of one to six guests. Your group will have the museum entirely to yourselves and will receive a custom program curated to your tastes.

Our experience with A Night at the Museum started with a guided cheese tasting. This was led by Amy Robert, owner of The Rind and Truckle, downtown Orillia’s artisanal cheese shop. Then, OMAH’s Executive Director Ninette Gyorody hosted a private unveiling and discussion of two paintings from local artists in the museum’s collection.

Finally, we had an opportunity to explore two of OMAH’s temporary exhibits. One exhibit celebrating the impact of teachers is on until January 11, 2025. It showcases the works of José Salas, who was an art teacher at Orillia’s Park Street Collegiate Institute from 1969 to 1994, as well as those of the many students he influenced. The Orillia: Then and Now exhibit features current and historic photographs of key landmarks in the city to show how it has evolved over time. This exhibit is on display until May 3, 2025.

This program offers such a wonderful and unique way to engage with the museum and its collections. From a date night to a gathering with friends or even a corporate event, the possibilities are endless! To inquire, email visitors@orilliamuseum.org.

Experience Orillia’s theatre and concert scene at the Orillia Opera House

The Orillia Opera House has been a fixture in the city since 1895. It’s the largest professional performing arts venue north of Toronto. The main stage has nearly 700 seats, and performances throughout the year include concerts, comedy acts, theatre, musicals, and more.

A favourite performance can become a great focal point for a weekend getaway. During our visit, the Mariposa Arts Theatre began its run of Gypsy: A Musical Fable, one of Broadway’s all-time great musicals. This production is wonderful, and tickets are very reasonably priced at $35 each. It’s well worth seeing before the show’s run concludes on November 17, 2024. A variety of performances is scheduled through the holiday season and again beginning in February 2025. Find a full list of upcoming shows at the Orillia Opera House here.

Discover a part of Canada’s heritage at Orillia’s Leacock Museum National Historic Site

When you visit Orillia, you’ll quickly notice the name Mariposa in use throughout the city. For this, we can thank Canadian humorist Stephen Leacock. His famous novel, Sunshine Sketches of a Little Town, features the town of Mariposa. Though Leacock reportedly denied it, Mariposa was clearly inspired by his adopted home of Orillia. Leacock and his wife built their summer home here in the 1920s on Old Brewery Bay. He lived here full-time later in life until his passing in 1944.

Leacock was a teacher, political scientist, and public speaker, though it was his humour writing that gained him notoriety around the world. For a time, he was considered the best-known English-speaking humorist on the planet.

Today, his home on Old Brewery Bay stands as Leacock Museum National Historic Site and is maintained and operated by the City of Orillia. The museum is worth visiting for several reasons. It’s an opportunity to learn more about Leacock’s legacy, but it also provides a chance to tour a beautifully preserved high-society 1920s vacation home and find out what life was like a century ago.

Check out Orillia’s cafés to see works created by local artists

As you walk through downtown Orillia, you’ll come across two wonderful coffee shops. Apple Annie’s is on Mississaga Street, Orillia’s main drag. It serves a variety of coffees and teas, sandwiches, and baked goods. The Lone Wolf Café is just around the corner on Matchedash Street. It offers classic café fare, and it becomes a cocktail bar in the evenings on Thursdays, Fridays, and Saturdays. Both locations showcase works by local artists that you can peruse during your visit.

Find unique gifts and treats in Orillia’s downtown shopping district

Orillia has a wonderfully vibrant downtown area that’s packed with unique shops selling all kinds of products. Whether you’re looking for baked goods and sweet treats, an independent bookstore, or gifts for the mystic or music enthusiast in your life, Orillia’s got you covered.

Mariposa Market, Orillia’s bakery destination

The amazing Mariposa Market has been a fixture in downtown Orillia for more than 35 years. This shop’s centrepiece is its unique range of fresh baked goods. These range from Chelsea buns and Muskoka berry pies to cookies, huge apple fritters, and their famous Texas donuts. There’s also a café at the back for grabbing a coffee or sandwich to go with your sweet treat. Up front, the bakery is flanked by a sweet shop packed with classic candies and a housewares store selling premium products and seasonal goods for the home. Repeat visitors to Orillia will tell you no tour of the town is complete until you’ve heard the creaks of this historic storefront’s wooden floorboards beneath your feet!

