Ontario is brimming with charm during the winter months, and the festive towns of the province offer a wide variety of events and things to do on any cold day. In this article, we’ll take a closer look at some of the most enchanting winter festivals and events that you can’t miss in these communities.

Towns featured in this article include:

• Niagara-on-the-Lake
• Blue Mountain
• Stratford
• Perth
• Kingston

Niagara-on-the-Lake Holiday Events

Niagara Icewine and Culinary Festival

Niagara-on-the-Lake is the perfect winter destination for a short getaway, especially during the Niagara Icewine Festival, which runs each January. In 2025, the festival will be held from January 10-12, 17-19, and 24-26. The town is renowned for its ice wine, and the festival allows you to sample some of the best. You can visit the participating wineries and enjoy the Icewine and Culinary Festival, which pairs delicious icewines with locally sourced gourmet food.

Cool As Ice Gala

If you’re looking for something more sophisticated, the Cool As Ice Gala on January 18, 2025, is a wonderful experience. Held at the Niagara Parks Power Station, this event combines a glamorous setting with live entertainment, fine dining, and tastings of rare icewines. Tickets for this gala typically start at $225 per person, and since much of the festival is outdoors, make sure to dress warmly—layering is key to staying comfortable as you wander between wineries. And since the town is a hot spot during this time, it’s wise to book your accommodations ahead of time to ensure you get the best options.

Blue Mountain Holiday Events

Holiday Magic at Blue Mountain

Blue Mountain Resort in Collingwood is a winter sports enthusiast’s dream, and from November 16, 2024, to January 5, 2025, the festivities around the resort make it a perfect winter getaway for everyone. The Holiday Magic festival fills the village with excitement, featuring live music, snow sculptures, and fireworks to brighten the long nights. Imagine standing in the village, surrounded by snow-covered peaks, sipping hot cocoa, and enjoying festive entertainment. It’s a family-friendly experience, with activities for all ages, from snowman contests to winter games. You can check the event schedule on the Blue Mountain website.

Winter Fest Day

Scheduled for January 25 and 26, 2025, this free, family-friendly event is the perfect way to embrace this winter season. During these two exciting days, the village will be buzzing with activity, featuring live music that sets a festive mood throughout the day and evening and offers a range of winter games and interactive activities such as snowball tossing, snowman-building contests, and fun challenges for all ages.

One of the biggest highlights of Winter Fest Day is the fireworks display that lights up the night sky. Make sure to find a spot with a clear view, as this spectacular show will leave you in awe. Additionally, Winter Fest Day will feature special appearances by members of the USA Luge Team, who will participate in demonstrations and meet-and-greets with visitors. This is a unique opportunity to learn about the exciting sport of luge from the athletes themselves and get a few tips if you want to try out some winter sports during your visit.

As a free event, it’s the perfect time to experience Blue Mountain Resort’s winter charm without any added costs. Be sure to bundle up, as the event takes place outdoors in the crisp winter air, and plan to arrive early to make the most of all the activities and performances.

Stratford Holiday Events

Lights on Stratford

The Lights On Stratford Winter Festival of Lights is an annual event that transforms the charming town of Stratford into a glowing winter wonderland. Running from December 13, 2024, to January 19, 2025, this vibrant festival features a variety of interactive light installations.

This year’s theme, “REIMAGINE,” invites visitors to experience Stratford in a completely new light. The festival’s light trail stretches from Market Square to Tom Patterson Island, where you can wander through beautifully illuminated displays. Visitors can enjoy large-scale art installations that use light, colour, and movement to create an immersive and magical experience.

Stratford Winterfest

If you’re looking for an exciting way to celebrate winter, Stratford Winterfest is the perfect event. Scheduled for January 25, 2025, Winterfest is a family-friendly celebration of all things winter, with activities designed to bring people of all ages together for a day of fun in the snow.

This free event features a variety of activities for all ages, including snow gliding on tubes and toboggans, snow golf, ice skating, and snowshoeing. Visitors can also enjoy live music, seasonal treats from local vendors, and family-friendly competitions. With plenty of opportunities for outdoor fun, Winterfest is the perfect way to embrace the season.

