DAY 1 – 9:00 AM: SPEND THE MORNING TAKING IN THE VIEW OF LAKE ONTARIO AT THE PICKERING NAUTICAL VILLAGE.

Pickering is your first stop on this journey from lake to lake, and where better to kick things off than on the shores of Lake Ontario? Like any settlement on the water, Pickering was and continues to be a nexus of trade, travel, and communication.

Sheltered along the coast of Frenchman’s Bay and watched over by a lighthouse, Pickering Nautical Village is a popular spot among locals and tourists alike. Picturesque buildings line the wide streets, housing boutique shops, restaurants, and spas.

Afterwards, make your way over to Millennium Square to enjoy the waterfront more thoroughly. The nearby marina is full of boats, yachts, and just about anything that floats. If you’re in the mood for a walk, consider the Waterfront Trail, but don’t go too far—it runs from Gros Cap in Sault Ste. Marie to Cornwall!

DAY 1 – 11:00 AM: EXPLORE THE HISTORY OF THE REGION AT THE LYNDE HOUSE MUSEUM

Jabez Lynde, a United Empire Loyalist, became one of the first landowners in the region. He helped develop the roads that became vital for trade, communication, and moving troops in the area. Lynde’s home, built in the infamous year of 1812, became a tavern and inn during the great war between British North America and the United States. General Brock was one of the many notable people who stayed within its walls. Now, at the Lynde House Museum, visitors can immerse themselves in the 19^th-century experience of the home and learn about the history of the area.

Be sure to keep an eye out for a pair of green spires and a curiously paint-splattered locomotive. The Station Gallery, formerly Whitby’s Grand Trunk Railway Station, is where local artists exhibit their work and teach their craft to the public. Come by at the right time, and you might just catch a concert taking place on the porch.

DAY 1 – 2:00 PM: CHECK OUT SOME LOCAL ART AND CULTURE 

Oshawa is a place built on getting people moving, which is fitting because the city’s name comes from an Ojibwe term which means “that point at the crossing of the stream where the canoe was exchanged for the trail.”

Downtown Oshawa is notable for the architecture of Oshawa City Hall and The Robert McLaughlin Gallery. The latter is named after the founder of General Motors Canada and has the most extensive collection of works by the Painters Eleven, a group of artists who helped make abstract art popular in Canada. One of the artists, Alexandra Luke (also known as Margaret McLaughlin), helped establish the gallery with her husband, Ewart McLaughlin.

The McLaughlin family’s fingerprints are all over Oshawa⎯⎯their former residence has been declared a National Historic Site. Darling and Pearson, the architecture firm responsible for the Royal Ontario Museum and Toronto General Hospital, designed the Parkwood Estate

. Its classical revival style and Georgian flares have made it an iconic structure⎯⎯it has been the backdrop for many productions, including X-Men, Anne of Green Gables, Chicago, and Murdoch Mysteries!

DAY 1 – 5:00 PM: BEFORE THE SUN SETS, HOP IN A CAR AND DRIVE NORTH.

Port Perry is a picturesque community nestled on the southwest shore of Lake Scugog. Take a stroll through the streets of its Victorian-era downtown, where there are plenty of shops, cafes and restaurants to cater to the weary traveller. The town is small enough that you can walk off dinner with a quick jaunt to the marina or through Palmer Park. Watching the sunset over the calm waters of Lake Scugog is the perfect way to end the night.

DAY 2 – 9:00 AM: CHECK OUT META4

Port Perry might be small, but it’s not without its own gallery. META4 is part art-supply shop, part studio, and part exhibition space. Local artists stop by to stock up on materials and talk shop while instructors teach a variety of techniques. And of course, there’s no shortage of art on display, with over 130 artists’ work available to view or purchase.

DAY 2 – 12:00 PM: THIS NEXT STOP IS A MUST FOR FANS OF ANNE OF GREEN GABLES.

Fans of Anne may not know that the author married Presbyterian minister Ewan McDonald and moved to Leaskdale, Ontario, when she was 37. Montgomery wrote 11 novels during her time there. In a testament to Montgomery’s significance to Canada’s literary tradition, her modest brick home, Leakside Manse, became a National Historic Site in 1997.  Just next door is St. Paul’s Presbyterian Church, where Montgomery’s partner was a minister. The church now serves as an interpretive centre and as a venue for local events.

No Anne super-fan should miss out on the chance to sneak a selfie with the likeness of this famous author¾ a life-sized, bronze statue of Montgomery sits in the Manse’s back garden.

DAY 2 – 5:00 PM: THE LAST STOP ON YOUR DURHAM EXCURSION IS THE THOMAS FOSTER MEMORIAL, WHERE FORMER TORONTO MAYOR THOMAS FOSTER NOW RESTS.

The building was inspired by Byzantine architecture and Foster’s visit to the Taj Mahal.  Outside, several minarets reach skyward, while inside, copper domes rise up, held aloft by thick marble columns and stone capitals.  Large stained glass windows fill the space with light, causing the mosaics to glimmer. Take a moment to reflect upon this solemn, but striking piece of Canadian architecture as you bring your journey to a close.