Planning a date in Toronto in 2026? Whether you are looking for a first-date icebreaker or a milestone anniversary celebration, the city has an incredible lineup of new venues and classic favorites to have a date at in 2026. Here are 27 ideas to make 2026 your most romantic year yet.
1. Catch a Global Superstar at the New Rogers Stadium
The biggest news for 2026 is the opening of the massive open-air Rogers Stadium at Downsview. This purpose-built venue is designed specifically for music, meaning the acoustics and sightlines are far superior to older stadiums. If your partner loves live music, this is the place to be. You can check the Rogers Stadium 2026 concert schedule for major tours from artists like Luke Combs, the Foo Fighters, and AC/DC who are already on the calendar for the summer season. With a 50,000-person capacity and a festival-like atmosphere, it is set to be the heart of Toronto’s entertainment scene.
2. Dine at the World’s 3rd Best Italian Restaurant: DaNico
For a high-end culinary experience, head to DaNico on College Street. It was recently ranked as the third-best Italian restaurant globally for 2026 by the prestigious 50 Top Italy guide. The setting, inside a restored historic bank building, features soaring ceilings and an intimate, sophisticated vibe. Under Michelin-starred Chef Daniele Corona, the menu offers a “MediterrAsian” fusion, blending traditional Italian techniques with subtle Asian influences. It is the ultimate choice for a luxury date night where every course feels like a piece of art.
3. Experience the White Garden at Queens Harbour
Running through January 2026, this winter pop-up at the waterfront offers a retractable roof and climate-controlled garden that feels like a storybook forest. The space is transformed with over 40 suspended flocked trees, snow-dusted foliage, and soft fur textures, creating an otherworldly atmosphere. It is the perfect spot to enjoy lake views and the CN Tower skyline without the winter chill. Their specialized feature menu includes shareable mezzes and charcoal-grilled dishes, making it as much a culinary destination as it is a visual one.
4. A Cozy Night at the Winterlicious Festival
From January 30 to February 12, 2026, Toronto’s premier food festival returns with over 200 participating restaurants. This city-wide event is the best way to enjoy a three-course prix fixe meal at the city’s top-tier restaurants for a fraction of the usual price, with dinner options ranging from $25 to $75. According to the official Winterlicious event page, it is an ideal opportunity to explore new neighborhoods and cuisines you might otherwise miss. Be sure to book your reservations early, as the most popular spots fill up weeks in advance.
5. Sunset and Skyline Views from the Toronto Islands
Take a water taxi to Ward’s Island in the late afternoon to skip the crowded main ferry lines. Once there, you can rent a tandem bike to explore the quiet, car-free streets filled with charming island cottages and lush gardens. Watching the Toronto skyline light up from the boardwalk as the sun sets behind the skyscrapers remains one of the most romantic and affordable dates in the city. End the night with a drink at the Island Cafe before heading back to the mainland under a canopy of stars.
6. Take it Up a Notch with the CN Tower EdgeWalk
For the adventurous couple, nothing beats walking hands-free 116 storeys above the ground on a 5-foot wide ledge. As the world’s highest full-circle hands-free walk, it offers a thrill that is guaranteed to be a lasting memory. Your guide will even encourage you to lean out over the edge for a photo that will definitely win your Instagram for the week. It is a high-adrenaline bonding experience that ends with a much calmer celebratory drink at the 360 Restaurant located just below.
7. Discover the Underground at Kensington Market
Spend a Sunday afternoon wandering through the eclectic vintage shops and narrow alleys of one of Toronto’s most storied neighborhoods. Start by grabbing a world-famous “Gobernador” taco at Seven Lives, then spend an hour browsing the hidden gems at Courage My Love. As evening falls, find a hidden corner for live jazz at Poetry Jazz Cafe, where the dim lighting and soul music create an intimate, “secret club” vibe that is perfect for getting to know someone new.
8. Skate the Bentway Figure Eight
Located right under the massive concrete pillars of the Gardiner Expressway, this skating trail offers a unique urban vibe that you won’t find anywhere else. The trail is a 220-metre figure-eight loop that often features large-scale art installations and light shows throughout the winter months. In early 2026, they will continue their tradition of hosting “Polar Bear Skates” and providing on-site warming stations with gourmet hot cocoa. It is a fun, active date that feels like a modern city adventure.
