Travel is fun and all — but how often have we wished we could dodge the airport lines and stingy baggage allowances, hop into a convertible and zip along the great open road, scarf flying behind us, à la Bridget Jones (pre-hair disaster)?
Vacation-wise, we may be looking inward for the second year running, but perhaps that’s not such a bad thing. There are plenty of places in Ontario just waiting to be discovered and rediscovered: hidden gems, local bites and craft brews (because beer just tastes better when your OOO is on, and that’s a scientific fact). From Ontario's coolest cabins to its most breathtaking beaches, you won't be hard-pressed to find an adventure during summer's second act.
Cash in your vacation days and explore some of the best places in Ontario, from Windsor’s vineyards to Cambridge’s cinematic cityscape. We’ve planned out the best three-day Ontario trips, so you can start booking hotels and perusing menus (just us?). Can’t squeeze it all in? Worst case Ontario, you’ll just have to extend your trip by a few days to fit in more fun...
Best places in Ontario: Windsor
Day One:
A straight shot down the 401, Windsor is best tackled by car to fully appreciate the quiet charm of its nearby towns. Check in to the Best Western PLUS Windsor Waterfront for spectacular views of (you guessed it) the waterfront and neighbouring Detroit’s skyline. Quickly drop off bags and zip around on a Bird Canada electric scooter tour, soaking up the incredible graffiti across five districts of Rose City while swotting up on the history of Canada’s southernmost city. Once you reach Ford City, park up and make a margarita and taco pitstop at The Grand Cantina, home to delicious Mexican fare and yet another mural on their stunning patio.
Day Two:
Extend your trip to a two-night stay and you’ll get $75 back as part of the Road Trip Windsor rewards. If time is limited, check out early and kickstart your day with a sunset paddle through the beautiful canals of Pike Creek and Lake St. Clair, courtesy of Urban Surf Co. Refuel with brunch at Toast, a friendly spot for waffles, eggs benny and lots of much-needed coffee.
Head south towards the vineyards, where 19 wineries sprawl along Lake Erie. Sprucewood Shores Estate Winery — a 52-acre farm and Ontario’s only walk-out, beachfront winery — is one of the best. To maximize your wine wandering, download the EPIC wine route map. Scoot along the water’s edge to Paglione Estate Winery for wood-fired pizza, Italian gelato and merlot, before checking into one of the 18 quirky suites at The Grove Hotel in Kingsville, a boutique accommodation on Main Street.
Day Three:
Once you’ve got your fill of the Grove’s 1854 building and its free coffee and tea, shuffle down the street to Dutch Boys Chocolate for award-winning handmade confections and truffles. Head east towards Leamington, stopping off for Lake Erie’s finest at Birdie’s Perch, a ‘bustaurant’ serving fish and chips out of a double decker bus at the foot of Point Pelee National Park.
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On your way home, make one final stop at Cured Craft Brewing Co., an old tobacco barn serving local bites and delicious pints (we call shotgun). If you're not imbibing, the brewery holds a farmers’ market on its patio every Saturday, so you can take home tasty local souvenirs like beer, cheese and honey for later.
Best places in Ontario: Kawarthas Northumberland
Day One:
This expansive area just east of Toronto offers the perfect Ontario long weekend escape for those looking to fill their days with outdoor adventure and their evenings with delicious food and drink. Base yourself in Bobcaygeon for the first leg of the trip. Easily accessible right downtown and on the water, Buckeye Surf & Snow Shop is the place to rent your gear before heading out to paddle the Trent-Severn Waterway. There are dozens of different routes ranging in length and difficulty, so know before you go. Once you’re all tuckered out from a day on the water, cozy in at the historic Bobcaygeon Inn. For dinner, take the scenic five-minute walk over the river to El Patio for locally-farmed Mexican fare, margarita pitchers and live music.
Day Two:
After a long night of live music and likely a few too many drinks, take the morning to sleep in and recover a little before making the 20-minute drive to Buckhorn. Enjoy a scenic lunch on the water at the newly-opened Mainstreet Bar & Grill, then the outdoor adventure is back on. The largest park in southern Ontario after Algonquin, Kawartha Highland Signature Site is where the Canadian Shield transitions into the St. Lawrence Lowlands — you’ll definitely want to hike this beauty.
