What's Happening in Durham West: September 2026

Whether it's a local event, farmers' market, fall festival, or simply getting out for a walk in your neighbourhood, there's plenty to enjoy in Whitby, Ajax, Pickering and Oshawa as summer winds down.

🌾 Whitby

Every Wednesday: Whitby Farmers' Market - All Ages
📍 Celebration Square, 905 Dundas St. W.
🕘 9:00 a.m.–3:00 p.m.
A great midweek stop for local produce, vendors and seasonal goodies. The market continues throughout September into October.

Every Saturday: Whitby Farmers' Market - All Ages
📍 Municipal Lot 9, 3 Vipond Rd, Brooklin
🕘 9:00 a.m.–2:00 p.m.
A great way to spend Saturday Mornings with friends and family; stop in for local produce, vendors and seasonal goodies. The market continues throughout September into October.

September 10: Seniors Active Living Fair - Ages 55+
📍 8 Vipond Rd, Whitby
Developed in partnership between the OACAO and Ministry for Seniors and Accessibility (MSAA), Seniors Active Living Fairs aim to increase awareness about available programs and services for seniors and share knowledge about healthy aging and active lifestyles. Generously funded by MSAA, they help reduce seniors’ social isolation, improve their overall health and well-being, and help them maintain their independence.

September 12: Fall Waterfront Market - All Ages
📍 Port Whitby Marina
🕙 10:00 a.m.–4:00 p.m.
A free, family-friendly indoor market. Spend the day shopping a curated lineup of local vendors offering handmade goods, seasonal finds, gifts, treats, and fall-inspired favourites. Enjoy music, delicious eats, and a welcoming, family-friendly atmosphere — all while staying warm and dry inside our beautiful waterfront venue.

September 12: CBC Kids Read Live - Intended for Families and Young Readers
📍 Whitby Public Library, Central Library
🕙 10:00 a.m.–2:00 p.m.
Join Gary the Unicorn, Cottonball and Paw Patrol’s Chase for a live celebration of reading, featuring fun activities, crafts and storytimes inspired by five amazing Canadian picture books! With crafts, photo opportunities, and interactive activities, this is a great family-friendly addition to the calendar.

September 19: Brooklin Harvest Festival - All Ages
📍Historic Downtown Brooklin and Grass Park, 41 Baldwin St
🕔 10:00 a.m.–4:00 p.m.
Enjoy the Adventure Zones with a rock wall, inflatable slides, bouncers, games, reptiles and much more. The streets will be lined with interactive games and activities, balloon artists, face painting, local entertainment, farmers' market and vendors. Enjoy Grass Park’s newly renovated pathways and seating, or relax in comfortable Adirondack chairs and take in the bountiful fall colours, local entertainment, and street performances throughout the day.

September 20: Whitby Terry Fox Run - All Ages
📍Heydenshore Pavilion, 589 Water St
🕔 8:00 a.m.–1:00 p.m.
This event celebrates community spirit and fundraising, featuring activities such as walking, running, rolling, a silent auction, children's games, and merchandise sales. By participating, you will be supporting Terry Fox's mission to find a cure for cancer. Choose a 1 km, 5 km or 10 km route while supporting cancer research.

September 27: Adaptive Climbing Try-Us-Out Night - All Ages and Skill Levels
📍 Aspire Climbing Whitby
🕔 5:00 p.m.
A pay-what-you-can ($20 suggested) introductory climbing session designed for first-timers of all abilities. Learn more and reserve your spot at Adaptive Climbing Try-Us-Out Night

🎨 Oshawa

September 10: Emerging Songwriters Showcase - All Ages
📍 Biltmore Theatre, 39 King St. E.
🕗 7:00 –11:00 p.m.
Emerging Songwriters Showcase is a new series highlighting the amazing up-and-coming talent of Durham Region and the GTA. Join us on the Biltmore Mezzanine for the fourth event in this series. Tickets cost $20

September 12: Sweet Serotonin Dance Party - Ages 19+
📍 BOND|ST Event Centre, 44 Bond Street East, Oshawa
🕗 10:00 pm –2:00 a.m.
A 19+ late-night dance party featuring the sweetest sounds from live DJ The Brooks Brother, who'll be playing pop bangers, throwbacks, hip-hop, diva anthems, dance, Jersey club and NOLA bounce tracks. Tickets cost $8

September 18: DREAMS! Music Awards 2026 - All Ages
📍 Biltmore Theatre, 39 King St. E.
🕗 8:00–10:00 p.m.
The annual DREAMS! Music Awards 2026 proudly continues a tradition of celebrating musical excellence across Durham Region.