9. Attend Nuit Blanche on October 3
This all-night contemporary art festival transforms the entire city—from downtown streets to Scarborough and Etobicoke—into a massive open-air gallery. Starting at sunset and running until sunrise, it is the perfect “late-night” date that costs nothing but your time. You can find more details on the City of Toronto Nuit Blanche page regarding the 2026 themes and locations. Walking through the city at 3:00 AM surrounded by glowing art installations and thousands of people is a surreal experience that every Toronto couple should try at least once.
10. Visit the New Waterworks Food Hall
The Waterworks Food Hall is a massive new addition to the city, housed in a beautifully restored 1930s machine shop. It is perfect for a low-pressure date because it allows you to both pick exactly what you want from dozens of high-end vendors like Union Chicken or Bello Pizza. The communal seating area features stunning industrial architecture and a massive glass ceiling, making it a great spot for people-watching. It’s located right next to St. Andrew’s Playground Park, so you can take your food outside if the weather is nice.
11. Stroll Through the High Park Cherry Blossoms
In late April 2026, the Sakura trees in High Park will reach peak bloom, painting the park in shades of soft pink and white. It is a Toronto tradition that never gets old and provides the perfect backdrop for photos. Because this event attracts huge crowds, the best way to make it a romantic date is to go on a Tuesday or Wednesday morning at sunrise. Pack a small breakfast and a thermos of coffee to enjoy under the trees before the rest of the city wakes up and the park gets busy.
12. Laugh it Out at Second City
The world-famous comedy troupe has a stunning, modern venue at York and Harbour that features multiple theaters and a full-service bar. A mainstage sketch comedy show is a foolproof way to ensure the conversation keeps flowing, as you’ll have plenty to talk about during the intermission. Many of their shows incorporate improv based on audience suggestions, making every performance a one-of-a-kind experience. It is a great way to break the ice on a first date or add some lighthearted fun to a long-term relationship.
13. Picnic at Riverdale Park East
Grab some Greek takeout from the nearby Danforth Avenue and head over to the hill at Riverdale Park East. This spot offers arguably the most iconic view of the Toronto skyline, especially as the sun sets and the lights of the financial district begin to twinkle. In the summer of 2026, you can also catch free outdoor movie screenings on the grass. It is a simple, classic date that relies on the natural beauty of the city’s landscape.
14. Explore the ROM After Dark
On select Fridays throughout 2026, the Royal Ontario Museum sheds its quiet daytime persona and turns into a 19-plus party. These events, known as ROM After Dark, feature themed cocktails, live DJs, and curated performances interspersed throughout the museum’s galleries. Imagine sipping a drink while standing next to a T-Rex or dancing in the world-class Bat Cave. It is a sophisticated yet high-energy way to experience history and culture without the usual museum crowds.
15. Catch the Paul McCartney Exhibition at the AGO
Starting in February 2026, the Art Gallery of Ontario will host “Eyes of the Storm,” an exhibition featuring intimate photographs taken by Paul McCartney during the height of Beatlemania. This is a must-see for music and history lovers alike. You can view the full AGO 2026 exhibition lineup to plan your visit. Afterward, walk through the Frank Gehry-designed “sculptural staircase” for some of the best interior architecture shots in Canada.
16. Walk the Scarborough Bluffs
For an escape from the city noise, head east to the Scarborough Bluffs. The towering white cliffs and turquoise water look more like the Mediterranean coast than Lake Ontario. You can walk the trails along the top for incredible views or head down to Bluffers Park for a walk along the sandy beach. It is a fantastic “adventure” date that provides a much-needed break from the urban grind, and it’s especially beautiful in the autumn when the leaves on the cliffs change color.
17. Spend a Night at the Drive-In
The CityView Drive-In at the Port Lands offers a nostalgic cinema experience with a modern twist. Instead of just a screen in a field, you get a massive outdoor movie screen with the literal Toronto skyline as your background. It is a private and cozy way to enjoy a movie from the comfort of your own car. In 2026, they will continue to host a mix of new blockbusters and classic “retro” nights, making it a versatile option for any film-loving couple.
18. Browse the St. Lawrence Sunday Antique Market
If you both love hunting for unique treasures and historical artifacts, the Sunday market at St. Lawrence is a goldmine. You can find everything from vintage jewelry and mid-century furniture to rare books and old vinyl records. It’s a great way to learn about each other’s tastes and styles. Follow up your morning of browsing with a walk through the nearby Distillery District events, which often feature seasonal markets and outdoor art displays.
