by Alex Kinsella | August 2026
September brings busy schedules, back-to-school routines and the feeling that summer disappeared overnight. Rush and routine become the order of the day. So why not make your weekends a chance to hit pause, get out and enjoy yourself? From live music and festivals to fall celebrations, immersive art and the return of Kitchener-Waterloo Oktoberfest, make your weekends (and event days in between) a chance to recharge and enjoy everything happening throughout Waterloo Region this month!
Scroll down for the full rundown and don’t forget to sign up for the TL;WR newsletter to get a weekly rundown of events across Waterloo Region.
This month discover:
- September events in Waterloo Region, including live music, comedy, cultural celebrations and community events.
- Fall activities and seasonal events, from harvest celebrations and food festivals to experiences in St. Jacobs, Wellesley and beyond.
- Arts, festivals and entertainment, including Lumen, live performances, exhibitions and immersive experiences.
- Big September events worth planning a weekend around, including Kitchener-Waterloo Oktoberfest, Fest2Fall and more.
September Events & Festivals in Waterloo Region
Summer Mosaic Sessions | September 2
You’ve got one more opportunity to create your own mosaic work of art this summer at the Canadian Clay and Glass Museum’s Summer Mosaic Session workshop on September 2. You choose the base and cut, arrange, glue, and grout your personal masterpiece with expert guidance from the museum’s team.
D.J. Demers live at the Registry Theatre! | September 3
Fresh off appearances on The Tonight Show with Jimmy Fallon and America’s Got Talent, D.J. Demers is bringing his award-winning comedy to the Registry Theatre in Downtown Kitchener. All five of Demer’s stand-up albums have been played millions of times on the major streaming platforms and his appearances on Fallon, AGT, and Conan have garnered tens of millions of views on Instagram, YouTube and TikTok.
Endless Summer | September 5
The leaves may be starting to turn colour, but that doesn’t mean summer is over. The City of Kitchener’s Endless Summer concert brings you some of Canada’s best-loved musical acts on stage in Victoria Park. This year, catch performances from SHEBAD, Valley, and headliners Mother Mother.
Candlelight: The Best of Hans Zimmer | September 5
Enjoy the music of composer Hans Zimmer surrounded by candlelight inside the St. Matthews Centre in Kitchener. The performance includes renditions of hits like “This Land” from “The Lion King” and “Cornfield Chase” from “Interstellar”. St. Matthews has some of the best acoustics in Waterloo Region and this is a concert not to be missed.
The Aud 75th Anniversary Open House | September 9
To be honest, The Aud doesn’t look a day over 50. On September 9, celebrate 75 years of musical history, epic wins, heartbreaking losses, and amazing memories at The Aud 75th Anniversary Open House from 5 to 8 P.M. Take a self-guided tour through five interactive stops and collect passport stamps at each destination along the way. Complete all five stops to unlock a photo opportunity with the Memorial Cup, and enjoy a free skate and complimentary popcorn.
SummerlooFest 2026 | September 9
Whether you enjoy riding on King Street or sitting in a high-rise looking at Laurier, the first-ever SummerlooFest has something for you. AJDIDIT, the rapper behind Waterloo’s official song of the summer, brings you an evening of live music and Tiktok-style challenges and games.
Rusty Nail Comedy presents Matt Wright | September 10
The Rusty Nail Comedy team is known for bringing some of the country’s best comedians to town for their Friday and Saturday night shows—but every so often, they go above and beyond for a special Thursday show, including this one with “two-time JUNO Award losing Canadian stand-up comedian” Matt Wright! Don’t miss this show with the writer and actor from “Son of a Critch” and “This Hour Has 22 Minutes”.
Cambridge Fall Fair | September 10–13
Discover the ultimate autumn celebration at the Cambridge Fall Fair from September 10 through September 13! Dickson Park will be packed with games, activities, live music and more. From carnival rides to delicious food vendors, there’s something for everyone to enjoy!
The Art Experience ’26 | September 11
Last Minute Gallery and the KWFamous Creative Cafe bring you a night where artists and art lovers come together to create, connect, and engage in a unique creative atmosphere. The Art Experience ‘26 features an exhibition showcasing inspiring works by artists, as well as an interactive live painting session where participants can create their own pieces of art while enjoying a beautiful and relaxing musical atmosphere.
Grandparents Day Heritage Hopper | September 12
Whether you call them nana and a poppa or opa and oma, the Grandparents Day Heritage Hopper is a special event train ride aboard the Waterloo Central Railway. Grandparents ride for 50% off when travelling with family! All aboard for lasting memories together as you journey through the beautiful countryside of Woolwich Township and Waterloo Region’s farm country aboard this historic railway.
Premier League games on The Big Screen | September 12
The Gaslight District is the place to be for exciting Premier League action! On September 12, they’ll have Liverpool vs. Fulham live starting at 10 A.M. on one of Canada’s largest outdoor screens. BYO chairs and show off your team spirit! Visit The Gaslight District’s website for other games in September.
Moore Farms 110th Anniversary | September 12
Celebrate 110 years of farming history at Moore Farms from 10 to 3 P.M. This one hundred and ten years-in-the-making bash includes a curated vendor market, Alexander Henry’s coffee, the ice cream truck, and live music! (And cake, of course there’s cake!)
Monarch Tagging Weekend | September 12–13
It’s fall, and that means the monarchs are migrating. No, we’re not talking about Harry and Meghan moving back to the UK. Monarch Tagging Weekend at the Cambridge Butterfly Conservatory is your chance to learn about their remarkable migration and how you can help support this at-risk species. There’s games, challenges, and you can even take home a complimentary packet of Common Milkweed seeds to help support monarchs at home.
