As April showers bring May flowers, Milton is filling up with exciting events to keep the community entertained. Don’t miss out on fun afternoons of painting with the family, thrilling concerts that will fill up your evenings, regular trivia nights, and so much more.
Here’s Milton’s roundup of all the can’t miss events for May.
Experience of the Month
- Monster Trucks All Out: It’s a Monster Truck event at the Milton Fairgrounds. Come see your favourite robot battle and monster truck collisions, including the T-Rex Canada debut tour on Saturday, May 9. It’s guaranteed to be a fantastic day of fun for the whole family.
Ongoing Events
- Happy Hour Wine & Beer Tasting in Milton: Come out every Friday at Vin Bon in Milton for a great way to pass a Friday night in a relaxing atmosphere with others who are just as curious as you are about winemaking and the brewing process. It’s your chance to ask questions and have an enjoyable tasting hour.
- Live Music @ Marquee Steakhouse & Piano Lounge: Dinner out is made for Friday and Saturday nights. Dress up and head on over to the Marquee for some delicious food and live entertainment as you dine with a loved one or friends.
- The Love List: Enjoy this humorous, thought-provoking comedy brought to you by The Milton Players Theatre Group in this multi-day show that runs from Friday, May 1, to Saturday, May 9.
- Graceway Baptist Church Women to Women Ministry: Join in this monthly fellowship for women who want to dig deeper into God’s teachings on the first Saturday of every month.
- Spirit of the Lake: Don’t miss out on the opportunity to visit Crawford Lake and see it from the perspective of the Indigenous people through their art and stories. This event runs on weekends until June 28.
- Neurodiverse Teen Hangout: If you know a neurodivergent teen who could use a safe space and a way to connect with others of a similar mind, then be sure to sign them up for this 2-hour Saturday get-together from 2:00 to 4:00 pm.
- Monday Night Trivia at Keenan’s Irish Pub in Milton: Trivia lovers, come out for Keenan’s Irish Pub Trivia Night from 7:30 to 9:30 pm with host master Colleen Whelpdale. Don’t forget to reserve your spot on Eventbrite and call Keenan’s at (905) 693-0030 to reserve your table.
- Tuesday Night Trivia at Shoeless Joe’s in Milton: Take your talent for knowing random facts to the next level at Trivia Night at Shoeless Joe’s. Reservations can be made via Eventbrite, but don’t forget to call Shoeless Joe’s at (905) 864-9779 to reserve your spot.
- Grace Church’s Walking Group at Mill Pond: Partake in Grace Church’s Walking Group for a nice, gentle stroll around Milton’s iconic Mill Pond. Meet up at Grace Church at 8:30 am or at the Mill Pond Gazebo at 8:45 am every Wednesday.
- Wednesday Night Trivia at St. Louis Bar & Grill in Milton: We’ve got another trivia event every Wednesday night at St. Louis Bar and Grill. This is your chance to show off your knowledge and potentially earn a prize, plus bragging rights. Don’t forget to call ahead at (905) 875-1333 to reserve your spot.
- Public Speaking & Leadership Skills- Supporting Women Entrepreneurs: Calling women who want to learn to bolden their voice and become better prepared at public speaking, come on out to the Toastmasters Club. These meetings take place every Wednesday from 7:30 to 9:30 pm, and the first one is free.
- The Thursday Fixe @ Marquee Steakhouse & Piano Lounge: Celebrate Thursdays with a visit to the Marquee. Experience a delicious dinner of an appetizer, entrée, and dessert for $78 per person every Thursday.
- Graceway Baptist Church Deep Roots Youth Night: A great way to occupy kids in grades 7 through 12 and deepen their faith in God in this Youth Night, every second Friday at 7:00 pm at Graceway Baptist Church.
- Graceway Baptist Church Men’s Fellowship: Join the fellowship of men and reconnect with God every second Saturday of the month from 7:00 to 8:00 pm.
- High School Musical 2 JR.: It’s time for dancing and music with the whole gang. Bring the family and come to one of these shows that run from May 21 to May 24.
Events by Date
Friday, May 1
- Feel the Rush Watch Party: Cheer on the Toronto Rush and their season opener in the company of like-minded ultimate frisbee fans at Luigi’s Lasagna and Pizzeria. The cost to attend includes unlimited pizza and two beverages.
- Kenny & Dolly: Enjoy the best of these iconic artists in this tribute show performed by award-winning artists Alan Turner and Laurie Lynn.
