2026 Festivals and Community Events in Pickering, Ajax, and Their Surrounding Areas
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.
Pickering, Ajax, and Surrounding Areas Festivals and Community Events
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February 28, 2026
Coldest Night of the Year Walk
Start Point: Peace Lutheran Church, 928 Liverpool Road, Pickering
In Support of Durham Youth Services
cnoy.org/location/pickering
The Coldest Night of the Year is a nationwide 2 or 5-km walk event raising funds for homeless and vulnerable individuals. Participants walk in the winter’s chill to raise awareness and funds for local charities providing critical services to those experiencing poverty and homelessness.
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February 15, 2026 | 1:30 pm - 4:00 pm
Snowshoes & Snow-Clues
Claremont Nature Centre, 4290 Westney Road, North, Pickering
calendar.trca.ca/event/snowshoes-and-snow-clues-claremont-nature-centre
Strap on snowshoes and follow winter clues to discover local wildlife in action. At Claremont Nature Centre, learn how animals leave tracks, adapt, and survive cold temperatures while creating tracks of your own. Guided activities make winter nature come alive, and warming hot chocolate and refreshments await after your snowy adventure. Perfect for families and curious explorers of all ages.
February 24, 2026 | 6:30 pm - 9:00 pm
Hoot & Howl
Claremont Nature Centre, 4290 Westney Rd N, Pickering
www.eventbrite.ca/e/hoot-and-howl-claremont-nature-centre-tickets-1981451450628
Guests embark on an exciting evening of exploration and discovery, diving into the mysterious world of nocturnal wildlife. The experience begins with an engaging presentation on the owls and coyotes of Southern Ontario. The night concludes with a guided walk, listening for eerie owl hoots and distant coyote howls—an unforgettable adventure for nature lovers of all ages, young and old.
March 16 - 20, 2026 | 9:00 a.m. to 4:00 p.m.
March Break Camp @ Claremont
Claremont Nature Centre, 4290 Westney Rd N, Pickering
calendar.trca.ca/event/march-break-camp-Claremont
March Break Camp @ Claremont offers children a fun, nature-filled school holiday at the Claremont Nature Centre in Pickering. Running March 16–20, 2026, the camp features outdoor exploration, hands-on activities, games and learning led by experienced staff. An optional overnight adventure adds extra excitement for older campers.
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March 7, 2026 | 9:00 am - 1:00 pm
Sports Club Open House and Registration Day
CHD Recreation Complex, 1867 Valley Farm Road, Pickering
events.pickering.ca/default/Detail/2026-03-07-0900-Sports-Club-Open-House-and-Registration-Day
This spring, the City of Pickering will host an open house highlighting local sports user groups. Residents can explore leagues and programs at the CHD Recreation Complex while enjoying free beginner squash clinics led by Pro Nicole Pirko. Participants of all ages will learn racquet skills, movement, and gameplay fundamentals in a fun, supportive environment with all equipment provided.
March 28, 2026
Riversong - 1st Session
Claremont Nature Centre, 4290 Westney Rd N, Pickering
calendar.trca.ca/event/riversong
Riversong is a four-Saturday forest program for female and non-binary participants who enjoy trail running, nature connection, and building friendships at Claremont Nature Centre. Expect muddy shoes, longer hikes, and joyful voices outdoors. 4 Sessions run March 28, April 11, May 9, and June 13. Riversong I (ages 8–13) and Riversong II (ages 14–18) run concurrently, offering mentorship and leadership opportunities.
April 4, 2026 | 10:00 am to 2:00 pm
Pickering Easter Parade
Begins at Annland Street and ends at Kinsmen Park
www.pickering.ca/easterparade
The City of Pickering and Royal Canadian Legion Branch 606 invite the community to the annual Easter Parade in Bay Ridges. Celebrate the arrival of spring with colourful bonnets, festive Easter baskets, and a lively parade atmosphere. Families and friends can enjoy a fun-filled morning as the parade winds through the neighbourhood, welcoming the season with joy and community spirit.
April 11, 2026
Riversong - 2nd Session
Claremont Nature Centre, 4290 Westney Rd N, Pickering
calendar.trca.ca/event/riversong
Riversong is a four-Saturday forest program for female and non-binary participants who enjoy trail running, nature connection, and building friendships at Claremont Nature Centre. Expect muddy shoes, longer hikes, and joyful voices outdoors. 4 Sessions run March 28, April 11, May 9, and June 13. Riversong I (ages 8–13) and Riversong II (ages 14–18) run concurrently, offering mentorship and leadership opportunities.
May 9, 2026 | 10:00 am - 5:00 pm
Petapolooza
Esplanade Park, 1 The Esplanade, Pickering
In Support of Pickering Animal Services
www.pickering.ca/petapolooza
Petapolooza brings pet lovers together for a fun-filled outdoor festival celebrating animals and community. Enjoy pet-friendly activities, local vendors, live entertainment, and family experiences at Esplanade Park, all while supporting Pickering Animal Services. It’s a joyful spring outing where pets take centre stage and animal welfare is at the heart of the celebration.
