Things to do this weekend in Pickering, Ajax, Whitby and Oshawa: Feb. 14 to Feb. 17
Published February 14, 2025 at 11:10 am
If you’ve had your fill of winter days—or simply want to make the most of the long weekend—Pickering, Ajax, Whitby, and Oshawa have you covered!
Whether it’s diving into immersive gaming, singing along at live concerts and musical tributes, getting creative with painting workshops, or lacing up for free public skate sessions, there’s something for every mood.
Here’s what’s on from Feb. 14 to Feb. 17:
February 14
Pickering:
Activate Brings Immersive Gaming to Durham Region
Celebrate the grand opening of Activate Pickering, an immersive gaming experience with 11 interactive rooms and hundreds of games.
Where: 1899 Brock Rd. (Activate Pickering)
When: 9:30 a.m. to 11 p.m.
Cost: $29.99
A1A Jimmy Buffett Tribute
Celebrate the music and legacy of Jimmy Buffett with A1A, the longest-running Jimmy Buffett tribute band. Featuring Jeff Pike and special guests from Jimmy’s Coral Reefer Band, this show brings the energy and excitement of Margaritaville to life.
Where: 888 Durham Live Ave. (The Arena at Pickering Casino Resort)
When: 7:30 p.m.
Cost: Tickets from $54.75
Whitby:
Valentine’s Day Social
Celebrate Valentine’s Day with music, dancing, and light refreshments at this special event for the 55+ community. Wear red and enjoy an afternoon of fun!
Where: 801 Brock St. S (55+ Recreation Centre)
When: 2 p.m. to 4 p.m.
Cost: $10
Oshawa:
Kebabs and More Oshawa – Free Meal Bowl for the First 50 Guests
Enjoy an evening of delicious flavours at Kebabs and More. Be among the first 50 guests to receive a free meal bowl.
Where: 804 Ritson Rd. S. (Kebabs and More Oshawa)
When: 4 p.m. to 8 p.m.
Cost: Free (first 50 meal bowls)
Laughter Ever After
Celebrate Valentine’s Day with a fun and lighthearted romantic comedy trivia night hosted by Doug Menzies. Enjoy great food, drinks and a chance to win a $50 gift certificate.
Where: 44 Bond St. E. (Local Lounge)
When: 6 p.m. to 10 p.m.
Cost: $10 per couple
Jersey Nights – A Valentine’s Tribute to Frankie Valli and the Four Seasons
Celebrate Valentine’s Day with an incredible musical tribute to Frankie Valli and The Four Seasons, presented by Blackrose Entertainment in association with CKDO 107.7 FM and 1580 AM.
Where: 50 King St. E. (Regent Theatre)
When: 8 p.m. – 10 p.m.
Cost: $51
February 15
Ajax:
Painting and drawing lessons for kids
Kids will enjoy drawing lessons and watercolour/acrylic painting projects, bringing home a new creation every week. All materials are provided and siblings receive 10% off.
Where: 250 Bayly St. W. Unit 7 (Arts on Fire)
When: 11 a.m. to 12 p.m.
Cost:$30.
Note: Pro-rated. Join anytime if space is available.
Accelerate Durham Pitch – Black History Month Event
Nobellum presents the Accelerate Durham Pitch, a live Innovation supporting Black entrepreneurs in the Durham Region. Black-owned startups will compete for $10,000 in prizes, fostering a thriving ecosystem for Black founders and innovators in STEM and beyond.
Where: 1955 Audley Rd. (Audley Recreation Centre)
When: 1 p.m. to 6 p.m. Registration required
Cost: Free
Your New Neighbors at The Edge Lounge
Get ready for a wild night of live rock music as Your New Neighbors return to The Edge Lounge for an electrifying performance.
Where: 250 Bayly St. W. (The Edge Lounge)
When: 9:30 p.m.
Cost: Unspecified
Whitby:
Tick, Tick… Boom!
A rock musical by Rent creator Jonathan Larson, following a struggling composer navigating love, friendship and artistic dreams in 1990.
Where: 416 Centre St. S. (Whitby Centennial Building)
When: 2 p.m. to 4 p.m. and 8 p.m. to 10 p.m.
Cost: Unspecified
Oshawa:
St. Valentine’s Dinner & Dance
All members of St. Mary of the People Parish are invited for an evening of dinner, wine and dancing. Enjoy a fantastic meal with wine included and a cash bar available.
Where: 570 Marion Ave. (St. Mary of the People Parish Hall)
When: 6 p.m. to 11 p.m.
Cost: $60 per person
Utsav – A Celebration
Celebrate talent and culture with a 1.5-hour showcase featuring CNSID students and community performers. Enjoy vibrant music, dance and cultural performances.
