Hamilton, with its vibrant mural arts scene and picturesque natural trails, has stolen my heart—not just as a city outside Toronto, but as a thriving community filled with hidden treasures waiting to be uncovered.

After a recent visit to Toronto, I hopped on a train from Union Station to Waterdown, a quick one-hour journey that was easy, and incredibly convenient.

Our mini-tour of the area kicked off with a visit to Smokey Hollow, a stunning waterfall and lookout. It was such a delightful surprise to find this serene natural gem so close to an urban center.

We took a scenic drive along “the back route” toward Hamilton, making a stop at Clara’s Climb. This lookout holds a special connection to Winnipeg-born cyclist and speed skater Clara Hughes, who passed by here countless times while training to become Canada’s most accomplished Olympian. The view was absolutely stunning!

Our final nature stop was Sherman Falls, a peaceful stroll into a charming spot where we could soak in the beauty of cascading waterfalls and the serene forest surroundings.

Next, we headed downtown for an urban mural tour, where Hamilton’s streets are full of unexpected artistic treasures waiting to be discovered.

After braving the chill, we wrapped up the day with dinner at Rapscallion & Co. – a chic, modern restaurant featuring an impressive wine list and expertly crafted cocktails to perfectly compliment their creative menu.

After dinner, we headed to Bar Sazerac for cocktails—a cozy, hidden gem just down the street from the restaurant. With its cozy setting and renowned modern, creative cocktails, it absolutely lived up to expectations.

Day 2

Next on the itinerary: a wine tour through the Niagara Escarpment and surrounding area! Just an hour southeast of Waterdown, the early October shoulder season offered a peaceful and uncrowded experience.

Here’s a link to a map & list of wineries.

We kicked off our tour at Creekside Estate Winery, where we enjoyed a tranquil patio with a beautiful view. It’s definitely a spot to visit in the spring or summer, when you can fully relax and soak in the atmosphere on their patio.

Our second stop was Vineland Estates Winery, a spacious property with a stunning loft overlooking the tasting floor, where we enjoyed our wine tasting.

Our final and favourite stop of the day turned out to be an unexpected gem—Redstone Winery. Here, a former wine colleague from Vancouver now manages the tasting room, and the experience was absolutely fantastic!

They also have a charming restaurant with breathtaking views of the vineyard and host special dinner events throughout the year.

Our mini-tour was just a teaser of this vast wine region, and I’m already looking forward to returning for a deeper exploration. I was pleasantly surprised to discover that this area offers so much more than it initially appears.

On our way back to Waterdown, we made a quick stop at Starsky, an Eastern European deli and grocery chain in Ontario, with lots of fun culinary finds.

Later, my cousins treated me to a beautifully prepared dinner inspired by Yotam Ottolenghi’s latest cookbook, Comfort. As someone who enjoys experimenting with new recipes and chefs, I found Comfort to be an intriguing and inspiring cookbook.

We uncorked a delightful Blanc de Noirs bubbly from Redstone Winery to toast to a wonderful visit.

I hope you get the chance to explore this area someday, it’s a peaceful escape from the big city, and there is much to see and do.

Until next time, keep exploring!

Cheers, Donita