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.
Want to skip to a specific section based on what you're most interested in? Click the links below if you love:
- Whisky, Wine, or Craft Beer Touring
- History
- Beachy Outdoor Fun
- Music
- The Farm-To-Table Food Scene
- Going Off The Grid
- Flowers and Gorgeous Gardens
- Knowing Where Your Food Comes From
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:
This beautiful area just beyond the U.S. border loves a night market, and the Night Market Hop is the perfect way to peruse all the excellent evening options available for you to time your trip around.
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.
Spirits
Spirit sippers won’t want to miss The Rum Runner’s Tour, which transports guests back in time to the Roaring Twenties on a captivating four-hour adventure that brings Prohibition-era Windsor to life! The immersive experience includes a two-hour bus tour through historic sites, followed by a lively speakeasy scene with a delicious hot meal accompanied by live music, singing, and comedy routines. Setting out on a self-guided Walkerville Heritage Walking Tour is another interesting way to learn the fascinating history of the Hiram Walker & Sons Distillery and dozens of other area landmarks. Touring Willistead Manor, a 15-acre park with a 36-room mansion that was built for one of Hiram Walker’s sons in 1906, is another must-visit stop for those serious about spirits!
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 six staples to 14 different premium whiskies, vodkas, gins, and specialty spirits. Tours are offered on Saturdays, and tastings and flights are always available at the on-site restaurant.
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 on August 2 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:
- Buxton National Historic Site and Museum in Merlin
- Josiah Henson Museum of African-Canadian History in Dresden
- Chatham-Kent Black Historical Society and Black Mecca Museum in Chatham, which also offers a wonderful walking tour of Chatham’s historically Black neighbourhood, including stops at the John Brown Meeting House, the BME Freedom Park and more.
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.
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 Trail, Canatara 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 Canada Life Place, London Music Hall, Aeolian Hall, Grand Theatre, Centennial Hall, and Wolf Performance Hall to score tickets to performances that coincide with your visit.
For a stay that keeps you close to the action, book a room at the Hard Rock Hotel London, located right on-site. This music-infused hotel blends modern luxury with iconic rock 'n' roll style, offering everything from memorabilia-lined walls to curated playlists and a vibrant atmosphere. Unwind at the bar or explore the hotel’s upscale dining and spa amenities.
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.
For a stay that keeps you close to the action, book a room at the Hard Rock Hotel London, located right on-site. This music-infused hotel blends modern luxury with iconic rock 'n' roll style, offering everything from memorabilia-lined walls to curated playlists and a vibrant atmosphere. Unwind at the bar or explore the hotel’s upscale dining and spa amenities.
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 Canada Life Place. 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 visit Canada’s Dairy Capital: Oxford County
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 agricultural 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:
- Field-to-table farm brunches
- Taste of farm life experiences
- Small-batch coffee roasting classes
- Tree-to-table charcuterie board crafting classes
- Berry patch picnics
If You Love: Going Off The Grid
Amazing Area To Explore: Middlesex County
Fun Events To Time Your Trip With:
Dorchester’s Art in the Barn event is the area’s largest summer arts and crafts festival with vendors from all over Ontario, Quebec, and Canada’s east coast selling a fabulous selection of soaps, jewelry, clothing, furniture, pet items, candles, pottery, stained glass, and up-cycled, recycled and vintage products.
Arrowwood Farm’s Blueberry Festival, in Melbourne, is a fun celebration of the blueberry harvest, complete with vendors, horse and carriage rides, farm tours and more.
Road trippers eager to discover off-grid adventures around every corner will find plenty to love in Middlesex County. Friendly farmers invite guests into their fields for hands-on harvesting fun of seasonal berries and flowers at Heeman’s, Kustermans, and Arrowwood Farm. Taking a sunflower or alpaca walk at The Crump Family Farm is another delightful option. You can find other adorable alpaca adventures in the area at S.A.M.Y.’s Alpaca Farm and Fibre Studio and Timbuktu Agri-tourism and Wellness Farm. Goat yoga sessions at Laughing Goat Yoga Studio or a scenic horseback ride with Willow and Water are two other fun ways for animal lovers to spend a few hours.
Extend your off-grid adventure by booking a night of glamping at Texas Longhorn Guest Ranch, Fernwood Hills, or Willow and Water.
If You Love: Flowers and Gorgeous Gardens
Amazing Area To Explore: Haldimand County
Fun Events To Time Your Trip With:
Take high tea in a sea of purple blooms set to a soundtrack of spoken word poetry at Purple Haven Lavender Farm’s Poet’s Garden Tea Party, or visit the farm on various dates throughout the summer for a guided forest bathing experience that includes a delicious lunch.
Head to Ruthven Park National Historic Site for a soul-nourishing blend of nature, creativity, and mindfulness at the restorative Wellness Retreat on Saturday, August 2nd, 2025. This retreat will be complete with guided Qi Hong, landscape painting, forest bathing, and a meditative labyrinth journey.
Get ready to breathe in the blooms! Haldimand County’s fields and flower beds ignite into a flurry of colour throughout the summer, and the passionate growers who call this area home are incredibly proud to share their gardening gifts with visitors. Canfield’s Purple Haven Lavender Farm invites guests to enjoy luxury lavender field picnics. Windecker Woods Flower Farm is a cut-your-own flower farm with a rotating crop of peonies, zinnias, dahlias, sunflowers and many more. Guests can also take part in on-site flower workshops or book a beautiful spot to enjoy a picnic. Concession Road Garden also offers hands-on flower workshops. The roadside stand at Buds and Blooms Flower Farm is the perfect spot for a flower-filled roadside selfie! Scroll through Tourism Haldimand’s dedicated Flowers page before your trip to find even more adventures for your garden-filled galavant!
If You Love: Knowing Where Your Food Comes From, Visit Ontario's Garden
Amazing Area To Explore: Norfolk County
Fun Events To Time Your Trip With:
Norfolk County Ribfest, from July 18-20, is an excellent way to discover a wide selection of local craft beverage makers while savouring delicious barbecue and enjoying live music.
The Norfolk County Fair and Horse Show, from October 8-14, is a seven-day celebration of all things Norfolk County featuring livestock and equine competitions, motorsports, major concerts, local exhibits, and a full midway.
Affectionately referred to as Ontario’s Garden, Norfolk County’s unique microclimate, sandy soils, and long growing season create the perfect conditions for a wide range of crops and incredibly tasty roadtripping adventures! Roadside stands and bustling farm markets overflow in the summer months with strawberries, tomatoes, sweet corn, and specialty crops like sweet cherries and lavender. Passionate chefs showcase these crops in delicious, farm-to-table dishes at area restaurants, and local craft beer, cider, and winemakers leverage these locally grown goods to create signature sippers.
Discovering farm markets, roadside stands and breweries, cideries and wineries with the help of the Visit Norfolk app is a fun way to spend the day. Those who prefer making fewer stops can head straight to weekly farmer’s markets in Simcoe (Thursdays), Port Rowan (Fridays), and Port Dover (Saturdays) to connect with a wide range of local vendors. There, you'll find everything from produce and artisan cheeses to freshly baked goods and locally raised meats.