Through its award categories, live performances, and community partnerships, the DREAMS! Music Awards shines a spotlight on the extraordinary talent, creativity, and collaboration that define the region’s cultural landscape. Tickets cost $45.20

September 19–20: Convergence 2026: Music + Art Festival - All Ages
📍 61 King St W, Oshawa, Downtown Oshawa
🕛 12:00–10:00 p.m.
A free downtown festival featuring live music, interactive art installations, local vendors, food and immersive experiences. The CONVERGENCE Music and Art Festival is more than an event; it's a movement that transforms Oshawa into a hub of creativity, connection, and cultural discovery. With bold programming and vibrant energy, the festival celebrates Oshawa's heart and soul through music, art, and immersive experiences.

September 30: Truth & Reconciliation Day Tours - All Ages
📍Oshawa Museum, 1450 Simcoe Street South, Oshawa
🕛 12:00–4:00 p.m.
The Oshawa Museum is commemorating Truth and Reconciliation Day (Orange Shirt Day). Miijim: Traditional Foods of the Lake of the Woods Anishinaabeg Exhibit will be on display. Visit and learn more about the Indigenous foods of the Anishinaabeg. The exhibit was collaboratively designed by Iskatewizaagegan #39 Independent First Nation, The Natural Resources Institute of the University of Manitoba, and The Lake of the Woods Museum.

🌊 Ajax

September 19: Wildflower Planting & Pollinator Garden Stewardship - All Ages
📍 Aldonschool Court
🕙 10:00 a.m.–1:00 p.m.
Don't miss this chance to connect with nature and contribute to a greener community. Join the Town of Ajax for a fun morning of native wildflower planting and pollinator garden stewardship. Plant wildflowers and help out the busy pollinators at the Aldonschool Community Pollinator Garden at Aldonschool Ct. Participating high school students will earn community service hours.

September 20: Ajax Terry Fox Run - All Ages
📍 Rotary Park Pavilion
🕤 9:30 a.m.–12:00 p.m.
No entry fee; fundraising is encouraged in support of cancer research.

September 25: Spirit Walk - All Ages
📍 Rotary Park Pavilion
🕖 7:00–9:00 p.m.
A free guided historical walking tour featuring "spirits" who share stories about the people, places and events that shaped Ajax. Step back in time to discover Ajax’s rich history and heritage. Along this free guided walking tour, you will meet ‘Spirits’ who will share historical details about the people, places, stories, and headlines that shaped Ajax. NOTE: This isn’t really a scary event; it's more about history and heritage involving “spirits.”

🚲 Pickering

September 12: Cultural Fusion - All Ages
📍 Pickering Museum Village / Dorsay Community & Heritage Centre
🕚 11:00 a.m.–5:00 p.m.
Celebrate Pickering's diversity with unique tastes from local food vendors, interactive activities, live entertainment, roaming performances, and a vendor market.

September 12: Take Pride in Pickering: Community Tree Planting & Litter Cleanup - All Ages
📍 2516 Tillings Rd Pickering, ON
🕚 11:00 a.m.–12:00 p.m
Get ready to roll up your sleeves and make a difference at our Community Tree Planting & Litter Clean-Up event! This is a joint partnership with the City of Pickering, Ontario Power Generation & Toronto and Region Conservation Authority.

September 23: Reels for Meals: Community Movie Night - All Ages
📍CHDRC Arena O'Brien Room A and B, Pickering
🕚 6:00 p.m.–8:00 p.m.
Grab your family, bring your friends, and join The City of Pickering at Reels for Meals: A Community Movie Night, in partnership with St. Paul’s on-the-Hill Community Food Bank.

This year, they are screening Disney and Pixar's Elio, a heartwarming adventure the whole family will enjoy.

Admission is simple. Just bring a non-perishable food item to help support local families experiencing food insecurity. Complimentary refreshments will be available, and monetary donations are also welcome by cash, debit, or credit.

With limited seating available, you won't want to miss this evening of movies, snacks, fun, and community spirit.

Register here.