October 14, 2026 | Community

Weekend Events in Burlington, Oakville and Hamilton: October 16th to 18th

Halloween season has officially arrived in Ontario. Pumpkins glow on porches and the leaves are at their peak. Best of all, local calendars are packed with fall events.

From candlelit pumpkin trails to ghost walks and harvest markets, there is something for everyone. Whether you want a cozy night out or a busy Saturday with the kids, these events make it easy to celebrate the season close to home. Here is your guide to the best events happening from Friday, October 16 to Sunday, October 18.

Burlington Weekend Events

Burlington is leaning into the spooky season this weekend. Here are the highlights.

The Great Pumpkin Trail

Thursday, October 15 to Sunday, October 18 | Entry from 5:30 to 8:30 p.m. | Hendrie Park, 680 Plains Road West

This beloved RBG tradition returns with thousands of real pumpkins on display. Follow a candlelit trail through the Hendrie Valley and enjoy live entertainment and seasonal treats along the way. Tickets are timed and must be purchased in advance. Also, the trail is dark and uneven, so bring a flashlight and wear sturdy shoes.

The Great Pumpkin Trail

Giant Indoor Community Garage Sale

Saturday, October 17 | 8:30 a.m. to 1:00 p.m. | Ukrainian Hall, 2077 Pine Street

Treasure hunters, take note. This popular indoor sale is celebrating its 20th year in Burlington. Arrive early for the best finds. Then, grab a coffee and stroll through the downtown core.

DreadCon Dark Fiction and Horror Convention

Saturday, October 17 | 11:00 a.m. to 5:00 p.m. | 3063 South Service Road | $10 general admission, kids free

Horror fans will love this one. Canada’s only dark fiction and horror convention returns to Burlington for its third year. Expect author signings, panels, workshops and a marketplace full of books and art.

Live Performances at the Burlington Performing Arts Centre

Saturday, October 17 | 440 Locust Street

Music lovers have two great options on Saturday. First, the Secret Path Cushion Concert with Kate Dickson and Shannon Thunderbird begins at 1:00 p.m. This pay what you can show marks Secret Path Week with Indigenous music and storytelling. Later, She Carries the Song takes the stage at 7:30 p.m.

Oakville Weekend Events

Oakville is full of Halloween spirit this weekend, with candlelit tours, markets and family fun.

Moonlight Market at Joshua Farm Gallery

Friday, October 16 | 4:30 to 8:30 p.m. | 1086 Burnhamthorpe Road East

Kick off your weekend at this unique evening market. Browse local vendors and meet tarot readers, astrologers and other mystical artisans. It is a fun and different way to start the weekend.

Oakville Historical Society Ghost Walks

Friday, October 16 and Saturday, October 17 | 6:30 and 8:00 p.m. | Starts and ends at 110 King Street

Explore the spooky side of Old Oakville on a guided evening walk. These seasonal tours are a fun way to celebrate Halloween while learning about local history.

Haunted Happenings: Candlelight Tour

Friday, October 16 and Saturday, October 17 | 7:00 and 8:00 p.m. | Oakville Museum, 8 Navy Street

See the Oakville Museum in a whole new light. Each candlelit tour runs about 30 minutes, so it pairs nicely with dinner downtown.

Haunted Happenings: Candlelight Tour

Oakville Civitan Farmer’s Market

Saturday, October 17 | 8:00 a.m. to 1:30 p.m. | 240 North Service Road West

Stock up on fall produce, baked goods and local favourites. As a result, it makes a great first stop before a busy Saturday.

Family Saturdays: Pumpkin Carving

Saturday, October 17 | 10:00 a.m. to 2:00 p.m. | Oakville Galleries in Gairloch Gardens, 1306 Lakeshore Road East

Get into the Halloween spirit with a creative family activity. Plus, the lakeside setting at Gairloch Gardens is beautiful this time of year.

