While the summer season is coming to an end, there’s still plenty of fun happening throughout town, with concerts, festivals, and family-friendly experiences. Mark your calendars for these exciting local events.
Experience of the Month
Pooch and Hearts: On September 13, leash up, load the treat pouch, and bring the whole pack to Halton’s biggest dog event, with play zones for pups, vendors, contests, and tail wags around every corner at the Milton Fairgrounds.
Ongoing Events
- Tuesday Night Trivia at Shoeless Joe’s in Milton: Enjoy a fun-filled evening of brain-teasing questions and great company during this unique visual trivia game shown on all the TVs in the venue, featuring digital scoring.
- Trivia Tuesday at Ned Devine’s: Bring your buds and put your brains together to make your best guesses for a chance at prizes at this fun weekly event.
- Walking Group Around the Mill Pond: Enjoy some company and a leisurely stroll around the picturesque Mill Pond on Tuesday mornings, starting at the Grace Anglican Church.
- Wednesday Night Trivia at St. Louis Bar & Grill in Milton: Join Host Neal Macfarlane for a fun-filled weekly trivia night, complete with a half-time game of Heads & Tails for a chance to win an additional prize.
- Date Night at The Note: Enjoy a specially curated date night menu at the Eighth Note every Thursday evening.
- Mom & Tots: Bring your little ones along to play with each other as moms hang out, build friendships, and share life at Milton Bible Church’s weekly Friday morning drop-in at The Connect Centre.
- Hands in Clay: On select Fridays in August, join Conservation Halton at Crawford Lake Conservation Area to learn the art of pinch pot making and shape your own piece of pottery to take home.
- Milton Farmers’ Market: The beloved annual market takes over Main Street every Saturday from 8:00 a.m. to 12:00 p.m., featuring over 40 farmers, vendors, florists, and artisans. Alongside the main market, explore Milton’s downtown businesses and attractions, including blacksmith demos at Milton Historical Society’s Waldie Blacksmith Museum.
Events By Date
Monday, September 1
- 🚜 Steam-Era 2025 – Labour Day Weekend at Hume’s Auction Farm! 🚜: Experience one of Ontario’s longest-running Heritage shows, featuring tractors in action, antique vehicles, miniature trains, a “trading post” market, and much more.
Monday, September 4
- Mental Health First Aid: Country Heritage Agricultural Society: Learn how to better manage potential or developing mental health problems in this full-day workshop.
- From Field to Vase Workshop @ The Barn Door Studio: Learn the art of creating a textured painted jar and spend an evening among the flowers, building a bouquet.
- Family Paint Party: Bring your family to Lone Star Texas Grill for a meal while painting, suitable for teenagers and adults.
Tuesday, September 5
- September Eco Film Night: Join Sustainable Milton for a viewing of Reflection: a walk with water, accompanied by the film’s director.
Saturday, September 6
- 5 Peaks Area 8: Join in this running adventure for all ages and abilities at Area 8.
- Milton Doggie Dip: Bring your pup for a tail-wagging day of dog-friendly swimming, exciting activities, and a vibrant vendor market—all in support of the animals at Oakville & Milton Humane Society, happening at Rotary Park.
- Family Paint Party: Head to Boston Pizza Milton for some family fun for teens and adults with a guided painting session.
- The Loonie Tunes (half of The 2 Dollar Bills) @ Ned Devine’s: Enjoy live music on the covered rooftop patio.
Saturday, September 6 – Sunday, September 7
- Fairy & Iron Renaissance Faire: Experience an immersive event celebrating community, creativity, and magic, with live sword fights, a magical marketplace, food vendors, and fun for the whole family.
Sunday, September 7
- Family Paint Party: Head to Boston Pizza Milton for some family fun for teens and adults with a guided painting session.
Wednesday, September 10
- The Moms Who Read Filth Book Club: Join Common Moms Milton for a casual night to connect, sip wine, and chat – no pressure, and no reading required.
Wednesday, September 10
- Sin Bin Comedy Show with Drew Behm at Keenan’s Irish Pub – Milton: Join Drew Behm, Monica Gross, and Greg Enwright for a night of laughs.
Friday, September 12 – Sunday, September 14
- Laos-C-Chef Weekend: Visit Third Moon Brewing all weekend for a tasty pop-up as Laos-C-Chef brings his unique food trailer.
Saturday, September 13
- 7th Milton Scouts Bottle and Can Drive: Bring your cans, bottles, and Tetra-Paks to Kinsmen Park to support the Scouts.
- Adam’s Legacy Walkathon: Honour the beautiful legacy of Adam Malki — a young man remembered for his kindness, leadership, and heart, in this day of love, community in kindness to raise funds for the Adam Malki Memorial Scholarship Fund through the Halton Learning Foundation.
- Family Paint Party: Teens and adults – unleash your inner artist at Shoeless Joe’s with an afternoon of creativity in a guided painting tutorial.
- Family Paint Party: Head to Boston Pizza Milton for some family fun for teens and adults with a guided painting session.
- Milton Praise Night: Join this annual worship concert at the FirstOntario Arts Centre Milton.
- ACME Hi-Fi Live @ Ned Devine’s Irish Pub: Enjoy a night filled with rock, pop, and Top 40 hits.
