Things To Do This Weekend in Durham Region (October 23-25, 2026)

Looking for things to do this weekend in Durham Region? The weekend of October 23 to 25, 2026 is the last full weekend before Halloween, and Durham Region leans right into it. The Booseum family Halloween event returns to the Scugog Shores Museum Village in Port Perry, the Uxbridge Farmers' Market holds its final outdoor market with a trick-or-treat theme, haunted attractions run in Cannington and Whitby, and the Oshawa Generals host two home games at the Tribute Communities Centre. Here is your weekend guide for Friday, October 23, through Sunday, October 25.

Friday, Oct-23

Friday is a night for hockey, live music and the first spooky events of the weekend. Families with older kids can start Halloween early at the haunts in Cannington and Whitby.

Oshawa Generals vs. Peterborough Petes

The Oshawa Generals open the weekend at home against the Peterborough Petes at the Tribute Communities Centre in Oshawa, with puck drop at 7:05 PM. It is one of Ontario Hockey League's classic rivalries and an easy, family-friendly night out in downtown Oshawa. See the Tribute Communities Centre events page for tickets.

Fleetwood Mac Mania at the Regent Theatre

The Regent Theatre at 50 King Street East in Oshawa hosts Fleetwood Mac Mania, a tribute to the rock legends, on Friday at 8 PM. It is a polished night of hits in one of Durham Region's grandest theatres, and a great pairing with dinner on King Street before the show. Tickets are on the Regent Theatre box office.

Cannington Haunted Attraction

The Cannington Haunted Attraction runs Friday and Saturday from 6:30 to 9:30 PM at MacLeod Park, 91 Elliot Street in Cannington, Brock Township. This volunteer-run Halloween haunt features two wooded trails, an indoor barn maze, a mini-escape game and axe throwing, with food and craft vendors on site. It is recommended for ages 8 and up, tickets are $20 each, and they are sold online only. See the Cannington Haunted Attraction listing for details.

Crocs After Dark at Reptilia Whitby

Reptilia Whitby at 1400 Victoria Street East in Whitby runs Crocs After Dark on Friday and Saturday from 7 to 9 PM, an after-hours program where crocodilians come to life under the lights with keeper-led feeding demonstrations and nocturnal shows. Tickets are $9 for children 2 to 6, $11 for youth 7 to 12, and $15 for adults. Book on the Reptilia Crocs After Dark page.

Spooktacular Light Show in Ajax

The Spooktacular Light Show, a drive-thru Halloween light display with animated scenes and a trick-or-treat stop, is open Friday, Saturday and Sunday at 462 Kingston Road East in Ajax. It is a car-friendly way to get the whole family in the Halloween spirit without leaving the front seat. Tickets and showtimes are on the Spooktacular Light Show website.

Saturday, Oct-24

Saturday is the biggest day of the weekend. Port Perry sits at the centre of family-friendly Halloween fun, while farms, museums, markets and music fill the rest of Durham Region.

Booseum at the Scugog Shores Museum Village (Headline)

The Booseum (Adventures at the Boo-seum) is a family-friendly Halloween event at the Scugog Shores Museum Village, 16210 Island Road in Port Perry, running Saturday from 1 to 4 PM. The historic village turns gently spooky for the afternoon, with the museum's heritage buildings and grounds ready for young visitors in costume. It is one of the most popular family events on the Scugog fall calendar, so check the Scugog Shores Museum events page for times and admission.

Candle Making Workshop at Kids Art Talks

Kids Art Talks at 175b Queen Street in downtown Port Perry hosts a Candle Making Workshop on Saturday from 1 to 3 PM. It is a hands-on craft hour in the heart of the historic main street, and a lovely way to slow down between the morning and evening of a busy weekend. See the Port Perry BIA featured events page for workshop details and registration.

Fall Fun on the Farm at Applewood Farm Winery

Fall Fun on the Farm continues Saturday and Sunday from 11 AM to 5 PM at Applewood Farm Winery, 2055 Saintfield Road in Seagrave, just north of Port Perry. Expect the 40-acre corn maze, a pumpkin patch, wagon rides and a sunflower walk, all in the golden October countryside that makes living on Lake Scugog so special. This year's run ends October 26, so it is one of your last chances. See the Applewood fall event page for hours and admission.

Prowl at the Park in Orono

Prowl at the Park returns to Jungle Cat World Wildlife Park, 3667 Concession Road 6 in Orono, Clarington, on Saturday from 4 to 8 PM. The park opens after hours with trick-or-treating stations and Halloween enrichment activities for the animals, costumes encouraged. Confirm the exact time on the Jungle Cat World programs page before you head out.