Wiggle Waggle Walk

Sunday, October 18 | River Oaks Community Centre, 2400 Sixth Line

Bring your four-legged friend to this community walk. The Humane Society of Oakville, Milton and Halton hosts it, so every step supports animals in need. Check the event website for start times.

Tony Bennett: 100 Years of the Good Life

Sunday, October 18 | 2:00 p.m. | Oakville Centre for the Performing Arts, 130 Navy Street

The Toronto All-Star Big Band celebrates the timeless music of Tony Bennett. It is a perfect way to spend a Sunday afternoon.

Hamilton Weekend Events

Hamilton rounds out the weekend with festivals, flowers and film.

Stoney Creek Pumpkinfest

Saturday, October 17 | 11:00 a.m. to 5:00 p.m. | Downtown Stoney Creek

The Stoney Creek BIA hosts this festive fall celebration. Spend the afternoon exploring downtown Stoney Creek and soaking up the harvest atmosphere with the whole family.

Fall Floral Mum Show at Gage Park

Daily from October 17 to 25 | 9:00 a.m. to 7:00 p.m. | Gage Park Tropical Greenhouse

Hamilton’s favourite fall show is back. The greenhouse bursts with colourful chrysanthemums, so it is a lovely indoor option on a chilly day.

Fall Floral Mum Show

Hamilton Film Festival

October 16 to 25 | Various locations

The Hamilton Film Festival opens this weekend. Catch independent films at venues across the city over the next ten days.

Gardens in the Fall at Westfield Heritage Village

Sunday, October 18 | 12:00 to 4:00 p.m. | Westfield Heritage Village

Step back in time as historic kitchens come alive. Visitors can watch traditional techniques like drying, salting and pickling the harvest.

TERRA Fall Market

Saturday, October 17 | From 10:00 a.m. | TERRA Hamilton

Browse seasonal finds and local vendors at this cozy fall market. It is also an easy way to support small businesses this weekend.

Tips for Enjoying Local Events This Weekend

A little planning goes a long way. First, book timed tickets early for popular events like the Great Pumpkin Trail. Next, check each event website before you go, since times and details can change. In addition, bring a flashlight for evening walks and trails. Finally, dress in layers, because October evenings cool down quickly.

Why Local Events Matter When Choosing a Home

Community events show what everyday life feels like in a neighbourhood. A busy fall calendar, walkable downtowns and beautiful green spaces all add to the appeal of Burlington, Oakville and Hamilton.

For many buyers, these moments are what make a city feel like home. So if you are thinking about a move, local events are a great way to get to know an area. Our team is always happy to share insider tips on the neighbourhoods we serve.

Frequently Asked Questions

What events are happening in Burlington this weekend?

Burlington events this weekend include the Great Pumpkin Trail at Royal Botanical Gardens, the Giant Indoor Community Garage Sale, DreadCon and two performances at the Burlington Performing Arts Centre.

What Halloween events are happening in Oakville this weekend?

Oakville offers the Historical Society Ghost Walks, the Haunted Happenings Candlelight Tour at the Oakville Museum, the Moonlight Market and a family pumpkin carving day at Gairloch Gardens.

Are there free events this weekend?

Yes. The Secret Path Cushion Concert at the Burlington Performing Arts Centre is pay what you can, including free. Kids also get into DreadCon for free. Always check the organizer’s website to confirm admission details.

What is happening in Hamilton this weekend?

Hamilton events include Stoney Creek Pumpkinfest on Saturday, the Fall Floral Mum Show at Gage Park, the Hamilton Film Festival and Gardens in the Fall at Westfield Heritage Village on Sunday.

Do I need tickets for the Great Pumpkin Trail?

Yes. The Great Pumpkin Trail uses timed tickets that must be purchased in advance. Last entry each evening is 8:30 p.m.

Get The Newsletter

Join our mailing list to get updates from our experts about the Toronto market, the latest listings, and our industry insights.

Weekend Events in Burlington, Oakville and Hamilton: October 16th to 18th