by Alex Kinsella | August 2025
September in Waterloo Region brings a mix of festivals, concerts, and community events to help you make the most of the season. From world-class performances at Centre in the Square and the return of local favourites like the Wellesley Apple Butter & Cheese Festival, to cultural celebrations, family-friendly activities, and the start of Kitchener-Waterloo Oktoberfest, something is happening almost every day of the month.
Whether you’re looking to dance in the streets, explore art and theatre, or savour the flavours of fall, you’ll find plenty to enjoy close to home.
September Events
Theresa Caputo Live! | September 3
Theresa Caputo, known worldwide as the Long Island Medium and star of the Lifetime Series Raising Spirits, is coming to Centre in the Square on Wednesday, September 3. Experience her messages of comfort and healing that she has shared with more than 1.5 million people around the world.
Learning to Love the Land Underfoot | September 6
The Art of Soil Collective and the Kitchener-Waterloo Art Gallery present “Learning to Love the Land Underfoot,” an event that encourages us to explore our connections to the land underfoot in an urban setting, reflecting on our biases, expectations, and assumptions.
Up to Here, a Tragically Hip Tribute | September 6
Maxwell’s Concerts & Events invites you to celebrate the music of the Tragically Hip with Up to Here on September 6. The Guelph‑based band captures the spirit and energy of Canada’s iconic rockers with explosive performances and powerful vocals.
Endless Summer | September 6
The weather is getting chillier, so the City of Kitchener is turning up the heat with Endless Summer, a free concert event in Victoria Park. Pick up something to eat from one of your favourite Downtown Kitchener restaurants and head to the park to hear live music from Canadian icon Feist, Liv Gains, Basia Bulat, and more!
Cambridge Hotel Wedding Show 2025 | September 7
Planning a wedding? You don’t want to miss the Cambridge Hotel Wedding Show. With a complimentary glass of bubbly in hand, explore the boutique-style show that brings together some of the region’s top wedding vendors, from florists and photographers to DJs, decorators, and more.
German Clothing Buy & Sell | September 7
Make KW Oktoberfest 2025 the year you’re decked out in traditional lederhosen or dirndls! The annual German Clothing Buy & Sell event is taking place at the Schwaben Club (50 Scheifele Place, Breslau) from 11:00 AM to 3:00 PM. Prost!
Waterloo Tech Week | September 8–11
Connect, celebrate, and be inspired by the Waterloo Region’s tech innovators at the inaugural Waterloo Tech Week. There are meetups, networking events, and showcases to explore the frontiers of tech, from advances in quantum computing and artificial intelligence to cybersecurity and robotics.
Free Outdoor Screening: Kung Fu Panda 4 | September 9
Bring the family, grab some snacks, and join Po on his epic adventure under the stars on one of Canada’s largest outdoor screens. Pizzeria Motola and the Collective Arts patio will be open, too!
Real to Reel: A Silver Screen Soirée | September 10
Walk the red carpet in support of oneROOF Youth Services at its inaugural Real to Reel: A Silver Screen Soirée benefit. This black-tie event includes a screening of “The Pursuit of Happyness” and a documentary showcasing oneROOF Youth Services and the realities of youth homelessness.
Mean Girls – High School Version | September 10–21
The Drayton Entertainment Youth Academy presents Mean Girls – High School Version at the Hamilton Family Theatre in Cambridge. It’s a fearless musical comedy about chasing popularity and being true to yourself, starring over 50 students on stage and backstage in the annual Drayton Entertainment Youth Academy High School Musical Production.
TriCity Improv Improv Comedy! | September 12
“Back to school” got you down? Turn those frowns upside down with a great evening of improv comedy presented by some of the most talented performers in the region! TriCity Improv is back at the Kitchener-Waterloo Little Theatre for a night of improv that will have you laughing all September long.
Latin Music on Queen | September 13
Latin Music returns on September 13 to Hespeler Village. It’s a free street dancing event with the hottest salsa, bachata, and merengue music! Come feel the emotion and energy while dancing the night away!
Monarch Tagging Weekend 2025 | September 13–14
Celebrate the incredible Monarch migration at the Cambridge Butterfly Conservatory with a weekend of learning, activities, and hands-on fun for the whole family. Explore how you can support this endangered species while enjoying special programs throughout the day.
Waterloo Terry Fox Run | September 14
Celebrate Terry’s legacy while raising funds for advancing cancer research at the annual Waterloo Terry Fox Run on Sunday, September 14. The walk starts and ends in Waterloo Park at Central and Albert Streets.
Taste the Countryside Harvest Dinner
Join in a farm-to-fork meal with fresh local flavours from Waterloo Region’s countryside, set in the beautiful Shuh Farms apple orchard! Enjoy the rustic charm of the orchard while listening to live music by Tyler Frey, a local Elmira artist, adding to the magic of the evening. Every ticket supports a greater purpose: all proceeds go toward tackling food insecurity in our townships.
Kitchener-Waterloo Art Gallery Opening Celebration | September 19
KWAG invites you to celebrate the opening of its Fall Exhibition Cycle on September 19. Meet the artists of Auto-Biography: Vehicles of identity, community, and globalization and enjoy live music from a Special Guest DJ Charlie Star.