Wind down with a visit to Whetung Ojibwa Centre, where you can shop through a beautiful collection of Native crafts, art, jewellery, leather work and more from the Curve Lake First Nation. Jump back in the car and drive down to Peterborough to lay your head to rest at the Holiday Inn Peterborough-Waterfront. From here, it’s a 15-minute walk over to Publican House Brewery & Pub, where you can enjoy their craft brews, each paired with a menu item to match.
Day Three:
In the morning, head over to the Silver Bean Café for classic breakfast dishes by the water. Follow that up with a leisurely stroll in downtown Peterborough where you’ll find unique shops and waterside vistas. You might even catch one of their Saturday farmers’ markets. If you’re all adventured out, spend the afternoon at Rolling Grape Vineyard tasting wine and snacking on charcuterie. Or, if you’ve still got the energy, make the winery a quick stop before going Treetop Trekking in Ganaraska Forest.
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The last town on the tour is Port Hope, where you can stop in at famous spot Olympus Burger. They’ve got a lengthy and interesting list of burgers to choose from and they were featured on the Food Network’s You Gotta Eat Here! If you’re too stuffed to drive home, opt to stay the night at the beautiful Hotel Carlyle and head home in the morning.
Best places in Ontario: Kitchener-Waterloo
Day One:
Who needs Europe? This summer, start your road trip in Cambridge, located at the confluence of the Grand and Speed rivers. A popular shooting destination, the city’s steeples and spires may be recognizable from TV shows like The Queen’s Gambit and The Handmaid’s Tale. Historic limestone buildings dating back to the mid 1800s populate the Dickensian Gaslight District, a regenerated area paying homage to its industrial past.
Cambridge has produced a Craft Beer Tour Map for self-guided suds sipping at spots like Foundry Brewing. Don’t miss their award-winning Beautiful Aurelia Hefeweizen on their equally stunning patio. Finally, head 10 minutes out of town to Langdon Hall Country House Hotel and Spa, a luxurious accommodation and restaurant nestled within the Carolinian Forest. It’s a destination in and of itself — so do NOT be late for check in.
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Day Two:
Pry yourself away from Langdon Hall's luxury linens and chef Jason Bangerter’s heavenly dishes, and head north towards Kitchener. Bingemans offers adventurers plenty of ways to explore the Grand River, from canoeing and kayaking to tubing or biking the Walter Bean Trail. Once you’ve dried off, head to midtown’s Belmont Village. Choose from the 18 rotating taps of craft beer and cider at Arabella Beer Park Bar, then grab a hole in one from Lady Glaze Doughnuts, with tempting flavours like blueberry maple or pistachio, coconut and coffee. Work off those carbs with some mural meandering along the DTK (Downtown Kitchener) Art Walk, which showcases local art installations. Drop your bags at the charming Walper Hotel then head to Swine & Vine for sustainable small plates, with a focus on charcuterie and tapas style dishes.
Day Three:
Enjoy brunch on Walper Hotel’s extended King Street patio, with handcrafted cocktails and a regional, seasonal menu from chef Nicole Hunt. Then pack up and head north to the charming village of St. Jacobs, a spot steeped in history along the Conestoga River. Step back in time by jumping in a buggy at St. Jacobs Horse Drawn Tours. Tours leave from the St. Jacobs Farmers’ Market (Canada’s largest year-round farmers’ market), where you can grab fruit, veggies, honey, maple-syrup and more from over 300 vendors. While you’re in the market district, go treasure hunting for vinyl records, art, books and vintage clothing at Market Road Antiques. Then celebrate your finds with authentic Mexican cuisine, craft beer and cider at the Village Biergarten’s sprawling patio before tootling on home.
Best places in Ontario: Ottawa
Day One:
Start off your capital journey at the boutique Le Germain Hotel on the edge of Ottawa’s historical, canal-side Sandy Hill neighbourhood. The hotel’s central location is within walking distance to the buzzing ByWard Market and the stunning Rideau canal (a UNESCO World Heritage site) which pulses through the city. Just beyond the hotel’s front door, the Mackenzie King Bridge leads to Confederation Park, a downtown oasis for picnicking and people watching before a stroll down Elgin Street. You could spend all afternoon on this iconic, village-like street lined with heritage buildings, restaurants and shops. You literally can’t miss the Elgin Street Diner because it’s always open; next door, get your fill of steamed buns, noodles and dumplings at Asian bar Datsun.