Saturday, May 2
- 40th Annual Charity Breakfast: Don’t miss out on the return of the Halton Sportsmen’s Association 40th Annual Charity Breakfast. In support of a great cause, you’ll also get a delicious breakfast and the potential to win a prize.
- 5 Peaks Kelso: Runners and trail blazers looking to challenge themselves, sign up for this trail run open to all ages and abilities.
- Milton Youth Market: Food trucks, vendors, and a chance to support the neighbourhood youth in this free event that runs from 10:00 am to 3:30 pm at the Milton Sports Centre.
- TeaFest 2026: Calling tea enthusiasts, come on out to Sherwood Community Centre for your chance to taste your way through over 30 vendors, watch a few demonstrations, and learn more about the history and culture of tea. This is a free event that runs from 10:00 am to 5:00 pm.
- Halton Country Radial Railway: The operating system for the Milton radial railway is back in action. Bring your family and friends for a fun ride along the tracks, and don’t forget to visit the museum.
- Family Paint Party: Great food, time with family, and artwork to bring home and display in your home, that’s what this paint party is all about. Sign up for your sport and come a few minutes early to order some food.
- Cozy Paint Night: Book your cozy paint night at Art Haven Café and get ready to paint, sip a hot beverage, and bring home your piece to display proudly in your home.
- Halton Fashion Show 2026: Fashion for a great charity. Enjoy a cocktail dinner, drink, and show – all while supporting the Milton District Hospital Foundation.
- MPO Symphonic Brilliance: Enjoy the Milton Philharmonic Orchestra as it presents its 12th season with the best of orchestral music, including pianist Sumi Kin.
Sunday, May 3
- Ward 2 Cleanup: If you find yourself driving or walking around Milton seeing garbage everywhere, come on out to the Clark Neighbourhood Park cleanup initiative. Gloves and bags are provided; simply bring a positive spirit and the readiness to clean.
- ODOC Tech Day – For DeLorean Owners: A day for ODOC members and those who own DeLoreans to get their car checked out.
- Turkish Mosaic Lamp Workshop: Sign up for this 2.5-hour workshop for those interested in making a Turkish lamp to bring home. You’ll receive all materials, a fun environment, and expert guidance.
- In-person Free Coding Workshop for Kids (7-14 yrs): If you have a kid who is interested in learning how to code, this is the free workshop for them! Please note there are different timeslots for each age group.
- In-person Free Robotics Workshop for Kids (7-14 yrs): Calling kids who have an interest in robotics. Come on out for this free workshop and learn more with this hands-on program.
- Clothed With Love Pop-Up Freestore – Prom/ Grad Edition: If your child is graduating this year, check out this clothing pop-up with grad clothes in mind.
- Spring Bouquet: Enjoy a spring-themed concert by the Milton Concert Band in this afternoon event at First Ontario Arts Centre.
- Family Paint Party: Gather the family for an afternoon of painting, food, and time spent together at Boston Pizza.
Monday, May 4
- Scholastic Book Fair: This is a two-day event showcasing the newest releases, bestsellers, and classics in the book world. Come on out and find your next favourite read.
- Paint On 2 Wine Glasses at East Side Mario’s: An early treat for the mother figures in your life. In this activity, you will paint two wine glasses at East Side Mario’s and enjoy some cocktails and food along the way.
Thursday, May 7
- Third Moon 6th Anniversary Weekend!: Third Moon Brewery is celebrating being a Milton Brewery for 6 years. Want to know what they’ve got planned? Check with their website on May 7 and see what fun they’ve got in store.
- Prompt Engineering for Real Life Scenarios (METM Spring Open House): If you find the idea of AI confusing and the words “prompt engineering” enough to send you into hiding, then this free workshop is for you. Learn how to use it for real-life scenarios and walk away with confidence.
Friday, May 8
- Night at the Races: Get yourself out of the house with a fun evening of exciting races at Woodbine Mohawk Raceway and show your support for the Hamilton Mountain EDA.
- Kala Colours of South Asia Art Exhibition: Focussed on the theme of Kshan, come and explore the beauty of South Asian artistry as SAMM celebrates 10 years of building community.
- HELLS BELLS: It’s the world’s longest touring tribute to rock band AC/DC – an event not to be missed!
Saturday, May 9
- Book Signing with Kristine Cieslok at Milton Indigo: Come and meet author Kristine Cieslok of the book DIY – Tools You Need to Fix Yourself at Indigo.
