Summer may be coming to an end, but some of the best local events of the year are just getting started.

September and October bring fall fair season to Durham Region and the surrounding communities, with agricultural shows, midway rides, demolition derbies, local vendors, live entertainment, harvest celebrations and, of course, plenty of fall food.

If you're looking for things to do in Durham Region this fall, there are events happening almost every weekend. We've rounded up some of the 2026 fall fairs and festivals in Durham Region, along with a few destinations in Kawartha Lakes and nearby Brighton that are worth adding to your fall calendar.

Port Perry Fair

September 5–7, 2026 | Port Perry Fairgrounds

Labour Day weekend marks the…

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 Oshawa is getting a full afternoon of food, activities, local businesses, prizes and community connections on August 15, 2026!

Join us at 785 Taunton Rd E (Torchbearer Taproom) from 12 PM to 4 PM for Meet Your Neighbours Community Day, an event designed to bring residents, families, local businesses and community organizations together in one place.

Throughout the afternoon, there will be scheduled meetup times for different interests and age groups, along with pop-ups, giveaways, food and other activities happening around the plaza.

Scheduled Meetup Times

12:00 PM – 12:45 PM | Parents & Young Kids
A chance for local families to connect while the kids enjoy activities and limited free kids packs.

1:00 PM – 1:45 PM | Dogs & Their…

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5 Fun Things to Do in Durham Region at the Height of Summer

The end of July and beginning of August can feel like the halfway point of summer. The first round of plans is over, the kids may be getting restless, and many people start wondering what they can do without driving into Toronto or spending an entire day in traffic.

The answer may be closer than you think.

From walking through thousands of sunflowers to cycling country roads and enjoying free live entertainment beside the water, Durham Region has several experiences that can turn an ordinary summer day into something memorable.

Here are five fun things to do in Durham Region while summer is still in full swing.

1. Walk Through Canada’s Only Sunflower-Shaped Trail

Most people…

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Few things feel more like summer in Durham Region than heading out for ice cream after dinner, after a walk by the water, after a day at the park, or on the way home from a weekend drive.

From gelato in Pickering to classic scoops in Ajax, Whitby favourites, a Brooklin stop, Oshawa treats, and small town gems through Clarington, Durham has no shortage of places worth adding to your summer list.

Here are some of the top ice cream spots to check out across Durham Region.

Belaggios Gelato, Pickering

Starting on the west side of Durham, Belaggios Gelato is a great Pickering stop for anyone who loves gelato, espresso, desserts, and café style treats. It has more of an Italian inspired feel, making it a nice option when you want something a…

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As the weather warms up, patios start filling up again, waterfronts get busier, and local spots become part of people’s routines again. Whether you’re looking for casual drinks, dinner with friends, or a summer-night atmosphere, Durham has no shortage of great patio options.

Here are a few local spots worth checking out this season.

The Courtyard

A Courtice favourite known for its lively patio, live music, and energetic atmosphere. It’s the kind of place that works just as well for a casual afternoon as it does for a busy Friday night.

The Canadian Brewhouse

Big screens, a large patio, and a high-energy atmosphere make Canadian Brewhouse a go-to for game nights and casual group outings.

Best for: Weekend drinks and sports nights

…

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The holiday season is one of the best times of the year in Durham Region, with local communities hosting Christmas markets, craft fairs, winter festivals, and family events throughout November and December. Whether you are looking for handmade gifts, festive food, live entertainment or just a way to enjoy the magic of the season, there are plenty of events happening in Oshawa, Whitby, Courtice, Bowmanville, Ajax, Pickering, Port Perry, and Uxbridge.

This guide highlights the top holiday markets and Christmas events in Durham Region for 2025.

Holiday Markets and Events:

Abilities Centre Holiday Market – Whitby

Date: Saturday, November 1
Time: 10 am to 4 pm
Location: Abilities Centre, 1 Jim Flaherty Street, Whitby
A fully accessible holiday…

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Fall in Durham Region means colourful leaves, crisp air, and pumpkin patches — but it also means spooky season. If you’re looking for something a little different than apple picking and hayrides, why not explore some of the region’s most haunted spots? From eerie old courthouses to ghostly pubs, Durham has plenty of places that will give you goosebumps.

Whitby Centennial Building (Courthouse Theatre), Whitby

Built in 1853 as a courthouse and jail, the Centennial Building is now home to the Whitby Courthouse Theatre. Over the years, visitors and staff have reported shadowy figures, flickering lights, and footsteps echoing through empty halls. Whether you’re attending a play or just walking by on Centre Street, this historic site has a reputation…

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The crisp air, vibrant leaves, and cozy sweaters can only mean one thing: fall has arrived in Durham Region. And with it comes some of the best festivals, pumpkin patches, and farm markets Ontario has to offer. Whether you’re searching for the perfect pumpkin, getting lost in a corn maze, or enjoying local food and harvest celebrations, there are plenty of places to explore this season.

Fall Festivals

Applefest – Downtown Bowmanville
On Saturday, October 18, 2025, Historic Downtown Bowmanville transforms into Applefest, a celebration of all things apple. Expect fresh cider, pies, crisps, candy apples, cider donuts, and the famous hot apple fritters. With artisan vendors, live entertainment, and family activities, it’s a true small-town…

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If you’re looking for the best places to go apple picking in Ontario, Durham Region should be at the top of your list. With family-friendly orchards, scenic farmland, and plenty of fall activities, Durham offers a true taste of autumn just east of Toronto. From wagon rides and pumpkin patches to fresh-pressed cider, here’s your guide to apple picking in Durham Region this fall.

Top Orchards for Apple Picking in Durham Region

Maple Grove Farm – Bowmanville
Maple Grove Farm is a local favourite for apple picking in Bowmanville. This family-run farm offers a wide variety of apples and expands into pumpkins as the season continues. Visitors enjoy the authentic country atmosphere and the chance to experience a traditional farm outing.

Watson Farms…

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August is here, and there’s no better time to enjoy everything summer has to offer. Whether you're planning a family outing, a relaxing solo day, or a spontaneous weekend adventure, Durham Region is home to some of the best beaches and parks—plus, a few hidden gems just under an hour away.

Here’s your guide to the top spots to unwind and soak up the season:

Lakeview Park Beach (Oshawa)

One of Durham’s most popular beach destinations, Lakeview Park Beach is perfect for families. This beautiful waterfront spot features a splash pad, shaded picnic areas, a playground, and a long boardwalk ideal for walks along the lake. The beach is supervised by lifeguards daily from 11:30 a.m. to 6:30 p.m., and there’s even a lifejacket loaner station for extra…

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