Things to do this weekend in Pickering, Ajax, Whitby and Oshawa: Nov. 15 to Nov. 17

Thinking of what to do this weekend? You’ll be surprised to see how many holiday events are bringing joy to Durham Region. From festive markets and creative workshops to free skating and community celebrations, there’s no shortage of activities in Pickering, Whitby, Ajax and Oshawa. You might even have a hard time deciding where to start!

Check out these happenings from Nov. 15 to Nov. 17:

November 15

Pickering: 

Black Joy Holiday Market 2024

Celebrate culture, community, and the holiday spirit at the 3rd annual Black Joy Holiday Market. Discover over 90 vendors offering unique gifts, fashion, food, skincare and more. The market features live entertainment, a drumming circle, children’s activities and festive surprises.

Where: 1867 Valley Farm Rd. (Chestnut Hill Developments Recreation Complex)
Time:  5:30 p.m. – 8:30 p.m. (Winter Night City Lights Festival with fireworks and tree lighting at 6 p.m.)
Cost: Free

PA Day Fun: Family Crafternoon

Get creative with your family during this fun-filled crafting session for kids ages 5-12. Enjoy a variety of craft supplies and let your imagination run wild. Supplies are provided.

Where: 470 Kingston Rd. (George Ashe Library, Quiet Study Room)
Time: 2 p.m. – 3 p.m.
Cost: Free

PA Days at Earthbound Kids

Earthbound Kids offers PA Day & School Break Day Camp programs for kids aged 4 to 12, featuring activities like horseback riding, sports, BMX biking, arts & crafts, and winter fun like snowshoeing. Saddle Club is available for kids 6 to 12 years, focusing on riding and horse care.

Where: 4100 Concession Rd. 8
Time: 9 a.m. – 4 p.m. (before and after care available)
Cost: Varies by program

Winter Nights, City Lights (Nov. 15 and Nov. 16) 

The City of Pickering invites you to experience Winter Nights, City Lights, a celebration of community and culture.

Where: 1 The Esplanade
Time: 5:30 p.m. – 8:30 p.m.
Cost: Free

LEGO Holiday Pop-Up Market (Nov. 15 and Nov. 16) 

Celebrate the holiday season with the LEGO Holiday Pop-Up Market in Pickering.

• Marvel at a life-size LEGO fireplace adorned with festive lights and decorations, perfect for holiday photos.
• Participate in interactive build activities and create your own LEGO ornaments for the Christmas tree.
• Explore a selection of LEGO sets available for purchase, with a special gift included for purchases over $35.

Where: 1 The Esplanade
Time: 5:30 p.m. – 8:30 p.m.
Cost: Free

Alex Monaghan Youth Mental Health Chat 

Learn effective tools to support youth mental health at this engaging community event.

Where: 1867 Valley Farm Rd. (Chestnut Hill Developments Recreation Complex— O’Brien Rooms A & B – Arena Entrance)
Time: 6 p.m. – 8 p.m.
Cost: Free

Ajax: 

Fall Heart Market

Discover a premium vendor market focusing on mental wellness and community building through the arts.

Where: Audley Recreation Centre, 1493 Audley Rd., Ajax, ON
When:

• Nov. 15 — 2 p.m. to 8 p.m.
• Nov. 16 — 11 a.m. to 5 p.m.

Cost: Free

Project Makerspace: Holiday Greeting Card Photo Shoot

Create a memorable holiday gift at this interactive photo shoot and card-making session at the Makerspace.

Where: 95 Magill Dr. (Ajax Public Library —McLean Branch)
When: 2 p.m. to 6 p.m.
Cost: Free

Workshop: Fresh Evergreen Urn

Learn the art of “greening” and create your unique holiday urn with expert guidance from Vandermeer Nursery designers.

Where:  588 Lake Ridge Rd. S. (Vandermeer Nursery & Garden Centre)
When:

• Nov. 15 — 6 p.m. to 7:30 p.m.
• Nov. 16 — 10 a.m. to 11:30 a.m.
• Nov. 17 — 3 p.m. to 4:30 p.m.

