Kitchener-Waterloo Region has a wide variety of events, festivals as well as outdoor activities, to do during the cold season. From trail walking, tobogganing & skating, to shopping at an outdoor farmers’ market & taking in the sights aboard a steam locomotive, here is a list of activities that has something for everyone.
Credit: Chicopee Tube Park
Winter Fun in Kitchener-Waterloo Region: Events, Festivals and Outdoor Adventures
Events & Festivals
Skate Night Date Night
Wednesdays in January and February | 6:00 PM to 8:00 PM
Waterloo Public Square Ice Rink, 75 King St S, Waterloo
Winterloo
Celebrate all things winter in Uptown Waterloo. This annual winter festival has a host of free activities that all ages can enjoy. Activities will include meeting the snow dogs, ice carving, snow sculptures, winter activities and much more! Details
Saturday, January 24, 2026 | 12:00 PM to 5:00 PM
Waterloo Park – Central Promenade & Other Venues
Galt Jazz
Enjoy top-quality live Jazz ensembles in a cozy and intimate setting on the last Sunday of every month. Details
2026 dates TBA
Sundays, December 29, 2024 & January 26, February 23, 2025 | 4:00 PM – 7:00 PM
Taproom at 13 Food&Beverage, 13 Main St, Cambridge
The Brush Off
At this original and premier live art-making event, guests will watch artists compete in an art competition while enjoying drinks, voting for their favorites, and bidding in a silent auction. Details
Saturday, January 31, 2026 | 7:00 PM
TheMuseum, 10 King St W, Kitchener
Cinderella: The Panto
The enduring fairy tale gets a clever and contemporary makeover in this glittering stage production that features all the classic elements you remember – the pumpkin, glass slipper, masked ball … plus some unexpected and surprising new twists! Whether you’re 9 or 99 – this show, filled with just the right amount of naughty and nice humour, is fun for the entire family. So join us at the theatre, and don’t worry – we’ll have you home well before the stroke of midnight!! Details
November 27, 2025 to January 11, 2026
St. Jacobs Country Playhouse, 40 Benjamin Rd. E., Waterloo
From Vienna with Love
Inspired by the world-renowned New Year’s concerts of Vienna and other great cities, the CSO proudly presents its second annual New Year’s Day celebration — a magical way to ring in the year together in community. This year’s program features the dazzling soprano Holly Chaplin, with a joyful selection of waltzes, polkas, and operetta favourites to welcome 2026 in style. Details
Thursday, January 1, 2026 | 3:00 PM
Tapestry Hall, 74 Grand Ave S, Cambridge
Blue Rodeo
January 9 – 10, 2026 | 8:00 PM
Centre in the Square, 101 Queen Street North, Kitchener
Woodstock Toy and Collectibles Expo
Join the Woodstock Toy and Collectibles Expo features over 200 vendor tables offering a wide range of old and new collectibles, including comics, retro video games, action figures, vinyl records, sports memorabilia, and more. Details
Sunday, December 28, 2025 | 9:30 AM to 2:30 PM
Oxford Auditorium and the Mutual/Market Buildings, on the Woodstock Fairgrounds, at 875 Nellis Street in Woodstock
Sing-A-Long Broadway
Get ready for a show-stopping night of song and community at Sing‑a‑Long Broadway on Saturday, January 31st. Join friends—new and old—as you belt out timeless Broadway hits like Memory, Defying Gravity, and Seasons of Love alongside a live band and spirited sing-along hosts. Details
Saturday, January 31, 2026 | 7:00 PM
Centre in the Square, 101 Queen Street North, Kitchener
The Prince
KWLT’s performance of The Prince will explore this unique twist on The Bard’s work and its relationship with gender like never before, as we enter the round to ask ourselves what it really means to play a role in today’s world. Details
January 30 – February 1, 6 – 8, 13 – 15, 2026
Kitchener-Waterloo Little Theatre, 9 Princess St. E., Waterloo
Noises Off
Noises Off is a side-splitting farce that takes you behind the scenes, and onto the stage, of a hilariously disastrous play within a play. From missed cues and misplaced props to romantic entanglements and backstage chaos, this fast-paced comedy delivers non-stop laughs. Enjoy sharp wit, madcap timing, and the unpredictable magic that only live theatre can deliver. Details
February 6 – 8, 13 – 15, 2026
Fergus Grand Theatre, 244 St. Andrew Street, Fergus
Swan Lake by International Ballet Stars
Experience the world’s most in-demand ballet, “Swan Lake,” presented by Classical Arts Entertainment and performed by International Ballet Stars. A full-scale production features Tchaikovsky’s legendary score and brings the masterpiece choreography by Marius Petipa and Lev Ivanov to life. Be spellbound by the iconic variation of Little Swans, Odile’s 32 fouettés, and the graceful movements of the talented ballet dancers. Details
