Bestival or Rusty Nail Comedy Fest? Both!
TL;WR for September 9 through September 15 2025
What to do.
Tuesday, September 9
The Waterloo Historical Society meeting on September 9 features Elysia DeLaurentis presenting "Tarred & Feathered: Rough Justice in 19th-Century Ontario" at the Maryhill Community Centre. Doors open 6:30; all welcome.
Bring the family, grab some snacks, and join Po on his epic adventure under the stars on one of Canada’s largest outdoor screens at the Gaslight District’s Free Outdoor Screening of “Kung Fu Panda 4”. Pizzeria Motola and the Collective Arts patio will be open, too!
Join special guest winemaker Daniel Kiowski at Blackshop! Restaurant & Wine Bar for German Wine Makers Dinner, a 6-course culinary journey paired with exceptional German wines.
The Duke of Wellington has Smarty Pants Trivia Night from 7 to 9 pm.
Wednesday, 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.
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.
Homework? That’s okay, so, we can do it on the boat. Check out a 40th anniversary screening of “The Breakfast Club” at 6:45 pm.
AOK and In4Questioning have High School Musical Trivia at AOK Craft Beer + Arcade at 8 pm.
Thursday, September 11
Launching this fall, Small Ideas is a fast-paced 30-minute live-audience show that explores innovation, technology, and ideas before they get BIG. Be part of the live audience and give real-time feedback to help shape the first episode taping in October. Tannery Event Centre (yeah, it’s back!) from 11:30 to 3:30 pm.
The University of Waterloo Art Gallery has an opening reception for Brenda Mabel Reid and Andrew McPhail on September 11, 5-8 pm.
It’s opening night of Rusty Nail Comedyfest 2025! Get ready to enjoy hilarious stand-up performances by top comedians in the beautiful Crystal Ballroom upstairs at the historic Walper Hotel. Your headliner is Martha Chaves, a Latin Canadian, award-winning stand-up comedian, actor, and comedy writer. Doors open at 7 pm.
The Rabbid Fox has 90s Music Bingo at 8 pm.
Friday, 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.
Emmanuel Concerts presents n interstellar night of song, sonorous therapy and whimsical wordplay with Graven, Stephen Stanley & Emily Gilbart at Emmanuel United Church starting at 8 pm.
The Rusty Nail Comedy Fest continues at TWH Social with Christophe Davidson, Brayn Hatt, Ryan Dillon, and Ernie Vicente. Doors open at 7 pm for the early show and 9:30 pm for the late show.
The Sundown Saints open the annual Belmont Village Bestival at 7:30 followed by Juno award nominated Whitehorse at 9 pm! Arabella Park also has the House of Kameleon drag show at 8 pm.
Saturday, September 13
The Belmont Village Bestival continues with a day of events, music, and more on Belmont Ave. Erick Traplin plays the Union Stage at 11 am, JP Sunga plays the same stage at 3 pm, Jesse Webber Presents closes out the night on the Glasgow Stage. Check their website for the full schedule!
Pink Crow Cafe has an outdoor craft market from 10 am to 2 pm.

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.
KW Creators and Studiocomix Press present the Illustrators Bazaar at 44 Gaukel in DTK. Illustrators Bazaar is a one-day celebration of art, creativity, and connection, bringing together the largest collection of artists from across the region to share their work with the community. From prints, stickers, and zines to commissions and original artwork, every booth is filled with imagination and skill.
The Knitters' Fair is fibre arts heaven: two arenas, over 80 artisan vendors, a fashion show, door prizes, and technique demos. Our vendors have everything from local wool and alpaca fibre, to exquisitely hand-dyed yarns, to handmade project bags, and even special eyes for making amigurumi. The event is hosted by the KW Knitters' Guild, which will be celebrating its 40th anniversary this coming year. 9:30 to 3:30 at The Aud.
Come see what the artists of Southern Ontario have for sale on the grounds at Homer Watson House & Gallery for the 5th annual Art Fair! From ceramics to canvas, you’ll find paintings, sculptures, prints, photographs, and more from over 40 vendors. Bring a picnic lunch, listen to local music talent, and bring the kids for a drop-in activity!
If that wasn’t enough to tempt you, this year, the Art Fair team are sharing the day with CreekFest happening down the street, celebrating Schneider Creek and the Grand River with community mural painting, musical, aerial, dance, and poetry performances, bike decorating, and local organisations sharing their own activities and information!
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!
The Rusty Nail Comedyfest 2025 closes out with an early show at 7 and late show at 9:30 pm.
Sunday, 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.
Also making me feel old, check out a 35th anniversary screening of “Teenage Mutant Ninja Turtles” at 2 pm. A UW student called me “sir” last night at a Waterloo Tech Week event and I haven’t gotten over it.
The Boathouse x The Lab x Labodega are back with Beats, Bites, and Pints. All vinyl hip-hop, R&B, and reggae on the patio at the Boathouse from 3 to 8 pm.
Monday, September 15
Join in Taste the Countryside Harvest Dinner 2025, 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.
Don’t sleep on these upcoming September events
Democracy in Action is a community-powered non-profit that shines a spotlight on the changemakers shaping a more informed, inclusive, and resilient democratic society. They’re having a launch event on September 17 at Kitchener Public Library from 5 to 7.
The Pinch Cabaret variety show is back from summer vacation! The 42nd edition of this legendary series features a surprising mix of comedy, music, analog projector art, storytelling, quantum physics, poetry & who knows what else!!! Sat September 20 - 8pm at Hepcat Swing Studio - 42 Erb St, Waterloo. Sliding scale tix $5-$30.
Ways to get involved
Cinema Under the Stars is an evening of laughter, games, and entertainment for the whole family! Presented by City of Kitchener Councillor Paul Singh in partnership with Country Hills Community Centre, Anglican Church in North America and Canadian Housing and Renewal Association, the Ward 6 Cinema Under the Stars kicks off at 6:30 p.m. and includes an outdoor screening of Paddington in Peru at dusk. Please consider bringing a cash donation in support of the Food Bank of Waterloo Region.
What to read.
Play-meets-exhibit project to unpack abuse at former Galt reformatory (Bill Jackson, The Record)
Unless you're a vampire, don't shy away from garlic (Jasmine Mangalaseril, CBC KW)
"The Garbage Man Can!" (pt 1) (Melissa Bowman, Citified)
It's Tech Week in Waterloo and organizers say it's a chance for everyone to check out 'cool things' (Joe Pavia, CBC KW)