While a trip to Toronto’s downtown core has its perks (iconic draws like the CN Tower and the Theatre District among them), heading a little further afield from the city offers the possibility of new experiences. Whether you’ve visited Toronto once or a few times, there’s likely lots left to see within three hours of its city limits, from appealing lakeside towns to winery-rich regions. On your next trip, do as the locals do and take your time to see the city’s surroundings with an afternoon or weekend away. As these four spots prove, travel has its rewards.
Drive time: Two to three hours
Best time to visit: Summer and fall
On summer weekends, trails of cars make the trip north from Toronto to the Muskoka District Municipality, also referred to as “cottage country,” thanks to its many summer residences that range from compact to palatial. The area spans 2,900 square miles with more than 650 lakes. Avoid Friday summer traffic by driving up during off hours. (There are often seasonal options for bus and train routes north, but if you plan on doing any extensive sightseeing in the area, a car is the better choice.)
Play or stay: Stay
If you are going to Muskoka, make it count by staying a few nights. Cottage rentals (including Airbnbs) are often snapped up long in advance of peak summer, so be sure to book early. Resorts, including Deerhurst, Touchstone, and Taboo, help ease capacity pressure.
Each of the towns and townships that make up the region has its own personality, but you might want to start with Gravenhurst—one of the closest towns to Toronto at just over a two-hour drive. Gravenhurst has six public beaches and hosts events like the Muskoka Music festival, showcasing a diverse lineup of performers, a vintage boat show, and a Ribfest, making for a perfect introduction to the area.
On the drive up, stop at Webers for a burger or Kawartha Dairy for an ice cream cone. Activities beyond Gravenhurst include walking the forested paths that abut Algonquin Provincial Park (especially when the leaves change color in the fall) or biking the great-for-all-levels (and all-seasons) trails in the riverside town of Bracebridge. Or follow the Muskoka Art Trail, where 32 studios and galleries display the work of resident amateurs and famous artisans.
South: The Toronto Islands
Drive time: None. Just head to the Jack Layton Ferry at the city’s waterfront terminal to catch your ride. Cars aren’t allowed.
Best time to visit: Summer
Known collectively as Toronto Island Park, these 15 islands may be the city’s best-kept secret. Covering 800 acres, they sit just off the southern edge of downtown Toronto. They were once connected to the mainland until an 1858 storm removed the peninsula and created the island chain.
Play or stay: Play
Three islands are the most frequented by the 1.4 million tourists who visit each year: Ward’s Island (home to about 650 residents), Centre Island (with the kid-friendly Centreville Amusement Park), and Hanlan’s Point (where you’ll also find the city’s only nude beach). To reach one of these islands, hop on a $9, 13-minute ferry across Lake Ontario. You can also opt for a $13 water taxi. Either option will quickly have you on a sandy beach hugging the shores of Lake Ontario or a comfortable patch of grass to view the iconic Toronto skyline.
Unless you know someone who lives on the island or have rented a room in advance, you’ll need to wrap up your fun in time to catch the last ferry home between 11 and 11:45 p.m. in the summer, depending on the island of departure. Pack a picnic and bring it with you or pop into the cozy Island Café (Ward’s Island) or eat on the giant patio at Toronto Island BBQ and Beer Company (Centre Island). The islands are covered in nature trails, so you can walk or bike your way around. Toronto Island Bicycle Rental offers singles ($10/hour), tandems ($19/hour), or quadricycles ($20 to $38/hour), while Toronto Islands SUP can set you up for either SUP Yoga tours ($49 per person) or a Sunset paddle ($85 per person) at a variety of island locations.
East: Prince Edward County
Drive time: 2.5 hours
Best time to visit: Summer and fall
With its collection of cideries, wineries, and farm-to-table restaurants, Prince Edward County is a foodie paradise. The area’s location at the eastern end of Lake Ontario makes it one of the best places in the province for orchard fruit, although the grapes have made it famous. And now a burgeoning beer and cider scene has introduced a younger crowd to its fields. A car is the best way to explore the area, but for tastings, signing on with a tour like Get Corked PEC means never having to worry about the ride home.
Play or stay: Stay
Book a room at the Royal in Picton, an 1800s-era railroad hotel that underwent an eight-year renovation and opened in 2022. Fill your days with walks around town, exploring antique shops and independent clothiers, and visits to the golden beaches at Sandbanks Provincial Park. Be sure to stop at Slickers for house-made ice cream.
Restaurants are hard to choose between. 7Numbers Picton’s Southern Italian dishes are a favorite, chef Jamie Kennedy’s pop-up French fry stands are worth scoping out, and Merrill House is ideal for fine dining, with a seasonal tasting menu that includes optional wine pairings. For memorable sips, pick from the almost 40 wineries in the area, which is known for its pinot noir and chardonnay grapes. Huff Estates is an appealing choice for a patio lunch on the edge of the vineyards. (Try the wood-fired Funghi pizza, perfectly paired with a pinot gris.)
Drive time: Two hours
Best time to visit: Spring through fall
People come to Stratford, Ontario, for a lot of things, but one reigns supreme: Shakespeare. The walkable town named for its England equivalent has celebrated all things Bard since the Stratford Festival was founded by journalist Tom Patterson in 1952. Now, every year between April and October, the annual theatrical festival draws crowds and notable actors; the latter have included Christopher Plummer, Sarah Polley, Jessica Tandy, and Christopher Walken. True theater lovers will want to sign up for a backstage tour of the Avon Theatre or the chance to experience a set changeover in a theater. Other reasons to visit include a robust food scene and an exhibit at the Stratford Perth Museum celebrating its other prized celebrity: Justin Bieber.
Play or stay: Both
Skipping the car rental and hopping on a bus from downtown Toronto to Stratford ($35 return) can make it an easy day trip. Pop over for a meal and a theatrical production at one of the four Stratford Festival stages before returning to the city.
But, if time allows, tuck in for a few days. Avonview Manor has both apartments and suites and an on-site outdoor pool, and more formal stays are available at boutique properties like the spacious the Bruce, or the quirky Edison’s Inn (where inventor Thomas Edison once lived). Whatever your choice, book early, as most theatergoers opt for an overnight.
When you’re not in a theater seat, enjoy a local restaurant like the intimate Bijou or burger-heavy Bentley’s. Or sign up for the Savour and Sip trail, which provides six vouchers to redeem at local businesses for picnic essentials like sausage rolls or warm olives with bread. And always check the Destination Stratford site before a visit for news about frequent gallery exhibitions, artist studio openings, and outdoor concerts.