Cycling the Cressy Loop

The ride naturally begins at Beacon Bike and Brew in downtown Picton. Early in the morning the café patio fills with cyclists checking tire pressure, discussing wind direction, and planning how many stops they will try not to make.

Coffee in hand, riders roll east along Main Street before turning at the flashing light. Within minutes, a short downhill carries you out of town and onto Union Street, which soon becomes County Road 8. Traffic fades, shoulders widen, and the ride begins to feel rural. 

This first stretch eases you into the County. The road undulates gently, passing farm fields and glimpses of water, giving legs time to warm before the day unfolds. After about 11 kilometres the route turns onto County Road 13 and enters Waupoos, where many riders realize they will need to abandon any strict schedule. Stops appear naturally — not as destinations, but as part of the ride itself. 

Cressy Mustard makes a perfect early pause, known as much for its specialty fish as its condiments.

 A little farther along, Waupoos Estates Winery sits right on the waterfront, its dock extending into Prince Edward Bay. Even riders who plan only a quick refill often linger here, drawn by the calm water and the sense of having arrived somewhere far removed from daily routine.

Soon after comes one of the ride’s iconic features: the climb up Bongards Hill to the County Cider Company. The ascent is short but memorable, and the reward is a sweeping view over the bay that encourages a longer rest than intended.

Leaving Waupoos, County Road 8 rolls quietly through farmland toward the midpoint of the ride. Fifth Town Artisan Cheese appears around a bend, often prompting riders to tuck a carefully wrapped purchase into a jersey pocket for later.

A few kilometres farther, the shoreline opens at Prinyers Cove, a natural photo stop where riders regroup and glance ahead toward the hills rising in the distance. Until this point the ride has been gentle and forgiving, but the terrain soon changes character. 

Gradually the road begins to climb toward Lake on the Mountain, one of the County’s defining landmarks. The ascent is steady rather than steep, allowing riders to settle into a rhythm while anticipation builds. At the top, the landscape suddenly drops away to reveal the Glenora Ferry crossing Adolphus Reach far below — an unexpected view in eastern Ontario and one that regularly stops cyclists in their tracks. It is a natural place for lunch, whether at the nearby restaurant or simply on a bench overlooking the water, watching boats and the ferry move through the narrow channel.

What follows is the emotional high point of the ride: the descent down Lake on the Mountain Road. Smooth pavement curves toward Loyalist Parkway in a sweeping drop that feels both thrilling and controlled, the kind of descent riders replay in conversation long after the day ends. At the bottom, the ride settles again into relaxed cruising along quieter roads toward Picton. The final kilometres bring a gentle return to town, but not without one more welcoming stop.

The Claramount Inn offers riders a place to refuel, whether with a full meal or a quick patio snack nearby. By now the ride has shifted from exercise to experience, and conversations begin to stretch — favourite views, hardest climb, best unexpected moment.

Soon the familiar streets of Picton reappear and the route closes where it began, back at Beacon Bike and Brew, often for a well-earned drink and a lingering discussion that lasts nearly as long as the ride itself.