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Jun 21, 2023

9 min. read

Forget NAFTA negotiations and politics, the real relationship between Canada and the United States is best experienced in the small towns and villages that dot the world’s longest ‘undefended’ border. From bootleggers’ trading posts to historic settlements that were split in two by a border redrawn by war, here is a collection of fascinating spots to visit – all less than a day’s drive away from South Central Ontario.


Stanstead, Quebec and Derby Line, Vermont.

Manitoba, Ontario and Lake of Woods, Minnesota.

Sault Ste. Marie, Ontario and Sault Ste. Marie, Michigan.

Fort Frances, Ontario and International Falls, Minnesota.

The Thousand Islands, Ontario and New York, U.S.

Free maps or tour books.

Plotting your border town adventure.

Stanstead, Quebec and Derby Line, Vermont.

One of the best examples of a border town shared by Canada and the U.S. is in Quebec’s Eastern Townships. About an hour and a half southeast of Montreal, the towns of Stanstead, Quebec and Derby Line, Vermont were founded as essentially one village. A former Stanstead resident explained, “When I went to school in nearby Sherbrooke back in the late 1990s, you could fill up the tank of your car in one country and then cross the street and buy groceries in the other.”

A street with a white line painted on it.

In recent years, due to increased security concerns post 9/11, the border has become less arbitrary and more protected. Still, this town is home to the Haskell Free Library and Opera House, a public library built right on the border that sits in two countries at once! While the entrance is in America, the books inside are technically located in Canada. Citizens of both countries are free to enter without going through customs. The borderline is actually painted along the floor. The opera space on the second floor is the only one in the world known to have the seats in one country and the stage in another.

A living room with a table and chairs.

With rolling green hills, forests, rivers and hundreds of lakes, this region is a great spot to visit for camping, going to the cottage and skiing. And while you’re there, be sure to stop by for a drink at Checkpoint Charlie. Just on the Stanstead side of the border, this bistro/bar was one of Canada’s very first banks and still has its original vaults in place.

Manitoba, Ontario and Lake of Woods, Minnesota.

This area includes the Northwest Angle on the shores of the region of Minnesota that is cut off by land from the rest of the U.S. by Canada and marks the northernmost point of the U.S. other than Alaska. Americans can only access the territory (without entering Canada) by crossing the Lake of the Woods, which borders on Manitoba, Ontario and Minnesota, or by flying in.

The Angle, as it is known locally, is cut off from the rest of the U.S. by Southern Manitoba. Accessing the region by road requires crossing the border using the only gravel road in and out. Checkpoints along this route are unmanned. Travellers are expected to use a dedicated telephone at Jim’s Corner, or Carlson’s Landing to call and check in when crossing.

Known as the “Walleye capital of the world,” this region is a top choice for fishing and boating enthusiasts, as well as for camping, going to the cottage and outdoor adventure-seekers looking to explore the more than 14,000 islands, surrounding forests and shorelines of Lake of the Woods.

A yellow tent sits next to a lake in the woods.

Sault Ste. Marie, Ontario and Sault Ste. Marie, Michigan.

Sault Ste. Marie, Ontario is just across the border from a twin city of the same name in Michigan. The two were actually one city up until the war of 1812 when the border was drawn along the St. Mary’s River, but they are still connected by the International Bridge across the river.

A bridge over a canal with a boat in the background.

Sault Ste. Marie has been a settlement for thousands of years, serving as a crossroads of fishing and trading around the Great Lakes. French explorers and missionaries founded one of earliest European settlements in North America here in the 1600s.

This area is home to the classic shores of two Great Lakes, sandy beaches, unspoiled forests, winding rivers and the natural beauty of Northern Ontario. It also boasts one of the largest towns in the region. The Sault (or the Soo) has a population of roughly 75,000 people.

Experience a Canada that is largely unchanged since it was captured by the Group of Seven and pop across the border for a visit to the U.S. just by crossing a bridge.

Fort Frances, Ontario and International Falls, Minnesota.

