Holiday Markets and Christmas Events in Durham Region 2025

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 market featuring handmade goods, local vendors and early-season shopping in support of community programs.

Brooklin Merry Market – Whitby

Date: Saturday, November 8
Time: 10:30 am to 3:30 pm
Location: Heydenshore Pavilion, Whitby
A popular one-day holiday market with indoor and outdoor local vendors, artisan products and festive shopping.

Bright and Merry Market – Oshawa

Date: Friday, November 14
Time: 5 pm to 9 pm
Location: Downtown Oshawa (City Hall to Memorial Park)
This is Oshawa’s official holiday season kickoff featuring a street market, live entertainment, seasonal displays, a holiday trolley and a tree lighting ceremony at 8 pm. Visitors are encouraged to bring a non-perishable food donation to support Feed the Need in Durham.

Downtown Whitby Christmas Market

Dates: Friday, November 14 and Saturday, November 15
Location: Whitby Public Library, Downtown Whitby
A festive two-day holiday market with local vendors, gift shopping and a seasonal atmosphere in the heart of downtown Whitby.

7th Annual Durham Region Holiday Pop-Up Marketplace – Ajax

Date: Sunday, November 16
Time: 11 am to 6 pm
Location: Ajax Community Centre, 75 Centennial Road, Ajax
A large indoor holiday marketplace featuring small businesses, handmade goods, gift items and festive treats.

St. John Bosco Christmas Market – Oshawa

Date: Tuesday, November 18
Time: 6 pm to 8 pm
Location: 1600 Clearbrook Drive, Oshawa
A community-focused market offering handmade crafts, baked goods, raffle baskets and local vendors. A great local event to support school fundraising.

Winterfest Vendor Market – Oshawa

Dates: Saturday, November 22 and Sunday, November 23
Time: 10 am to 3 pm
Location: Parkwood National Historic Site, 270 Simcoe Street North, Oshawa
A traditional holiday vendor market hosted at Parkwood Estate, one of Oshawa’s most historic landmarks. Features seasonal vendors, décor and holiday atmosphere.

Whitby Lights the Night Festival

Date: Friday, November 21
Location: Whitby Civic Park, 555–575 Rossland Road East
A magical holiday celebration featuring live entertainment, a Christmas farmers’ market, festive displays and a tree lighting ceremony. 

Brooklin Holiday Market – Brooklin

Opens: Saturday & Sunday November 29-30
Location: Brooklin High School, 20 Carnwith Dr W, Brooklin
With over 120 vendors, candy cane cafe, appearance from Santa and fun activities for all, you don't want to miss this holiday market. 

Holiday in the Hills – Orono

Opens: Saturday, November 22
Location: Orono Fairgrounds, Orono
A winter festival experience with themed holiday displays, vendor shopping, kids' attractions and seasonal treats.

Classic Holiday Market – Oshawa Centre

Dates:

• November 22 and 23

• November 29 and 30

• December 6 and 7

• December 13 and 14

Time: 10 am to 5 pm
Location: Oshawa Centre – upper level of the former Sears building (outside access only)
One of the largest recurring Christmas markets in Durham Region, featuring rotating vendors each weekend and a wide selection of handmade goods and holiday gifts.

Moonlight Magic and Christmas Market – Bowmanville

Date: Friday, December 5
Time: 5 pm to 9 pm
Location: Downtown Bowmanville, Temperance Street
Moonlight Magic is Bowmanville’s annual holiday kickoff celebration, featuring a Christmas tree lighting ceremony at 6:30 pm, children’s entertainment, live music, carol singing and a visit from Santa. The event also includes complimentary horse-drawn wagon rides, a festive outdoor Christmas market with handmade vendors, food stalls and hot drinks. Downtown Bowmanville shops will be open late for holiday shopping and donations will be accepted in support of local food and toy drives.

2025 Two-Day Holiday Pop-Up Market – Ajax

Dates: Saturday, December 6 and Sunday, December 7
Time: 12 pm to 7 pm
Location: Audley Recreation Centre, 1955 Audley Road, Ajax
A family-friendly market featuring artisan vendors, holiday accessories, handmade décor and local businesses.

If you enjoy supporting local creators and small businesses during the holiday season, these markets and events across Durham Region offer the perfect opportunity. Whether you are searching for unique gifts, enjoying festive entertainment or looking for a fun family outing, there is something happening every weekend in November and December.

Looking for more things to do in Durham Region this season? Check back for our upcoming guides on Christmas light displays, Santa Claus parades and holiday festivals across local neighbourhoods.