whitby ontario winter day

How to spend a winter day in and around Whitby Ontario

As someone who loves escaping the hustle of Toronto for a day of exploration, I recently set out for Whitby, Ontario, eager to immerse myself in both the natural beauty and the charm of historic downtown Whitby. 

The day unfolded as a delightful mix of serene wilderness, thrifty discoveries, and a step back in time.

Starting the day with a morning hike

My first destination was the Herber Down Conservation Area, 10 minutes north of downtown Whitby. Navigating the Lyndebrook Road access point per my maps, I discovered it was closed for the winter season. 

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The Railway Trail in Herber Down Conservation Area, layered with heavy slush during an unprecedentedly mild January.

Undeterred, I rerouted to the year-round open access point at 5000 Cochrane St, a short five-minute drive around the park. 

The weather, however, had a different plan - mild temperatures and steady rainfall transformed the snow into a cold, slushy challenge that seeped into my boots. 

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The pine trail on the eastern side of Herber Down Conservation Area offered a break from my trudge through the slush found throughout other trailways.

Despite the less-than-ideal conditions, my determination to relish the tranquility of trees and solitude prevailed.
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This is the view out across one of the fields at Herber Down Conservation Area from the entrance to the pine corridor trail-head at the south-west corner of the Cochrane Street parking lot.

Herber Down Conservation Area, spanning 687 acres and featuring three trail loops totalling over 5 kilometres, was a haven of diverse landscapes - forests, meadows, and wetlands. 

Opting for an aimless stroll, I meandered through the wilderness, embracing the freedom to explore at my own pace. Once partly farmland, this area was acquired from Heber Down in 1967 by the Central Lake Ontario Conservation. 

It now boasts intriguing trails like Devil's Den and Railway Trail, the former earning its name from historical horse-thieving rumours.

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Growing up, my father and I would spend many winter days standing at the back window of our kitchen watching cardinals pick berries from our winter garden. Cardinals now always make me think of him, and one day I will get one to eat out of my hand on camera, just for him.

During my return to the car, elusive cardinals made brief appearances amidst the towering pine trees surrounding the trail. Despite my attempts to capture them on camera and share some berries as a gesture of friendship, their cautious nature thwarted my efforts and patience.

An afternoon of shopping and dining in Whitby

Soaked through from the chilly wet conditions, I decided to continue my Whitby adventure with a visit to Talize, my preferred second-hand shop in town, offering a superior alternative to Value Village. 

An hour of treasure-hunting rewarded me with barely-worn Sorel boots, cozy track pants, kids' clothing, and household items - all under $100.

Rejuvenated by my thrifty finds, I proceeded to historic downtown Whitby.

whitby ontarioAround the Brock Street centre, I discovered historical plaques narrating the city's unique heritage and events, emphasizing its distinct identity despite now being viewed by some as an extension of Toronto.

Downtown Whitby offers many activities, including a visit to 8 Bit Beans, a nostalgic restaurant celebrating the '80s and '90s with over 10,000 retro video games. 

For a more relaxed experience, numerous pubs, vintage shops, unique boutiques, and tattoo studios await visitors exploration.

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A delicious chai latte and lemon cranberry scone always brightens my day. Brock St. Espresso was a delightful pitstop on my Whitby daytrip.

Opting for a cozy cafe experience, I savoured a delicious chai latte and pastries at Brock St. Espresso, surrounded by calming music and vibrant greenery this cafe made for an excellent and warming break in my day.

An afternoon filled with nature

Completing my day, I headed south to Lynde Shores Conservation Area, where the winter magic unfolded with close encounters with bunnies, deer, squirrels, waterfowl, and songbirds that ate right from my hand.

This gem was established in 1972 and today spans 272 hectares with an adjacent 40-hectare Cranberry West Tract. Its 5-km looping trails, especially the family-friendly Chickadee Trail, offer an enchanting experience.
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During my trip to Lynde Shores Conservation Area I was lucky to have such a close encounter with a small group of white-tailed deer.

Perfect for wildlife enthusiasts, Lynde Shores is a vital stop for migrating birds, in addition to being home to many other beautiful creatures like white-tailed deer.

All together, Whitby, a short trek from Toronto, proved to be a captivating day trip, blending the tranquillity of nature with the charm of historic downtown, offering a well-rounded escape for any explorer.

Photos by

Erin Horrocks-Pope


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