Adventure lovers will find plenty to be excited about in the off-the-beaten-path border town of Fort Frances, Ontario. Founded in 1731 as the first European settlement west of Lake Superior, this destination is located where the Rainy River meets the waters of Rainy Lake. It is connected to International Falls, Minnesota by the aptly (if not succinctly) named Fort Frances–International Falls International Bridge.

The region is a haven for outdoor enthusiasts of every stripe. The waters of Rainy Lake – and literally thousands of other nearby bodies of water – make this area a top spot for fishing, boating and swimming.

In the winter months, Northwestern Ontario offers an abundance of snowshoeing, cross-country skiing and snowmobile trails, as well as ice-fishing opportunities on frozen lakes.

The region is also renowned for its spectacular sunsets, star-filled night skies and views of the Northern Lights. Enjoy the best of the great outdoors and, for a quaint visit to small town America, head across the river. International Falls was the inspiration for the fictional small Minnesota town of Frostbite Falls, the hometown of cartoon moose and squirrel of *The Adventures of Rocky and Bullwinkle and Friends *and is the gateway to Voyageurs National Park.

Fort Frances invites you to explore the Great Canadian Experience.

An aerial view of a city and river.

The Thousand Islands, Ontario and New York, U.S. 

Southern Ontario shares a unique border crossing with New York state along the St. Lawrence River and through the Thousand Islands. These are actually a collection of over 1,800 large and small islands dotting the waters of St. Lawrence for 80 kilometres from Kingston to Brockville.

The Thousand Islands region played a prominent part in the war of 1812 and many historic forts and military outposts remain to this day. The area was also widely used by bootleggers to move liquor across the river during prohibition, so the islands are home to mansions and castles built by the booze barons of the era.

For those not crossing by water, the Thousand Islands Bridge connects the town of Ivy Lea, Ontario with Alexandria Bay, New York. While the entire region is a haven for sightseers, explorers and fans of water-based activities, the Canadian side of the border tends to be more tranquil and laid back, while Alexandria Bay has more nightlife and action in the summer months. It is also home to a 10-day pirate festival every August, celebrating the nefarious history of the region.

An aerial view of a bridge over a body of water.

If you’re planning on visiting the region, and prefer to stay on dry land, take a detour off the 401 and enjoy the winding Thousand Islands Parkway, which runs along the river for nearly 55 kilometres between Gananoque and Brockville.

A house on an island in the middle of the water.

Free maps or tour books.

You know what they say, a little preparation goes a long way.

Besides the obvious (don’t forget to bring your CAA Membership card and your Canadian passport) we’ve got some great FREE tools that can help make getting to any one of these cool border towns a lot easier.

Whether you’re driving your own vehicle or taking advantage of one of our CAA Rewards® rental partners, be sure to pop into a CAA Store before you go to get FREE maps or tour books of the area.

A screen shot of a map showing a map of a city.

Plotting your border town adventure.

Besides the complimentary maps and tour books, CAA can help take the guesswork out of plotting the route for your excursion with our TripTik® Travel Planner.

TripTiks are customized direction maps that include driving instructions to your predetermined destinations in Canada and the U.S. They’re available in print and by email.

Your TripTik® Travel Planner comes with a ton of great info that will enhance your road trip experience, including:

  • Written instructions and full-colour maps to direct you from your starting point all the way to your destination, notifying you of detours and construction concerns along your route

  • Locations for CAA Rewards® partners, CAA and AAA approved hotels, restaurants and attractions on your journey

  • Available gas stations across North America (with current gas prices for most), electric vehicle charging stations and CAA partner vehicle rental locations

  • Travel advisories, strict speeding enforcement areas and more

You can create your TripTik® Travel Planner online at caasco.com or through the CAA App on your smartphone or iPad. You can also order one through your local CAA Store or by calling 1-800-268-3750.

What’s great about living in South Central Ontario is just how close we are to the U.S. border, where towns on either side have so much to offer. So when planning your next road trip, don’t forget to consider a quick jaunt to visit our neighbour to the south.

Photo credits: U.S. Canada border line drawn on the pavement image, courtesy of the Haskell Free Library & Opera House. Borderline running directly through the library image, courtesy of the Haskell Free Library & Opera House.

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