Day Two:
You don’t have to talk (or even like) politics to admire the neo-Gothic Parliament buildings and the symbolic Peace Tower overlooking the Ottawa River. A five-minute walk from Parliament’s Centennial Flame is Escape Bicycle Tours where you can rent a bike for the day or join a small-group guided tour through Ottawa’s must-see sites like Sussex Drive, the Notre-Dame Cathedral and Rideau Falls.
Stop for a lunch of seasonal share plates at Play Food & Wine and save room for all the snacks and shops at ByWard Market, one of Canada’s oldest and largest public markets with a daily farmers’ market and over 600 businesses from local artisans to breweries. Cross the Alexandra Bridge to explore Hull, Quebec or stay for sunset from the bridge’s lookout. Then, toast the day with a glass from Tavern on the Hill’s garden patio in Major Hill’s Park or a treat-yo-self dinner at Restaurant e18hteen.
Day Three:
Three words: Bank Street brunch. If you’re looking for a fix of eggs benny and mimosas, get yourself to the charming Glebe-Landsdowne neighbourhood for brekky at Eldon’s, Banditos, Eddy's Diner or Kettleman's Bagel Co. Then, walk it all off with a scenic stroll to Dow’s Lake where you can rent canoes, kayaks or paddle boards on the picturesque man-made marvel. Or, float to Dow’s Lake on a Rideau Canal Cruise which departs near the National Art Centre and takes you past landmarks such as the Château Laurier Hotel enroute to the lake. You can’t go wrong with Mexicali Rosa’s for tacos and tequila after a day on the water or the coastal-cool Umbrella Bar on the lake’s pavilion. End your day with sultry cocktails at The Moonroom.
Best places in Ontario: Durham
Day One:
Just about everything east of Toronto is included in this region, so we’ve narrowed down a small slice of it for a selection of unique food and drink experiences (emphasis on the drinking part). Start with a visit to the enchanting Parkwood Estate. Tour the mansion and beautifully manicured grounds, then take afternoon tea here. After this posh afternoon, switch gears with Drama in Durham’s War on Whisky 1920s prohibition series. Their self-guided South Durham tour takes you to three breweries nearby: Brock Street Brewing Company, Town Brewing and Little Beasts Brewing Company. Then, cap things off at the Pickering Museum Village with their 1920’s prohibition-themed escape room. For Dinner, PORT in Pickering is a relaxing waterfront spot to unwind from the day’s adventures over pizza and pasta. Lay your head to rest at The Tartan House Bed & Breakfast in Ajax for a charming overnight stay.
Day Two:
Enjoy a leisurely Inn-Keepers Choice breakfast of mouthwatering entrees in the morning before you hit the road for Port Perry. Ditch the car at the historic Piano Inn & Café, where you’ll be staying the night, and strike out on foot for the day in the beautiful waterside town. Snack on an incredible selection of cheese and small bites paired with wine at The Port Cheese Co. Then, stroll about town and grab an ice cream from Louie’s Café and Dessert, or save this for an after dinner treat later. Spend the afternoon sipping on brews at Old Flame Brewing Co. — they’ve got live music every Saturday afternoon. Once you’ve worked up an appetite, head to Foundry Kitchen & Bar for local dishes served in a casual fine dining atmosphere.
Day Three:
Start the day out with a trip to Willowtree Farm. Take breakfast from their café and bakery out on the patio, then shop their farm store for preserves and other goods. If you’re here in September, you can pick your own strawberries. Keep the farm tours coming with a drive up to Villa Vida Loca. They’ve also got plenty of local delights to shop through, like honey, handcrafted soaps and pure maple syrup. You’ll want to have a delicious barbecue lunch from their weekend smoke shack. Stop in at Second Wedge Brewing for unique brews and Slabtown Cidery for craft cider and a bite before heading home.
