From fall fairs to farmers markets, family fun to music nights, there's something for everyone this September! Get out and explore all the community has to offer.
🍂 Durham Region Events
🎡 Uxbridge Fall Fair
📅 September 5–7, 2025
📍 Elgin Park, Uxbridge
🥕 Whitby Farmers Market
📅 Every Wednesday: Sept 3, 10, 17, 24 | ⏰ 9:00am–3:00pm
📍 Celebration Square, Whitby
🍎 Mobile Food Market (Ajax)
📅 Wednesdays: Sept 3, 10, 17, 24 | ⏰ 11:30am–2:00pm
📍 Ajax Community Centre
🍗 Wing Wednesdays at Ajax Legion
📅 Wednesdays: Sept 3, 10, 17, 24 | ⏰ 4:00pm–8:00pm
📍 111 Hunt Street, Ajax
🃏 Euchre Night at Torchbearer Taproom
📅 Thursdays: Sept 4, 11, 18, 25 | ⏰ 6:30pm–9:30pm
📍 785 Taunton Rd E Unit 2, Oshawa
🎶 Rum Ragged @ BOND|ST Event Centre
📅 Thursday, Sept 4 | ⏰ 7:00pm–11:59pm
📍 44 Bond St E, Oshawa
🔮 Theresa Caputo Live: The Experience
📅 Thursday, Sept 4 | ⏰ 8:00pm
📍 The Arena at Pickering Casino Resort
🌽 Bowmanville Farmers Market
📅 Fridays & Saturdays: Sept 5, 6, 12, 13, 19, 20, 26, 27 | ⏰ 9:00am–2:00pm
📍 Garnet B. Rickard Complex, 2440 Hwy 2, Bowmanville
🐟 Fish Frydays at Ajax Legion
📅 Fridays: Sept 5, 12, 19, 26 | ⏰ 12:00pm–8:00pm
📍 111 Hunt Street, Ajax
🥕 The Stouffville Market
📅 Saturdays: Sept 6, 13, 20, 27 | ⏰ 9:00am–2:00pm
📍 6240 Main St, Stouffville
🥍 Queens U Lacrosse (W) vs Trent Excalibur
📅 Saturday, Sept 6 | ⏰ 10:15am–1:15pm
📍 Oshawa, ON
🎨 Family Paint Party – Thornton Arms
📅 Sunday, Sept 7 | ⏰ 2:00pm–4:15pm
📍 Oshawa, ON
🎶 Last Days of Summer – Aquário Beach Club
📅 Sunday, Sept 7 | ⏰ 6:00pm
📍 949 Dillingham Road, Pickering
🍞 Beginner Sourdough Workshop – Parkwood Estate
📅 Thursday, Sept 11 | ⏰ 6:30pm–8:30pm
📍 270 Simcoe St N, Oshawa
🧘♀️ Meditation with the Horses
📅 Thursday, Sept 11 | ⏰ 7:00pm–8:30pm
📍 2677 Audley Rd, Ajax
🤠 Country Night + Line Dancing – Market at 70 King
📅 Thursday, Sept 11 | ⏰ 9:00pm
📍 70 King St E, Oshawa
🎬 Family Movie Night – Columbus Park
📅 Friday, Sept 12 | ⏰ 8:00pm–10:00pm
📍 3265 Simcoe St N, Oshawa
💍 The Wedding Expo – Ajax
📅 Sept 12–13
📍 Arthur Murray Dance Centre, Ajax
🦸♀️ Whitby ComiCon
📅 Sunday, Sept 14 | ⏰ 10:00am–3:00pm
📍 Heydenshore Pavilion, Whitby
📚 Durham Comic Book Show
📅 Sunday, Sept 14 | ⏰ 10:00am–4:00pm
📍 Legion Branch 43, Oshawa
🎨 Paint Your Pet Night – Lobby Bar
📅 Thursday, Sept 18 | ⏰ 6:00pm–9:00pm
📍 70 King St E, Oshawa
🎸 Lynyrd Skynyrd 50th Anniversary Tour
📅 Thursday, Sept 18 | ⏰ 7:30pm
📍 Tribute Communities Centre, Oshawa
🎉 Ajax Fairgrounds 70th Anniversary
📅 Friday, Sept 19 | ⏰ 6:00pm–9:15pm
📍 500 Kingston Rd E, Ajax
🔮 Oshawa Psychic & Crystal Fair
📅 Friday, Sept 19 | ⏰ 2:00pm
📍 Oshawa Convention Centre
🎤 Winding Roads Country Festival
📅 Saturday, Sept 20 | ⏰ 6:00pm–1:00am
📍 1401 Scugog Line 6, Port Perry
🎪 Brooklin Agricultural Fair – Fall Mini Fest
📅 September 21–22
📍 Luther Vipond Memorial Arena, Brooklin
🚶♂️ Explore the Trail – Autumn Edition
📅 Tuesday, Sept 23 | ⏰ 11:00am–2:00pm
📍 Riverside Park, Ajax
🎨 Paint Nite – Boston Pizza Whitby
📅 Tuesday, Sept 23 | ⏰ 6:00pm–8:30pm
📍 905 Dundas St W, Whitby
🧱 LEGO and Lagers
📅 Wednesday, Sept 24 | ⏰ 6:00pm–7:30pm
📍 Chronicle Brewing, Clarington
🎤 LUKE COMBS UK–Canada Tribute Tour
📅 Wednesday, Sept 24 | ⏰ 6:30pm–11:30pm
📍 BOND|ST Event Centre, 44 Bond St E, Oshawa
🎤 AQUA – 2025 Canada Tour
📅 Wednesday, Sept 24 | ⏰ 8:00pm
📍 The Arena at Pickering Casino Resort
🍳 Whitby Cooking Class (13+)
📅 Thursday, Sept 25 | ⏰ 5:30pm–7:00pm
📍 Longo's, 5550 Baldwin St S, Whitby
🎮 Discord Gaming Night
📅 Thursday, Sept 25 | ⏰ 6:30pm–7:30pm
📍 Oshawa Public Libraries – Online Event
🐍 PA Day with Reptilia!
