January: Niagara-on-the-Lake
Address: Niagara-on-the-Lake, ON
Why You Need To Go: There's no better way to kick off 2024 than with a trip to Niagara-on-the-Lake. The historic village transforms into a frosty paradise each winter and it's full of cozy experiences and stunning views.
One of the biggest January events in the area is the Icewine Festival, running on select dates from January 12 to 28, 2024. The boozy event transforms the heart of Niagara-on-the-Lake into a glistening "Icewine Village" complete with ice sculptures, samples and more.
There are also specialty programs, galas, and events happening at participating wineries and locations throughout the festival.
Aside from the Icewine Festival, you can explore the many local shops in the town's charming core, indulge in meals at the restaurants and explore the surrounding wineries.
Tourism Niagara website
February: Ottawa
Address: Ottawa, ON
Why You Need To Go: In February, you'll want to bundle up and take a trip to Canada's capital city, Ottawa. The area is home to so many winter activities and it's worth braving the cold for.
The biggest draw is Winterlude, an annual event running from February 2 to 19 this year. The "can’t-miss winter event" features endless cold-weather attractions, from snow tubing to art installations and more.
You'll also want to lace up your skates and glide along the Rideau Canal, the "world’s largest skating rink."
Ottawa Tourism website
March: Almonte
Address: Almonte, ON
Why You Need To Go: March is maple season in Ontario and Almonte is a great spot to experience this sweet Canadian delicacy.
The charming small town is close to several sugar bushes where you can live out your maple dreams. Fulton's boasts a 400-acre sugar bush and many maple experiences during the spring and winter months. From sleigh rides to a maple shop, you can dive into a maple wonderland.
You can also head to Fortune Farms for more maple fun.
Almonte is a stunning village complete with quaint boutiques, cozy cafes and more. It's surrounded by stunning countryside where you can enjoy a late winter or early spring walk.
Almonte website
April: Stratford
Address: Stratford, ON
Why You Need To Go: A spring trip to Stratford is worth adding to your 2024 bucket list. The gorgeous city will make you feel like you're in Europe and has so many charming restaurants and shops to explore.
April marks the start of the city's annual Stratford Festival, an iconic theatre series featuring a mix of Shakespearean and other exciting plays. From classics like Romeo & Juliet to musicals like The Sound of Music, there's something for everyone.
Visit Stratford website
May: Burlington
Address: Burlington, ON
Why You Need To Go: April showers bring May flowers, so during this month, you'll want to check out some gorgeous gardens and blooms. Burlington is a great spot to get lost in blossoms and breathe in the sweet smell of spring.
Spencer Smith Park is a popular spot for cherry blossom viewing. The area boasts a tunnel of trees where you can wander beneath a dreamy canopy of petals.
You can also head to the Royal Botanical Gardens and "experience one of the largest and most diverse lilac collections in the world," which typically blooms in May, according to the website.
Tourism Burlington website
June: Kingston
Address: Kingston, ON
Why You Need To Go: With the weather heating up, it's time to take a trip to Kingston. The historic city, dubbed the "Limestone City," offers tons of sunny-weather excitement.
Whether you're wandering by the waterfront with a sweet treat from Mio Gelato, indulging in a meal on one of the many patios, or browsing through the array of shops downtown, you're in for a good time.
Keep an eye out for experiences like Movies in the Square, cruises, trolley tours and more.
Visit Kingston website
July: Elora
Address: Elora, ON
Why You Need To Go: According go the Elora website, this town has been dubbed "Ontario's most beautiful village" and it's easy to see why.
The quaint streets, boutiques and eateries all have a European vibe, making this small town an idyllic spot to spend a summer day.
Not only can you enjoy the sun-filled streets and patios, you can also head to the iconic Elora Quarry and take a dip in the stunning turquoise swimming hole.
Elora Fergus website
August: Prince Edward County
Address: Prince Edward County, ON
Why You Need To Go: Boasting dreamy small towns, picturesque wineries and gorgeous beaches, Prince Edward County has "summer getaway" written all over it.
You can enjoy a movie under the stars at the Mustang Drive-In PEC, ride your bike along scenic trails, or spend a day in a sweet small town like Picton.
Sandbanks Provincial Park is one of the biggest highlights of the area during the summer months. The destination is home to three white sand beaches and tropical-blue waves.
Visit the County website
September: Tobermory
Address: Tobermory, ON
Why You Need To Go: While Tobermory is typically a July or August-type destination, it's worth planning a visit during September. The little beach town tends to get pretty crowded during the peak summer months, but in September, you can potentially enjoy a quieter atmosphere while still soaking up that warm weather.
From diving into crystal-clear waters to visiting the iconic grotto, exploring Flowerpot Island or cruising over shipwrecks, this enchanting destination is a nature-lover's paradise.
Tobermory website
October: Muskoka
Address: Muskoka, ON
Why You Need To Go: Muskoka is known for its rugged beauty, array of celebrities and incredible year-round attractions. If you want to experience the fall foliage to the fullest, this destination is the place to be.
The landscape transforms with vibrant colours of red, orange and gold, making it an autumn wonderland. You can take part in fall driving routes, climb lookout towers to take in the colours and more.
There are many small towns to visit for all your shopping and dining needs. You can also head to Sandhill Nursery for their annual Fall Festival.
Discover Muskoka website
November: Toronto
Address: Toronto, ON
Why You Need To Go: Toronto offers endless things to do year-round, but if you're obsessed with Christmas, then November is the time to visit the province's capital city.
There are so many fun holiday events to enjoy and you can easily fill up a weekend with festive activities.
The iconic Winter Village at the Distillery District is a must-visit for every Christmas-lover. You can also head to WinterFest at Canada's Wonderland, see the Santa Claus Parade, enjoy the decor at Casa Loma or visit one of the city's many Christmas bars.
Destination Toronto website
December: Blue Mountain Village
Address:
Why You Need To Go: Bring on the Christmas cheer! This enchanting pedestrian village transforms into a real-life Christmas town each holiday season and you won't want to miss out on a trip here.
The Holiday Magic at Blue event typically runs from November to January and it's brimming with festive magic. You can wander along a glowing trail of lights, sip cozy drinks, shop for gifts and take in the decor.
The charming town of Collingwood is located nearby and has lots of shops and eateries which come alive during the holiday season. You can even take a trip to the Scandinave Spa for a day of relaxation.
Blue Mountain Village website
Before you get going, check out our Responsible Travel Guide so you can be informed, be safe, be smart, and most of all, be respectful on your adventure.
