Philipsburg offers what is probably Montana's most picturesque outdoor skating experience at Winninghoff Park. The Missoulian newspaper described the rink, and the backdrop of century old buildings nearby, as 'a scene from Currier & Ives.' Built in the National Historic District, it is only a block from Philipsburg's famous candy store, lodging, restaurants and other downtown amenities. This NHL-sized natural ice rink is also the newest in the state and was erected on a 40-year-old rink site. The new facility is made of a special rink liner with 24-inch boards. Ice conditions vary with the weather but the town does have its own Zamboni for ice maintenance. There is also a sledding hill adjacent to the rink. Children under 16 must wear helmets. Helmets are available for use at the rink.

The Philipsburg rink is open to the public seven days a week until 10pm in the evening. It has a lighting system for week nights and is turned on from 6pm to 10pm Friday, Saturday and Sunday evenings or by arrangement for scheduled events.