Bolton Midnight Madness
Midnight Madness is back again for 2026, proudly celebrating their 50th year. Bring the whole family, your friends, neighbours and even your pets for a night of great food, live music, outdoor marketplace and so much more.
10 events found.
Events
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Downtown Bolton
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Authors in the Hills of Mulmur
The Foley Barn 587146 Sideroad 10, Mulmur, Ontario, CanadaThe brainchild of Mulmur mayor, Janet Horner, this is now a literary sense of occasion with tickets selling out early. This annual event is a collaboration between the Township of Mulmur, Shelburne Public Library, BookLore and hard-working volunteers. This year our author lineup includes Terry Fallis, Linwood Barclay and Heather Marshall. $40, includes an after-party…
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Legacy Golf Classic
TPC Toronto at Osprey Valley 19131 Main Street, Caledon Village, Ontario, CanadaExperience a premier, pro-tour-style tournament at TPC Toronto at Osprey Valley, the home of the 2025, 2026 and 2027 RBC Canadian Open. The 2nd Annual Legacy Golf Classic combines world-class golf with meaningful community stewardship. Following a spectacular inaugural year, this event brings together local leaders and partners for a championship-grade day on the greens.…
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Peel-Dufferin Plowing Match
Drummearl Farm 5754 Old School Rd, Caledon, Ontario, CanadaCome out for a day of fun in the fields at the annual plowing match featuring horse plowing, tractor plowing and the Queen of the Furrow Competition. BBQ chicken lunch available for $20 — pre-orders preferred by contacting Mel Karpenko at pdplowmens@gmail.com or calling 647-229-3326.
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The 21st Anniversary Jim Cuddy Jamboree
Lyric Pond 597425 2nd Line West, Mulmur, Ontario, CanadaJuno-award-winning musician Jim Cuddy takes to the stage in Mulmur for the 21st Annual Jim Cuddy Jamboree. This cherished tradition brings together talented musicians, local supporters, and community members for an evening of unforgettable music, exceptional food, and warm hospitality. For 2026, proceeds will directly support the Honeywood Arena, the Honeywood Fire Fighters Association, and…
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Orangeville Fair
Orangeville Agricultural Society Event Centre, 247090 Side Rd 5, Mono, Ontario, CanadaMark your calendars for the Orangeville Fair. Join the Orangeville Agricultural Society for a celebration of agriculture, entertainment, and community spirit. Experience the best of local culture, and traditions including a classic car show, petting zoo, wagon rides, demolition derby, live entertainment and more.
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Island Lake Classic
Island Lake Conservation Area 673067 Hurontario Street, S., Orangeville, Ontario, Canada14th annual Island Lake Classic 5K & 10K starts and ends in picturesque Island Lake Conservation Area. Groomed trails and numerous bridge crossings along the Vicki Barron Lakeside Trail highlight the natural elements that this park has to offer. Free Kids Fun Run. Finisher medals, great swag, fun for the whole family! Participants can add…
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motionball Caledon
Caledon East Community Complex 215 Old Church Rd, Caledon East, Ontario, CanadaGet ready to move, play, and make an impact. Sign up as a team captain and recruit up to 10 participants to join your team. When you arrive onsite at Marathon of Sport, you will be joined by one to two local Special Olympics athletes from the community. Together you will participate in a variety…
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Golf 4 Bethell Hospice
TPC Toronto at Osprey Valley 19131 Main Street, Caledon Village, Ontario, CanadaThe 7th Annual Golf 4 Bethell Hospice Tournament features 18 holes with shared power carts, delicious breakfast, barbeque lunch, cash bar, great prizes, and both live and silent auctions. All proceeds to support Bethell Hospice. Go online for more information or to register.
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Shelburne Fall Fair
Shelburne Fairgrounds 377 William Street, Shelburne, Ontario, CanadaCelebrating 159 years, the fair kicks off with the Fair Ambassador Program Friday evening and continues Saturday with classic fair events like livestock shows, contests, demolition derby and more. This year’s theme is ‘Harvest, Honey, & Home.’