Perth Holiday Events

Festival of Lights

Beginning November 15, 2024, the downtown streets of Perth are adorned with thousands of twinkling lights that create a festive ambiance throughout the winter months. The lighting ceremony on December 6, 2024, marks the official start of the season, with everyone coming together for a spectacular display. Throughout downtown, you’ll find the town’s historic buildings and trees lit up in vibrant colours creating the perfect backdrop for some holiday shopping, with local shops offering unique gifts and delicious treats. Additionally, the event includes a variety of special activities such as caroling and holiday performances so be sure to visit after dark for the best experience!

Santa Claus Parade

The Santa Claus Parade in Perth is a beloved community tradition that kicks off the holiday season. Happening on December 7, 2024, the parade will feature beautifully decorated floats, marching bands and of course, Santa himself. It’s a family-friendly event that brings the whole town together, and it’s a great way to get into the holiday spirit.

Polar Bear Plunge

For the brave and adventurous, the Polar Bear Plunge on January 1, 2025, is a must-see (or take part in!). This annual event sees participants dive into the icy cold waters of the Tay River, all in the name of charity. Spectators gather along the river to cheer on the brave souls who take the plunge. If you’re planning to join in, be sure to dress warmly before the event and bring a change of clothes—those icy waters are sure to give you a shock! Even if you’re not participating, it’s a fun event to watch, and it’s a great way to start your year off with a splash.

Kingston Holiday Events

Kingston Holiday Market

If you’re looking for local handmade finds this holiday season, check out the Kingston Holiday Market. Taking place over three weekends (November 30–December 1, December 7–8, and December 14–15, 2024), this market features an impressive lineup of local artisans and craft vendors, offering a variety of handcrafted items such as:

• Pottery
• Paintings
• Candles
• Delicious foods
• And much more!

Whether you’re searching for handmade jewelry, artisanal foods, or festive décor, this market offers a little something for everyone. Visitors can shop for unique gifts, enjoy live music, and enjoy delicious seasonal treats. The market is a great place to pick up one-of-a-kind gifts while supporting local businesses.

Kingston Canadian Film Festival

Set between February 26 to March 2, 2025, the Kingston Canadian Film Festival is a must-visit event for film lovers and film-buffs alike. This festival showcases the best in Canadian cinema, featuring films from established and emerging filmmakers. Here are some of the highlights you can expect:

• Feature Film Screenings
• Short Film Programs: Curated collections of short films will be presented, including programs like “Canadian Shorts: Beyond,” “Canadian Shorts: Northern Refractions,” and the “Slaight Music Video Showcase.”
• Workshops and Panels
• Special Events: The festival will host events such as the “25 Years 25 Minutes” pitch competition, where filmmakers with significant connections to Kingston can pitch short film projects for a chance to receive $25,000 towards production.
• Live Performances: The festival will feature live music events, including a performance by Dwayne Gretzky at the Grand Theatre and a conversation with Carolyn Taylor.

KCFF has a history of hosting esteemed guests, and the 25th anniversary is expected to continue this tradition. While specific guests for 2025 have yet to be announced, past attendees have included notable figures such as Gordon Pinsent, Deepa Mehta, and Elliot Page. As for event admissions, tickets and festival passes will be available for purchase starting February 1, 2025. For those planning to attend multiple screenings, the festival offers film passes that provide access to a selection of films at a discounted rate.

*Please note that the above activities and events may be updated without notice. We encourage all patrons to follow up with the business directly before attending. 

Final Thoughts

These festive towns invite visitors to experience Ontario’s winter unforgettably. From holiday markets and cultural festivals to winter sports and film workshops, there’s truly something for everyone. So, bundle up, grab your loved ones, and set off to explore these small towns this winter—you’ll create memories that will last long after the snow melts.

Are you looking to enter the real estate market this winter? Give us a call today! One of the experienced agents at Zoocasa will be more than happy to help you through the exciting home-buying process!

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