Love is in the air as Windsor-Essex prepares for a bustling weekend filled with Valentine's Day and Family Day celebrations. From live music performances to cozy pop-up events, residents have a variety of ways to enjoy the occasion with loved ones or solo. Looking ahead to Monday, Family Day offers a perfect opportunity to slow down and cherish meaningful time together.
Valentine's Day Events in Windsor
Valentine's Day brings a full slate of events this weekend, ranging from live music and pop-ups to low-key gatherings. There are numerous ways to share the occasion with a special someone or even enjoy it solo.
Live Music and Performances
CROSSFADE Live Show at Ekō: For a unique Valentine's Day plan beyond dinner and a movie, CROSSFADE returns with a live performance at Ekō (261 Pelissier St.). Detroit's Allen Dennard will perform on trumpet while Windsor's Justin James handles synths and decks, creating a dynamic live soundscape. The night promises a jazzy, groovy, and relaxed atmosphere. The show runs from 7 to 10 p.m., with tickets available on eventbrite.ca.
Soul Delegration at Dominion House Tavern: Soul Delegration brings its nine-piece ensemble back to Dominion House Tavern (3146 Sandwich St.) on Sunday, Feb. 15. The late-night set features classic soul, R&B, funk, and Motown, with dancing strongly encouraged. Instead of a cover charge, the band will accept donations at the door. Music runs from 10 p.m. to 12:30 a.m.
Valentine's Jazz Night at Walkerville Brewery: Walkerville Brewery (525 Argyle Rd.) hosts an intimate Valentine's Jazz Night on Saturday, Feb. 14. Enjoy a candle-lit performance by local jazz ensemble, The Coffee House Combo. Doors open at 8 p.m., with music starting at 8:30 p.m. Tickets are $10 each and can be purchased at valentines-jazznight.eventbrite.ca.
Pop-Up Events and Activities
Love Hurts Valentine Pop-Up and S'mores & Cocoa Fest: WindsorEats Food Hall (400 Erie St. E) embraces the season with back-to-back free winter events. Stop by the Love Hurts Valentine Pop-Up on Friday, Feb. 13, then warm up at the S'mores & Cocoa Fest, a three-day winter celebration running from Feb. 14 to 16. Expect fireside treats and hot chocolate, welcoming all ages. Visit windsoreats.com for more details.
Urban Art Market Pop-Up: Urban Art Market (548 Chilver Rd.) celebrates Valentine's Day weekend with a special pop-up featuring local makers. Drop in on Feb. 13 or Feb. 14 between 11 a.m. and 6 p.m. for handmade gifts, pottery, and sweet treats, whether shopping for someone else or yourself.
Family Day and Outdoor Activities
City Hall Square Ice Rink: Windsor's new City Hall Square Ice Rink, which opened on Dec. 13, 2025, has special activities planned for the Family Day long weekend, offering fun for all ages.
Forest Therapy and Connections Series: The Ojibway Prairie Complex continues its six-week Forest Therapy and Connections series, with new participants still welcome. The next session on Feb. 14 focuses on starting a nature journal and exploring how time outdoors can ground and restore. Each class includes a short indoor activity and a slow, guided walk. Visit citywindsor.ca for more information.
This weekend in Windsor-Essex is packed with opportunities to celebrate love, family, and community through diverse events and activities.
