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