What To Do This Weekend in Durham Region (October 16-18, 2026)

Looking for things to do this weekend in Durham Region? The weekend of October 16 to 18, 2026 is one of the biggest of the fall: the Bowmanville Applefest fills historic downtown with apples, cider and family fun, Pumpkinville returns to Greenwood Conservation Area in Ajax, the Uxbridge Farmers' Market celebrates its annual Pumpkin Festival, and Port Perry adds a chocolate and cheese tasting at The Port Cheese Co. Here is your weekend guide for Friday, October 16, through Sunday, October 18.

Friday, Oct-16

Friday is a gentle start to a very full weekend. Grab local produce at the Friday market in Bowmanville, snag a bargain at a community rummage sale in Port Perry, then settle into a comedy night, a concert or a movie.

Bowmanville Farmers Market

The Bowmanville Farmers Market runs Friday from 2 to 7 PM, connecting local makers, farmers and the community in Clarington. It is a relaxed way to pick up autumn produce, preserves and handmade goods before the weekend's big events, and a perfect warm-up for the Applefest on Saturday. See the market's page for the weekly lineup and location.

Port Perry United Church Rummage Sale

The Port Perry United Church Rummage Sale runs Friday from 9 AM to 7 PM at 294 Queen Street in downtown Port Perry. It is a classic small-town treasure hunt with a good cause behind it, and a lovely way to spend a morning browsing the stalls on the historic main street. Proceeds support the church and its community work.

Comedy Night with Debra DiGiovanni in Oshawa

Canadian comedian Debra DiGiovanni headlines at the Biltmore Theatre, 39 King Street East in Oshawa on Friday night, with doors at 6 PM and the show at 7 PM. It is a 19-plus, general admission evening in one of downtown Oshawa's classic theatres. Grab tickets on the Biltmore Theatre website, and check the Oshawa community guide for what else downtown has to offer.

Collective Soul at Pickering Casino Resort

The multiplatinum rock band Collective Soul plays The Arena at Pickering Casino Resort, 888 Durham Live Avenue on Friday at 8 PM, with doors at 7 PM. It is a big arena night in Pickering and one of the biggest concerts of the weekend anywhere in Durham Region. Tickets are on the Pickering Casino Resort events page.

A Movie at The Roxy Theatres of Uxbridge

The Roxy Theatres of Uxbridge at 46 Brock Street West starts screening Sense and Sensibility on Friday, October 16. It is the town's beloved heritage cinema, and a movie here is a cozy way to ease into the weekend in Uxbridge. See the Roxy website for showtimes.

Saturday, Oct-17

Saturday is the headliner of the weekend. The Bowmanville Applefest takes over historic downtown, Pumpkinville returns to Ajax, the Oshawa Halloween Boo Bash fills King Street East, heritage buildings open across Whitby, and pumpkin farms around Port Perry are in full swing.

Bowmanville Applefest (Headline)

The Bowmanville Applefest runs Saturday from 9 AM to 5 PM in historic downtown Bowmanville, in Clarington. Four city blocks on King Street line up with local apple growers selling fresh apples, cider, pies, candy apples, caramel apples and donuts, along with vendors, food and family activities. Admission and parking are free, and King Street closes from Scugog Street to George Street on Friday evening so the festival can set up. See the official Applefest page for the full lineup, and the Clarington Post road closure notice if you are driving in.

Pumpkinville at Greenwood Conservation Area in Ajax

Pumpkinville, presented by TD Bank Group, runs Saturday from 11 AM to 5 PM at Greenwood Conservation Area, 2290 Greenwood Road in Ajax. This free, all-ages Halloween festival features pumpkin patch activities and food vendors, all set on the green conservation lands along Duffins Creek. It is one of the best-value family outings of the weekend. See the Town of Ajax Pumpkinville page for details.

Oshawa Halloween Boo Bash on King Street East

The Oshawa Halloween Boo Bash returns to downtown Oshawa on Saturday from 1 to 10 PM on King Street East, presented by Oshawa Tourism. It is a free, family-friendly festival with family activities through the afternoon and scare actors joining the fun after 3 PM. The street closes to traffic for the day, so the whole downtown becomes the party. Follow the Boo Bash page for the schedule, and browse our Oshawa community guide to plan around it.

Doors Open Whitby

Doors Open Whitby runs Saturday from 10 AM to 4 PM, opening the doors of the town's heritage buildings to the public, including the 1855 Burr Lodge. It is a free, self-guided look at Whitby's history and architecture, and a relaxed way to spend an afternoon in Whitby. See the Doors Open Ontario Whitby listing for participating sites.

