Living in Durham Region means the holiday season arrives with real community spirit. From small-town morning parades to glowing evening processions, there is something happening almost every weekend from mid-November to mid-December.

I have pulled together the highlights so you can plan your weekends, bring the family and enjoy the season close to home. Save this one. You will want it handy.

Tip: Parade routes often involve road closures, so give yourself extra time to park and find a good viewing spot. It is also worth checking each event’s official page for last-minute updates.

Week of November 9: The Season Kicks Off

Winter Nights, City Lights | Pickering
Friday, November 13 and Saturday, November 14 | 5:30 PM to 8:30 PM
The Esplanade Park, Pickering

Pickering opens the season with two nights of tree lighting and fireworks, both at 6 PM. You will also find live entertainment, food vendors, art installations, photo spots, a market tent and roaming characters.
Make an evening of it: Browse the shops at Pickering Town Centre first, then head to the park. Leave time to park before the 6 PM lighting.

Winter Wonder Lights | Newcastle
Sunday, November 15 | 5:15 PM
Newcastle Community Hall, 20 King Ave. West

The historic Community Hall, the Christmas tree and the nearby parkette all get lit up for the season. Stroll the storefronts along King Avenue beforehand.

Newcastle Santa Claus Parade
Sunday, November 15 | Fireworks at 5:30 PM, parade to follow
King Avenue, from North Street east to Arthur and Brookhouse Streets

Expect fireworks, illuminated floats, marching bands and plenty of fun parade entries. Grab an early dinner on King Avenue and claim your spot along the route.

Week of November 16: Oshawa Lights Up

Bright and Merry Market and Tree Lighting | Oshawa
Friday, November 20 | 5 PM to 9 PM, tree lighting at 8:30 PM
Memorial Park, Downtown Oshawa

This downtown market blends holiday shopping, live entertainment, food vendors, community activities and a visit with Santa. Come early to explore, then stay for the tree lighting.
Make an evening of it: Visit the Robert McLaughlin Gallery or the Canadian Automotive Museum, then have dinner on Simcoe Street before the market.

Santa’s Parade of Lights | Oshawa
Saturday, November 21 | 6:30 PM
King Street West, from Gibbons Street to Division Street

An after-dark parade of illuminated entries through the heart of downtown. Plan to arrive early for a good viewing spot, and enjoy a bite on King Street before the road closures.

Christmas in the Village | Brooklin, Whitby
Saturday, November 21 | 9 AM to 4 PM
Grass Park, 41 Baldwin Street

A full day of seasonal activities in the heart of historic Brooklin. Shop the independent businesses along Baldwin Street and take a walk around Grass Park.

Bowmanville Santa Claus Parade
Saturday, November 21 | 10:30 AM
King Street, from Scugog Street to Simpson Avenue

Bring your letters for Santa. The Salvation Army will also be collecting non-perishable food donations, so it is a lovely chance to give back. Browse the bakeries and shops on King Street while you are there.

Uxbridge Santa Claus Parade
Saturday, November 21 | 11 AM
Brock Street, from the arena to Uxbridge Secondary School

A late-morning parade through the centre of town. Explore the independent shops on Brock Street beforehand.

Week of November 23: A Packed Weekend

Whitby Lights the Night and Holiday Festival
Friday, November 27 | 5 PM to 9 PM
Whitby Civic Park, 575 Rossland Rd E

Illuminated public spaces, an evening market and live music. Kids can enjoy cookie decorating, maple taffy and photo ops, plus a visit with Santa. Pair it with an early dinner in downtown Whitby.

Saturday, November 28 is a big day across the region:

• Pickering Santa Claus Parade | 10 AM. This year’s theme is Holiday Storytime. The route starts at Sheppard Avenue near Dunbarton High School, turns onto Whites Road and finishes at St. Mary Catholic Secondary School. A morning walk along the Frenchman’s Bay waterfront makes a nice pairing.
• Orono Santa Claus Parade | 10:30 AM. The route begins near the cemetery at Mill Lane, heads south on Mill Street and finishes at the Orono Fairgrounds. Stop at a village bakery or café first.
• Cannington Lions Santa Claus Parade | 11 AM. A Candy Land Christmas theme, starting and ending at Cannington Arena. Leave time to explore the village centre.
• Ajax Santa Claus Parade and Tree Lighting | 6 PM to 7:30 PM. The procession begins at Bayly Street and Mackenzie Avenue and ends at Ajax Town Hall, where the tree lighting and after-party follow.
• Beaverton Santa Claus Parade | 6 PM. Community floats travel through the village, and you can visit Santa afterward at the Fire Hall.

Early December: Lights, Tractors and More Parades

THEE Farmers Parade of Lights | Clarington
Wednesday, December 2 | approx. 5:30 PM
Old Scugog Road and Concession 9, north of Enniskillen

One of the most charming local traditions. Farmers from Tyrone, Haydon, Enniskillen and Enfield decorate their farm equipment with Christmas lights as a thank-you to neighbours for sharing the roads all year. Plan an early meal in Bowmanville or Orono, then drive out for the show.

Christmas Moonlight Magic and Tree Lighting | Bowmanville
Friday, December 4 | 5 PM to 9 PM
Downtown Bowmanville

Enjoy the tree lighting on Temperance Street, children’s entertainment, carol singing and a Santa visit. Arrive early for the Christmas Market and free wagon rides.

Whitby Santa Claus Parade
Saturday, December 5 | 10 AM to noon
Brock Street, from Manning Road to Trent Street

Organized by the Optimist Club of Brooklin, this morning parade runs through the centre of town. Browse downtown Brock Street before or after.

Port Perry Santa Claus Parade of Lights
Saturday, December 5 | 5 PM
Downtown Port Perry, starting at the fairgrounds

An evening parade through the lakeside downtown. Browse the boutiques and cafés on Queen Street and walk through Palmer Park beside Lake Scugog before the parade begins.

Fantasy of Lights | Uxbridge
December 5 to January 2, 2027
Elgin Park

Drive through more than 100 displays created by community groups, businesses, schools, churches and families. It is one of the largest free Christmas light displays in Ontario, and a great option when you want to enjoy the season on your own schedule.

Mid-December: The Final Parades

Courtice Santa Claus Parade
Saturday, December 12 | 12 PM
Nash Road, between Townline Road and George Reynolds Drive

Sunderland Santa Claus Parade
Saturday, December 12 | 7 PM
Starting at Sunderland Memorial Arena and traveling through the village

Enjoy shopping and dining along Highway 2 before the Courtice parade, and a stroll down River Street before Sunderland’s evening procession.

Still to be announced: Port Perry’s Christmas Tree Lighting and Candle Light Walk, with a holiday farmers’ market, carolling and live music at Queen Street and Palmer Park. The date is not yet confirmed, so watch for updates.

Why These Moments Matter

I have lived and worked in Whitby for over 26 years, and these events are a big part of why Durham Region feels like home. They are small-town traditions with real heart. The volunteers, the service clubs, the local businesses and the neighbours lining the streets are what make our communities special.

If you are thinking about a move in the new year, whether you are buying, selling or simply curious about what your home is worth, this season is a wonderful time to see our neighbourhoods at their warmest. Take a drive, stroll the main streets and notice which community feels like yours.

When you are ready to talk, I am always happy to chat, with no pressure and no pitch.

Which of these events is a tradition for your family? Tell me in the comments, and tag a friend you would bring along.