An Insider’s Guide To Building A Canadian Road Trip Filled With All The Things YOU Love


Popular navigation apps like Google Maps and Waze have ushered in a whole new era of freewheeling road trips. While crossing the border for a Canadian adventure once involved a lot of planning, pre-determined routes, and printed maps, today’s road-trippers can simply plug in a list of stops, set their driving preferences, and download the responsibilities of route planning to their navigation app.


But even the most intelligent navigation apps need some solid direction. One sure-fire formula for a fun-filled road trip route is to build a collection of stops around the things you love. Scan through the list below to help narrow down some options that reflect a few of your favourite ways to relax. Pick as many or as few as you like, depending on how action-packed you prefer your agenda and how long you’d like your road trip to last. Then, simply load your stops into your navigation app and let it create a customized road trip route that’s a perfect match for your preferences. Once your route is set, browse and book nearby accommodations.


Back Roads - car driving


If You Love: Whisky, Wine, or Craft Beer Touring

Amazing Area To Explore: Windsor, Essex, and Pelee Island


Fun Events To Time Your Trip With:


The monthly LaSalle Night Market, on select Sundays from May through September, features live music, vendors, and delicious food. 


The wine, craft beer, and spirit scene on the Canadian side of the border is so spectacular you’ll want to designate a driver or even park the car and opt for a touring route that allows you to explore some stops on foot or by bike.




Spirit sippers won’t want to miss the opportunity to learn about the vibrant past of Canadian whisky craftsmanship at The Chimczuk Museum's temporary exhibition "Beyond the Barrel: Windsor’s Whisky History" which explores the region's whisky-making heritage, from early production to post-Prohibition, through artifacts and photographs. This exhibit is on until January 26, 2025, so make sure to visit before it's gone!

To discover the next chapter in the story of Canadian spirits, plan a stop at Wolfhead Distillery in Amherstburg. Thanks to the fabulous response to its creative craft spirits, the distillery has grown its sipping selection from 6 staples to ten premium whiskies, vodkas, and gins. Tours are offered on Fridays and Saturdays, and tastings and flights are always available at the gift shop and on-site restaurant.



Windsor, Essex and Pelee Island’s world-class wine scene may come as a surprise to American visitors, but the region’s incredible reds, whites, rosés, and sparkling wines are sure to delight. An EPIC Tasting Pass is an excellent option for those who want to dedicate some serious time to touring, as it includes tastings at six different wineries. If you’d prefer to limit your tasting to one or two stops, excellent options include:

  • Muscedere Vineyards in Harrow, where guests can also snack on delicious wood-fired pizzas.
  • Oxley Estate Winery in Harrow, which is home to picture-perfect patios for sunny afternoon sipping.
  • Pelee Island Winery, which is Canada’s southernmost winery and has two locations: a winery and retail store in Kingsville and a Tasting Pavilion on Pelee Island, which visitors are often surprised to learn is further south than Northern California.
  • Sprucewood Shores Estate Winery in Harrow, where visitors can also enjoy the incredible Lake Erie view at Ontario’s only beachfront winery.

Craft Beer


The best way to get a taste of the hopping craft beer scene in these parts is to do a little exploring along the Barrels, Bottles and Brews Trail, which includes a tasty collection of 11 craft breweries, as well as the two distilleries highlighted in the spirits section above. Purchase a Flight Log touring pass if you’re interested in making multiple stops, or choose one or two crowd favourites to visit, like Windsor’s Walkerville Brewery, and Sandwich Brewing Co., Leamington’s Cured Craft Brewing Co., or Kingsville’s Banded Goose Brewing Co.


If You Love: History

Amazing Area To Explore: Chatham-Kent


Fun Events To Time Your Trip With:


Emancipation Day festivities at Josiah Henson Museum in July and Buxton National Historic Site’s Homecoming festivities on Labour Day weekend.