Kitchener Rangers Home Opener | September 19
Your Kitchener Rangers are back for the 25/26 season with an exciting roster of some of the best young hockey talent in the OHL! On September 19, head to the Aud for their home opener against the visiting Brantford Bulldogs.
St. Jacobs Market Harvest Hoedown | September 19
Pull on your boots, break out your denim and flannel, and get ready for an evening of country charm and lively fun at Harvest Hoedown 2025 on Friday, September 19, from 5:00–10:00 PM. With live music, great food, dancing, and local vendors, Harvest Hoedown 2025 is the perfect way to kick off the season.
Fest2Fall | September 19–20
Cambridge’s Dickinson Park comes alive with music, entertainment, and great friends at Fest2Fall. This year’s two-day festival features the Barenaked Ladies, Dwayne Gretzky, Sloan and more!
All That Worldly Jazz Festival 2025 | September 19–21
Nerdua Arts presents the All That Worldly Jazz Festival 2025 in St. Jacobs. It’s three days of music celebrating diverse cultural expressions of jazz.
Whimsical Weekends: Handmade Hobbies Edition | September 20–21
Enjoy a guided tour of Castle Kilbride and its exhibit. After the tour, participants will create a watercolour book to take home!
Rookie + Ace Multi-Sport Challenge for KidsAbility | September 20
Rookie + Ace is hosting a Multi-Sport Challenge on Saturday, September 20, where ten teams of four will battle it out in friendly competition across six different sports—Padel, Pickleball, Mini Pickleball, Ping Pong, Cornhole, Basketball—racking up points to win the top team prize. Net proceeds go to KidsAbility.
3rd Annual Multicultural Festival of Elmira | September 20
Head to Gibson Park in Elmira for the 3rd annual Multicultural Festival of Elmira on September 20, presented by Hearts Open for Everyone (HOPE). The festival celebrates and raises awareness of diversity and inclusion through performances, workshops, services, and vendors so everyone can feel a sense of belonging.
Lumen Festival | September 20
Lumen is an immersive festival celebrating light, art and technology. Experience awe-inspiring installations as you explore the shops, cafes, and restaurants of Uptown Waterloo.
Let’s Get Retro! 90’s Video Dance Party | September 20
Party like it’s 1999 at Maxwell’s Concerts and Events with the Let’s Get Retro! 90’s Video Dance Party. All your favourite 90’s party hits will be on the playlist—it’s the best boom box in town!
rare 2025 Trail Party | September 21
rare’s 16th annual walk, hike, and run fundraiser is your chance to help raise funds to protect environmentally sensitive lands in our community today and for the future. End the day with a celebratory BBQ at the rare ECO Centre.
The Australian Pink Floyd Show | September 23
The Australian Pink Floyd Show has been recognized as the gold standard of Pink Floyd tributes, having sold over four million tickets worldwide. Experience their renditions of Floyd classics on September 23 at Centre in the Square.
IMPACT 25 | September 23–28
The International Multicultural Platform for Alternative Contemporary Theatre (IMPACT), presented by MT Space, is a five-day festival featuring local, national, and international work by Indigenous, Black, and Racialized artists, with a special emphasis on interdisciplinary, intercultural, and physical productions. Festival passes and individual show tickets are available.
The Creative Trip | September 26
Looking for a high-energy, art-fuelled outdoor experience? Look no further than The Creative Trip, brought to you by Collective Arts Brewing and The Gaslight District. The event features a blend of alternative rock, melodic punk, and edgy pop from some of Canada’s most popular indie acts, including Rare Americans, NOBRO, and Weird Nightmare. There are limited tickets available for The Creative Trip Afterparty featuring Kardinal Offishall, too!
Menopause The Musical | September 26
The hilarious celebration of women and the change takes the stage at Centre in the Square on September 26. “This musical parody set to classic tunes from the ‘60s, ‘70s and ‘80s will have you cheering and dancing in the aisles!”
Kitchener-Waterloo Oktoberfest | September 26–October 18
Be Bavarian with friends new and old at Canada’s Greatest Bavarian Festival! The 57th annual edition of Kitchener-Waterloo Oktoberfest takes place from September 26 to October 18. Check out the first-ever Basstoberfest on September 13 at Wildwood Conservation Area and live music at Bingemans KoolHaus featuring Theory of a Deadman on September 26 and I Mother Earth on September 27. For a complete list of events taking place throughout the Festival and information on what’s happening at Festehallen throughout the region, visit www.oktoberfest.ca.
Bales & Boots Bluegrass Bash | September 27
The Village of St. Jacobs invites you to the first-ever Bales & Boots Bluegrass Bash featuring the music of The Never Willbillies Bluegrass Band. With great music and amazing fall vibes, it’s the perfect way to celebrate fall in true St. Jacobs style.
Wellesley Apple Butter & Cheese Festival | September 27
You had me at apple butter. That’s right, the Wellesley Apple Butter & Cheese Festival is back with a day of apple fritters, cider, and butter—and its famous Pancake and Sausage Breakfast! Bring the family for a day of festive fun in Wellesley.
Galt Jazz Live Latin Jazz | September 28
Part of the Galt Jazz Live Music on Main series, this month features a performance by Order of Canada recipient Alfredo Caxaj and his 7-piece Latin Jazz Band. Encore Threads and Treasures will be rolling out their ever-popular Kids Zone for kids to enjoy while the adults take in the music for FREE! Bring a chair, relax, enjoy!