Cost: $91.86

Whitby:

Downtown Whitby BIA’s 6th Annual Christmas Market (Nov. 15 and Nov. 16) 

Experience the holiday spirit at Whitby’s 6th Annual Christmas Market featuring performances, entertainers and unique holiday gifts and items.

Where: 405 Dundas St. W. (Celebration Square)
When: 5 p.m. – 8 p.m.
Cost: Free

Oshawa: 

Durham York Energy Centre Public Event

Residents are invited to visit the Durham York Energy Centre to learn about transforming household waste into valuable resources through guided tours, interactive activities, and informational displays.

Where: 1835 Energy Dr., Courtice, Ontario
Time: 10 a.m. – 3 p.m.
Cost: Free

Christ Church Weekly Market

Discover something new every visit at the Christ Church Weekly Market. Browse an array of items and enjoy a welcoming community atmosphere. Proceeds support outreach to those in need.

Where: 81 Hillcroft St.
When: 10 a.m. to 2 p.m.
Cost: Free

Oshawa’s Bright and Merry Market

Kick off the holiday season with the City of Oshawa’s Bright and Merry Market, presented by TRREB. This festive outdoor event features the annual tree lighting, a “Makers Market” showcasing local food and artisans, live entertainment and a chance to meet Santa.

Where: 110 Simcoe St. S.
When: 5 p.m. to 9 p.m.
Cost: Free

November 16

Pickering: 

St. Martin’s Holly Bazaar

Join the annual Holly Bazaar at St. Martin, Bay Ridges, featuring Granny’s Attic, a jewelry table, bake table, and the popular Bottle Boutique Game. New this year: enjoy a chilli lunch alongside refreshments from Café By The Bay. Debit and credit now accepted!

Where: 1203 St Martin’s Dr.
Time: 9 a.m. – 1 p.m.
Cost: Free

Christmas Craft Market (Nov. 16 and Nov. 17) 

Explore unique handmade crafts and gifts from local vendors at this festive community market.

Where: 1867 Valley Farm Rd. (Chestnut Hill Developments Recreation Complex)
Time: 10 a.m. – 4 p.m.
Cost: Free

Ajax: 

Journey into Enchantment – Christmas Light Show

Experience the magic of dazzling Christmas lights and festive decorations at this enchanting light show.

Where:  50 Alexander’s Crossing (Casino Ajax)
When: 5 p.m. to 7 p.m. (multiple 30-minute slots available)
Cost: $ 27.63

St. George’s Fall Fair & Bazaar

At this vibrant community event, explore vendor tables, a silent auction, treasures, crafts, and baked goods. Refreshments are available onsite.

Where: 77 Randall Dr. (St. George’s Church)
When: 9:30 a.m. to 2 p.m.
Cost: Free

Green Storage Ajax Christmas Food and Toy Drive (Nov. 14 to Dec. 15)

Join Green Storage Ajax in spreading holiday cheer by contributing to their Christmas Food and Toy Drive. Help brighten the season for families and children in need with your donations.

Where: 180 Station St.
When: 10 a.m. to 4 p.m.
Cost: Free

Whitby:

Lost in Yonkers

Bella, a socially awkward thirty-five-year-old, lives with her strict Grandma Kurnitz. When her brother Eddie leaves his two young sons with Grandma to go on the road, the boys must adjust to life with their tough grandmother, Bella’s hidden love life and their shady Uncle Louie—all in the unfamiliar world of Yonkers.

Where: 416 Centre St. S.
Time:

• 2 p.m. – 4:30 p.m.
• 8 p.m. – 10:30 p.m.

St. Leo the Great Annual Vendors’ Fair

Discover unique gifts and treasures at the St. Leo the Great Annual Vendors’ Fair. Explore a variety of vendor tables featuring handcrafted items and local goods.

Where: 130 Watford St.
When: 9 a.m. – 3 p.m.
Cost: Free

Whitby Train Show

Explore the fascinating world of trains at the Whitby Train Show, featuring vendors and interactive layouts for train enthusiasts and families.