Susie Q Fudge and Gifts, for handmade fudge and sweet treats

Walking into Susie Q Fudge and Gifts feels like stepping back in time. Located directly below Mariposa Market, the shop’s counters display more than a dozen varieties of fudge. On the walls, you’ll find nostalgic candies, coffees and teas, and a variety of housewares and other gifts. When you stop in, just ask and you’ll receive a free sample of their creamy and delicious fudge. Go ahead and try to leave without buying some to take home!

Manticore Books, the largest independent bookstore north of Toronto

Hands up if you love supporting independent bookstores! Manticore Books in Orillia is the largest independent bookshop north of the GTA. This cozy space features titles under categories ranging from fiction to crafts, recipes, wellness, and more. There are also multiple displays highlighting books by local, Canadian, and Indigenous authors. Step inside this heritage building and dive into a wonderful world of words.

Alleycats Music, for vinyls, band shirts, and more

This eclectic music store comes by its name honestly: it really did originate in a closed-in alleyway between storefronts when it opened in 2012. Alleycats Music has since expanded to fill the spaces on either side of that alley, filling three storefronts in total! You could spend all day browsing through the crates upon crates of records, the many band t-shirts hanging from the walls, and the hundreds of posters. You’ll sometimes encounter live music happening in the shop. If you miss it, pick up the monthly newsletter produced by the shop to learn about live performances happening throughout the region.

One of the coolest offerings at Alleycats is their gift cards. Instead of the typical piece of plastic, you’ll be invited to pick out a free 45 and it will become the gift card for you to pass on to the lucky recipient.

My Moon Collective, an Orillia shop for the modern mystic

Modern mystics, channels and diviners, this shop is for you! My Moon Collective is a downtown Orillia shop dedicated to all things spirituality, wellness, and ritual self-care. Its shelves are stocked with crystals, tarot cards, herbs and incense, talismans and spell jars, as well as housewares such as candles, soaps, and hand-painted mugs.

DWN Craft Chocolatier

At DWN Craft Chocolatier, chocolate is a canvas for creative expression. This award-winning chocolate maker loves to experiment with different flavour profiles and combinations. Some earn evocative names, such as “sitting at a cozy dark bar in Toronto sipping a toasted Old Fashioned,” which combines dark chocolate with maple whisky and tart buckthorn berries. Alongside these unique chocolate creations, you’ll also find locally made products such as jams, handmade cards, flavour-infused Ontario honey, and others.

Here are a few more shops in Orillia that we haven’t had a chance to visit but come highly recommended: The Rind and Truckle cheese shop, The Kitchen Shop for kitchen products and housewares, and the Cards and Coasters board game café.

Check out Orillia’s great food scene

Orillia is home to some excellent restaurants that will make a great addition to your visit. Picnic Wine and Tapas Bar brings a Spanish flair to its concept, menu, and decor. Combine classics like olives and jamón with unique takes such as the patatas bravas pancakes and duck confit with pickled Saskatoon berries, and enjoy with a glass of wine, a cocktail, or a non-alcoholic negroni.

FARE Restaurant is located next door to the Leacock Museum National Historic Site. These two spots make a perfect combination. Grab a crafted cocktail, alcoholic or not, and enjoy a bite to eat in their cozy dining room to fuel up for your museum tour. During the warmer months, the tables on the patio overlook Old Brewery Bay on Lake Couchiching.

Stay in the heart of Orillia at the Champlain Waterfront Hotel

If you’ll be spending most of your time downtown during your Orillia getaway, an overnight stay at the Champlain Waterfront Hotel is an easy choice. The rooms are cozy and well-appointed, and it’s located just a block from Orillia’s revitalized waterfront parks and within walking distance to downtown Orillia’s shopping and theatre district. We found the room rates to be extremely reasonable during our weeknight shoulder season stay!

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