Dunedin is the most rider-friendly town along the Pinellas Trail and a logical base or lunch stop. The trail cuts directly through the compact downtown, with the path widening into a linear plaza of patios, breweries, and bike shops. Dunedin Brewery, the oldest microbrewery in Florida, sits a block off the trail; Caledonia Brewing, HOB Brewing, and several others are within a five-minute walk.
The town earns its Scottish character from a wave of settlers in the 1870s, and the annual Highland Games in April still fill the streets with kilts and bagpipes. From Dunedin the trail continues north toward Palm Harbor through the prettiest section of the entire route — heavy shade, old wooden bungalows, and glimpses of the bay between live oaks.