Milton real estate agents may tell you that the market has cooled down a bit in 2026, but the community has definitely warmed up, and the days are starting to get longer. Spring is a wonderful time to get out and enjoy everything our community has to offer. From family-friendly festivals and live entertainment to markets, workshops, and outdoor events, there’s no shortage of things happening around Milton this season. Whether you’re looking for something fun to do with the kids, a unique local experience, or a great night out, here are some upcoming spring events happening in and around town.
Trivia Night
Every Tuesday | 7:30 PM
Ned Devine’s Irish Pub | 575 Ontario St S, Milton
Grab your smartest friends and test your knowledge at weekly Trivia Night at Ned Devine’s. Teams compete across a variety of fun and challenging categories in a lively pub atmosphere. It’s a great mid-week outing whether you’re playing for bragging rights or just enjoying a night out with friends, food, and drinks. More info at HERE
Autism Awareness Flag Raising
Thursday, April 2, 2026 | 9:30 AM – 10:30 AM
Milton Town Hall | 150 Mary St, Milton
Join the community for the Autism Awareness Flag Raising as Milton comes together to promote inclusion, understanding, and support for the neurodivergent community. The event will feature remarks from local advocates, including the Neurodivergent Community of Milton, Special Friends Network, and author Mary Barnes. Attendees can also connect with local resources such as Pivot Point, Autism Ontario, and Town of Milton Recreation. Light refreshments and community networking will follow, and all are welcome to attend.
Maple Town at Mountsberg
Weekends and holidays until April 5, 2026
Mountsberg Conservation Area | 2259 Milburough Town Line, Campbellville
Experience a classic Canadian spring tradition at Maple Town at Mountsberg. Visitors can learn how maple syrup is made while exploring the process from tree tapping to sap collection and syrup production. Along the way, guests can also visit the Animal Barn, walk the Raptor Trail and Raptor Centre, and let the kids enjoy the natural playground. Food is available for purchase, making it a great family outing to celebrate the maple syrup season. Tickets and info HERE
Sweet Water at Crawford Lake
Weekends and holidays until April 5, 2026
Crawford Lake Conservation Area | 3115 Conservation Rd, Milton
Discover the Indigenous origins of maple sugaring at Sweet Water at Crawford Lake. Visitors can enjoy maple and birch syrup tastings, gather for a Sweet Water Talk in the Longhouse Village, explore the Spirit of the Lake Exhibit, and walk the scenic trails. Families can also enjoy children’s crafts, maple taffy on snow (available for purchase), and browse maple treats in the gift shop. An optional Sweet Traditions Tour is also available for an additional fee. Tickets and info HERE
Dough Bowl Candle Pouring Workshop
Wednesday, April 1, 2026 | 6:00 PM – 8:00 PM
The Barn Door Studio | 327 Steeles Ave E, Milton
Create your own beautiful, handcrafted candle at this Dough Bowl Candle Pouring Workshop. Participants will learn the basics of candle making while pouring their own candle into a rustic wooden dough bowl. With guidance throughout the process, this relaxing and creative workshop is perfect for a fun night out, whether you’re coming with friends or looking to try something new. Purchase tickets HERE
Milton Comedy Show
Thursday, April 2, 2026 | 8:00 PM
Ned Devine’s Irish Pub | 575 Ontario St S, Milton
Enjoy a night of laughs at the Milton Comedy Show, featuring a lineup of stand-up comedians bringing sharp humour, quick wit, and hilarious storytelling to the stage. Held at Ned Devine’s Irish Pub, this lively comedy night offers a relaxed atmosphere with great food, drinks, and plenty of laughs for a fun night out in Milton. Info and tickets HERE
Family Paint Party
Saturday, April 4, 2026 | 2:00 PM – 4:00 PM
Boston Pizza Milton | 1085 Maple Ave, Milton
Bring the whole family for a fun and creative Family Paint Party where participants can enjoy a guided painting session together. No experience is necessary, just come ready to paint, relax, and create your own masterpiece. It’s a great opportunity for families to spend quality time together while enjoying an afternoon of creativity. Tickets HERE
The 2 Dollar Bills Live at The Ivy Arms
Saturday, April 11, 2026 | 9:30 PM – 1:30 AM
The Ivy Arms | 201 Main St E, Milton
Enjoy a night of live music as The 2 Dollar Bills return to The Ivy Arms for an energetic performance. Guests can expect great food, drinks, and a lively atmosphere while the band plays crowd-favourite hits late into the evening. A perfect way to spend a Saturday night with friends in downtown Milton.