- Mother’s Day Brunch @ Marquee Steakhouse & Piano Lounge: Why wait until Sunday to celebrate mom when you can get a jump on celebrating her with a Mother’s Day Brunch at Marquee Steakhouse? Enjoy delicious food and talented musical acts.
- The Barn Door Studio Custom Charcuterie Board Workshop: If you love to entertain but want to add some pizzazz to your next cheese and wine tasting night, sign yourself up for this charcuterie board workshop.
- Mother’s Day (moms and kids): A creative celebration for moms and kids in this Mother’s Day paint along at Art Haven Café. Each ticket covers mom and one child, a 9×12 canvas, painting supplies, and step-by-step instructions. Extra sibling spots can also be bought.
- The Pottery Hut Grand Opening: It’s the grand opening of The Pottery Hut. Come out to try some pottery for free with drinks and food. Reserve your spot on Eventbrite.
- Repair Café: If you have something lying around the house that isn’t working anymore and you’re wondering if it’s possible to fix, come out to the repair café. Let them know what you’d like repaired and reserve your spot.
- Paint Nite Brand Creative Events: Another fantastic early Mother’s Day event to spend some quality time with mom and give her a gift all in the same breath. Reserve your spot soon! *Note, there are two locations for this event, Shoeless Joe’s and Boston Pizza.
- The 68 Comeback & ALOHA from Hawaii Double Bill: Come out and see the most-watched concert in television history, featuring Elvis Presley in one of his most incredible performances ever.
Sunday, May 10
- Mother’s Day Dinner @ Marquee Steakhouse & Piano Lounge: Treat mom to some delicious food and music this Mother’s Day with a custom menu designed specially for her.
- Milton’s Annual Premium Mother’s Day Brunch: Celebrate the mother figures in your life with this special brunch at the Milton Banquet and Conference Centre. Tickets include a kid buffet, brunch station, fresh seafood, a sweets table, and more. Multiple time slots available.
- Mother’s Day Mats and Mimosas: Give mom more than flowers in this mat and mimosa event at The Barn Door Studio. Don’t forget to book your spot.
- Floral Dough Bowl Candle & Mimosas Mothers Day Workshop: Candles are soothing, and so are mimosas. Combine the two this Mother’s Day for an event she’ll swoon over. Be sure to book your ticket before they sell out.
- Mother’s Day Paint Nite at Boston Pizza Milton!: Let mom paint her worries away and have some fun time to simply enjoy herself in this paint night at Boston Pizza.
Tuesday, May 12
- CFHN Showcase Event: Come to this demonstration and celebration of the hardworking charities that serve Milton and Halton Hills in this free CFHN Showcase.
- Wednesday, May 13
- Oh Look, Fabric! Level 2 – Learn to Sew Workshop (Adult): If you took the Level 1 workshop, then you’ll want to be sure to take this learn to sew workshop, too, to continue in your learning journey.
Thursday, May 14
- Custom Corn Hole Set Workshop: If you’ve admired a neighbour’s corn hole board and thought, I’d like to have my own, then this is the workshop for you. Book your ticket with the Barn Door Studio and get yours made just in time before the warm weather sets in.
Friday, May 15
- Sonic Curators @ Uncle Sam’s Bar & BBQ: Come out for a great night of rock and pop hits from the past five decades alongside great food.
Saturday, May 16
- 3D Archery Shoot: Test your archery skills at this month’s archery tournament. Payment includes 40 individual targets and lunch. If you can’t make this one, don’t fret. You can catch one of the other ones later this year.
- Designers Merge Spring / Summer Exhibition Milton: Don’t miss out on this Spring/Summer Eid Edit showcase at the Holiday Inn Express & Suites.
- Family Paint Party: Paint the afternoon away with the family at Boston Pizza in this instructor-led paint night for all ages.
- The Barn Door Studio Pick Your Project Crafty Workshop: If you have a project you’ve had your eye on, then this is the workshop you want to attend. Come and create your custom project among popular projects like signs, mats, boards, and more.
- Tarot Reading Night: Want to know what the future holds for you? Join Dee the tarot reader for a private session at Third Moon Brewing while you partake in a delicious beer.
- Grease Live: It’s electrifying! Unleash your inner Danny and Sandy in an evening of music and dance from the popular musical Grease.
Sunday, May 17
- Family Paint Party: It’s another family paint afternoon for all ages at Boston Pizza with artist Disha Sharma. Don’t forget to come early to reserve your spot and order some food.
