Entertainment
2026 Entertainment
House of Chords Friday Night Musical Showcase
House of Chords, back for another year, is Milton’s favourite local music school, providing private lessons, recording, and vibrant student band programs. At the Milton Fall Fair, they are proud to power the Market Stage on Friday night, featuring up-and-coming local youth bands rocking the crowd with high-energy live covers and original hits.
You don’t want to miss some of Milton’s best up and coming talent on Friday night at the Fair!
Friday Night – Market Stage 5:00 pm
Urban Cowboy
Mario has always had an interest in leading a crowd and making sure everyone is involved and having fun. At a young age, Mario came to the hard realisation that he couldn’t dance and that he had no rhythm. Shortly after, he started spending endless hours on the dance floor; learning each dance and steps to various songs. He has been instructing for 10 years and throughout these years, he has acquired a unique style of teaching. In other words, he put in the hard work, now he’s making it easier for others to learn the moves!!
www.urbancowboyld.com
Friday Night – Main Stage (Beer Tent) 5:00 pm
Mackenzie Leigh Meyer
Multi-instrumentalists and CMAO award winning Mackenzie Leigh Meyer is one of the most unique up and comers in country music today. Her captivating talent and strong presence was an instant stand out; quickly getting her billed on famed stages like Boots and Hearts, Lucknow’s Music in the Fields and Nashville’s Whiskey Jam to name a few. Currently Mackenzie is promoting her latest single “In Love with a Loser” and gearing up to release her highly anticipated sophomore EP “Bar Star”. Playing your favourite country and classic rock hits at the 2026 Milton Fall Fair, whether it’s her velvety vocals, or unapologetic lyrics, when Mackenzie Leigh Meyer sings, people listen.
Friday Night – Beer Tent 8:00 pm
INJUNCTION: Ontario’s Ultimate Rock Cover Experience
Ontario’s Ultimate Rock Cover Experience INJUNCTION is Ontario’s powerhouse rock cover band that transcends generations with their electrifying performances and unparalleled musical prowess. Born from a shared passion for rock ‘n’ roll’s rich history and its timeless appeal, INJUNCTION is more than just a cover band—they are a sonic journey through the greatest decades of rock music. From intimate venues to large festivals, INJUNCTION has been rocking stages across Ontario, leaving a trail of satisfied audiences and unforgettable performances.
Saturday – Market Stage 5:00 pm
Greg Williams
Greg Williams is a multi-instrumentalist singersongwriter hailing from Woodstock, Ontario. His Roots-Rock sound nods to his influences of Southern Rock, Electrified Americana, Heartland Rock ‘n’ Roll, and Country & Western while creating something uniquely and unequivocally his own alongside his band ‘The Dirty Magnolias.’ He has performed with acts like George Canyon, The Hunter Brothers, The Reklaws, and Grammy-Award Winning Legendary Country Band Confederate Railroad. With over 25 years of Live Show experience across North America – this is one show you don’t want to miss out on!
Saturday – Beer Tent 9:00 pm
Milton Academy of Music
Established in 1982 by founder Joanne Parker, the Academy of Music is a family-run music school, celebrating over 40 years in the Milton community. We believe that learning music should be structured, welcoming, and above all, fun! Our teachers have extensive training and specialize in working with beginners of all ages, helping each student learn at their own pace. We are incredibly proud of our talented students performing at the Fall Fair today— please give them a round of applause as they take the stage!
Sunday – Market Stage 11:00 am
The Mighty Ship
The Mighty Ship is Fredericton, New Brunswick’s Rick Morgan. When the pandemic hit, it severed him from musical connection and collaboration. His ability to return home to the sights and sounds of Atlantic Canada was negated. As a coping mechanism, he launched a creative voyage to reconnect himself to his Celtic and East Coast Folk musical roots. Using his multi-instrumentalist abilities, he began recording himself playing instrumental loops that he combined to create master backing track MP3s for some of his favourite Celtic music from across The Pond and beyond. Acting as his own band playing these pre-recorded parts, he sings and plays guitar live in unison. The result is a full and diverse sound so if you enjoy a hand-clappin’, toe- tappin’, foot-stompin’ good time, get on board with The Mighty Ship today!
Sunday – Beer Tent 11:00 am
Crash Rhythm Drums
CRASH represents an alternative, dynamic and engaging approach to music education and exploration. CRASH uses bucket drumming to tie together teamwork, creativity and fun while also learning the basics of music, composition, rhythm and drumming. CRASH teaches the importance of music in a fun environment where every question is explored and all ideas are welcomed. The skills learned in CRASH benefit children already studying an instrument while offering a wonderful interactive introduction to new students of music. No matter how old or young, everyone can benefit from CRASH!!
