The bustling towns of Pickering and Ajax, along with their surrounding areas, are alive with festivals and community events that bring residents and visitors together in celebration. From lively cultural festivals to seasonal markets and family-friendly fairs, these events offer a chance to experience the unique character and diversity of the region. Whether you’re exploring an artisan market, enjoying live entertainment at a waterfront event, or taking part in a food festival, there’s always something happening to spark joy and create cherished memories.
Signature events like the Pickering Village JAM Festival and Ajax Rotary Ribfest showcase the vibrant energy and local pride that define these communities. Throughout the year, you’ll find everything from outdoor concerts and heritage celebrations to holiday parades and multicultural showcases, each designed to bring people together and highlight the area’s rich cultural heritage. With activities for all ages, these festivals and events provide the perfect backdrop for forging connections, celebrating traditions, and discovering all that Pickering, Ajax, and their neighbouring communities have to offer.
November 15 – 16, 2024 | 5:30 – 8:30 pm
Winter Nights, City Lights
Esplanade Park & Chestnut Hill Developments Recreation Complex
https://www.pickering.ca/en/discovering/winter-nights-city-lights.aspx
Participate in the annual winter season celebration! Watch the City of Pickering light up Esplanade Park with festive decor and fireworks. Enjoy live entertainment, food vendors, a new art installation, Instagram-worthy photo ops, artisan markets, and more.
St. Paul’s on the Hill Food Bank will be collecting Food & Toy Donations.
Free parking is available at Chestnut Hill Developments Recreation Complex. Parking is limited – if possible, please walk, take transit, or ride share. Dogs are welcome but must be leashed at all times.
November 15, 23, and 24, 2024
Black Joy Holiday Market 2024
Chestnut Hill Developments Recreation Complex, 1867 Valley Farm Road. Pickering
In Support of the Afro-Caribbean Food Baskets
Get ready for the 3rd edition of this amazing holiday event, and it’s going to be bigger and better than ever! Gather your family and friends for a festive celebration of culture, community, and entrepreneurship that you won’t want to miss!
Proceeds from the market support the 2024 Afro-Caribbean Food Baskets, providing culturally appropriate food to Black families in need this holiday season.
November 23, 2024
Pickering Santa Claus Parade
Glenanna Road, Pickering
www.pickering.ca/en/living/santa-claus-parade.aspx
Join the City of Pickering, The Shops at Pickering City Centre and the Kinsmen & Kinette Club in celebrating the highly anticipated return of the Santa Claus Parade. With extravagant floats from Pickering businesses and community groups, marching bands, and Santa Claus himself, the Santa Claus Parade is the spectacle to kick off everyone’s holiday season. A joyous celebration that will impress all ages. The Parade will begin at Dixie and Glenanna and end in Pickering’s City Centre. Be sure to mark your calendars now! It’s a day not to be missed.
November 23 – 24, 2025 | 10:00 am and 1:00 pm
Swag Making Workshop 16+
Pickering Museum Village, 3550 Greenwood Rd., Greenwood
Deck your halls with traditional evergreen swag – made by you! Join our Museum Interpreter and harvest fresh greenery from our museum site. Add in ribbon and natural accents like pinecones and other natural bits you collect. Learn some history about the materials and how they were used for holiday decorating in the past. This program is completed outdoors, so come dressed for the weather. Bring your family and friends for a creative and fun workshop, just in time for the holidays!
November 30, 2024 | 10:00 am to 3:30 pm
Pet & Family Photos with Santa
Pickering Museum Village, 3550 Greenwood Rd., Greenwood
Join us for your annual holiday photo with Santa! Bring all your loved ones (even the furry ones) for this magical experience. Pickering Animal Services will be on site to accept donations of pet food, supplies, or monetary contributions for the fuzzy friends in their care!
Tickets are timed entry. You may arrive between the times listed on your registration.