- Crochet Workshop (Thistle Flower Stem): Expand your crochet knowledge in this workshop. This is a beginner-friendly class hosted by The Way to You.
Tuesday, May 19
- Paint Nite Brand Creative Events: Unleash your inner artist on canvas and paint a landscape to take home while you nosh on some food at Keenan’s Irish Pub.
Wednesday, May 20
- The Barn Door Studio Petals and Pour Workshop: Enjoy an evening of candle making and flower arranging for the perfect take-home décor item.
Thursday, May 21
- Paint Nite Brand Creative Events: Create a painting of Misty Mountain Sunrise to take home. All supplies are provided by this instructor-led class at Montana’s BBQ & Bar.
- The Rise of Cinematography, Kodak and Leica: Join speaker Mike Miller in the third part of this captivating series of photography through the 1870s to 1932 at the Milton Historical Society.
Saturday, May 23
- Milton Mosaic Eid Bazar 2026: Join in the Eid Al-Adha shopping bazaar at the Milton Sports Centre. The event includes food stalls, cartoon mascots, competitions, and more. Entry is free.
- Singles Hike at Hilton Falls: Single and looking to mingle? Drop the traditional ways to meet people and try the singles hike at Hilton Falls. This is a guided social hike with mini cocktail sandwiches included in the cost. Please note that park admission is to be paid separately from the event payment.
- Family Paint Party: It’s another chance to paint with the family guided by artist Disha Sharma at Shoeless Joe’s.
- Lights! Camera! Sing!: Sing along with familiar tunes from cinema and theatre at Knox Presbyterian Church.
Sunday, May 24
- The Barn Door Studio Mats and Mimosas: Create your personalized mat while sipping away at mimosas alongside creative-minded folks.
Tuesday, May 26
- Eid Adha Gala Milton 2026: It’s the 14th anniversary of the Eid Gala in Milton. Join in the fun and shop for jewellery, bangles, clothing, and more at the Milton Sports Centre.
- UK Pink Floyd Experience _ The Authentic Tribute: Experience an evening of Pink Floyd as the band pays tribute to all the hits at the First Ontario Arts Centre.
Thursday, May 28
- Tropical Coastal Vibe Coaster Set Dot-Painting Workshop: Come and learn dot painting in this evening workshop. You’ll walk away with a set of 2 4” coasters to bring home and a delicious meal while you work.
- Oh Look Fabric! Level 3 – Learn to Sew Workshop (Adult): If you took levels 1 and 2, then be sure to attend level 3 in this learn to sew workshop for adults.
Friday, May 29
- Jerk Chicken Pop-up with Grant’s Gourmet: It’s the collaboration you love, Grant’s Gourmet and Third Moon Brewing. Enjoy some delicious jerk chicken alongside thirst-quenching beer.
- Fleetwood Mac Mania – Fleetwood Mac Tribute (1 HR Show): Come out and hear long-time favourites from this iconic band in this 1-hour show at Chudleigh’s Entertainment Farm.
Saturday, May 30
- Men’s Breakfast: Calling men 18+ looking for connection in uncertain times. Head on over to The Connect Centre and have a delicious breakfast as you share stories and laughter.
- UCHS Rabies & Microchip Clinic: If you have a cat or dog who is due for their rabies vaccine or you want to get them microchipped, this is the clinic for you. Please remember to register beforehand.
- Family Paint Party: It’s another fun afternoon of painting with the family at Boston Pizza. Come early to order some food and reserve your spot.
- Christian Spring Singles Mixer and More: Christians looking to meet someone within the same faith, this is the mixer you’ve been looking for. Register for this event and come ready to enjoy some games, treats, and good company.
- U2 Tribute – Desire (1 Hr Show): Performing some of their biggest hits, you’ll get swept away in this 1-hour show in the opening weekend of Summer Cider Nights.
Sunday, May 31
- The Little Blossom Children’s Musical 🎶 The Petting Zoo (ages 0-10): What better way to spend some time with the kids than apple picking, running around the playground, and visiting the farm animals at Chudleigh’s Entertainment Farm.
- Holding Space: If you are struggling with grief over the loss of a loved one, then this is a program to help you. This is the second-last session of this series. This one will focus on Pet loss: My furry friend is gone. Is my grief real?
- And The Award Goes To…: It’s a two-day event that celebrates the talent and love of dance in this recital inspired by past and present Tony Award-winning musicals.
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:
