September
- 21-24: Ancaster Fair
- 21: Niagara Falls Night of Art @ 5943 Sylvia Pl (Niagara Falls) FREE
- Sep 22-Oct 15: Culture Days (Across Canada)
- Sep 22 -Oct14: Oktoberfest (Kitchener)
- 22-24: Milton Fall Fair @ Milton Fairgrounds
- 22-24: Niagara Grape & Wine Festival
- 22-23: Enchanted Forest of Fergus
- 23 (3-8pm): Claridge Street Party with music by the Killin' Time Band @ Claridge Rd (Burlington Beach)
- 23: Oakville Fall Celtic Festival @ Toronto Rock Athletic Centre (Halton County)
- 23-24 (12-6pm): Flamborogh Chili Fest @ West Avenue Cider House
- 23 (2-6pm): Schneider Creek Porch Party (Kitchener)
- 23: Beerstock (Port Dover) $38.42
- 24: Tesla Electric City Festival (Hamilton)
- 24, 1-5pm: Appleby Street Festival (Burlington)
- Sep 28-Oct 1: Caledonia Fair @ Caledonia Fairgrounds $?
- 29-30: Paris Night Market (Fall Edition) $10
- 30 (10am-4pm): Ottawa Street Sidewalk Sale (Hamilton)
- 30 (10am-4pm): Taste Real Fall Rural Romp (Wellington Region)
- Sep 30-Oct 1: Cicada Music Festival (St. Catharines)
October
- Sep 22-Oct 15: Culture Days (Across Canada)
- Sep 22 -Oct14: Oktoberfest (Kitchener)
- Sep 28-Oct 1: Caledonia Fair
- Sep 30-Oct 1: Cicada Music Festival (St. Catharines)
- 1 (10am-2pm): Applefest Fall Fair (Burlington)
- 3-9: Norfolk County Fair (Simcoe)
- 5 (4-11pm): Oktoberfest Block Party @ Oktoberfest Platz (Kitchener) $20
- 6-9: Balls Fall's Thanksgiving Festival
- 6-9: Erin Fall Fair
- 6-9: Rockton World's Fair
- 12-21: AGH (Art Gallery of Hamilton) Festival
- 13: Artcrawl (Hamilton)
- 13-15: Hops and Harvest Festival (Milton)
- 13-15: Waterford Pumpkinfest
November
- 10: Artcrawl (Hamilton)
- 17-19: Handmade Market (some Live Music) (Niagara Falls)
- Boris Brott Music Festival
- Arts Dundas Weekend
- Fresh Up R&B Festival (Hamilton)
- Pints & Plaid: Beer Festival (Port Dover)
- Winter Wonders (Live Music Tent) (Burlington)
- International Pop Overthrow (Hamilton)
- Winter Wander (Hamilton)
December
- 8: Artcrawl (Hamilton)
- Winter Wonders (Live Music Tent) (Burlington)
- Let it Glow - A Celebration of Light (with some Live Music) @ St. Catharines & Port Dalhousie
- Downtown Milton Holiday Fest
- Winter Wonders (Live Music Tent) (Burlington)
- Let it Glow - A Celebration of Light (with some Live Music) @ St. Catharines & Port Dalhousie
- Wrapped in Local (Caledonia)
- Niagara Falls Music Live
2024
January
- 14: Artcrawl (Hamilton)
- 12: Winter Wonders (Live Music Tent) (Burlington)
- Let it Glow - A Celebration of Light (with some Live Music) @ St. Catharines & Port Dalhousie
- Niagara Icewine Festival
- ArtsEverywhere Festival (Guelph)
February
- 9: Artcrawl (Hamilton)
- Hillside Inside (Guelph)
- Hamilton Winterfest
- Frost Bites (Hamilton)
- Taste of Oakville (some live music)
- Inside & Outside Family Day Festival (Dundas)
- I Heart Beer & Taco Festival (Hamilton)
- Soupfest (Hamilton)
March
- 15: Artcrawl (Hamilton)
- Winter Beer Festival (Burlington)
- Taste of Oakville (some live music)
- Irish Life Festival (Kitchener)
- Food & Drink Fest (Hamilton)
- Heart of Ontario Tour (Paris)
- Heart of Ontario Tour (Milton)
- Heart of Ontario Tour (Binbrook)
- KW Wine & Food Show
April
- 12: Artcrawl (Hamilton)
- SCHTICKY FEST - Rural Roots Music Festival (Elmira)
- Eat and Drink Norfolk
- Hamilton Music Festival
- Elvis Festival (Niagara Falls)
- Gainfest (Guelph)
- Doors Open Guelph
May
- 10: Artcrawl (Hamilton)
- 2Rivers Festival (Guelph)
- Why Not Wine, Wine Tasting Festival (Hamilton)
- Sew Hungry (Hamilton)
- Binbrook Ribfest
- Concession Street Sidewalk Sounds (Hamilton)
- Mel Brown Festival @ Kitchener-Waterloo
- Hohner Avenue Porch Party (Kitchener)
June
- 14: Artcrawl (Hamilton)
- Open Ears Festival (Kitchener)
- Niagara Regional Exhibition (Welland)
- Handmade Market (some Live Music) (Niagara Falls)
- Battle of Stoney Creek Re-Enactment
- Downtown Milton Summer Fest
- Hamilton Arts Week
- Mudcat Festival (Dunnville)
- In the Soil Arts Festival (St. Catharines)
- Handmade Market (some Live Music) (Niagara Falls)
- Multicultural Festival (Guelph)
- Norfolk Night Market with Live Music
- Norfolk Country Fairground Festival $25
- Concession Streetfest (Hamilton)
- Ancaster Heritage Days
- Georgetown Highland Games
- Grand Porch Party (Waterloo)
- Sound of Music Festival (Burlington)
- FrancoFEST (Hamilton)
- Niagara Falls Ribfest
- Cambridge Celebration of the Arts @ City Hall
- Concession Street Sidewalk Sounds (Hamilton)
- Crafters Corner Market (Waterloo)
- Open Streets Hamilton
- For the Love of Fathers and Food Trucks (Milton)
- Oakville Film Festival
- Artsfest (Hamilton)
- Something Else! Festival of Creative Music (Hamilton)
- Fresh Up R&B Festival (Hamilton)
- KW Multicultural Festival (Kitchener)
- Holi Festival of Colour (St. Catharines)
- African Caribbean Food & Music Festival (St. Catharines)
- Art on the Street (Guelph)
- Crown Point Music Crawl (Hamilton)
- Street Sale & Party (St. Catharines)
- Boris Brott Music Festival
- Hamilton Mountain Ribfest
- Oh Canada Ribfest (Waterdown)
July
- 1: Burlington Canada Day Celebrations
- 1: Oakville Canada Day Celebrations
- 1: Brantford Canada Day Celebrations
- 1: Cambridge Canada Day Celebration
- 1: Kitchener Canada Day Celebrations
- Hamilton Mountain Ribfest
- Rock N Blues on the Battlefield (Thorold)
- Oh Canada Ribfest (Waterdown)
- It's Your Festival (Hamilton)
- Brantford International Villages Festival
- International Villages Cultural Festival (Brantford)
- Georgetown Ribfest
- The Grimsby Cheesecake X Food Truck Fest (with some live music) @ West Niagara Fairgrounds (Grassie) $5
- Ridgeway Art & Music Festival
- Cruising on King (Kitchener)
- Welland Floatfest
- HexStock (Milton)
- Pelham Summerfest
- Kultrún World Music Festival (St. Jacobs)
- Artcrawl (Hamilton)
- Davids & DeLaat's Block Party @ St. Catharines
- Hagersville Rocks
- Cambridge Scottish Festival
- Because Beer Festival (Hamilton)
- Norfolk Ram Rodeo
- Kitchener Ribfest & Craft Beer Show
- Concession Street Sidewalk Sounds (Hamilton)
- Sundays Unlocked @ Locke Street (Hamilton)
- Open Streets on Barton @ Barton Street (Hamilton)
- Mackenzie Creek Music Festival @ 72 King St. N (Oakland)
- Ancaster Ribfest
- Burlington Food Truck Festival @ Downtown Waterfront
- Grand River Pow Wow (Ohsweken)
- Uptown Waterloo Jazz Festival
- Wayback Festival @ City Hall, Carl Zehr Square (Kitchener)
- Boris Brott Music Festival
- Niagara Jazz Festival
- Hamilton Fringe
- Dusk Dances (Hamilton)
- Lions Carnival (St. David's)
- Milton Ribfest @ Community Sports Park
- CrewFest Music Festival @ Lion's Park (Brantford)
- Hillside Festival @ Guelph Lake Island (Guelph)
- Oakville Family Ribfest @ Sheridan College, Trafalgar Road
August
- Boris Brott Music Festival
- Food Day Canada Community BBQ with Live Music @ The Bridge (Downtown Elora)
- Festival of Friends @ Gage Park (Hamilton)
- St. Catharines Ribfest
- Canal Days Marine Heritage Festival (Port Colbourne)
- Simcoe Friendship Festival
- Six Nations Music Festival (Osweken)
- Halton Black History Awareness Freedom Celebration Festival (Burlington)
- Pirate Festival (Guelph)
- The Past is Present Heritage Festival (some live music) @ NOTL Museum (Niagara-on-the-Lake)
- Art in Park @ Bronte Heritage Waterfront Park (Oakville)
- Guelph Fringe Festival
- Kitchener Blues Festival
- Artcrawl (Hamilton, Upper James)
- ArtsWest @ Westdale (Hamilton)
- South Coast Jazz (Brantford/Port Dover)
- Brantford Ribfest @ Brantford Civic Centre
- Grand Railroad Music Festival @ 516 Old Onondaga Rd E (Brantford) $?
- Fergus Scottish Festival
- Dunnville Fair
- Cambridge Ribest & Craft Beer Show @ Riverside Park
- Doors Open Burlington
- 4EVRFEST @ Bridgeworks (Hamilton) FREE
- Summer Patio Party @ Clifford Brewing Co. (Hamilton)
- Niagara Sunflower Festival for Ukrainian Relief 2023 @ London Born Wine Co (Lincoln) $15
- Jazz on the Plaza @ Burlington Performing Arts Centre
- Cops N' Rodders Car Show (with some live music) @ Bayfront Park (Hamilton)
- Hamilton Latino Festival @ Gage Park
- Dundas Cactus Festival
- Boots in the Creek Country Music Festival @ Downtown Stoney Creek
- Paris Drinks Fest @ Lion's Park $?
- Riverfest @ Bissell Park (Elora) $?
- Jalopy Jam Up @ Rockton Fairgrounds
- Norwich Tractor Pull
- Jarvis Fest @ Lion's Park
- Concession Street Sidewalk Sounds (Hamilton)
- Port Dover Summer Festival
- Strummerfest (In memory of Joe Strummer) @ Waterloo Public Square (Waterloo)
- Sundays Unlocked @ Locke Street (Hamilton)
- HipFest @ Harmony Square (Brantford)
- Living Rock presents Arts of August (some live music) @ Gasworks (Hamilton) FREE
- Waterloo Busker Carnival
- Hamilton Ribfest @ Gage Park
- Winona Peach Festival
- Niagara Irish Festival @ Firemen's Park (Niagara Falls)
- Guelph Ribfest @ Riverside Park
- Three Fires Homecoming Pow Wow and Traditional Gathering @ 2789 Mississauga Road (Hagersville)
- AFROJAZZ FEST @ Milton Community Sports Park
- Worship in the Wild with some live music @ Safari Niagara (Stevensville) FREE with park admission
- African Women Acting Festival @ Riverbrink Art Museum (Queenston) $25 online/$35door
- Hamilton Greek Fest
September
- Canada's Largest Ribfest @ Spencer Smith Park (Burlington) $2
- Niagara Greek Festival @ St. Katharine Greek Orthodox Church (St. Catharines)
- Stupercrawl @Landsdale Fairground (Hamilton)
- Labour Day Parade and Picnic @ Bayfront Park (Hamilton)
- Arthur Fall Fair
- Cambridge Fall Fair @ Dickson Park $?
- Supercrawl @ James Street (Hamilton)
- Georgetown Fall Fair $?
- The West Niagara Fair (Grassie, ON)
- Welly Cask Fest @ Wellington Brewery (Guelph) $?
- Radfest @ The Rad Brothers Sports Bar and Tap House (Milton)
- Kerrfest Kids @ Westwood Park (Oakville) FREE
- Wellesley Township Fall Fair
- Binbrook Fall Fair
- Guelph Jazz Festival $?
- Niagara Grape & Wine Festival
- Grand River Arts Festival @ Glenhyrst Art Gallery (Brantford)
- Hope in the Street (Guelph)
- Fergus Fall Fair $?
- Belmont Village Bestival (Kitchener)
- Concession Street Sidewalk Sounds (Hamilton)
- Head for the Hills Craft Beer Festival (Georgetown) $?
- Harvest Pioneer Day (Lincoln)
- The Great Canadian Butter Tart Festival incl live music @ West Niagara Fairgrounds $5
- Telling Tales Festival (Rockton)
- Biketoberfest @ Welland County Motorcycle Club
- Sundays Unlocked @ Locke Street (Hamilton)
- Brantford International Jazz Festival
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