Week of September 7-13, 2026

Hey hi hello, Durham,

I missed a week because I was finally on PTO, able to enjoy the summer days with my kids, but we're back, baby.

Labour Day long weekend is officially over (RIP), which means one thing: school's back tomorrow for most Durham District School Board kids. If yours goes to Brock, Henry Street, or Maxwell Heights, you already survived week one — teach the rest of us your ways.

The last week of summer always hits different. Equal parts "let's savour every last popsicle" and "please, for the love of god, give me a Tuesday with a schedule again." This week gives you a bit of both: one more weekend of fair-season chaos, plus a genuinely huge opening in Whitby that's going to make the first week back a lot more bearable.

Here's what's on.

🗓️ This week in Durham

Ajax

• 🎤 Thursday, Sept 10 (doors 8pm, show 8:30pm) — Ajax Comedy Club: Eastern Promises 3 — local talent showcase inside Lumbini Restaurant's banquet hall (60 Randall Dr), $10. They're booked out for weeks after this: Habib Siam (Sept 17, $15–19), Ben Albert (Sept 24, $23.50). More on this one below.
• 👗 Sunday, Sept 13 — Durham Fashion Week — Audley Recreation Centre, kids showcase included, tickets on Eventbrite.
• 🎤 Fridays — karaoke with Rob and Lorraine (I don't know who y'all are, but I'm in) — Ajax Legion, weekly.

Clarington

• 🎪 Thursday–Sunday, Sept 10–13 — Orono Fall Fair — the 172nd year of it, at the Orono Fairgrounds. Adult day admission $15 (weekend pass $50), kids 6–13 $5/day ($15 weekend), 5 and under free. Friday's Farm Fest (10am–4pm) is free for the first 150 kids, and Friday night's concert headlines Tenille Townes with Nate Haller and Alycia Hebert.
• 🌽 Ongoing through Nov 1 — Pingle's Harvest Festival — corn maze, pick-your-own flowers, wagon rides, in Hampton.

Oshawa

• 🧠 Wednesdays & Thursdays — trivia nights — Wednesday at Torchbearer Taproom or BOND|ST Snack Bar, Thursday at Bollocks Pub.
• 🏒 Sunday, Sept 13, 4:05pm — Oshawa Generals preseason home game.

Pickering

• 🌍 Saturday, Sept 12, 11am–5pm — Pickering Cultural Fusion — free multicultural food, music, and performances.
• 🪄 Sept 12–13 — Magic at the Museum — spellbook workshop and potions class at Pickering Museum Village.
• 👻 Thursdays through October, 9:15–10:15pm — Pickering Paranormal Waterfront Tours — starts at Millennium Square for 12y+, $25 (but there's a waitlist already!)
• 🧚🏻‍♀️ Saturday and Sunday September 19 and 20th, Pickering's also doing ✨ Enchanted Fairy Tours for the whole family from 10-3pm. Kids under 3 are free!

Scugog

• 🧠 Wednesdays — trivia — Old Flame Brewery, Port Perry.
• 🍷 Weekends — wine tasting and railway-history tours — Ocala Winery, worth a look if you haven't been.

Uxbridge

• 🎪 Friday–Sunday, Sept 11–13 — Uxbridge Fall Fair — Elgin Park. Tractor pull Friday, demolition derby Saturday, SuperDogs and a cruise-in car show Sunday.

Whitby

• 🎉 Saturday, Sept 12 (ribbon-cutting 9:30am, runs to 4pm) — Fieldgate Sports Complex Grand Opening — free, all-day, family event: drop-in skating, swimming, pickleball, arts and crafts, food trucks, and a special appearance from Olympic figure skater Elvis Stojko.
• ✈️ Tuesday, Sept 8, ~1pm — Snowbirds flyover — over Captain Michael VandenBos Public School (3121 Country Lane). Time may shift with weather. This isn't my thing (loud, scary for the littles), but it may be for youuuu.
• 🧠 Tuesdays — trivia — Town Brewery.
• 🍔 Rosie's Burgers just opened its 15th Canadian location here, part of the chain's Ontario expansion — for the burger-curious. We tried these this summer while heading to a park and man, that sauce is delicious.

