What To Do This Weekend in Durham Region (September 25-27, 2026)

Looking for things to do this weekend in Durham Region? The last full weekend of September is a wonderful one to be out in the region. It brings the Songs of Summer season finale to downtown Port Perry, the Parkwood Beer Fest to the lawns of Oshawa's historic estate, a big live music festival to the Ajax Fairgrounds, and the Uxtober Fest celebration to downtown Uxbridge. Here is your weekend guide for Friday, September 25, through Sunday, September 27.

Friday, Sept-25

Ease into the weekend with a night out in downtown Oshawa, where the Regent Theatre opens its weekend with a favourite touring show.

Seven Drunken Nights at the Regent Theatre

Friday night, the Regent Theatre at 50 King Street East in Oshawa presents Seven Drunken Nights: The Story of The Dubliners at 7:30 PM. The show is celebrating 10 years on the road with the songs that made the band famous, including Whiskey in the Jar, The Irish Rover and Rocky Road to Dublin. It is a warm, lively start to the weekend, and the Oshawa community's downtown is full of dinner spots within a short walk of the theatre. Tickets are on the Regent Theatre ticketing site.

Ontario Culture Days is Underway

Ontario Culture Days runs September 18 to October 4, so the entire weekend sits inside the province-wide festival of free arts, culture and heritage events. Durham Region communities from Port Perry to Oshawa and Clarington are in the program, and the official Culture Days finder lets you filter events by municipality, date and interest.

If you are staying in North Durham, save the biggest moment for Saturday: the Songs of Summer season finale lands in downtown Port Perry.

Saturday, Sept-26

Saturday is the biggest day of the weekend. The Songs of Summer finale headlines in Port Perry, while Parkwood Beer Fest, the Kulture Series Festival, markets, museums and hands-on programs fill the day across the region.

Songs of Summer Season Finale in Port Perry (Headline)

The headline moment for Port Perry is the Songs of Summer season finale, the Port Perry BIA's free music in the street series that has run all summer in the historic downtown. Local musicians perform along Queen Street in the Port Perry community's heritage core, and Saturday, September 26, wraps up the 2026 series. It is a lovely way to spend an afternoon between market stops and a walk along the Lake Scugog waterfront. Details are on the Port Perry BIA website.

Port Perry Lakefront Farmers' Market

The Port Perry Lakefront Farmers' Market runs from 8 AM to 3 PM at the foot of Queen Street on Lake Scugog, one of the largest markets in Durham Region. Expect early-fall apples, squash, honey, maple syrup, artisan baking and crafts, plus live entertainment. The 2026 season runs from May 9 to October 10, so this is one of the last Saturdays before the market closes for the year. See the market's website for the vendor lineup.

Parkwood Beer Fest in Oshawa

The Parkwood Beer Fest takes over the grounds of the Parkwood Estate National Historic Site (270 Simcoe Street North) in Oshawa on Saturday from noon to 4 PM. Expect craft beer tastings from local breweries and food vendors set against one of Canada's grandest historic estates. Note that guided estate tours are not running that day because of the event. Full details are on the Parkwood Estate website.

Kulture Series Festival at Ajax Fairgrounds

Music fans can head to the Kulture Series Festival at the Ajax Fairgrounds on Saturday at 2 PM, a live music festival billed as Where Kultures Collide. It brings a broad lineup of artists to the heart of the Ajax community. Tickets, lineup and schedule are on the Kulture Series website.

Blacksmithing at Pickering Museum Village

Families in Pickering can try something hands-on at Pickering Museum Village (2365 Concession Road 6), which runs a blacksmithing program on both Saturday and Sunday where you shape a forged bottle opener while learning essential techniques. It is one of the most memorable family activities in the region. Programs are listed on the Pickering Museum Village programs page.

Evening Program at Scugog Shores Museum Village

In Port Perry, the Scugog Shores Museum Village (16210 Island Road) lists an evening program on Saturday starting at 6 PM. Check the Township of Scugog museum programs page for the program name and booking details.

Free Tree-Pruning Demonstrations in Clarington

For something a little different, the Municipality of Clarington's forestry team hosts free tree-pruning demonstrations on Saturday at four parks, one each in Courtice, Newcastle, Orono and Bowmanville, marking National Forest Week. It is free, family-friendly, and a great chance to learn how to care for the trees on your own property. Find the park locations on this Clarington Post story.

Sunday, Sept-27

Sunday is made for a slow market morning in Uxbridge, the Uxtober Fest trail walk, a cheese pairing in Port Perry, and an early evening show in Oshawa.

Uxtober Fest in Downtown Uxbridge (Headline)

The Uxtober Fest takes over downtown Uxbridge on Sunday, September 27, as part of Uxbridge Local Food Month. Expect a community trail walk, a keepsake souvenir, live music, and German beer and eats in the heart of the Uxbridge community. It is a cheerful way to close out the weekend, and the fold of the Oak Ridges Moraine around town makes for a beautiful walk this time of year. Details are on the Discover Uxbridge website.

Uxbridge Farmers' Market

The Uxbridge Farmers' Market runs Sunday from 9 AM to 2 PM at 14 Victoria Street, beside The Second Wedge Brewing Co. It is one of the region's friendliest markets, with local produce, artisan baking, crafts and live music, and the outdoor season runs every Sunday through October 25. We have written about The Second Wedge Brewing Co. in our community spotlight, and it is worth stopping in for a pint and a wood-fired pizza after the market. See the market's website for the full vendor list.

Fall Wine and Cheese Pairing at The Port Cheese Co.

In Port Perry, The Port Cheese Co. (203 Queen Street) holds a Fall Wine and Cheese Pairing Night on Sunday at 2 PM, part of the shop's Wine and Cheese Nights series. It is a cosy way to spend a fall afternoon on Queen Street, just steps from the waterfront in the Port Perry community. The event is listed among the Port Perry BIA's featured fall events.

Relive the Music at the Regent Theatre

The Regent Theatre in Oshawa closes its weekend with Relive the Music 50s, 60s and 70s Show on Sunday at 7 PM. The revue covers the biggest hits of those decades, from rock and roll to disco and funk, in one energetic night. Tickets are on the Regent Theatre ticketing site.

Culture Days programming continues all weekend, with free museum and gallery events listed for Oshawa and Clarington on the Culture Days finder.

Plan Your Weekend

Whether you are catching the Songs of Summer finale in Port Perry, tasting local brews on the lawns of Parkwood Estate, dancing at the Kulture Series Festival in Ajax, or walking the market with a coffee in Uxbridge, there is plenty to do across Durham Region this weekend. New to the area? Our Port Perry community guide, Uxbridge community guide and Ajax community guide introduce the towns hosting the biggest events, and the Weekend Guide archive holds every edition we have published so far.

If a slower weekend sounds better, the maples around the Port Perry waterfront are just starting to turn, and the Lake Scugog shoreline and trails are always open. Our guide to living on Lake Scugog explains what waterfront life in this corner of Durham Region really involves, and if you are thinking of putting down roots, the moving to Port Perry guide covers the town from the historic downtown to the lakeshore. Wherever your weekend takes you, we hope you have a safe and happy one in Durham Region.