Where:  1020 Dryden Blvd., (Father Leo J. Austin Catholic Secondary School— accessible entrance on the west side)
When:

• Nov. 16— 10 a.m. to 4 p.m.
• Nov. 17 —10 a.m. to 3 p.m.

Cost: Unspecified

Oshawa: 

Joseph & The Amazing Technicolor Dreamcoat

Experience the captivating tale of faith and forgiveness in this timeless musical as Joseph’s journey unfolds with humour, wit, and vibrant storytelling.

Where: 62 Russett Ave. (Oshawa Little Theatre)
When: 7:30 p.m.
Cost: $30 – $40 (including fees)

Ontario Philharmonic Gala

Join the Ontario Philharmonic Gala for an evening of music, fine dining, and fundraising at a reception-style event. Guests will enjoy appetizers, drinks and fundraising activities in the mezzanine before heading to their reserved seats for the concert.

Where: 50 King St. E. (Regent Theatre)
When: 5:30 p.m
Cost: Unspecified

Oshawa Valley Botanical Garden Winter Tree ID Tour

Discover the art of identifying trees in winter during this guided tour. Learn how to recognize trees by their buds, bark and evergreen needles while exploring the Oshawa Valley Botanical Gardens.

Where: 155 Arena St. ( Oshawa Valley Botanical Gardens)
When: 11:30 a.m. to 1 p.m.
Cost: Free

The Trojan Women

Durham Shoestring Performers presents The Trojan Women, adapted by Ellen McLaughlin and directed by Andra Kelly. This anti-war story portrays the resilience and struggles of displaced women.

Where: 45 Queen St. (Arts Resource Centre)
Time: 2 p.m. to 4 p.m.
Cost: Unspecified

November 17

Whitby:

13th Annual Christmas Craft Bazaar

Discover unique handmade crafts and gifts at the 13th Annual Christmas Craft Bazaar, featuring an array of artisan items and festive treats.

Where: 117 Byron St. S. (Royal Canadian Legion Branch 112)
When: 10 a.m. – 3 p.m.
Cost: Free

Oshawa: 

Christmas Mini’s

Capture festive memories with Christmas mini-photo sessions. Choose from four unique holiday-themed sets: a green candy cane PJ setup, a formal dark fireplace set, a colourful white fireplace setup or a white setup with trees. Each session includes access to two sets of your choice.

Where: 450 Emerald Ave. (Lake Vista Park)
When: 12 p.m. to 5 p.m.
Cost: $200 + HST (includes ten edited images and an online viewing gallery)

The Best Is Yet to Come – A Tribute to Tony Bennett by Matt Dusk

Presented by Blackrose Entertainment in Association with CKDO 107.7 FM 1580 AM, join Matt Dusk, one of Canada’s most beloved vocalists, as he pays tribute to the legendary Tony Bennett. Featuring timeless classics like I Left My Heart in San Francisco, The Way You Look Tonight, and The Good Life, this show is a captivating celebration of Bennett’s legacy.

Where: 50 King St. E., Oshawa
When: 8 p.m. to 10 p.m.
Cost: $63.50

Free Public Skate sponsored by Durham Children’s Aid Society

Enjoy a free public skate at Delpark Homes Centre Arena 2, sponsored by Durham Children’s Aid Society. Regular leisure skating rules will apply. Children six years and under must be accompanied by a parent or guardian on the ice.

Where: 1661 Harmony Rd. N.
When: 1 p.m. to 2:20 p.m.
Cost: Free

OPG’s Darlington New Nuclear Project Free Family Skate

Enjoy a fun-filled afternoon at the Newcastle Memorial Arena with a free family skate, courtesy of OPG’s Darlington New Nuclear Project. Meet project team members and learn about how OPG drives innovation.

Where: 103 Caroline St. W., Newcastle
When: 1:30 p.m. to 3 p.m.
Cost: Free

—Cover photo via eventbrite.ca