Where: 45 Queen St. (Arts Resource Centre)
When: 3 p.m. to 4:30 p.m.
Cost: $13 (General Admission)
Love Celebration (Ages 21+)
Spread joy and celebrate all things love—romantic, platonic and self-love—at this vibrant evening event. Enjoy live music, dinner and an after-party with plenty of opportunities to connect with others.
Where: 67 Simcoe St. N. (Oshawa Convention Centre)
When: 6:30 p.m. to 11:30 p.m. (Doors open at 6 p.m.)
Cost: $107.83
Galentine’s Day
Celebrate friendship with brunch, drinks and karaoke! Enjoy a continental brunch with pastries, desserts, and mimosas, followed by guided cider or beer and cheese pairings and end the night with karaoke fun.
Where: 785 Taunton Rd. E, Unit 2 (The Torchbearer Taproom)
When: 12:30 p.m. to 11:30 p.m.
Cost: From $36
A Tribute to Grease and the Music of the 50’s & 60’s’
Presented by Blackrose Entertainment in association with CKDO 107.7 FM and 1580 AM, this all-Canadian professional concert production celebrates Grease and the iconic sounds of the 50’s and 60’s with stunning multimedia performances.
Where: 50 King St. E. (Regent Theatre)
When: 8 p.m. – 10 p.m.
Cost: $46
February 16
Pickering:
Special Family Sunday with Chris Evans
Spend the afternoon listening to adventure stories and live music with local singer, songwriter and author Chris Evans.
Where: 617 Liverpool Rd. (Open Studio Art Cafe)
When: 2 p.m. to 5 p.m.
Cost: Free (RSVP recommended)
Ajax:
Meditate ‘n Heal
Join the first Meditate ‘n Heal Full Moon Healing Circle of 2025 and harness the energy of the full moon to manifest dreams, set intentions and welcome abundance.
Where: 845 Westney Rd. S. Unit 7 (Riddim Fitness Wellness Centre)
When: 1 p.m. – 2:30 p.m.
Cost: $27.96
Whitby:
Free Public Skate Event
Enjoy a free public skate session with family and friends. No registration required.
Where: 222 McKinney Dr. (McKinney Centre)
When: 11:15 a.m. to 1 p.m.
Cost: Free
Free Public Skate Event
Enjoy a free public skate sponsored by the Brooklin Spring Fair. No registration required.
Where: 67 Winchester Rd. (Luther Vipond Memorial Arena)
When: 2:30 p.m. to 4 p.m.
Cost: Free
Oshawa:
Family Day at the Oshawa Museum
Celebrate Family Day with a fun-filled afternoon exploring the Oshawa Museum and discovering the history behind its artifacts. Enjoy guided tours of Henry House and Robinson House.
Where: 1450 Simcoe St. S. (Oshawa Museum)
When: 12 p.m. – 4 p.m.
Cost: $5 per person
Hotel California – The Original Eagles Tribute
Experience the legendary sound of The Eagles with Hotel California, performing their greatest hits in this tribute presented by Blackrose Entertainment.
Where: 50 King St. E. (Oshawa)
When: 8 p.m. – 10 p.m.
Cost: $61
February 17
Pickering:
Pickering Family Day Tobogganing
Join the Sanctus Pickering family for some winter fun on Family Day! Bring your sled and enjoy tobogganing on the hill with friends and family.
Where: 1571 Ravenscroft Rd. (Paulynn Park)
When: 10 a.m. to 11:30 a.m.
Cost: Free
Family Day at the Rec
Have fun with full day of activities with family at the Rec, including free skating, swimming and other special programs.
Where: 1867 Valley Farm Rd. (Chestnut Hill Developments Recreation Complex)
When: 7 a.m. to 5 p.m.
Cost: Free
Ajax:
WinterFest Ajax
Enjoy the winter season with your family at the Town of Ajax’s Family Day WinterFest. Presented by TD Bank Group, the event features winter-themed activities, shows, and fun for all ages.
Where: 95 Magill Dr. (McLean Community Centre)
When: 11 a.m. – 4 p.m.
Cost: Free (nominal fees apply for food)
Whitby:
Town of Whitby Family Day Events
Enjoy Family Day fun with activities at multiple locations throughout Whitby. Presented by Gerdau with support from Renewal by Andersen and Stylux Homes.
Where: 500 Victoria St. W. (Iroquois Park Sports Centre, Brooklin Community Centre, McKinney Centre, Luther Vipond Memorial Arena, Whitby Civic Recreation Centre)
When: 10 a.m. to 4 p.m.
Cost: Free