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May 9, 2026
Riversong - 3rd Session
Claremont Nature Centre, 4290 Westney Rd N, Pickering
calendar.trca.ca/event/riversong
Riversong is a four-Saturday forest program for female and non-binary participants who enjoy trail running, nature connection, and building friendships at Claremont Nature Centre. Expect muddy shoes, longer hikes, and joyful voices outdoors. 4 Sessions run March 28, April 11, May 9, and June 13. Riversong I (ages 8–13) and Riversong II (ages 14–18) run concurrently, offering mentorship and leadership opportunities.
May 23, 2026 | 11:00 am - 5:00 pm
Artfest
Esplanade Park, 1 The Esplanade, Pickering
events.pickering.ca/default/Detail/2026-05-23-1100-Artfest2
Artfest is a lively celebration of creativity and community at Esplanade Park. Discover inspiring works by emerging and local artists, artisans, independent authors, and performers. With art displays, live performances, and a welcoming festival atmosphere, Artfest offers a weekend filled with imagination, connection, and creative expression for visitors of all ages to enjoy.
June 9 – October 6, 2026 | 9 am to 2 pm
Pickering City Centre Farmers’ Market
Chestnut Hill Developments Recreation Complex, 1867 Valley Farm Road
www.pickering.ca/en/FarmersMarket.aspx
The Pickering City Centre Farmers’ Market is a welcoming outdoor community hub in the northwest parking lot of the Chestnut Hill Developments Recreation Complex. Browse stalls filled with fresh produce, baked goods, quality meats, and local specialties while enjoying a lively market atmosphere in the heart of the city. It’s a perfect place to shop local, connect with neighbours, and savour seasonal flavours.
June 13, 2026 - Last Sessions
Riversong - 4th Session
Claremont Nature Centre, 4290 Westney Rd N, Pickering
calendar.trca.ca/event/riversong
Riversong is a four-Saturday forest program for female and non-binary participants who enjoy trail running, nature connection, and building friendships at Claremont Nature Centre. Expect muddy shoes, longer hikes, and joyful voices outdoors. 4 Sessions run March 28, April 11, May 9, and June 13. Riversong I (ages 8–13) and Riversong II (ages 14–18) run concurrently, offering mentorship and leadership opportunities.
To October 6, 2026 | 9 am to 2 pm
Pickering City Centre Farmers’ Market
Chestnut Hill Developments Recreation Complex, 1867 Valley Farm Road
www.pickering.ca/en/FarmersMarket.aspx
The Pickering City Centre Farmers’ Market is a welcoming outdoor community hub in the northwest parking lot of the Chestnut Hill Developments Recreation Complex. Browse stalls filled with fresh produce, baked goods, quality meats, and local specialties while enjoying a lively market atmosphere in the heart of the city. It’s a perfect place to shop local, connect with neighbours, and savour seasonal flavours.
July 2, 9, 16, 23, 30, 2026 | 7 to 9 pm
Annual Waterfront Summer Concerts
Millennium Square, 505 Liverpool Rd, Pickering
www.pickering.ca/parks-recreation-culture/festivals-and-events/summer-concerts
Pickering’s Annual Waterfront Summer Concerts bring live music to Millennium Square on warm summer evenings. Enjoy a rotating lineup of performers in a relaxed, lakeside setting that’s perfect for families, friends, and music lovers. Bring a chair or blanket, soak up the atmosphere, and experience free outdoor concerts with scenic views along the Pickering waterfront.
July 3, 10, 17, 24, 31, 2026 | 5:30 pm - 7:30 pm
Rick Johnson Summer Concerts
Rick Johnson Memorial Park, 2631 Sapphire Dr, Pickering
events.pickering.ca/default/Detail/2026-07-03-1730-Rick-Johnson-Summer-Concerts
The City of Pickering presents the Rick Johnson Summer Concerts as part of the 2026 Summer Concert Series. Held on Fridays at Rick Johnson Memorial Park, these free outdoor concerts invite residents to enjoy live music in a relaxed setting. Bring lawn chairs, gather with friends, and dance the evening away to a lively mix of performances all summer long.
July 5, 12, 19, 26, 2026 | 2 to 4 pm
Esplanade Summer Concerts
Esplanade Park, 1 The Esplanade, Pickering
events.pickering.ca/default/Detail/2026-07-05-1400-Esplanade-Summer-Concerts
The City of Pickering’s Esplanade Summer Concerts return for 2026 with lively Sunday performances in Esplanade Park. Enjoy a season of free live music featuring diverse sounds and local talent. Bring lawn chairs, gather with friends and family, and dance along in a relaxed outdoor setting as summer evenings fill the park with rhythm and community spirit.
