September is here, but there’s still plenty happening across Durham Region and the GTA.

From traditional country fairs and classic cars to fall family activities, cultural celebrations, live music and an adults-only comedy night, the next two weeks offer plenty of reasons to get out and enjoy the community.

Whether you’re looking for something to do with the kids, planning a date night or simply looking for somewhere different to spend the day, here are some events worth checking out from Saturday, September 5 through Friday, September 18, 2026.

Port Perry Fair – Small-Town Labour Day Tradition

Port Perry Fairgrounds
15835 Old Simcoe Road, Port Perry

Saturday, September 5 – Monday, September 7

Hours:
Saturday: 11:00 a.m.
Sunday: 9:30 a.m.
Monday: 8:00 a.m.

Admission: Paid

If a traditional country fair sounds like your kind of Labour Day weekend, the Port Perry Fair is a great place to start.

One of Durham Region’s favourite annual traditions, the fair brings together agricultural exhibits, livestock, midway rides, food, vendors, entertainment and plenty of family-friendly activities.

It’s also a chance to experience the community atmosphere and small-town charm that make Port Perry such a popular destination in north Durham.

Best for: Families, couples, all ages and anyone who enjoys a traditional country fair.

Magic at the Museum: Wand Workshop – Pickering

Pickering Museum Village
2365 Concession Road 6, Pickering

Saturday, September 5

10:00 – 11:00 a.m.

Admission: Paid

Have a young witch, wizard or fairy in the family?

Kids can let their imaginations take over during Magic at the Museum: Wand Workshop at Pickering Museum Village.

Participants get the opportunity to create their own magical wand while enjoying a hands-on activity in the unique surroundings of the historic museum village.

Best for: Children and families looking for a creative Saturday morning activity.

Pickering Car Show – Classic Cars & Family Fun

Dorsay Community & Heritage Centre
2365 Concession Road 6, Pickering

Saturday, September 5

11:00 a.m. – 4:00 p.m.

Admission: FREE

Classic-car fans may want to make their way to Pickering for this one.

The Pickering Car Show brings together antique and classic vehicles for an afternoon that both serious car enthusiasts and families can enjoy.

It’s free to attend and offers an easy way to spend part of your Saturday checking out some beautiful automobiles while enjoying a community event close to home.

Best for: All ages, families and car enthusiasts.

Canadian Opera Company Open House – Toronto

Four Seasons Centre for the Performing Arts
145 Queen Street West, Toronto

Saturday, September 5

3:00 – 5:30 p.m.

Admission: FREE

Looking for something a little different?

The Canadian Opera Company Open House offers a free opportunity to step inside the Four Seasons Centre for the Performing Arts and discover more about the world of opera.

It could be particularly interesting if you’ve always been curious about opera but have never attended a performance, or you're simply looking for a cultural experience while spending the day downtown.

Best for: Families, adults, culture lovers and first-time opera visitors.

Orono Fair – Four Days of Fall Fair Fun

Orono Fairgrounds
2 Princess Street, Orono

Thursday, September 10 – Sunday, September 13

Hours:
Thursday: 5:00 – 9:00 p.m.
Friday: 9:00 a.m. – 9:00 p.m.
Saturday: 8:00 a.m. – 9:00 p.m.
Sunday: 8:00 a.m. – 3:00 p.m.

Admission: Paid

Another long-running Durham Region tradition returns in September.

The Orono Fair features agricultural exhibits, livestock, midway rides, food, vendors, demonstrations and live entertainment over four days.

There’s also a Friday night concert, giving adults and music fans another reason to add the fair to their weekend plans.

For anyone who enjoys the atmosphere of Ontario’s traditional agricultural fairs, this is one of the bigger local events during this two-week period.

Best for: Families, couples, all ages and live-music fans.

Great Outdoors Comedy Festival – An Adults-Only Date Night

Erindale Park, Mississauga

Friday, September 11 – Sunday, September 13

Date-Night Pick: Friday, September 11 at 7:30 p.m.

Adults only

Admission: Paid

Want to trade the usual dinner-and-a-movie date for something different?

The Great Outdoors Comedy Festival brings a weekend of live comedy to Erindale Park in Mississauga.

The Friday night lineup includes John Mulaney, Stavros Halkias, Fred Armisen and James Austin Johnson, combining big-name comedy with an outdoor festival atmosphere.

It’s farther from Durham Region than most of our picks, but it could make for a fun night out for couples or groups of friends looking to do something beyond the usual weekend routine.

Best for: Adults, couples and groups of friends.

Paul Anthony – I'm Not Johnny Cash

Regent Theatre
50 King Street East, Oshawa

Saturday, September 12

8:00 p.m.

Admission: Paid

Johnny Cash fans can spend Saturday night in downtown Oshawa enjoying a tribute to the legendary Man in Black.

Paul Anthony – I'm Not Johnny Cash comes to the Regent Theatre for an evening of classic country music and live entertainment.

If you enjoy Johnny Cash, country music or tribute performances, this could be a good excuse for a night out without leaving Durham Region.

Best for: Country-music fans, couples and live-music lovers.

Cultural Fusion – Celebrate Pickering's Diversity

Dorsay Community & Heritage Centre
2365 Concession Road 6, Pickering

Saturday, September 12

11:00 a.m. – 5:00 p.m.

Admission: FREE

Experience some of the cultures and traditions that help make Pickering such a diverse community at Cultural Fusion.

The event features food, interactive activities, live entertainment, performances and a vendor market, creating plenty to see and experience throughout the day.

Best of all, admission is free, making this an easy addition to a family weekend.

Best for: Families, all ages and anyone interested in experiencing different cultures.

Falls Fun Festival at Brooks Farms – Welcome Fall

Brooks Farms
122 Ashworth Road, Mount Albert

Beginning Saturday, September 12

9:00 a.m. – 4:00 p.m.

Admission: Paid

Summer may not officially be over just yet, but fall fun is already getting underway.

The Falls Fun Festival at Brooks Farms offers families a full day of seasonal farm activities, including animals, wagon rides, jumping pillows, slides, a corn maze and more.

It’s a chance to get outside, enjoy the early harvest season and start getting into the fall spirit.

Best for: Families with children and anyone looking for an outdoor fall activity.

Bad to the Bone & Bootleg Credence – Classic Rock in Oshawa

Regent Theatre
50 King Street East, Oshawa

Friday, September 18

8:00 p.m.

Admission: Paid

Classic-rock fans can wrap up this two-week period with a night of familiar music at Oshawa's Regent Theatre.

Bad to the Bone pays tribute to George Thorogood, while Bootleg Credence brings the music of Creedence Clearwater Revival and John Fogerty to the stage.

It’s an easy Friday-night option for anyone who enjoys classic rock and live tribute performances.

Best for: Classic-rock fans, couples and adults.

Something for Everyone

One of the things I enjoy about putting these lists together is seeing just how much there is to do close to home.

Over these two weeks alone, you can experience the small-town atmosphere of the Port Perry Fair, see classic cars in Pickering, spend a fall day at the Orono Fair, experience different cultures at Cultural Fusion, enjoy live music in Oshawa, or make the trip into the GTA for something completely different.

Whether you're planning a family outing, looking for something free to do, arranging a date night or simply want to get out and enjoy September, there are plenty of choices between Saturday, September 5 and Friday, September 18.

And that's one of the many benefits of living in Durham Region – there's always something happening close to home, with even more to explore throughout the GTA.

Please remember that event dates, times, admission prices and programming can change. Check directly with the event organizer before heading out.

Thinking About Making a Move?

If you're considering buying or selling a home in Durham Region or the GTA, knowing the communities is just as important as knowing the real estate market.

If you'd like to talk about your plans or find out what your current home may be worth, feel free to reach out.

Or, if you'd prefer to speak with me directly, please call me at 905-683-7800.

Thanks For Reading Today’s Blog!

Brian Kondo
Sales Representative / Team Leader
The Brian Kondo Real Estate Team
Re/Max Hallmark First Group Realty Ltd.
905-683-7800 office
905-426-7484 direct
brian@briankondo.com
www.BrianKondo.com
www.BrianKondoTeam.com


If you or anyone you know is considering making a move in the next little while, give me a call or pass on my number ... 905-683-7800 (Office) or 905-426-7484 (Direct).

If you would like to see any of my previous blog posts, please click here!