There’s something interesting happening around every corner in Toronto. From an incredible culinary scene to every type of festival you could imagine, to world-class sports (go Raps/Leafs/Jays/Wolfpack/Rock/Argos/ Reds etc.) and an abundance of concerts, shopping and traffic. Sometimes, you just need to get away from it all to appreciate it even more. To help you escape the chaos, here’s our round up of The Best Weekend Getaways from Toronto You Haven’t Thought Of.

1. Waterloo Region
Even when Oktoberfest isn’t happening, the Waterloo Region is an incredible place to escape to for a couple of days. Just a quick 1.5 hr drive and you’ll arrive at the birthplace of the apple fritter and a bit of a slower, more relaxed pace. St. Jacobs Market is an obvious stop, but go here on your way home and pick up fresh produce, honey and maple syrup to take back to Toronto. Carve out some time and bike the incredible trails the region has to offer, take the fascinating tech tour or take in some local live theatre and performances. If you’re a fashionista, you’ll want to check out the Fashion History Museum in Cambridge, home to over 10,000 garments dating back to the 1600s. We suggest staying at Homewood Suites by Hilton Waterloo St. Jacobs so you’re centrally located across from St. Jacobs Market.

Photo Credit: Gatineau Park

2. Gatineau
Across the bridge from Ottawa, you’ll find a place that can be sometimes be overlooked due to Ottawa’s popularity. A 4.5 hr drive from Toronto will get you to the rolling parklands, lush golf courses, sparking lakes, exciting casinos and the world-class dining of Gatineau, Quebec. Nature lovers will enjoy the wildlife reserves, national parks and of course Gatineau Park. Golf lovers will want to practice their swing at the Number 1 ranked downtown golf course at the DoubleTree by Hilton Gatineau/Ottawa. Once you’ve worked up an appetite, you’ll find that the Gatineau food scene does not disappoint. Check out these 10 restaurants to try or treat yourself and indulge in some Five Diamond dining at Le Baccara followed by a night at Casino Lac Leamy.

3. Washington, DC
If you want to take your weekend adventure a bit further try Washington, DC. A quick 1.5 hr flight will have you immersed in this US capital and surrounded by the headline making political activity to our south. Hit the ground running after your flight and explore US monuments and memorials at the National Mall, then head over to the Smithsonian Museums to take in some history. If you’re looking to stay close to all of the attractions Washington has to offer, stay at the Capital Hilton for easy access. Leaf fans – it’s much cheaper to cheer on the boys in blue here so bring your jersey! Stay at the Canopy at The Wharf and you’ll be just 10 minutes away from the arena. Foodies will want to check out Midtown which is where all the young, innovative chefs cook up a storm. Check out Hazel for an easygoing meal or Iron Gate for an upscale experience. Washington is also a fun place for a distillery crawl. You’ll find four within walking distance from each other in the Ivy City area, each offering spirits you can’t find in Canada. Hit up Green Hat for gin, One Eight and Jos. A. Magnus for whiskey and Republic Restoratives for rye, bourbon and brandy.

4. Chicago
Ok, you might have thought of Chicago as a weekend getaway already, but have you spent time in the coolest neighbourhoods of the Windy City? With flights from the Island that are less than 2 hours, it’s an easy fun-filled weekend getaway. There’s tons to see downtown including Broadway plays you didn’t get to see in Toronto (pro tip: check Hot Tix out for half-price tickets), incredible museums and  historic architecture. Whatever you do, make sure you don’t miss out on the following cool kid neighbourhoods. Wrigleyville is home to the Chicago Cubs and the second oldest ballpark in the US (catch the Jays here when they are in town). Explore Pilsen’s is vibrant murals, art, and restaurants all celebrating the area’s Latino community. West Loop is home to the city’s Restaurant Row, including Stephanie Izard’s Girl and the Goat and Au Cheval’s legendary burger. Wicker Park is teeming with bars, restaurants, and intimate music venues. To keep your bank account in check, get a 3-day CTA pass for easy access to downtown from the airport and so you can easily get to all of these great neighbourhoods. We suggest staying at the LondonHouse Chicago for some of the best views of the city to fill your IG feed. In the warmer months, don’t miss having a drink on the hotel’s rooftop!

5. Boston
Another quick flight option from the Island is Boston. And really, who wouldn’t love to go back to work on Monday and tell their colleagues they spent the weekend in Beantown? After a quick 1.5 flight, it won’t be hard to fill your weekend in the charming streets of Beacon Hill, browsing renowed museums or the taking in a game at TD Gardens (another great place to catch the Leafs play an away game). Freedom Trail is a must-see, but if you’re looking to get off the beaten path and blow up your IG feed, check out the Ruins of Schoolmaster Hill, the Sacred Cod of State House and Ether Dome. Beer lovers, rejoice! Sam Adams Brewery offers free tours that includes free samples. Before you leave, make sure you indulge in some fresh lobster rolls, fried clams and clam chowder and keep an eye out for 1-Buck Shucks if you’re an oyster lover. The seafood here rivals only that of Atlantic Canada. Our favourite seafood restaurants in Boston are The Beach Plum for overloaded lobster rolls, Clam Box for fried clams and Cunard Tavern for a juicy burger topped with a clam roll and tartar sauce. We suggest booking a stay at Hilton Boston Logan Airport so you’re close to the airport (connected by indoor walkways) and just over 3km to downtown Boston. Plus, if you’re looking for a great pic for Instagram – check out the view from the 9th floor!

Previous Article

Finding the Unusual in Waterloo/St. Jacobs

Next Article

24 Hours in Ottawa-Gatineau

Related Guides