The Chatham-Kent area is home to an impressive collection of historic sites and museums dedicated to telling the stories of those who escaped to Canada to find freedom from slavery. If you’d like to really dive deep into the region’s Black history, consider our two-day Showcase of Stories itinerary, which also includes sites in Windsor and Amherstburg. If you’d like to set your own course, excellent stops to incorporate into your route include:


If You Love: Beachy Outdoor Fun

Amazing Area To Explore: Sarnia-Lambton


In addition to the incredible beaches and sunsets courtesy of Lake Huron and the St. Clair River, this area is home to beautiful trails for hiking and cycling, 13 scenic golf courses, and a collection of relaxed craft breweries and rural wineries that offer really fun outdoor spaces for sunny weather sipping.


Canatara aerial


Best-bet beaches to consider incorporating into your route include Sarnia’s Canatara Beach, Grand Bend Beach, Ipperwash Beach, which is one of Ontario’s longest freshwater beaches, and the beach at Highland Glen Park. We recommend visiting beaches during weekdays to avoid crowds. 


Excellent trails in the area for hiking and biking include Sarnia’s Howard Watson Nature TrailCanatara Park Trail, the St. Clair River Trail, which is a 35-km path stretching from Corunna to Port Lambton, Lambton Shores’ many nature trails, and Pinery Provincial Park’s Old Ausable Channel


When it’s time to take a break from the outdoor action, enjoy some downtime at one of the 15 stops along the Cheers To The Coast Drink Trail that winds through this area. Choose from craft breweries and cideries, an artisanal mead maker, and cool-climate wineries that all share one thing in common: a passion for introducing visitors to their delicious products!


Outdoor adventure seekers who want to add a day or two onto their trip for some additional hiking or biking will find excellent trails throughout Ontario’s Southwest, including in London, Windsor Essex, and Oxford County.


If You Love: Music

Amazing Area To Explore: London


Fun Events To Time Your Trip With:


Sunfest Concert Series events, Rock The Park Music Festival, Elevate Electronic Dance Music Festival, City of Music Concert Series Events


Americans eager to tune into the Canadian music scene must plan a stop in London. The beat of the music industry here is so swift that in 2021, London was Canada’s first city to be recognized as a UNESCO City of Music.

In addition to great summer festivals, the city’s many live music venues host a wide range of acts. Be sure to check the event calendars at Budweiser Gardens, London Music Hall, Aeolian Hall, Grand Theatre, Centennial Hall, and Wolf Performance Hall to score tickets to performances that coincide with your visit.


London’s renowned concert venues aren’t the only place to catch a show in the Forest City. London’s many breweries often feature live music acts. 100 Kellogg Lane, a world-class entertainment complex housed in a historic cereal factory, also hosts outstanding musical events.


While you’re in London, other must-see stops for music lovers include the London Music Hall of Fame and iconic music murals such as the towering Johnny & June, located just down the road on the north side of Budweiser Gardens. This three-story mural captures the historic moment where Johnny Cash proposed to June Carter in London during a concert in 1968. The UNESCO City of Music Murals act as a bold welcome to the city, spanning across locations such as the downtown VIA Rail station and the London International Airport.


If You Love: The Farm-To-Table Food Scene

Amazing Area To Explore: Oxford County


Fun Events To Time Your Trip With:


Cowapolooza, Woodstock’s favourite summer festival in August, features free music, family fun, and delicious eats.


American road-trippers looking for one of Canada’s most historic farm regions will be thrilled to discover Oxford County. Home to almost 100 cheese factories in the 1800s, this friendly collection of small communities is so incredibly proud of its reputation for producing world-class dairy products that it’s even created a dedicated touring trail celebrating the cheeses made here. The Oxford County Cheese Trail invites guests to visit their choice of over 30 stops, which include everything from cheese factory tours to restaurants with decadent cheese dishes and shops featuring wares that passionate foodies will love. Whether looking for just a taste or diving deep into the dairy scene with a day or two dedicated entirely to touring, foodies will have no problem finding fun stops with friendly hosts who can’t wait to welcome them.

But Oxford’s rich agriculture scene isn’t limited to dairy farms. A healthy crop of creative agritourism entrepreneurs now call this area home and proudly showcase their passions through a wide range of hands-on experiences, including:


For additional inspiration for your next Canadian road trip, be sure to check these articles: