Things To Do in Durham Region and the GTA - September 19, 2026 - Friday, October 2, 2026

Fall is arriving, and there are plenty of reasons to get out and enjoy Durham Region and the GTA over the next two weeks.

From music and art festivals to family adventures, local history, live theatre, books, food and home-improvement inspiration, there’s something for just about everyone.

Here are some of our picks for things to do in Durham Region and the GTA from Saturday, September 19 through Friday, October 2, 2026.

Convergence Music & Art Festival

Location: Downtown Oshawa
Dates: Saturday, September 19 & Sunday, September 20, 2026
Time: Festival programming throughout the weekend
Cost: Free festival activities available

Downtown Oshawa comes alive for a weekend celebrating music, art and creativity during the Convergence Music & Art Festival.

Enjoy live music, visual art and immersive experiences throughout the downtown, along with interactive art activities and a temporary exhibition at Veterans Square.

It’s a great opportunity to experience Oshawa’s growing arts and culture scene while supporting local artists and exploring downtown.

Pickering Fairy Tour

Location: Pickering Museum Village, 2365 Concession Road 6, Pickering
Dates: Saturday, September 19 & Sunday, September 20, 2026
Time: 10:00 a.m. – 3:00 p.m.
Cost: Paid event

Step into a magical world of fairies, gnomes and other mythical creatures at Pickering Museum Village.

Families can explore themed stations, hear stories inspired by folklore, participate in interactive activities and create take-home crafts as part of this imaginative outdoor experience.

It’s an especially fun choice for families with younger children and a different way to experience one of Durham Region’s unique local attractions.

Roncesvalles Polish Festival

Location: Roncesvalles Avenue, Toronto
Dates: Saturday, September 19 & Sunday, September 20, 2026
Time: Saturday 11:00 a.m. – 11:00 p.m.; Sunday 11:00 a.m. – 7:00 p.m.
Cost: Free admission

Celebrate Polish culture as the Roncesvalles Polish Festival returns for its 20th anniversary.

The neighbourhood will be filled with live music, dancing, entertainment and family activities, along with plenty of food, including favourites such as pierogis.

With activities taking place throughout the weekend, you can stop by for a few hours or spend the afternoon exploring Roncesvalles Village.

Ajax Terry Fox Run

Location: Rotary Park Pavilion, 177 Lake Driveway West, Ajax
Date: Sunday, September 20, 2026
Time: 9:30 a.m. – 12:00 p.m.
Cost: No entry fee; fundraising encouraged

Join the Ajax community for the annual Terry Fox Run in support of cancer research.

Walk, run or come out to support participants while enjoying a Sunday morning along the Ajax waterfront.

It’s a meaningful community tradition and an opportunity for people of different ages and abilities to participate together.

Spirit Walk

Location: Rotary Park Pavilion, 177 Lake Driveway West, Ajax
Date: Friday, September 25, 2026
Time: 7:00 – 9:00 p.m.
Cost: Free; registration required

Take a step back in time and discover some of the people, places and stories that helped shape Ajax.

During this guided evening walking tour, participants encounter costumed “spirits” who share stories and historical details from the community’s past.

Despite the name, this isn’t really intended to be a scary ghost walk. It’s focused on local history and heritage, making it an interesting evening out for anyone curious about the community.

The Word On The Street

Location: David Pecaut Square, 215 King Street West, Toronto
Dates: Saturday, September 26 & Sunday, September 27, 2026
Time: Saturday 11:00 a.m. – 6:00 p.m.; Sunday 10:00 a.m. – 5:00 p.m.
Cost: Free admission

Book lovers can spend the weekend discovering authors, publishers, stories and ideas at one of Toronto’s longstanding literary festivals.

The Word On The Street features author appearances, readings, conversations, workshops, children’s programming and plenty of opportunities to browse books.

Whether you’re an avid reader or looking for a family-friendly downtown outing, there’s lots to explore throughout the weekend.

Relive the Music – 50s, 60s & 70s Show

Location: Regent Theatre, 50 King Street East, Oshawa
Date: Sunday, September 27, 2026
Time: 7:00 p.m.
Cost: Paid event

Take a musical trip through three unforgettable decades at the Regent Theatre in downtown Oshawa.

Relive the Music brings together singers, dancers, a live band, period costumes, music trivia and memorable songs from the 1950s, ’60s and ’70s.

For anyone who enjoys nostalgia and classic hits, this could make for a fun Sunday evening close to home.

Food Truck Spotlight

Location: Dorsay Community & Heritage Centre, 2365 Sixth Concession Road, Pickering
Date: Friday, October 2, 2026
Time: 5:00 – 8:00 p.m.
Cost: Free admission; food and drinks available for purchase

Bring your appetite to Pickering for an evening featuring food trucks, live entertainment and family activities.

Visitors can choose from a variety of food and drinks while enjoying entertainment and a kids’ zone at the new Dorsay Community & Heritage Centre.

It’s an easy local option for families and friends looking to kick off the weekend without travelling far from home.

Styx / Journey – Featuring Grand Evolution

Location: Regent Theatre, 50 King Street East, Oshawa
Date: Friday, October 2, 2026
Time: 8:00 p.m.
Cost: Paid event

Classic-rock fans can spend Friday night revisiting the music of two legendary bands at Oshawa’s Regent Theatre.

Grand Evolution brings the music of Styx and Journey to the stage with a tribute performance featuring familiar favourites from both bands.

If classic rock is your kind of music, this could be a great way to start the weekend right here in Durham Region.

Fall Home Show 2026

Location: Enercare Centre, Exhibition Place, 100 Princes’ Boulevard, Toronto
Dates: Friday, October 2 – Sunday, October 4, 2026
Friday Hours: 11:00 a.m. – 7:00 p.m.
Cost: General admission starts at approximately $15 + HST online; children 12 and under are free

Thinking about renovating, decorating or simply looking for new ideas for your home?

The Fall Home Show brings together more than 225 home and lifestyle vendors and experts under one roof, with renovation advice, decorating inspiration, products, demonstrations and opportunities to speak directly with industry professionals.

Even though the show continues beyond the dates covered by this roundup, it opens Friday, October 2, making it a fitting way to finish our list, particularly for homeowners considering their next project.

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 music and art at Convergence in downtown Oshawa, take the family on the Pickering Fairy Tour, support a great cause at the Ajax Terry Fox Run, discover local history during the Ajax Spirit Walk, enjoy live music at the Regent Theatre, or head into Toronto for festivals, books and home-improvement inspiration.

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 the beginning of fall, there are plenty of choices between Saturday, September 19 and Friday, October 2.

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, call 905-683-7800. I'd be happy to answer your questions, with absolutely no obligation.

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!