Latin Music On Queen | September 12 and 29
There are two nights left this season for Latin Music On Queen in Cambridge! Salsa, bachata, and merengue fill the air as dancers of all skill levels come together for an evening of fresh-air, good-music, and good vibes. No experience needed. Just show up and move.
Punk Rock Flea Market | September 13
The Kitchener Market is the new home of the KW Punk Rock Flea Market. Explore over 40 weird and alternative vendors, live music from Nova Kate, Your Pal Bill, and Heir Loom, and beers from Short Finger Brewing and coffee from Streets Ahead Coffee Roasters.
LYNC Porch Music Fest | September 13
New Hamburg rocks on September 13 with LYNC’s Annual Porch Music Fest. It’s a free community event featuring live music, local food and drinks, and family fun. The fest is an awesome way to explore New Hamburg, with four locations—the Waterlot, the Imperial Market Patio, Puddicombe House, and LYNC Station.
Rusty Nail Comedyfest ’26 | September 16–19
TWH Social in Downtown Kitchener is the home of the Rusty Nail Comedyfest ’26 from September 16 through September 19. Kick off this four-day comedy festival with the opening night show featuring hometown hero Rob Bebenek and “Canadian-born interracial love child” Landry, best recognized for his likeable hair.
Together for Care Fashion Show | September 17
The catwalk is back for the second annual Together for Care Fashion Show in support of the Waterloo Regional Health Network’s new campus on, well, the campus of the University of Waterloo. The evening features a fashion show, dinner, and a fabulous silent auction to help build a stronger future for healthcare in Waterloo Region.
Harvest Hoedown | September 18
Giddy up—it’s time for the annual Harvest Hoedown at the St. Jacobs Market. It’s a “boot-stompin’, toe-tappin’ good time” as the market brings the spirit of the countryside to life in a night filled with live country music, line dancing, and the ultimate challenge of the mechanical bull!
Kitchener Rangers Hockey | September 18
Fresh off their Memorial Cup championship, your Kitchener Rangers are back for another season at The Aud. Get your tickets for the home opener versus the Owen Sound Attack on September 18 and don’t forget to check out the 2026 Fan Fest and Summer Showcase on September 6.
The 29th Annual Royal Medieval Faire | September 19
Hear ye, hear ye—it’s time for the 29th Annual Royal Medieval Faire inside Waterloo Park. This year’s event brings you everything you’ve come to expect, from storytelling and swordplay to games, music, and dancing. Entry is only $10, cash at the gate.
Multicultural Festival of Elmira | September 19
HOPE’s Multicultural Festival of Elmira is back for its fourth year! This year’s theme is “Rooted Here. Growing Together” and is meant to show how shared presence and care create vibrant, connected communities. 12 to 6 P.M. in Gibson Park.
Craftoberfest – THEMUSEUM x TWB | September 19
Sample the best of local craft breweries, grab a pretzel, and challenge your friends to some classic party games at Craftoberfest. This year, the event moves to THEMUSEUM in Kitchener with live music from Toronto’s best Beatles cover band, The Sh•tty Beatles and a live DJ keeping the fest going all night long.
Lumen Festival | September 19
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.
Cambridge Terry Fox Run | September 20
The annual Terry Fox Run in Cambridge happens at Riverside Park starting at 11 A.M. Whether you walk, run, or roll, join them in celebrating the community’s impact on raising funds for cancer research in Canada.
VANCAMP, I, the Mountain, and Painting Pelicans | September 24
VANCAMP is bringing his mix of modern country, rock, folk, and pop to Emmanuel United Church on September 24. Special guests are I, the Mountain and Painting Pelicans. Doors at 6:45 P.M., music and memories at 7:30 P.M.
Fest2Fall Music Festival | September 25 & 26
Welcome the arrival of fall at Fest2Fall Music Festival, a two-day celebration of live music, great food and drinks at Dickinson Park in Cambridge’s historic Galt neighbourhood. Friday goes country with performances from The Reklaws and Dean Brody, while Saturday turns up the volume with The Glorious Sons, The Trews, Texas King, Feral Minks and Ella Ruth.
Kitchener Waterloo Oktoberfest | September 25–October 17
Oktoberfest in September? That’s right, Canada’s Greatest Bavarian Festival returns for another year of celebrating German heritage, culture, food, and beer across official festhallen at historic German clubs and the Willkommen Platz in Downtown Kitchener. This year, Oktoberfest returns to Cambridge at the Gaslight District’s Prostgarten, a free-to-attend event that transforms the district into Cambridge’s “go-to” Oktoberfest Festhallen starting on September 25!
Bales & Boots in St. Jacobs Village | September 26
You don’t need to go to Kentucky to enjoy old fashioned bluegrass tunes. St. Jacobs Village comes alive with the sounds of bluegrass music, cozy autumn decor, and laid-back country charm. Whether you’re a fan of banjos, fiddles, or just soaking in the season, this is your chance to celebrate fall in true St. Jacobs style.
Wellesley Apple Butter and Cheese Festival | September 26
As if you needed another reason to visit Wellesley. The annual 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.
Gluten Free Fest | September 27
Celiacs of Waterloo Region, head to Bingemans and try our tasty treats with wild abandon at the annual Gluten Free Fest on September 27. Whether you’re newly diagnosed or have been living gluten free for years, the festival brings together some of Canada’s best gluten-free vendors to find your new favourites. Tickets are $8 in advance or $10 at the door.
King StrEATery Food Truck Festival | September 27
Eat on the street at the annual King StrEATery Food Truck Festival in Downtown Kitchener. Over 15 food trucks are rolling into DTK’s Eastend for a celebration of food, community, and fun. There’s also vendors, live music, and games for the whole family.
**The fun doesn’t stop here! Explore even more festivals, concerts, markets, and community events on the Explore Waterloo Region Events Calendar.