Southwestern Ontario Road Trip Guide: 6 Must-Visit Cities
Southwestern Ontario Road Trip Guide: 6 Must-Visit Cities
Southwestern Ontario is one of Canada's best-kept secrets for local travel. Tucked between Lake Huron and Lake Erie, this region combines tech hubs, deep history, outdoor adventure, culinary scenes, and fantastic local shopping destinations.
Whether planning a weekend escape or a full cross-region road trip, here is a guide to six distinct hubs across Southwestern Ontario—including a central stop to refresh your wardrobe.
1. Kitchener-Waterloo: The Tech & Heritage Hub
Known as Canada’s Silicon Valley, the Twin Cities blend innovation with deep historic roots.
-
What to Do: Explore Doon Heritage Village, a living history museum showing life in 1914, or walk the tech corridor downtown. Just 15 minutes north, visit the famous St. Jacobs Farmers' Market for fresh produce, local crafts, and traditional Mennonite baked goods.
-
Local Flavor: If visiting in autumn, Kitchener-Waterloo hosts the largest Oktoberfest celebration outside of Germany.
2. Guelph: The Royal City
Guelph offers historic limestone architecture, active green spaces, and a thriving farm-to-table culinary scene.
-
What to Do: Marvel at the Gothic revival architecture of the Basilica of Our Lady Immaculate overlooking the city. Take a peaceful stroll through the University of Guelph Arboretum or wander around Riverside Park along the Speed River.
-
Local Flavor: Grab a craft pint downtown—Guelph has a strong independent brewing culture fueled by local agriculture.
3. London: The Forest City & Style Destination
Positioned right in the geographic center of Southwestern Ontario, London offers the amenities of a large urban center alongside extensive parkland—making it the ultimate mid-trip stopover.
-
What to Do: Visit 100 Kellogg Lane, Canada's largest indoor entertainment complex featuring indoor ropes courses, arcades, and craft breweries housed in a historic cereal factory. For history lovers, stop by Banting House, the birthplace of insulin.
-
Shop & Refresh Your Style: Take a short drive over to Big & Tall London's Menswear (located at 2205 Wharncliffe Rd S). Because London sits at the crossroads of the region (just a short drive under an hour from Kitchener-Waterloo, and around an hour and a half from Windsor or Sarnia), it's a convenient pitstop to pull up, step inside, and try on clothing in person.
-
Sizes for Menswear: Finding proper-fitting extended sizes while traveling can be a challenge, but this local favorite carries hard-to-find options, including:
Skip the guessing games of online shopping, take advantage of their in-house tailoring services, and walk out with a tailored fit before continuing your trip.
-
Local Flavor: Walk along the Thames River at Springbank Park before grabbing dinner at Covent Garden Market downtown.
4. Chatham-Kent: History & Great Lakes Coastlines
Stretching between Lake St. Clair and Lake Erie, Chatham-Kent is packed with rich Canadian history and scenic rural drives.
-
What to Do: Explore the Uncle Tom’s Cabin Historic Site (Josiah Henson Museum) in Dresden to learn about the Underground Railroad history in Canada.
-
Local Flavor: Head south to Rondeau Provincial Park for birdwatching, sandy Lake Erie beaches, and hiking through rare Carolinian forest.
5. Windsor: Border Culture, Pizza & Craft Spirits
Canada’s southernmost city sits right across the river from Detroit, offering iconic waterfront views, rich history, and a distinct food identity.
-
What to Do: Stroll through the Windsor Sculpture Park along the waterfront, or take a distillery tour through historic Walkerville, the neighborhood founded by Hiram Walker of Canadian Club whisky fame.
-
Local Flavor: You cannot leave without trying Windsor-style pizza—famous for its shredded pepperoni, canned mushrooms, and sweet galati mozzarella.
6. Sarnia: Lake Huron Waterfront & Blue Water Views
Located at the mouth of the St. Clair River on Lake Huron, Sarnia is the ultimate stop for freshwater views and beach town vibes.
-
What to Do: Walk along the waterfront under the Blue Water Bridge connecting Canada to Michigan. Spend a summer day swimming or sunbathing at Canatara Park Beach.
-
Local Flavor: Grab a bag of fresh, vinegar-soaked fries from the famous chip trucks parked under the Blue Water Bridge.
Quick Southwestern Ontario Road Trip Route
To turn this into a seamless loop itinerary, start in Guelph or Kitchener-Waterloo, take the short drive down Hwy 401 into London (where you can stop at Big & Tall London's Menswear to try on clothing and pick up new menswear sizes), continue southwest to Chatham-Kent and Windsor, then loop back north along the St. Clair River through Sarnia before heading back east.