📅 Friday, Sept 26 | ⏰ 10:30am–11:30am
📍 Newcastle Library, Clarington
🎨 Get Creative! (PA Day)
📅 Friday, Sept 26 | ⏰ 10:30am–11:30am
📍 Courtice Branch Library, 2950 Courtice Rd, Courtice
🧱 LEGO Blast (PA Day)
📅 Friday, Sept 26 | ⏰ 11:30am–12:30pm
📍 Bowmanville Branch Library, 163 Church St, Bowmanville
🎨 Sips & Sunflowers Paint Nite
📅 Saturday, Sept 27 | ⏰ 3:00pm–5:00pm
📍 Sabina's Casual Dining & Pub, 1755 Pickering Parkway #20
🎶 Grease & Music of the 50s & 60s
📅 Saturday, Sept 27 | ⏰ 7:30pm
📍 The Arena at Pickering Casino Resort
🕺 Totally 80's Night
📅 Saturday, Sept 27 | ⏰ 8:00pm
📍 Regent Theatre, 50 King St E, Oshawa
🎃 Caregiver & Tot Happy Harvest
📅 Sunday, Sept 28 | ⏰ 10:00am–11:00am
📍 Pickering Museum Village, 3550 Greenwood Rd, Pickering
🍂 Northumberland County Events
♟️ Chess Club at Cobourg Library
📅 Tuesdays: Sept 2, 9, 16, 23, 30 | ⏰ 4:00pm–5:30pm
📍 Cobourg Public Library, 200 Ontario St, Cobourg
🧘 Orchard Yoga + Apple Picking
📅 Wednesday, Sept 3 | ⏰ 6:00pm
📍 West Wind Farm at Blue Barn Cidery, Hilton, ON
🌾 Lakefield Farmer’s Market
📅 Thursdays: Sept 4, 11, 18, 25 | ⏰ 9:00am–1:00pm
📍 Lakefield Arena Parking Lot, 20 Concession St, Lakefield
☕ Coffee Club – Colborne
📅 Friday, Sept 5 | ⏰ 8:30am–9:30am
📍 Colborne, ON
📖 Family Storytime – Bewdley Library
📅 Fridays: Sept 5, 12, 19, 26 | ⏰ 10:00am–11:00am
📍 Alice D. Behan Bewdley Branch, 7060 Lake St, Bewdley
🎡 173rd Warkworth Fall Fair
📅 Sept 5–7
📍 Warkworth Fairgrounds, 24 East St, Warkworth
🐱 Motor City Cat Show
📅 Sept 6–7 | ⏰ 9:00am–4:30pm
📍 Cobourg Community Centre, 750 D’Arcy St, Cobourg
🥩 Legion Steak Dinner – Bewdley
📅 Saturday, Sept 6 | ⏰ 4:00pm–7:00pm
📍 Legion Branch 577, 5063 Main St, Bewdley
🧺 Millbrook Farmers Market
📅 Sundays: Sept 7, 14, 21, 28 | ⏰ 10:00am–1:00pm
📍 Millbrook Public School, 10 Tupper St, Millbrook
🎬 Monday Movies – Cobourg
📅 Mondays: Sept 8, 15, 22, 29 | ⏰ 2:00pm–4:30pm
📍 Cobourg Public Library, 200 Ontario St, Cobourg
✂️ Youth Sewing Studio
📅 Monday, Sept 8 | ⏰ 3:00pm–3:30pm
📍 Trenton Branch, 7 Creswell Dr, Quinte West
💃 Square Dancing – Otonabee Squares
📅 Mondays: Sept 8, 15, 22, 29 | ⏰ 6:00pm–9:00pm
📍 Emmanuel United Church, 534 George St N, Peterborough
🎨 Joyful Art – Trenton
📅 Mondays: Sept 8, 15 | ⏰ 10:00am–11:00am
📍 Trenton Branch, 7 Creswell Dr, Quinte West
👶 Move and Groove
📅 Tuesdays: Sept 9, 16 | ⏰ 10:30am–11:00am
📍 Trenton Branch, 7 Creswell Dr, Quinte West
🧶 Introduction to Knitting
📅 Tuesdays: Sept 9, 16 | ⏰ 1:30pm–3:30pm
📍 Trenton Branch, 7 Creswell Dr, Quinte West
🎲 Tuesday Teen Takeover: Games Night
📅 Tuesday, Sept 9 | ⏰ 5:30pm–7:30pm
📍 Trenton Branch, 7 Creswell Dr, Quinte West
🏃 Running Club – Trenton
📅 Tuesday, Sept 9 | ⏰ 6:00pm–7:00pm
📍 Trenton Branch, 7 Creswell Dr, Quinte West
📚 Preschool Storytime – Trenton
📅 Wednesday, Sept 10 | ⏰ 10:00am–10:30am
📍 Trenton Branch, 7 Creswell Dr, Quinte West
👶 Babytime – Trenton
📅 Wednesday, Sept 10 | ⏰ 11:00am–12:00pm
📍 Trenton Branch, 7 Creswell Dr, Quinte West
🎨 Open Art Studio (Adults)
📅 Wednesday, Sept 10 | ⏰ 11:00am–12:00pm
📍 Trenton Branch, 7 Creswell Dr, Quinte West
👧 Creative Kids – Frankford
📅 Wednesday, Sept 10 | ⏰ 4:30pm–5:00pm
📍 Frankford Branch, 22 North Trent St, Frankford
🎡 Port Hope Fall Fair
📅 Sept 13–15
📍 Port Hope Agricultural Park
🎨 Fall Makers Market
📅 Saturday, Sept 13 | ⏰ 11:00am–3:00pm
📍 Peterborough Retirement Residence, 1039 Water St, Peterborough
🎤 Rod Stewart Tribute – Forever Young
📅 Saturday, Sept 13 | ⏰ 7:00pm
📍 Lions Club of Cobourg, 157 Elgin St E, Cobourg
🥗 Peterborough VegFest
📅 Sunday, Sept 14 | ⏰ 11:00am–4:00pm
📍 Millennium Park, 131 King St, Peterborough
🍳 Little Chefs Series
📅 Monday, Sept 15 | ⏰ 4:30pm–5:30pm
📍 Trenton Branch, 7 Creswell Dr, Quinte West
🍷 WLAM Wayne: Wine & Garden Party
📅 Wednesday, Sept 17 | ⏰ 8:00pm
📍 Welcome, ON
😂 Comedy Night – Cobourg
📅 Friday, Sept 19 | ⏰ 8:00pm–10:00pm
📍 Best Western Plus, 930 Burnham St, Cobourg
🛍️ Fall-ing into Autumn Market
📅 Saturday, Sept 20 | ⏰ 10:00am–4:00pm
📍 Trenton Curling Club, 293 King St, Trenton
🍻 Hops on the Water – Craft Beer Finale
📅 Saturday, Sept 20 | ⏰ 11:00am–7:00pm
📍 67 Front St, Trenton
🥍 U of T Women’s Lacrosse vs Guelph
📅 Saturday, Sept 20 | ⏰ 12:00pm–3:00pm
📍 Peterborough, ON
🥍 Queen’s Lacrosse vs McMaster
📅 Sunday, Sept 21 | ⏰ 9:00am–12:00pm
📍 Peterborough, ON
🌿 PA Day Nature Camp – Sun School
📅 Friday, Sept 26 | ⏰ 8:00am–5:00pm
📍 Westdale United Church, 1509 Sherbrooke St, Peterborough
🍂 PA Day Autumn Scavenger Hunt
📅 Friday, Sept 26 | ⏰ 10:00am–5:00pm
📍 Cobourg Public Library, 200 Ontario St, Cobourg
👢 Country Line Dancing at Rolling Grape
📅 Friday, Sept 26 | ⏰ 5:00pm–10:00pm
📍 Rolling Grape Vineyard, 260 County Rd 2, Bailieboro
🍎 Brighton AppleFest
📅 Sept 27–29
📍 Downtown Brighton