What To Do This Weekend in Durham Region (October 2-4, 2026)

Looking for things to do this weekend in Durham Region? The first full weekend of October brings the final days of Ontario Culture Days, one of the last Saturdays of the Port Perry farmers market season, two weekend-long fall art festivals, and pumpkin season opening across Scugog and near Port Perry. Here is your weekend guide for Friday, October 2, through Sunday, October 4.

Friday, Oct-2

Ease into the long weekend ahead with a tribute concert in downtown Oshawa, or simply enjoy the final Culture Days weekend getting underway.

Grand Evolution: A Tribute to Styx and Journey at the Regent Theatre

Friday night, the Regent Theatre at 50 King Street East in Oshawa presents Grand Evolution: A Tribute to Styx and Journey at 8 PM. The show brings the arena-rock catalogues of both bands to the stage, from Renegade and Blue Collar Man to Don't Stop Believin' and Open Arms. It is a lively way to open the weekend, and downtown Oshawa is full of dinner spots within a short walk of the theatre. Tickets are on the Regent Theatre ticketing site, and we have written a full guide to the Oshawa community if you are not familiar with the city.

The Final Weekend of Ontario Culture Days

Ontario Culture Days runs through Sunday, October 4, so the whole weekend sits inside the province-wide festival of free arts, culture and heritage events. Durham Region communities from Port Perry to Pickering and Clarington are in the program, and the official Culture Days finder lets you filter events by municipality, date and interest. If you plan one Culture Days stop, make it the art festivals on Saturday.

Saturday, Oct-3

Saturday is the biggest day of the weekend. The Port Perry farmers market runs in the morning, two free art festivals open, pumpkin season starts at two farms, and live music fills the afternoon in downtown Port Perry.

Port Perry Lakefront Farmers' Market (Headline)

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 October apples, squash, pumpkins, honey, maple syrup, artisan baking and crafts, plus live entertainment. The 2026 season ends on Saturday, October 10, so this is one of the last two chances to visit before winter. See the market's website for the vendor lineup, and our Port Perry community guide covers the historic downtown around it.

Port Perry Artists' Association Semi-Annual Art Exhibition

In the heart of Port Perry, the Port Perry Artists' Association holds its Semi-Annual Art Exhibition and Sale at the Latcham Centre, 121 Queen Street, from 10 AM to 6 PM on both Saturday and Sunday. Members of the association show and sell original work, and it is a relaxed, family-friendly way to support local artists in the Port Perry community. Admission is free. Details are on the Port Perry Artists' Association website.

Oshawa Art Association Fall Art Festival at Camp Samac

The Oshawa Art Association celebrates its 43rd annual Fall Art Festival at Camp Samac, 275 Conlin Road East in Oshawa, from 10 AM to 5 PM on Saturday and Sunday. More than 50 local and emerging artists from Durham Region show and sell original art in watercolours, oils, acrylics, pottery, linocuts and sculpture, with live entertainment and free admission. It is a registered Culture Days event and one of the most popular art weekends in the region. Full details are on the Oshawa Art Association website.

Fall Fun on the Farm at Applewood Farm Winery

Pumpkin season opens this weekend at Applewood Farm Winery (2055 Saintfield Road) in Seagrave, just north of Port Perry in Scugog. Fall Fun on the Farm runs Saturdays and Sundays from 11 AM to 5 PM between September 20 and Halloween, with a 40-acre corn maze, a pumpkin patch, wagon rides, a sunflower walk, farm animals and a children's play area. Farm wristbands cover entry to the farm, patch and maze, and advance booking is recommended on busy weekends. See the Applewood Farm fall event page for tickets and details.

Pumpkin Palooza at Willowtree Farm

Willowtree Farm (975 Regional Road 21), just outside Port Perry, opens its Pumpkin Palooza this weekend from 9:30 AM to 4 PM, with a corn maze, pumpkin patch and family activities for the fall season. Tickets start at $12 per person online for ages two and up, with on-site tickets limited. The farm runs Pumpkin Palooza on select weekends through October, so if Saturday or Sunday is full, later weekends are an easy fall plan. Book on the Willowtree Farm Pumpkin Palooza page.