19. Sip Cocktails at Writers Room Bar
Located on the 17th floor of the Park Hyatt, this bar has been a legendary haunt for Canadian writers and thinkers for decades. Recently renovated, it maintains its literary charm while offering a sleek, dark-wood interior and a stunning outdoor terrace. The terrace provides one of the most sophisticated views in Yorkville, looking straight down Avenue Road toward the legislative buildings and the CN Tower. It’s the perfect spot for a “nightcap” date where the focus is on good conversation and even better drinks.
20. Play Arcade Games at Tilt
For a casual and playful date, head to Tilt on Dundas West. For a small flat cover fee of around $5 to $10, you get unlimited access to dozens of vintage arcade games, pinball machines, and old-school consoles like the N64. It’s a high-energy environment that takes the pressure off making constant small talk. They also have a solid menu of “arcade food” like corn dogs and poutine, along with a great selection of local craft beers on tap.
21. Visit the Aga Khan Museum
Located in North York, the Aga Khan Museum is a masterpiece of modern architecture. The building itself is stunning, featuring white granite walls and serene reflecting pools that provide a peaceful atmosphere for a date. Inside, you’ll find a world-class collection of Islamic art and history. In 2026, the museum is expected to host several international touring exhibitions that blend traditional art with modern technology. It is a cultured and quiet date spot that feels worlds away from the busy downtown core.
22. Hike the Evergreen Brick Works
Evergreen Brick Works is a former industrial site turned into an environmental center and park. You can hike the trails that lead up to a lookout point with a great view of the city or wander through the old kiln buildings. On Saturdays, they host one of the city’s best farmers’ markets, where you can grab fresh pastries and local coffee. It’s an ideal date for a couple that likes to stay active and enjoys supporting local artisans and sustainable living.
23. Go Record Shopping in Dundas West
Dundas West is home to some of the best independent record stores in Canada. Spend an afternoon flipping through vinyl at stores like Rotate This or Tiny Record Shop. It’s a great way to share your musical tastes and discover new artists together. Afterward, you can grab a drink at one of the many nearby “hole-in-the-wall” bars like Get Well, which even has its own selection of vintage arcade games to keep the fun going.
24. Take the Glass-Bottom Floor at Ripley’s Aquarium
While it’s a popular tourist spot, Ripley’s Aquarium is an undeniably cool date location. The “Dangerous Lagoon” features a slow-moving sidewalk that takes you through a glass tunnel surrounded by sharks, sea turtles, and sawfish. In 2026, keep an eye out for their “Friday Night Jazz” events, which offer a more adult-focused atmosphere with live music and bars set up throughout the aquarium. It is a visually stunning experience that provides plenty of “wow” moments.
25. Experience Salsa on St. Clair
Every July, a massive stretch of St. Clair Avenue West is shut down for Canada’s largest Latin-themed street festival. Salsa on St. Clair is a high-energy date full of live music, professional dance performances, and incredible street food from across Latin America. Even if you have two left feet, the atmosphere is so infectious that you’ll likely find yourselves joining in on a public dance lesson. It is a vibrant, colorful celebration of the city’s diversity that makes for a fantastic summer date.
26. Relax at Vetta Nordic Spa
If you are looking to truly disconnect, take a short drive north of the city to Vetta Nordic Spa. Based on authentic Finnish traditions, the spa offers a series of hot and cold pools, steam rooms, and wood-coded saunas designed to relax the body and mind. It is a “silent” or “quiet” spa, which encourages you to focus on the experience and each other without the distraction of phones or loud noise. It is the ultimate relaxation date for a couple that needs a break from the fast-paced city life.
27. Watch the Toronto FC at BMO Field
Even if you aren’t a hardcore sports fan, the energy of a live Toronto FC match at BMO Field is something everyone should experience. The stadium is located right on the lakefront, providing a cool breeze and great views on a spring evening. The “Supporters Section” provides a constant soundtrack of chants and songs that keeps the energy high from start to finish. It’s a great outdoor date that combines the excitement of the game with the beauty of the Toronto waterfront.
Bonus: Check out a Community Event on AdmitONE
For a date that feels truly local and unique, browse the community listings on AdmitONE. This platform is where independent organizers host everything from intimate small shows and trivia nights to high-energy parties and fascinating speaker series. It is the best way to find a one-of-a-kind event in Toronto that you won’t find on the typical tourist maps. You can see the full calendar of upcoming local gatherings at the AdmitONE Toronto community events page. Whether you want to attend a DIY art show or a niche documentary screening, this is your gateway to the city’s underground pulse.