Friday, February 6, 2026 | 7:00 PM
Centre in the Square, 101 Queen Street North, Kitchener
Coldest Night of the Year
The Coldest Night of the Year is a winterrific family-friendly walk to raise money for local charities serving people experiencing hurt, hunger, and homelessness. Details
Saturday, February 28, 2026 | 4:00 PM
Various locations
Jeans ‘N Classics: Heartland – Current & Classic Country
From Nashville’s hottest stars to timeless country legends, Heartland is a thrilling journey through the best of contemporary and classic country music. This high-energy concert blends the heart and soul of country with the grandeur of the orchestra for a night of unforgettable music!! Details
Thursday, February 26, 2025 | 8:00 PM
Centre in the Square, 101 Queen Street North, Kitchener
KW Mac & Cheese Festival
Treat yourself to deliciously warm, cheesy creations paired with craft beer and cocktails from local breweries. It’s the ultimate comfort food celebration you won’t want to miss! Details
February 27, 2026 | 6:00 PM – 11:00 PM
TheMuseum, 10 King St W, Kitchener
Gabby’s Dollhouse Live!
Gabby, Pandy Paws and friends travel to the Cat-O-Sphere, Mermaid-Lantis and some favorite Dollhouse locations in search of the colors that will make rebuilding the rainbow, possible. Gabby’s Dollhouse Live! Presented by Walmart brings to life an exciting original story featuring incredible puppets, dynamic staging, a talented live show cast of singer-actor-puppeteers and songs from the beloved series, including “Hey Gabby”, “You Can’t Spell Meow Without Me” and “Sprinkle Party”. Details
Saturday, February 28, 2026 | 4:00 PM
Centre in the Square, 101 Queen Street North, Kitchener
Valentine’s Day Dinner with Chef Rob
On Valentine’s Day, treat your sweetheart to a romantic dinner, beer pairings and charcuterie made with local meats and cheeses. Chef Rob will prepare a multi-course meal for you to enjoy a special evening with your loved one. Details
Saturday, February 14, 2026 | 6:00 PM – 8:00 PM
Kitchener Market, 300 King St E, Kitchener
The Tragedy of Hamlet, Prince of Denmark
Created by choreographer Guillaume Côté and stage director Robert Lepage, Hamlet, Prince of Denmark pulls the audience deep into a world of deceptiveness, where phantoms and humans mingle on a minimalist set where light, shadow and transparency play a central role. This metaphorical reinterpretation of the Shakespearian drama draws a fine line connecting movements of the body with what may or may not be lurking within the corners of the mind. Details
Thursday, March 5, 2026 | 8:00 PM
Centre in the Square, 101 Queen Street North, Kitchener
Seedy Saturday
Join us Saturday, March 7th, to share and exchange seeds! Meet fellow gardeners and find exciting seed varieties that other seed savers are sharing! Whether you are a first-time gardener or a seasoned expert, everyone is welcome! Details
Saturday, March 7, 2026 | 10:00 AM to noon
rare ECO Centre and Slit Barn, 768 Blair Road, Cambridge
Misatango
Join the Wellington Wind Symphony for an inspiring evening that combines the traditional beauty of the Latin Mass with the emotional intensity and rich, dramatic colours of Argentinian tango! Details
March 7, 2026 | 7:30 PM
St. Matthews Centre, 54 Benton Street, Kitchener
Kitchener I❤︎BEER & Taco Festival
Enjoy a fun-filled day or night of beer, cider and spirits sampling, games, dancing and tacos! Details
Saturday, March 14, 2026 | 12:00 PM to 5:00 PM and 5:00 PM to 10:00 PM
Bingemans Conference Centre, 425 Bingemans Centre Drive, Kitchener
Femme Folks Fest 2026
Over 9-days Femme Folks Fest 2026 will present 30+ new art imaginings including: Performance, Public Creation, Incubation, Installation, Conversation Cafés, and Professional Development for Creators. . Details
March 7, 9 – 14, 2026 | 7:30 PM
Centre in the Square, 101 Queen Street North, Kitchener
Chris de Burgh 50LO
To celebrate 50 remarkable years in music, legendary singer-songwriter Chris de Burgh embarks on a Canadian Tour in 2026. Fans will be treated to an intimate solo performance featuring his greatest hits. This special evening offers audiences the chance to experience de Burgh’s iconic storytelling and unforgettable melodies in a one-of-a-kind celebration of his extraordinary career. Details
Monday, March 9, 2026 | 7:30 PM
Centre in the Square, 101 Queen Street North, Kitchener
Attractions & Outdoor Adventures
Outdoor Skating and Tobogganing Hills
- The city of Kitchener operates 30+ free outdoor skating rinks that are open from December till March. Rinks are operated by volunteers and are weather-dependent.