Live Music at Old Flame Brewing Co. in Port Perry

After the market, head to Old Flame Brewing Co. (135 Perry Street) in downtown Port Perry, where Saturday afternoon live music runs from 1 to 5 PM every weekend. It is a local favourite for a pint on the patio and a relaxed start to the evening. The brewery keeps the full fall lineup on its news and events page.

Culture Days in Pickering

In Pickering, Pickering Museum Village (2365 Concession Road 6) is part of the Culture Trek Durham program on the festival's final weekend, running Saturday with heritage programming and activities. The museum also hosts special evening programs through October, including the lantern-lit Pickering Ghost Walk on select October evenings. Current opening hours and programs are listed on the Pickering Museum Village programs page.

Cartwright Fall Festival and Classic Car Show in Nestleton

Saturday brings the Cartwright Fall Festival and Classic Car Show to Cartwright Fields, 3971 Highway 7A in Nestleton, in the Township of Scugog, about 10 minutes from Port Perry. The annual, family-friendly fall festival is paired with a classic car show open to all makes, models and years, with food, family fun and entertainment, held as a fundraiser by Cartwright Sports & Recreation Inc., the volunteer-run, not-for-profit organization that maintains the fields. Since start time and admission details have varied in past years, confirm both on the Cartwright Fields website before you head out.

Sunday, Oct-4

Sunday belongs to a slow market morning in Uxbridge, the final day of both art festivals, pumpkin farms, and a farewell to Ontario Culture Days along a Bowmanville trail.

Uxbridge Farmers' Market (Headline)

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, and our Uxbridge community guide for more on the town.

Both Art Festivals Continue

The Oshawa Art Association Fall Art Festival runs its second day from 10 AM to 5 PM at Camp Samac (275 Conlin Road East), and the Port Perry Artists' Association exhibition continues from 10 AM to 6 PM at the Latcham Centre (121 Queen Street). With free admission at both, Sunday is the perfect day for a two-festival art crawl across the region.

Pumpkin Farms, Both Days

Fall Fun on the Farm at Applewood Farm Winery runs again Sunday from 11 AM to 5 PM, and Pumpkin Palooza at Willowtree Farm continues from 9:30 AM to 4 PM. Both farms book ahead on weekends, so grab tickets online before you go.

Culture Days Trailside Finale in Bowmanville

The Municipality of Clarington closes out Ontario Culture Days with a Trailside Finale along the Marie Hubbard Trail in Bowmanville on Sunday from 10 AM to 2 PM, with art and heritage programming on the trail. See the Municipality of Clarington festivals and events page for the full lineup.

Fall Colours Drive Through Brock Township

If the weather cooperates, the country roads of Brock Township, through Cannington, Beaverton and Sunderland, hit their peak colour around the first weekend of October. It is a free afternoon of red maples and golden fields, with a stop at Canter Coffee in Cannington for a warm drink along the way. No tickets, no lineup, just the best of North Durham in October.

Culture Days programming continues through Sunday across the region, with free museum, gallery and trail events listed on the Culture Days finder.

Plan Your Weekend

Whether you are stocking up at the Port Perry farmers market, browsing art at the Latcham Centre and Camp Samac, walking a corn maze in Seagrave, or taking the slow road through Brock Township, there is plenty to do across Durham Region this weekend. New to the area? Our Port Perry community guide, Uxbridge community guide and Oshawa community guide introduce the towns hosting the biggest events, and the Weekend Guide archive holds every edition we have published so far.

If you are new to the area and thinking about making it home, the fall is a wonderful time to explore. Our moving to Port Perry guide covers the town from the historic downtown to the lakeshore, and the guide to living on Lake Scugog explains what waterfront life in this corner of Durham Region really involves. Wherever your weekend takes you, we hope you have a safe and happy one in Durham Region.