Pumpkin Farms Around Port Perry

Pumpkin season is in full swing around Port Perry. Willowtree Farm (975 Regional Road 21) runs its Pumpkin Palooza Saturday and Sunday from 9:30 AM to 4 PM, with a corn maze, pumpkin patch and family activities, booked on the Willowtree Pumpkin Palooza page. Applewood Farm Winery (2055 Saintfield Road) in Seagrave runs Fall Fun on the Farm weekends from 11 AM to 5 PM, with a 40-acre corn maze, pumpkin patch, wagon rides and a sunflower walk; see the Applewood fall event page. And Nature's Bounty Farm (651 Scugog Line 2) is open daily from 9 AM to 5 PM through October with a corn maze, pumpkin patch and apples, a short drive from the Port Perry waterfront.

Live Music at Old Flame Brewing Co. in Port Perry

After a day at the farms, Old Flame Brewing Co. (135 Perry Street) in downtown Port Perry hosts live music on Saturday afternoon, as it does most weekends. It is a local favourite for a pint on the patio and a relaxed start to the evening. The brewery keeps the fall lineup on its news and events page.

An Evening of Boston and Kansas Greatest Hits in Oshawa

Saturday night, The Regent Theatre (50 King Street East) in Oshawa hosts An Evening of Boston and Kansas Greatest Hits at 8 PM. The band "More Than A Feeling" delivers the high-energy hits of the 70s rock giants, a night of nostalgia in one of Durham Region's grandest theatres. Tickets are on the Regent Theatre box office.

Sunday, Oct-18

Sunday eases the pace with a market morning in Uxbridge, a chocolate and cheese tasting in Port Perry, a comic convention in Whitby, and an evening of junior hockey in Oshawa.

Uxbridge Farmers' Market Pumpkin Festival (Headline)

The Uxbridge Farmers' Market celebrates its annual Pumpkin Festival on Sunday from 9 AM to 2 PM at 14 Victoria Street, beside The Second Wedge Brewing Co. Expect more than 50 local vendors, farm-fresh pumpkins both culinary and decorative, seasonal baked goods and pumpkin-themed art, live music from 10 AM to 1 PM, and a pumpkin scavenger hunt for the kids. We have written about The Second Wedge Brewing Co. in our community spotlight, and it is worth stopping in for a pint and wood-fired pizza after the market. See the market's Pumpkin Festival page, and our Uxbridge community guide for more on the town.

Chocolate and Cheese Pairing at The Port Cheese Co.

The Port Cheese Co. at 203 Queen Street in downtown Port Perry hosts a Chocolate and Cheese Pairing on Sunday from 2 to 4 PM. It is a tasty, grown-up afternoon in one of the town's favourite shops, and a lovely way to close the weekend on Queen Street. See the Port Cheese Co. website for tickets and details.

Whitby ComiCon at Heydenshore Pavilion

The Whitby ComiCon comic convention runs Sunday from 10 AM at the Heydenshore Pavilion in Whitby, with entry around $7. Expect comics, collectibles, cosplay and creators in a relaxed waterfront setting. It pairs well with a walk along the Whitby waterfront afterwards.

Oshawa Generals vs. Kitchener Rangers

Sunday evening, the Oshawa Generals host the Kitchener Rangers in Ontario Hockey League action at the Tribute Communities Centre in Oshawa, with puck drop at 6:05 PM. Tickets run roughly $29 to $46, and it is one of the most family-friendly ways to spend a Sunday night in Durham Region. See the Tribute Communities Centre event page for tickets.

Pumpkin Farms, Both Days

Pumpkin Palooza at Willowtree Farm continues Sunday from 9:30 AM to 4 PM, and Fall Fun on the Farm at Applewood Farm Winery runs again from 11 AM to 5 PM. Forsythe Family Farms in Uxbridge is open weekends through the end of October with its pumpkin patch, corn maze and wagon rides. Both local farms book ahead on weekends, so grab tickets online before you go.

Plan Your Weekend

Whether you are walking the Applefest in downtown Bowmanville, carving a pumpkin at Pumpkinville in Ajax, joining the Boo Bash on King Street, browsing the Uxbridge market, or tasting chocolate and cheese on Queen Street in Port Perry, there is plenty to do across Durham Region this weekend. New to the area? Our Port Perry community guide, Uxbridge community guide, Oshawa community guide and Clarington 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 great one in Durham Region.