Durham Holiday Markets and Events: Your 2026 Planner

A holiday calendar is easier to use when it separates a quick shopping stop from an outing that needs tickets and several hours. Durham Tourism’s seasonal guide brings together markets, light displays, performances and farm experiences across the region. Here is a planning index drawn from that guide, with direct organizer links for the next step.

Dates below refer to the 2026 holiday season; January end dates fall in 2027. A date range does not mean an attraction operates every day. Check individual performance dates, opening sessions, admission and availability before travelling.

Markets, lights and performances

• Beaverton Christmas Market: November 28 | Simcoe Street, Beaverton. Read the individual article.
• Bright & Merry Market: November 20 | City Hall’s Civic Square and North Parkette, Oshawa. Read the individual article.
• Brooklin Merry Market: November 7 | Heydenshore Pavilion, Whitby. Read the individual article.
• Candlelit Christmas Concerts: November 28 to December 20 | Across Durham Region. Read the individual article.
• Christmas at Parkwood Estate: November 7 to January 3 | Parkwood Estate, Oshawa. Read the individual article.
• Christmas Cheer Mingle & Jingle: November 29 to December 20 | Applewood Farm & Winery, Scugog. Read the individual article.
• CPKC Holiday Train: November 29 | Oshawa and Bowmanville. Read the individual article.
• Deer Creek’s Brunch With Santa: December 13 | Deer Creek Golf Club, Ajax. Read the individual article.
• Downtown Whitby Christmas Market: November 13 and 14 | Celebration Square, Whitby. Read the individual article.
• Frozen: The Broadway Musical: November 12 to December 5 | Oshawa Little Theatre, Oshawa. Read the individual article.
• Holiday In The Hills: November 21 to December 22 | Orono Fair Grounds, Orono. Read the individual article.
• How The Gretsch Stole Christmas: November 29 | The Biltmore Theatre, Oshawa. Read the individual article.
• Jinglefest Holiday Concert: December 19 | Beaverton Town Hall, Beaverton. Read the individual article.
• Jingle & Roar Christmas Market: November 28 | Beaverton Fair Grounds, Beaverton. Read the individual article.
• Journey Into Enchantment: November 20 to December 26 | Ajax Downs Casino, Ajax. Read the individual article.
• Knox Farm Christmas: December 5 to 20 | Knox Pumpkin Farm, Hampton. Read the individual article.
• Ladies Christmas Crawl: November 6 | Simcoe Street, Beaverton. Read the individual article.
• Market at 70 King’s Holiday Cheer Market: November 21 | Market at 70 King, Oshawa. Read the individual article.
• Markets Ontario Holiday Pop-Ups: December 4 to 20 | Markets Ontario, Bowmanville. Read the individual article.
• Mary Street Winter Market: November 14 | Unique Town Boutique, Whitby. Read the individual article.
• Moonlight Magic & Christmas Market: December 4 | King Street and Temperance Street, Bowmanville. Read the individual article.
• Old Scugog Road Christmas Lights: December 1 to 31 | Old Scugog Road, Bowmanville. Read the individual article.
• Ontario Philharmonic: December 12 and 18 | Regent Theatre, Oshawa. Read the individual article.
• Picks & Giggles Classic Holiday Market: December 13 | Kingsway College, Oshawa. Read the individual article.
• Port Perry Lakefront Farmers’ Market: November 20 | The Latcham Centre, Port Perry. Read the individual article.
• Royal Ashburn Christmas Event: December 13 | Royal Ashburn Golf Club, Whitby. Read the individual article.
• Santa’s Cottage: November 1 to December 23 | 4405 Ritson Road North, Oshawa. Read the individual article.
• Snow White Panto: December 27 to 31 | Town Hall 1873 Theatre, Port Perry. Read the individual article.
• Stars on Ice: Holiday Tour: December 10 | Tribute Communities Centre, Oshawa. Read the individual article.
• Sugar & Snow Holiday Market: November 28 and 29 | Chestnut Hill Developments Complex, Pickering. Read the individual article.
• The Merry Little Market: December 12 | Little Beasts Brewing Co., Whitby. Read the individual article.
• Tindall Farm Christmas Markets: November 21 to 22 and December 5 to 6 | Tindall Farm & Market, Uxbridge. Read the individual article.
• Uxbridge Farmers’ Market’s Holiday Edition: November 1 to December 13 | Uxbridge Arena, Uxbridge. Read the individual article.
• Uxbridge Holiday Trail: December 4 and 5 | Brock Street, Main Street and Toronto Street, Uxbridge. Read the individual article.
• Uxbridge Optimist Fantasy of Lights: December 5 to January 2 | Elgin Park, Uxbridge. Read the individual article.
• Vintage Holiday Weekend in Port Perry: December 11 to 13 | Queen Street, Port Perry. Read the individual article.
• Whitby Lights The Night Festival: November 27 to January 4 | Civic Park, Celebration Square and Grass Park , Whitby. Read the individual article.
• Willowtree Farm’s Adventures with Santa: December 5 to 20 | Willowtree Farms, Scugog. Read the individual article.
• Winter Nights, City Lights: November 13 and 14 | Esplanade Park, Pickering. Read the individual article.
• Winter Wonderland: December 5 and 12 | Millennium Square (Liverpool Road), Pickering. Read the individual article.

Build a realistic day, not a packed checklist

Start with one anchor: a market, a booked show or a light display. Add a nearby café or shop only after checking the timing. Markets are useful for browsing gifts from several makers, while theatre performances and farm experiences may need advance booking. Do not assume that a free public gathering makes parking, food or optional activities free.

For an early start to holiday planning, look at the November markets. If you prefer a December outing, compare the festive farm experiences, performances and light displays rather than choosing on the event name alone.

Check these details before booking

• Whether admission is per person, per vehicle or by timed session.
• Which activities are included and which cost extra.
• Accessibility, washrooms, seating and indoor warming areas.
• Weather cancellation, rescheduling and refund policies.
• Any age limits, photography policies or pet restrictions.

Our existing Oshawa Bright and Merry Market report and Whitby November events story provide additional local context.

Sources and planning notes

Prepared November 3, 2026. Durham Tourism holiday guide · City of Oshawa market information.

Illustration: original AllAboutDurham editorial artwork, not a photograph of a venue or event.

Updated November 3, 2026: Event listings now link to individual AllAboutDurham articles with organizer sources. See The Durham Calendar for confirmed event-date listings.