To October 6, 2026 | 9 am to 2 pm
Pickering City Centre Farmers’ Market
Chestnut Hill Developments Recreation Complex, 1867 Valley Farm Road
www.pickering.ca/en/FarmersMarket.aspx
The Pickering City Centre Farmers’ Market is a welcoming outdoor community hub in the northwest parking lot of the Chestnut Hill Developments Recreation Complex. Browse stalls filled with fresh produce, baked goods, quality meats, and local specialties while enjoying a lively market atmosphere in the heart of the city. It’s a perfect place to shop local, connect with neighbours, and savour seasonal flavours.
August 2, 16, 23, 30 2026 | 2 to 4 pm
Esplanade Summer Concerts
Esplanade Park, 1 The Esplanade, Pickering
events.pickering.ca/default/Detail/2026-07-05-1400-Esplanade-Summer-Concerts
The City of Pickering’s Esplanade Summer Concerts return for 2026 with lively Sunday performances in Esplanade Park. Enjoy a season of free live music featuring diverse sounds and local talent. Bring lawn chairs, gather with friends and family, and dance along in a relaxed outdoor setting as summer evenings fill the park with rhythm and community spirit.
August 6, 13, 20, 27, 2026 | 7 to 9 pm
Annual Waterfront Summer Concerts
Millennium Square, 505 Liverpool Rd, Pickering
www.pickering.ca/parks-recreation-culture/festivals-and-events/summer-concerts
Pickering’s Annual Waterfront Summer Concerts bring live music to Millennium Square on warm summer evenings. Enjoy a rotating lineup of performers in a relaxed, lakeside setting that’s perfect for families, friends, and music lovers. Bring a chair or blanket, soak up the atmosphere, and experience free outdoor concerts with scenic views along the Pickering waterfront.
August 7, 14, 28, 2026 | 5:30 pm - 7:30 pm
Rick Johnson Summer Concerts
Rick Johnson Memorial Park, 2631 Sapphire Dr, Pickering
events.pickering.ca/default/Detail/2026-07-03-1730-Rick-Johnson-Summer-Concerts
The City of Pickering presents the Rick Johnson Summer Concerts as part of the 2026 Summer Concert Series. Held on Fridays at Rick Johnson Memorial Park, these free outdoor concerts invite residents to enjoy live music in a relaxed setting. Bring lawn chairs, gather with friends, and dance the evening away to a lively mix of performances all summer long.
To October 6, 2026 | 9 am to 2 pm
Pickering City Centre Farmers’ Market
Chestnut Hill Developments Recreation Complex, 1867 Valley Farm Road
www.pickering.ca/en/FarmersMarket.aspx
The Pickering City Centre Farmers’ Market is a welcoming outdoor community hub in the northwest parking lot of the Chestnut Hill Developments Recreation Complex. Browse stalls filled with fresh produce, baked goods, quality meats, and local specialties while enjoying a lively market atmosphere in the heart of the city. It’s a perfect place to shop local, connect with neighbours, and savour seasonal flavours.
September 12, 2026 | 11:00 am - 5:00 pm
Cultural Fusion
Dorsay Community & Heritage Centre, 2365 Concession Rd 6, Pickering
www.pickering.ca/parks-recreation-culture/festivals-and-events/cultural-fusion
Cultural Fusion is a vibrant community celebration highlighting Pickering’s rich diversity at the Dorsay Community & Heritage Centre. Enjoy flavours from local food vendors, browse a lively market, and take part in interactive activities. Live entertainment and roaming performances fill the day with music, movement, and cultural expression for visitors of all ages to enjoy.
To October 6, 2026 | 9 am to 2 pm
Pickering City Centre Farmers’ Market
Chestnut Hill Developments Recreation Complex, 1867 Valley Farm Road
www.pickering.ca/en/FarmersMarket.aspx
The Pickering City Centre Farmers’ Market is a welcoming outdoor community hub in the northwest parking lot of the Chestnut Hill Developments Recreation Complex. Browse stalls filled with fresh produce, baked goods, quality meats, and local specialties while enjoying a lively market atmosphere in the heart of the city. It’s a perfect place to shop local, connect with neighbours, and savour seasonal flavours.
October 17 and 24, 2026 | 11:30 am - 3:00 pm
Fall Fling
Millennium Square, 505 Liverpool Rd, Pickering
www.pickering.ca/parks-recreation-culture/festivals-and-events/fall-fling/
Fall Fling brings seasonal fun to Millennium Square with a festive celebration of autumn. Enjoy pumpkin painting, creative crafts, charming photo stops, and colourful fall décor. Families can take miniature train rides, join Halloween costume contests, and go trick-or-treating while browsing a market featuring local artisans. It’s a cosy, cheerful way to celebrate the sights and sounds of fall.
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