Planning ahead?

• Sunderland Fall Fair, Sept 15–16, in Brock.
• Beaverton Fall Fair, Sept 18–19 — worth double-checking closer to the date, the fair's own page had some inconsistent info when I looked.
• Fat Lip Friday, Sept 18 — Convergence Weekend's kickoff at BOND|ST, with Cone from Sum 41 DJing. 👀
• Convergence 2026, Sept 19–20 — Oshawa's music, art, and culture festival, downtown. Volunteer applications are open at convergenceoshawa.com/volunteer.
• Oshawa Culture Days / Ontario Culture Days, Sept 18–Oct 4, across Oshawa, Bowmanville, Courtice, and Newcastle.
• Brooklin Harvest Festival, Sept 19, 10am, Grass Park.
• Oshawa Generals regular-season home opener, Sept 20, 6:05pm.
• Little Shop of Horrors, Sept 24–26, Oshawa Little Theatre — tickets via ci.ovationtix.com.
• Glaze & Graze, Sept 25, 6:30pm, Downtown Whitby — a $120/person skincare-meets-social night, two small plates and a drink included, if that's your thing.
• Jay Rainville at Ajax Comedy Club, Oct 8, 8:30pm — the headliner night they've been teasing all summer finally has a date.

📍 Local gem: Ajax Comedy Club (Ajax)

Tucked into the banquet hall of Lumbini Restaurant on Randall Drive — not exactly where you'd expect to find a comedy club — this weekly Thursday night show has quietly become one of the region's best-kept nightlife secrets. Doors at 8pm, show at 8:30, tickets $10–23.50 depending on the night.

It's the kind of place that doesn't announce itself — no flashy signage, just a solid, weeks-deep lineup of touring comics (though I'd love to see more women on the rostaaa) and local talent in a room that seats a few dozen people who all showed up because someone told them about it. Consider this me telling you about it.

This week it's Eastern Promises 3, a local talent showcase (Sept 10, $10). After that: Habib Siam (Sept 17) and Ben Albert (Sept 24) — and yes, the Jay Rainville headliner night is finally locked in for Oct 8.

💚 Why I love it: it's proof you don't need a Yonge Street postal code for an actual night out. Durham Region has real nightlife — you just have to know which banquet hall to walk into.

👨‍👩‍👧 This weekend, with littles

• 🎉 Saturday, Sept 12 — Fieldgate Sports Complex Grand Opening, Whitby — free, all day, and there's a literal Olympic figure skater there. Hard to beat for a first-week-of-school reward.
• 🌍 Saturday, Sept 12 — Pickering Cultural Fusion, 11am–5pm — free food and performances, about as low-effort-high-payoff as a weekend outing gets.
• 🪄 Sept 12–13 — Magic at the Museum + Enchanted Fairy Tea Party, Pickering Museum Village — spellbooks, potions, and a tea party for the very small among us.
• 🐕 Sunday, Sept 13 — SuperDogs at the Uxbridge Fall Fair, Elgin Park — pair it with the cruise-in car show happening the same day.
• 🌽 Ongoing through Nov 1 — Pingle's Harvest Festival, Hampton — corn maze, wagon rides, pick-your-own flowers. A solid any-weekend option for the rest of fall.

Before you go — a few things with a deadline

• 🍔 Through Sept 13 — Kids Eat Free at Symposium Cafe — one free kids' meal with an adult food purchase of $15.99+.
• 🛒 This week — Longo's BOGO — lunchbox snacks, produce, pantry staples, back-to-school desserts.

Know a hidden gem (or just an obvious, but well-loved rock) in Durham Region I should feature, profile, or talk to?

Talk soon, Arina from Whitby