- See You in September Car Show in Downtown Milton: Experience Milton’s biggest car night featuring classic and unique cars, live entertainment, food, prizes, and family fun.
Sunday, September 14
- Family Paint Party: Bring your family to Lone Star Texas Grill for a meal while painting, suitable for teenagers and adults.
Wednesday, September 17
- Mindful Meetup @ Sherwood: Learn and discuss techniques to cultivate present moment awareness, reduce stress, and enhance overall well-being with Milton Public Library.
Thursday, September 18
- Family Paint Party: Bring your family to Lone Star Texas Grill for a meal while painting, suitable for teenagers and adults.
- 2 Mediums. 1 Night. Live Audience Mediumship Readings: Visit Keenan’s Irish Pub for an intimate evening with Mediums Barbara Quinton and Trish Finch.
- Milton Comedy Show: Enjoy a night of laughs at Ned Devine’s with a hilarious line-up of comics seen on Just For Laughs, CBC Comedy, Comedy Central, and Sirius XM.
Friday, September 19
- Comedy Night w/ Dan Brennan + Friends: Head to Third Moon Brewing for a night of big laughs and fresh beers.
- Salsa at Champs: Experience an electrifying evening of high-energy vibes and passionate rhythms at Milton’s ultimate Salsa destination, featuring DJ Gio – Toronto’s legendary DJ, spinning the hottest Salsa beats.
Saturday, September 20
- Grace Anglican Church Presents: A Fall Market: Browse a variety of vendor tables and shop for unique items, handmade creations, and favourite brands.
- Family Paint Party: Head to Boston Pizza Milton for some family fun for teens and adults with a guided painting session.
Sunday, September 21
- Mudskipper Milton and the Milton Open Water Swim: Try a 10K or 20K individual swimrun where participants alternate between swimming in the Kelso Quarry and Kelso trail runs, or join for an open water swim.
- ARTifacts Re-Imagined: Take part in a one-of-a-kind artistic experience, including sunflower field photos, interactive education, kids’ activities, and more at Country Heritage Park.
- Marshall Dane with ASL Interpretation-All Access Tour: Visit the FirstOntario Arts Centre as Canadian independent country recording artist Marshall Dane brings heartfelt storytelling to life in a captivating theatre-style concert with full ASL interpretation.
- Family Paint Party: Head to Boston Pizza Milton for some family fun for teens and adults with a guided painting session.
- Crystal Journey at Life Yoga Studio: Experience a sonic sound concert featuring Quartz crystal bowls, paiste planet gongs, Persian santoor, and harmonica.
Tuesday, September 23
- The Writer’s Circle @ Sherwood: Join this self-directed group at Sherwood Library to work on and share your writing.
Thursday, September 25
- Collaborations in Urban Riparian Restoration & Site Monitoring: Join the Society For Ecological Restoration Ontario and key consultants to learn about efforts in urban restoration and monitoring alongside commercial development.
- Sushi Making Class at Third Moon Brewery: Learn how to make California rolls, spicy salmon rolls and tuna hand rolls with Joyce of Cooking.
Friday, September 26
- Epic Elton: Experience the magic of Elton John in this incredible tribute performance by Jeff Scott at the FirstOntario Arts Centre.
Saturday, September 27
- Repair Café: Give broken goods a new lease on life before you toss them with some help from the volunteers at Sustainable Milton.
- Family Paint Party: Head to Boston Pizza Milton for some family fun for teens and adults with a guided painting session.
- Family Paint Party: Teens and adults – unleash your inner artist at Shoeless Joe’s with an afternoon of creativity in a guided painting tutorial.
- The Reba, Dolly and Shania Tribute Show: Celebrate the 100th anniversary of the Grand Ole Opry with a a high-energy tribute show that brings the best of Reba McEntire, Dolly Parton, and Shania Twain to the stage in one unforgettable performance at the FirstOntario Arts Centre.
- Glow Disc Golf at Kelso – One Night Only: Experience a unique glow-in-the-dark disc golf round on the scenic “Blue 9” layout at Kelso Conservation Area.
Saturday, September 27 – Sunday, September 28
- The 25th annual Putnam County Spelling Bee: Join Milton Community Theatre for its latest show where an eclectic group of mid pubescents vie for the spelling championship of a lifetime, happening at the FirstOntario Arts Centre.
Sunday, September 28
- Cycle 4 St. Joe’s: Sign up to ride 10km, 25km, 50km, 75km, or 100km through the scenic countryside to support St. Joseph’s Health Centre Foundation at this fundraiser starting at Mattamy National Cycling Center.
- Diwali Artisan Bazaar: Celebrate the Festival of Lights with creativity and community at Milton Mall’s first-ever Diwali Artisan Bazaar.
- Family Paint Party: Bring your family to Lone Star Texas Grill for a meal while painting, suitable for teenagers and adults.
- Take It To The Limit – A Tribute To The Eagles: Get ready for an unforgettable night of live music as some of Canada’s most talented musicians and vocalists bring to life your favourite Eagles hits at FirstOntario Arts Centre.
Tuesday, September 30
- Sechile Sedare: Enjoy a free musical performance at FirstOntario Arts Centre by a duo that transcends genre.
New events are continually being added to our event calendar, so make sure to stay tuned for all the latest festivals and community connections! For more Milton activity inspiration, check out our blog and explore our guides:
