Leave Brampton around 7:00 AM, taking Highway 401 east toward Belleville, then County Road 49 south toward Picton. The drive is usually 2½–3 hours, but a Sunday in August can be slower, so bring coffee, water, and a quick breakfast for the car. Continue straight to Sandbanks Provincial Park rather than stopping in Picton first; day-use parking can fill by late morning, and entry is subject to the park’s daily capacity and vehicle-permit system. Spend about two hours at the West Lake beach swimming and walking the broad sandy shoreline. Wear water shoes if you have them, bring shade and plenty of water, and expect limited food options inside the park.
From Sandbanks Provincial Park, drive roughly 30 minutes east to The County Cider Company in Waupoos. Settle in for a relaxed tasting and light lunch with vineyard and Lake Ontario views; allow approximately $25–45 per person, and check the current Sunday kitchen and tasting hours before leaving, since seasonal service changes. Afterward, continue toward Lake on the Mountain Provincial Park, where a short stop of 30–45 minutes is enough to see the striking elevated lake and viewpoints. There is little shade, so this is best as a scenic pause rather than a long walk. Then return toward Picton for Macaulay Mountain Conservation Area. Its woodland trails and lookouts over Picton Harbour make a pleasant late-afternoon walk; allow about an hour, wear proper shoes, and keep an eye on trail conditions and daylight.
Leave Picton around 6:30–7:00 PM, following Highway 62 north to Highway 401 west toward Brampton. Plan on another 2½–3 hours, with longer travel possible after a summer weekend. If everyone needs food or coffee, stop around Belleville before settling into the 401; it is easier than waiting until you reach the busier Toronto-area stretch. Refuel before leaving the County, and expect to arrive in Brampton around 9:30–10:30 PM.