Pick Your Project Crafty Workshop
Saturday, April 11, 2026 | 1:00 PM – 4:00 PM
The Barn Door Studio | 327 Steeles Ave E, Milton
Get creative at this Pick Your Project Crafty Workshop, where participants can choose from a variety of DIY projects and create something unique to take home. With guidance from the studio team and all materials provided, it’s a fun and relaxed environment to explore your creativity, whether you’re a beginner or an experienced crafter. Purchase tickets HERE
Family Paint Party
Saturday, April 11, 2026 | 2:00 PM – 4:00 PM
Shoeless Joes Milton | 800 Main St E #3, Milton
Bring the whole family for a fun and creative Family Paint Party where participants can enjoy a guided painting session together. No experience is necessary, just come ready to paint, relax, and create your own masterpiece. It’s a great opportunity for families to spend quality time together while enjoying an afternoon of creativity. Tickets HERE
Ladies Pink PJ Party
Friday, April 17, 2026 | 6:00 PM – 12:00 AM
Carlisle United Church | 1432 Centre Rd, Carlisle
Grab your favourite pink pajamas and join this fun evening designed just for the ladies. The Ladies Pink PJ Party features a relaxed night of socializing, entertainment, and community connection in a welcoming atmosphere. Guests can expect a lively event filled with laughter, themed activities, and opportunities to connect with friends old and new while supporting a great cause. Tickets HERE
Team Relay Challenge
Saturday, April 18, 2026 | 9:00 AM
Milton Sports Centre | 605 Santa Maria Blvd, Milton
Hosted by the Milton Speed Skating Club, the Team Relay Challenge is a short track speed skating event where teams compete in fast-paced relay races throughout the day. Skaters of various age groups come together for a competitive and exciting event that showcases teamwork, speed, and strategy. Spectators are welcome to attend and cheer on the athletes. More info HERE
Family Paint Party
Saturday, April 18, 2026 | 2:00 PM – 4:00 PM
Boston Pizza Milton | 1085 Maple Ave, Milton
Bring the whole family for a fun and creative Family Paint Party where participants can enjoy a guided painting session together. No experience is necessary, just come ready to paint, relax, and create your own masterpiece. It’s a great opportunity for families to spend quality time together while enjoying an afternoon of creativity. Tickets HERE
Sourdough School
Sunday, April 19, 2026 | 11:00 AM – 2:00 PM
Marquee Steakhouse & Piano Lounge | 204 Main St E, Milton
Learn the art of baking delicious sourdough bread at this hands-on Sourdough School workshop. Participants will be guided through the fundamentals of sourdough, including starter care, fermentation, shaping techniques, and baking tips. It’s a fun and interactive experience perfect for beginners or anyone looking to sharpen their bread-making skills while enjoying a unique culinary experience in Milton. Tickets HERE
Mill Pond Free Children’s Fishing Derby
Saturday, April 25, 2026 | 6:00 AM – 1:00 PM
Mill Pond | 50 Martin St, Milton
Families are invited to the annual Mill Pond Children’s Fishing Derby, a fun community event where kids can enjoy a morning of fishing at one of Milton’s most scenic spots. Hosted by the Halton Sportsmen’s Association, the event encourages young anglers to get outdoors and experience fishing in a welcoming environment. A non-perishable food donation for the food bank is appreciated, making it a great opportunity to support the community while enjoying a memorable family outing. More info HERE
Family Paint Party
Saturday, April 25, 2026 | 2:00 PM – 4:00 PM
Shoeless Joes Milton | 800 Main St E #3, Milton
Bring the whole family for a fun and creative Family Paint Party where participants can enjoy a guided painting session together. No experience is necessary, just come ready to paint, relax, and create your own masterpiece. It’s a great opportunity for families to spend quality time together while enjoying an afternoon of creativity. Tickets HERE
Fleetwood Mac Mania
Friday, April 24, 2026 | 7:30 PM
FirstOntario Arts Centre Milton | 1010 Main St E, Milton
Fleetwood Mac Mania brings the iconic music of Fleetwood Mac to life with an electrifying tribute performance. Fans can expect to hear beloved classics like Go Your Own Way, Dreams, Rhiannon, and The Chain, delivered with the energy and authenticity that have made Fleetwood Mac one of the most celebrated bands of all time. A must-see show for rock and classic music lovers. Tickets HERE
The Men of the Deeps
Saturday, April 25, 2026 | 7:30 PM
FirstOntario Arts Centre Milton | 1010 Main St E, Milton
Experience a powerful performance by The Men of the Deeps, a world-renowned choir made up of working and retired coal miners from Cape Breton. Through traditional songs and storytelling, the group shares the rich culture and history of mining communities in Nova Scotia, creating an unforgettable evening of music and heritage. Tickets can be purchased HERE
Just For Laughs Road Show
Sunday, April 26, 2026 | 7:30 PM
FirstOntario Arts Centre Milton | 1010 Main St E, Milton
Enjoy a night of stand-up comedy as the Just For Laughs Road Show brings some of Canada’s top comedians to Milton. Featuring a lineup of performers from the world-famous comedy festival, the show promises an evening full of big laughs and great entertainment, perfect for a fun night out with friends or a date night. Tickets HERE
TeaFest 2026
Saturday, May 2, 2026 | 10:00 AM – 5:00 PM
Sherwood Community Centre and Library | 6355 Main St W, Milton
A celebration of all things tea featuring local tea vendors, samples, demonstrations, and community activities. A welcoming event for both tea enthusiasts and families looking for a unique spring outing. More info HERE
5 Peaks Trail Running Series – Kelso
Saturday, May 2, 2026 | 8:00 AM
Kelso Conservation Area | 5234 Kelso Rd, Milton
The 5 Peaks Trail Running Series returns to Kelso for a full day of trail racing set against the scenic backdrop of the Niagara Escarpment. Known as Canada’s largest trail running series, the event features multiple race distances suitable for beginners through experienced runners, along with a kids’ race and a welcoming festival atmosphere. It’s a great opportunity to enjoy Milton’s beautiful trails while cheering on runners tackling the challenging and rewarding course. More info and registration HERE
Symphonic Brilliance
Saturday, May 2, 2026 | 7:30 PM
FirstOntario Arts Centre Milton | 1010 Main St E, Milton
Enjoy an afternoon of beautiful orchestral music with Symphonic Brilliance, featuring a captivating performance by the Oakville Symphony. The program showcases powerful classical works performed by talented musicians, offering an inspiring and elegant concert experience for music lovers of all ages. Tickets HERE
MY 80s House Party Live!
