Cycling the Cressy Loop

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. 

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.

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. 

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.