- Opened in 1896 and named after Queen Victoria in honour of her diamond jubilee, Victoria Park is a favourite destination amongst couples to take a romantic walk around the lake, visit the clock tower relocated to the park from the original city hall, and go skating hand-in-hand at the parks’ outdoor rink. Learn more about this historic part of town with a free self-guided walking tour available from the city of Kitchener.
Credit: City of Kitchener
- McLennan Park, located on the South end of Kitchener has one of the best tobogganing hills in KW. Known by locals as Mt. Trashmore, this former landfill site is now a scenic vantage point to take in a sunset and a view of the entire city. A couple of other tobogganing options include Foxglove Park and Hillside Park.
- Waterloo Public Square is a popular date night destination in Uptown Waterloo. The city’s largest Christmas tree, an outdoor skating rink and the many coffee shops and restaurants in this area keep it buzzing all winter long. Enjoy a romantic evening of skating, live music and food at the popular Skate Night, Date Night, every Wednesday in January and February from 6:00 p.m. to 8:00 p.m.
- A short walk from Waterloo Public Square, the Waterloo Park offers lots to see and do. Stop by outdoor Eby Farm to see some llamas and alpacas, visit the oldest log house school in Waterloo Region, circa 1820 or stroll along the wooden boardwalk and enjoy the holidays lights.
Experience an Adrenalin Rush
Credit: Chicopee Ski & Summer Resort
- Chicopee ski hill draws in skiers and snowboarders from all over Southern Ontario. Whether you are a beginner or a pro, there is a hill here with your name on it. And when you are done for the day, enjoy a relaxing après ski bite or drink by a cozy fireplace at the Silvertip Lounge.
- If skiing or snowboarding is not for you, why not give snow tubing a shot?! Located on the other side of the ski hill, Chicopee Tube Park is a popular destination amongst youngsters and adults alike. Zip down one of the six chutes and ride the magic carpet back to the top.
Winter Fun at Grand River Conservation Parks
Credit: Grand River Conservation Authority
- Located in North Waterloo, Laurel Creek is part of Grand River Conservation Authority. Their 4.5 km groomed and tracked pine forest trail network is ideal for hiking, snowshoeing and bird watching. Equipment rental is available on site.
- Belwood Lake Conservation Area, located in the town of Fergus, features a 12km reservoir created during the construction of the Shand Dam in 1942 and is ideal spot for ice fishing, hiking and bird watching.
- Another Grand River Conservation Authority area worth mentioning is Pinehurst Lake. In addition to ploughed hiking trails, groomed and tracked cross country skiing trails, snowshoeing trails, this conservation area offers ice fishing and bird watching. Equipment rental is also available on site.
- South of Kitchener, Shade’s Mill Conservation Area offers the longest trail network of all Grand River Conservation Authority winter trails. The 10km groomed and tracked trail network is ideal for hiking, snowshoeing, cross country skiing and bird watching. Ice fishing is available on the reservoir when conditions are suitable. Day use of fish huts is allowed and skiing and snowshoeing equipment rentals are also available.
- A little less known Grand River Conservation Area is Snyders Flats. It’s a former gravel pit that’s been transformed into a looped hiking trail with ponds, forests and meadows.
