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Top Cycling Dates in Toronto

Couple Ride Along Fencing

Photo Credit: Destination Ontario

Finding the perfect date spot can be a bit overwhelming in a city as big as Toronto, with such a huge selection of incredible restaurants and bars, magical outdoor spaces, and so many things to see and do. And what if you want the journey to be part of the fun? Cycling is the ideal way to experience Toronto if you’re looking to both cover some distance plus see all the hidden corners and local gems that other forms of transportation just can’t quite reach. Let us guide you to some of the top cycling date options for Toronto.

West End Wandering

If you’re looking for an urban cycling date, Toronto’s West End is the place. The last few decades have solidified the neighbourhoods of the West End as some of Toronto’s coolest, and it also happens to have some of the best bike infrastructure. Add to that some of the best restaurants and bars in the city and you have the perfect place for an urban cycling date. If you don’t have bikes of your own, be sure to rent one from the ever-increasing number of Bike Share Toronto locations across the city.

Photo Credit: Destination Toronto

The Annex and Korea Town

First up, starting at Spadina, bike west along the Bloor Street bike lanes through the historic Annex neighbourhood and stop at one of many cafes, take a stroll through the stacks at BMV Bookshop, or stop for a drink at neighbourhood institution Victory Cafe. Next up, west of Bathurst Street is Toronto’s famous Korea Town, with so many restaurants to choose from, with local favourites Korean Village Restaurant or Buk Chang Dong Soon Tofu, or try the sweet fish-shaped waffles at PAT Central grocery store. If it’s a Sunday evening in the summer make plans to check out the free film screenings at Christie Pits Park for a super cozy time (bring blankets!).

Photo Credit: Destination Toronto

West Toronto Rail Path and Ossington

Cycle further west along Bloor and share a sunset bike ride on the West Toronto Rail Path, with great westward views and a picturesque mix of nature, street art, and many former industrial buildings. If it’s a Friday night, visit the Museum of Contemporary Art (open and free admission till 9pm Fridays) located in an early 20th century former factory, adjacent to the Rail Path on Sterling Road. Continue cycling south on the path to Dundas Street, where you can ride east and go for a drink on the popular Lower Ossington strip. If you’re in the mood for live music, the hip country and western inspired Dakota Tavern is always a good bet, or The Painted Lady just across the intersection. Recently expanded into the adjacent storefront, Bellwoods Brewery is always a great date spot, with a unique atmosphere, renowned beers brewed in-house, and delicious and upscale pub food. Continue west to West-Queen-West and Parkdale for more interesting eats and hip late-night spots for drinks.

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Winter Cycling in Toronto

Thanks to milder temperatures compared to the rest of the province, Toronto is a great place to keep riding together all year long. And when the snow does fall, the City clears 776km of bikeways and major trails including the West Toronto Rail Path and Waterfront Trail. Getting out to cycle together in the winter is a great way to experience trails when they’re a little less busy, and see a different side of the city and its urban and natural spaces. Many of the cycling date ideas in this blog can be ridden at any time of year, but you do want to do a bit of planning before setting out.  Make sure to dress for the weather and wind, be visible (lights, bright colours), and bike more slowly and cautiously than you would in the warmer months. Colder temperatures can also mean frigid winds along the lakeshore, so on windy days sticking to cycling on protected trails and city streets can be the best way to have a relaxing ride together. Bike Share Toronto, available all year long, is a great option for winter riding if you don’t want the salt and snow to put wear on your own bike. Plus Bike Share bikes have wide tires and built-in lights for stability and safety in different conditions.

Photo Credit: Bike Share Toronto

Hidden Ravines and Quiet Trails

If you’re looking for some nature to set the mood, you’re in luck as Toronto is blessed by an incredible network of multi-use trails throughout its extensive ravines, perfect for relaxed dates on a bike. One of the most picturesque and hidden is the Moore Park Ravine, an incredibly lush, forested ravine trail with steep banks making it feel separated from the busy city above. While the trail is popular on summer weekends during the day and during peak fall colours, most other times the trail is a really peaceful natural experience. In the summer, try evenings for the most solitude – you’ll instantly feel like you’ve been transported out of the city. The ravine trail connects to and forms part of the Beltline trail through the Mount Pleasant Cemetery and is the most scenic cycling route to get to the Evergreen Brickworks, a reclaimed quarry and brick foundry which is a stunning reimagining and restoration of urban and natural space, with a cafe open daily and farmers’ market every Saturday throughout the year. It might be the ultimate date spot, with a slow walk through its wetland trails and brick structures, and a great place to grab a coffee, snack or lunch mid-ride. The Brickworks is also a great hub to expand your cycling date into a longer cycling adventure, connecting to the Don River Trail where you can cycle north or south to the Waterfront Trail, or loop back up to Midtown Toronto via the Beltline Trail section along the Yellow Creek, a tributary of the Don.

