Discover Historic Charm in Kingston This Summer

Midway between Toronto and Montreal, this region is packed with outdoor adventure, historical landmarks, heavenly food and small-town charm

By Doug Wallace

Posted: August 03, 2021 01:40 PM ET

Port Hope, Cobourg and Kingston deliver a trifecta of Ontario-proud things to do. Map out your adventure and make it an extra-long weekend if you can.

Explore charming heritage buildings
See a Rideau Canal landmark
Take in the history of Kingston
Take in the scenic views of the 1000 Islands

Explore charming heritage buildings

An overhead view of a store. In the middle is a blue, red and black robot figure that is taller than the building. There are three people standing on the ground looking up at it. To the right of them are retro looking signs. The right of them are other items for sale, like a colourful rooster.

When you begin exploring downtown Port Hope, it won’t take long to discover that it has some of the most engaging heritage homes in Ontario. The Heritage Tour map will take you past iconic landmarks to carefully restored buildings such as the Hotel Carlyle and the Waddell Hotel. Make a point have a look around the family-owned Primitive Designs on County Road 28, which is filled with eclectic treasures from all around the world.

Next, head to picturesque Cobourg to discover its historic downtown, and stroll through Victoria Park or along the boardwalk. If you’re staying overnight, book a room at the Northumberland Heights or the Best Western Plus, where CAA Members can save up to 15 percent.

See a Rideau Canal landmark

A bridge overhead and below it, a small dam with blue gates over it, and two flights of concrete steps next to it with a walkway.

Departing Cobourg, your first pit stop is The Big Apple for a cider-tasting and snack—like an apple turnover or fritter.

Next, head to the historic Kingston Mills Locks 46-49, which is one of 24 lockstations on the Rideau Canal, a UNESCO World Heritage Site. Beginning in 1827, the area was cleared to build these locks to allow boats to bypass the Cataraqui Falls.

Take in the history of Kingston

A row of soldiers standing in a line. They are dressed in red jackets with bands of white criss crossing their chest and a white belt. They are wearing black hats with a ball that is half white on top and half red on the bottom.

Continue on to Kingston—dubbed the “Limestone City” because many of its historic buildings were constructed with the sedimentary rock that is abundant in the region.

Hop aboard a Kingston Trolley Tour, a bright red bus that takes you through the Old Town, and makes stops at the 19th-century Fort Henry, the Pump House museum, the Murney Tower and the notorious Kingston Penitentiary.

Take in the scenic views of the 1000 Islands

A man holding a cellphone up to take a photo of a stone building with turrets in the distance. He is on a boat, surrounded by water.

Wind down your getaway with a tranquil tour of the 1000 Islands. There are two options to see this destination nestled along the St. Lawrence River. Explore the region by boat with an audio guide, listening to tales of lost ships and passing by Boldt Castle. Alternatively, take a helicopter tour for a bird’s-eye view of the private island homes and the glistening waterways that stretch to the horizon and beyond.

Get expert advice

Looking for more ideas in Ontario? Visit Hidden Gems or speak with a CAA Travel Consultant who can help plan your ideal trip. Visit

Looking for more ideas in Ontario? Visit CAA Travel or call 1-800-992-8143 to start planning.

Image credit: Ben Flock, Port Hope Tourism, ArchonCodex/Alamy, Destination Ontario