This is the official bike route through the Parco della Collina del Penz (Penz Hill Park). It's a mishmash of various trail surfaces and it doesn't have a real beginning or endpoint. It's not the best ride in the area, but it is the most likely to be rideable in the dead of winter. It's accessible from the Chiasso train station using via Luigi Favre, so that's where this GPS starts.
Heading clockwise, the route starts with an easy forest road. This deposits you onto a perfectly-flat, perfectly-straight stretch with a nice view of a concrete water channel and part of the Chiasso rail yard.
The most/only difficult part of the ride is next with a 0.5-mile (0.8 km) climb of about 100 m (300 ft) of the side of the Collina del Penz (Penz Hill), which is the high point in the local area. This takes you to the paved Strada Regina (Queen's Street), which you follow into the village of Pedrinate. From the roundabout in the center of town, continue on via al Laghetto. This takes you to a singletrack section that runs along the Italian border.
The start of the singletrack represents the high point along the route and from here you'll enjoy about 250 m (700 ft) of descent back to the starting point. The singletrack becomes a forest road that loops back almost to the center of Pedrinate. From there, the paved via Oscar Camponovo takes you back to the starting point.