Halloween at the Harbour in Oshawa

The Oshawa Museum hosts Halloween at the Harbour on Saturday from 6 to 8 PM at its three historic buildings in Lakeview Park in Oshawa. It is an evening of Halloween-themed experiences in the museum's heritage houses at the water's edge. Tickets are $7.50 per person and $5 for children under 5, with members and children under 2 free. See the Oshawa Museum What's On page for details.

Ajax Pumpkin Giveaway

The 18th Annual Pumpkin Giveaway runs Saturday from 10 AM to 2 PM in Ajax, with free pumpkins, face painting, a hot-dog BBQ, a bake sale and raffle prizes in support of the Jennifer Ashleigh Children's Charity. It is a free, family-friendly morning that gets your carving pumpkin sorted well before Halloween. See the Town of Ajax Pumpkin Giveaway listing for the location and full details.

Born Ruffians at the Uxbridge Music Hall

Saturday night in Uxbridge, the Born Ruffians headline the Springtide Music Festival fall concert at the Uxbridge Music Hall at 7:30 PM. It is a big-name indie show in one of North Durham's favourite live venues, and the festival runs a shuttle from Port Perry for anyone coming from the lake. See the Springtide fall concert announcement for tickets.

Oktoberfest Weekend at Pingle's Farm and Brawley Woods in Whitby

In Whitby, Pingle's Farm Market at 1805 Taunton Road celebrates an Oktoberfest themed weekend on October 24 and 25, with apple and pumpkin picking, a 6.5-acre circus corn maze, wagon rides, farm animals, seasonal food and live music. And for brave older kids and adults, Brawley Woods Haunted Halloween Walk at 1320 Brawley Road West runs its 30-minute forest haunt with live scare actors and movie-style scenes all weekend, from $35. See the Pingle's Harvest Festival page and the Brawley Woods listing.

Sunday, Oct-25

Sunday winds the weekend down with a market morning in Uxbridge, farm fun in Seagrave and Whitby, and a family-friendly hockey game in Oshawa to close it out.

Uxbridge Farmers' Market Final Outdoor Market (Headline)

The Uxbridge Farmers' Market holds its final fully outdoor market of the season on Sunday from 9 AM to 2 PM at 14 Victoria Street, beside The Second Wedge Brewing Co. in Uxbridge. It carries a trick-or-treat Halloween theme: more than 50 vendors selling produce, artisanal food and handcrafts, free kids' activities, and plenty of candy stops, so bring the costumes. After the market, the season moves indoors to the Uxbridge Arena for the Holiday Markets. We wrote a community spotlight on The Second Wedge Brewing Co., and it is worth a pint and wood-fired pizza after you shop. See the market's special events page for the full lineup.

Oshawa Generals vs. Sudbury Wolves

Sunday evening, the Oshawa Generals host the Sudbury Wolves at the Tribute Communities Centre in Oshawa, with puck drop at 6:05 PM. After a weekend of farm visits and markets, a junior hockey game is one of the most family-friendly ways to close it out. See the Tribute Communities Centre events page for tickets.

Farm Fun, Both Days

Fall Fun on the Farm at Applewood Farm Winery continues Sunday from 11 AM to 5 PM, and Pingle's Farm in Whitby keeps its Oktoberfest weekend going with pumpkin picking, the corn maze and wagon rides. Both farms book up on weekends in late October, so grab tickets online before you go. If you are new to the countryside, our moving to Port Perry guide explains what life in this corner of Durham Region is really like.

A Movie at The Roxy Theatres of Uxbridge

The Roxy Theatres of Uxbridge at 46 Brock Street West screens Sense and Sensibility on Sunday at 1 PM and 7:15 PM, and all weekend long. The town's beloved heritage cinema is a cozy way to round out the weekend in Uxbridge. See the Roxy website for showtimes.

Plan Your Weekend

Whether you are hunting for pumpkins at the Booseum in Port Perry, trick-or-treating through the final Uxbridge Farmers' Market, cheering the Generals in Oshawa, or braving the haunts in Cannington and Whitby, 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 Whitby community guide introduce the towns hosting the biggest events, and the Weekend Guide archive holds every edition we have published so far.

Halloween itself lands next Saturday, October 31, and our 2026 Trunk-or-Treat and Trick-or-Treat Guide rounds up the family Halloween events across Oshawa and Durham Region so you can plan ahead. Wherever your weekend takes you, we hope you have a great one in Durham Region.