Saturday, May 2, 2026 | 8:30 PM
Champs Family Entertainment Centre | 300 Bronte St S, Milton
Step back in time for a high-energy 80s dance party featuring the sounds of New Wave and iconic movie soundtrack hits from the decade. MY 80s House Party Live! brings a fun retro atmosphere with nostalgic music, vibrant energy, and a lively crowd ready to dance the night away. Perfect for anyone who loves the unforgettable music and style of the 1980s. More info HERE
Spring Bouquet
Sunday, May 3, 2026 | 2:00 PM
FirstOntario Arts Centre Milton | 1010 Main St E, Milton
Celebrate the beauty of the season with Spring Bouquet, a delightful performance by the Milton Philharmonic Orchestra. This uplifting concert features a selection of classical favourites and vibrant orchestral pieces that capture the fresh energy and renewal of spring, making it a wonderful afternoon of music for the whole community. Tickets HERE
Monster Trucks All Out – Milton
Saturday, May 9, 2026 | Various start times
Milton Fairgrounds | 136 Robert Street, Milton
Get ready for high-energy family fun with massive monster trucks performing stunts, crushing cars, and racing in nonstop action. This event includes meet-and-greet pit parties, ride-along experiences, and entertainment for all ages. Children ages 2 and under sit free on an adult’s lap. Rain or shine with ticket options ranging from general admission to VIP experiences. Tickets can be purchased HERE
Cornhole Workshop
Thursday, May 14, 2026 | 6:00 PM – 9:00 PM
The Barn Door Studio | 327 Steeles Ave E, Milton
Build your own custom cornhole boards at this hands-on workshop at The Barn Door Studio. Participants will be guided step-by-step through the process of assembling and finishing their boards, creating a fun backyard game set to take home. It’s a great experience for anyone who enjoys DIY projects, crafting, and creating something both practical and personal. Tickets HERE
Milton Farmers’ Market
Saturdays starting May 16, 2026 | 8:00 AM – 12:00 PM
Downtown Milton | Main Street East, Milton
The Milton Farmers’ Market returns for the season with fresh local produce, baked goods, artisan products, and ready-to-eat treats. Stroll through downtown Milton, meet local vendors, and enjoy a vibrant community atmosphere while supporting local farmers and small businesses. More info HERE
High School Musical 2 JR.
May 21-24, 2026 | Multiple Shows
FirstOntario Arts Centre Milton | 1010 Main St E, Milton
Enjoy a fun-filled theatrical performance as local young performers bring High School Musical 2 JR. to the stage. Based on the hit Disney Channel movie, the show features catchy songs, energetic dance numbers, and a lively story about friendship, teamwork, and summer fun. A great outing for families and musical theatre fans alike. Tickets HERE
5 Peaks Trail Running Series – Crawford Lake
Saturday, June 6, 2026 | 8:00 AM
Kelso Conservation Area | 3115 Conservation Road, Milton
The 5 Peaks Trail Running Series returns to Crawford Lake for a full day of trail racing set against the scenic backdrop of the Niagara Escarpment. Known as Canada’s largest trail running series, the event features multiple race distances suitable for beginners through experienced runners, along with a kids’ race and a welcoming festival atmosphere. It’s a great opportunity to enjoy Milton’s beautiful trails while cheering on runners tackling the challenging and rewarding course. More info and registration HERE
All Colours Agricultural Fair
June 12 – June 14, 2026 | TBD
Country Heritage Park | 8560 Tremaine Rd, Milton
The All Colours Agricultural Fair returns to Country Heritage Park for a weekend celebrating agriculture, education, and family-friendly fun. Visitors can explore historic buildings, enjoy live demonstrations, browse a vendor market, and participate in educational workshops. Hosted by the Country Heritage Agricultural Society, this vibrant community event highlights farming traditions while offering interactive experiences for all ages. More info HERE!
Milton is such a vibrant community, and these events are a great way to connect with neighbours, support local organizations, and enjoy everything the season has to offer. Be sure to check event pages for the most up-to-date details before attending.