$42.25 + tax per group (up to six people)
December 1, 2024 | 10:00 am to 3:30 pm
Pet & Family Photos with Santa
Pickering Museum Village, 3550 Greenwood Rd., Greenwood
Join us for your annual holiday photo with Santa! Bring all your loved ones (even the furry ones) for this magical experience. Pickering Animal Services will be on site to accept donations of pet food, supplies, or monetary contributions for the fuzzy friends in their care!
Tickets are timed entry. You may arrive between the times listed on your registration.
$42.25 + tax per group (up to six people)
December 7 & 14, 2024 | 11:30 am – 3:00 pm
Winter Wonderland
Millennium Square, Pickering
https://www.pickering.ca/en/discovering/winter-wonderland.aspx
Join the City of Pickering and Nautical Village businesses for an event in Millennium Square this Winter. Enjoy an opening day of live ice carving, select holiday vendors, buskers, s’mores stations, miniature train rides through Nautical Village, and the Public Art installation “Same Material / Different Time” by Studio Jordan Shaw.
December 7, 8, 14 & 15 | 10:00 am – 4:30 pm
A Storybook Christmas
Pickering Museum Village, 3550 Greenwood Rd., Greenwood
Get ready for a magical experience at Pickering Museum Village as we proudly unveil: A Storybook Christmas – featuring an exciting new tale for 2024! Join Teddy on yet another enchanting holiday adventure that promises to delight visitors of all ages. Immerse yourself in the festive spirit as you wander through the village, discovering a wealth of interactive activities, festive treats, creative crafts, fun trivia, lively music, and so much more. And remember, your visit wouldn’t be complete without a special appearance from the jolly man in red himself!
$11.40 + tax for Adults
$9.60 + tax for Seniors (65+ years old)
$7.30 + tax for Children (3-17 years old)
Children under 3 are free and do not require a ticket.
Note: Purchase of a ticket will allow entry into this event at any time between the hours listed above. It is recommended that entry occurs prior to 3:30 pm to ensure the full experience as the event is fully closed at 4:30 pm.
June – October 2025
Pickering City Centre Farmers’ Market
Chestnut Hill Developments Recreation Complex, 1867 Valley Farm Road
https://www.pickering.ca/en/FarmersMarket.aspx
Happening every Tuesday starting from June to October between the hours of 9 am and 2 pm. Come out and enjoy fresh produce, baked goods, meats and more in the heart of our City Centre.
Weekly entertainment 10:00 am – 1:00 pm
To October 2025
Pickering City Centre Farmers’ Market
Chestnut Hill Developments Recreation Complex, 1867 Valley Farm Road
https://www.pickering.ca/en/FarmersMarket.aspx
Happening every Tuesday starting from June to October between the hours of 9 am and 2 pm. Come out and enjoy fresh produce, baked goods, meats and more in the heart of our City Centre.
Weekly entertainment 10:00 am – 1:00 pm
To October 2025
Pickering City Centre Farmers’ Market
Chestnut Hill Developments Recreation Complex, 1867 Valley Farm Road
https://www.pickering.ca/en/FarmersMarket.aspx
Happening every Tuesday starting from June to October between the hours of 9 am and 2 pm. Come out and enjoy fresh produce, baked goods, meats and more in the heart of our City Centre.
Weekly entertainment 10:00 am – 1:00 pm
To October 2025
Pickering City Centre Farmers’ Market
Chestnut Hill Developments Recreation Complex, 1867 Valley Farm Road
https://www.pickering.ca/en/FarmersMarket.aspx
Happening every Tuesday starting from June to October between the hours of 9 am and 2 pm. Come out and enjoy fresh produce, baked goods, meats and more in the heart of our City Centre.
Weekly entertainment 10:00 am – 1:00 pm
To October 2025
Pickering City Centre Farmers’ Market
Chestnut Hill Developments Recreation Complex, 1867 Valley Farm Road
https://www.pickering.ca/en/FarmersMarket.aspx
Happening every Tuesday starting from June to October between the hours of 9 am and 2 pm. Come out and enjoy fresh produce, baked goods, meats and more in the heart of our City Centre.
Weekly entertainment 10:00 am – 1:00 pm