Market Stage – Sunday 2:00 pm
Station 31
Station 31 is a cover band based in Ontario’s Halton Region, formed in 2023 by longtime collaborators Shaun Kazemi and Jody Hayes. The two first met in 2003 while playing in separate original bands and reconnected years later, leading to the start of Station 31 and a renewed focus on playing live music together. With a focus on live performance and connecting with audiences, Station 31 takes pride in showing up prepared and delivering a fun, reliable show. If you’re curious to hear them live, check the Upcoming Shows section to see where Station 31 is playing next.
Sunday – Market Stage 3:00 pm
Hands on Exotics – EXHIBIT and SHOWS!
Seth’s Amazing Pets – Seth’s Amazing Pets is filled with exciting magic tricks, special props and comedy! This hour-long experience features a group performance followed by an animal and trainer meet and greet.
https://handsonexotics.com/seths-amazing-pets
Exhibit in Exhibition Theatre – Friday 4:00 pm – 6:30 pm, Saturday 10:00 am – 8:00 pm, Sunday 10:00 am – 4:00 pm
Marvellous Moments Face Painting
Making your event a success by creating a Marvellous Moment for everyone! So many services to choose from, it will be the event everyone raves about.
Exhibition Theatre – Saturday 12:00 pm – 5:00 pm and Sunday 11:00 am – 4:00 pm
Starry Party
Starry Party is all about bringing magic, smiles, and unforgettable moments to your events! We’ve brought joy to thousands of kids through expert face painting, glitter tattoos, and creative balloon characters. Beyond entertainment, we design custom party and event decorations—from weather resistant backdrops to grand illuminated installations—that turn festivals into vibrant, photo-worthy destinations!
Exhibition Theatre – Saturday 12:00 pm – 5:00 pm and Sunday 11:00 am – 4:00 pm
Rimsha Henna Art
Rimsha is a highly skilled professional henna (mehndi) artist based in Milton with over 10 years of experience in the industry. Her work includes collaborations with top beauty parlours and appearances at major exhibitions and festivals throughout the Greater Toronto Area. Rimsha is dedicated to providing safe and high-quality services by exclusively using organic henna. Her expertise spans multiple henna design styles, including Indian, Arabic, Freestyle, Moroccan, Pakistani, African, Contemporary, and more. Fluent in English, Urdu, Hindi, and Punjabi, Rimsha offers her services for a wide range of private events.
Exhibition Theatre – Saturday 12:00 pm – 5:00 pm and Sunday 11:00 am – 4:00 pm
Agricultural Education Tent
The Agricultural Education Tent features information and interactive exhibits and resources from across Ontario, helping our visitors to learn more about farming practices’, farm safety, and where their food comes from! This year, the Agricultural Education Tent features Durham Farm Connections, Aubrey from Little Musicians, Tinkerlabs Inc., Backed by Bees and so much more! Don’t forget to take in a demonstration from the Halton 4H Bunny Hopping Club of 2026!
Located at the south end of the grounds between the Display Barns
Open Friday 3:00 pm – 7:00 pm, Saturday 9:00 am – 7:00 pm, Sunday 10:00 am – 4:00 pm
FireSword Forge Blacksmith: David Brandow
David is a part-time blacksmith who does custom, traditional, hand-crafted functional art, tools and demonstrations. He does custom commissions, the occasional craft show, many public demonstrations and the occasional class. On the executive of the Ontario Artist Blacksmith Association for many years, he believes strongly in upholding traditional techniques and educating the public while simultaneously entertaining them. A teller of bad jokes and stories of dubious authenticity, with copious amounts of real information buried in and between them. A strong believer that the things you own should be built to last, should have beauty to them and should be functional.
Located at the south end of the grounds
Friday 5:00 pm – 8:00 pm, Saturday 10:00 am – 6:00 pm, Sunday 10:00 am – 4:00 pm
KR Horsemanship
Tom has been running petting zoos for many years, and caring for animals has always been his passion. He loves to share that passion with others and seeing the smiles that animals bring to families. Making those memories and connecting people with animals is what makes every event so rewarding.
Dawn till Dusk Enchanted Princesses
Tom has been running petting zoos for many years, and caring for animals has always been his passion. He loves to share that passion with others and seeing the smiles that animals bring to families. Making those memories and connecting people with animals is what makes every event so rewarding.
Making dreams come true is our ultimate goal. All children deserve something special and to feel like they have someone to believe in. At Dawn Till Dusk Enchanted Princess Parties, we take the time, care and attention to ensure every party feels special and one of a kind.
Roaming Sunday 12:00 pm – 3:00 pm