Photo Credit: Destination Ontario

Island Getaway

If you’re looking for a romantic natural getaway that feels far away but is close to the city, look to the Toronto Islands. Getting to the Jack Layton Ferry Terminal by bike is a breeze being just next to the excellent Queen’s Quay separated bike path, part of the Waterfront Trail, which connects to other great bikeway routes across the city. The ferry ride itself is scenic and romantic, especially in late afternoon and sunset, where you’ll get gorgeous light casting onto Toronto’s epic downtown skyline. Take your pick of ferries, or take a water taxi, to one of three of islands – Centre Island, Hanlan’s, and Ward’s.

Photo Credit: Destination Toronto

The Toronto Islands are even more appealing for a relaxed cycling date as the largest car-free neighbourhood in North America. You can take your bike directly on the ferry, or rent a bike from Toronto Island Bicycle Rental (open May 1st until fall) if you’re taking the ferry to Centre Island. They rent single and tandem bikes, plus covered two-seater quadcycles (four wheels). Once you’re on the Island, take your pick of fun things to do: cycle leisurely amongst the beautiful tall willow trees, lounge or picnic on the lawns, gardens and greenspaces, visit the Centreville Amusement Park, or check out interesting historic sites like Gibraltar Point lighthouse, the oldest existing lighthouse on the Great Lakes. And when you’re ready for a rest and refreshment, hit up the Island Cafe on Ward’s Island for great cafe and pub fare and drinks, or The Riviera Ward’s Island Kitchen with a waterside patio with amazing ambiance.

Photo Credit: Destination Ontario

Secret and Quiet Beaches

The beach is a great place for a date, and a fun destination bike ride, but sometimes the crowds can kill the vibe. If you’re looking for a quieter scene, the Toronto Islands is a good place to start. Take the Hanlan’s or Centre Island ferry (if you’re renting a bike) and once you’re off the ferry cycle to Gibraltar Point. Here along the south shore of the islands is a long stretch of sandy beach that’s much less crowed than Hanlan’s or Centre Island Beach. The trees overhang the thin stretch of beach, and it’s a great place to hang out, enjoy the sun, and relax care-free. Ward’s Island beach is another great option, especially on a summer evening. It’s a little more popular, but far enough from the main attractions on the Island that it’s not on everyone’s radar.

Photo Credit: Ontario By Bike

Tommy Thompson Park on the Leslie Street Spit, known as “Toronto’s Urban Wilderness” is another magical destination date spot with kilometres of shoreline for a private beach hangout or picnic with epic views over the city or across Lake Ontario. But while the shoreline views are great, swimming is not permitted in the park. As it’s a car-free park, it’s a great place to ride side-by-side and chat while having a leisurely cycle. On summer weekends there are quadcycles available for rent, and also a Bike Share station at the entrance of the park. Note that the park is only open weekday evenings 4-9PM and weekends and holidays 5:30-9PM.

If you’re game for a waterfront bike ride west out of the city, there are so many incredible beaches as you cycle west on the Waterfront Trail through Etobicoke and Mississauga, including Marie Curtis Park Beach or Lakefront Promenade Park Beach, which has a Florida-esque inlet with beach on all sides. And you’ll be able to tell all your friends that you found the best secret beaches in “Toronto”.

Photo Credit: Destination Ontario

Cycling is the great way to share experiences together on a date and have the journey be part of the experience. Being on a bike lets you see more and access all of the interesting hidden corners of this great city. Toronto is home to beautiful cycling trails, parks, beaches and urban neighbourhoods, and cycling is the perfect way to see it all together. Why not make your next date one on a bike.

More information:

  • Cycling in Toronto – City of Toronto webpage for all things cycling – maps, bike parking and helpful resources.
  • Destination Toronto – Explore Toronto By Bike – Discover more blogs and ideas for cycling and other activities, bike tour and rental information, plus transportation and accommodations.
  • Ontario By Bike – Great Places to Cycle: TorontoFind road and trail routes and itineraries, major off-road trails in the city, maps, and links to bike shops, rental and tour companies.
  • Bike Share Toronto – Bike Share Toronto offers 24/7 convenient access to 7,185 bikes and 630 stations across the city, all year round.
  • GO Transit – Getting to Toronto – Consider a weekend pass to get to the city using the GO train, if arriving from one of the many stations out of the city. Bikes are allowed on trains during non-peak travel times, free of charge.


Sponsored Content Partner: Destination Toronto

Published On: January 31, 2023Categories: News

About the Author: Ontario By Bike