More Hiking Trails
Credit: City of Kitchener
- An oasis in a busy metropolis, Huron Natural Area is a network of scenic hiking trails, running along provincially significant wetlands, forests, and meadows. While this area is undergoing a transformation to make it a space that represents past and present Indigenous communities, it is also ideal for winter biking, bird watching or simply having a play date at the children’s natural playscape.
- The Kiwanis Park is a great starting point for a hike along the scenic Grand River and if you have a four legged friend with you, there is also a leash-fee dog park on-site.
- On the outskirts of Kitchener, the trails belonging to the RARE Charitable Research Reserve are a hiker’s paradise. Winding through the forests and moss covered stone formations; the trails converge for a stretch along the Grand River. This conservation area is used to preserve the native plant and animal species and is a popular spot for bird watching.
Explore Culture and History
Credit: Waterloo Central Railway
- Go back in time and experience an authentic steam engine locomotive ride at Waterloo Central Railway. The non-profit heritage short line railway operates between Northfield Dr., Waterloo, the St. Jacobs Farmers’ Market, the Village of St. Jacobs, and the town of Elmira. A variety of themed train excursions are offered throughout the year.
- Open every Thursday and Saturday all year round the St. Jacobs Farmers’ Market is a great place to shop for fresh produce, indulge your sweet tooth with a famous apple fritter, and meet some Old Order Mennonites who still travel to the market by horse and buggy. Explore the Market Building, the Peddlers Village and the Market Tent for locally grown or freshly made eats or browse through hundreds of one-of-a-kind gifts from local artisans.
- Originally built in 1885 and restored in 2015, The Old Post Office is one of the many architectural marvels in the Historic Downtown Cambridge. Located just a short drive from Kitchener, this area is popular amongst film makers and wedding photographers, who like use the historic buildings and the bridge over the Grand River as their backdrop. Watch visual effects transform the Old Post Office every Thursday, Friday, Saturday, and Sunday night during winter nights.
- Another popular film backdrop is the West Montrose Covered Bridge. Located in the nearby Township of Woolwich, this 19th century bridge is the last remaining covered bridge in Ontario. It spans the Grand River and has been designated as a cultural heritage site in 2007.
- In the heart of Kitchener, you’ll find the childhood home of William Lyon Mackenzie King, Canada’s tenth, and longest-serving Prime Minister. There is an admission fee to visit the museum inside, but access to the grounds and the trails around Woodside National Historic Site is absolutely free.
- Kitchener Farmers’ Market is open on Saturday’s year round. There are activities for children and classes for adults, plus lots of fresh produce, mouth-watering desserts and delicious smelling gourmet coffee.
- The Waterloo Pioneers Memorial Tower is a tribute to the Pennsylvania-German pioneers who settled in Waterloo Region in the early 1800s. Overlooking the Grand River, the tower is a good access point to the Walter Bean Trail.
- On the other side of the Grand River, the Walter Bean Trail continues through the Old Mill Ruins. Considered haunted by some, this site represents the conflict between the Six Nations of Grand River who originally occupied this land, and the German-Dutch settlers who began to harness the water power of the Grand River in the 1800s and build the many mills, whose foundations are still scattered along the mighty river.
- Part of the Trans Canada Trail, the Iron Horse Trail connects the cities of Kitchener and Waterloo along the former railway corridor. While you walk or cycle along this paved trail, you’ll come across industrial artifacts from KW’s industrial heritage and pass through popular destinations like Victoria Park and Waterloo Park.
- See drive-thru light show at Bingemans. Gift of Lights is a family-friendly drive-thru holiday light display with two tunnels and over 300 animated and static light displays! Enjoy this holiday spectacle from inside the comfort of your own vehicle and tune into Gift of Lights Radio at 103.3 FM.
- Get out your fishing gear and auger then head to Pinehurst Lake to catch lunch. You can easily snag bluegill or black crappie during the winter months.
Credit: Chicopee Tube Park
Kitchener-Waterloo Region has a wide variety of events, festivals as well as outdoor activities, to do during the cold season. From trail walking, tobogganing & skating, to shopping at an outdoor farmers’ market & taking in the sights aboard a steam locomotive, here is a list of activities that has something for everyone.