I'm from just across the lake (>>Wisconsinite<<) and there is no reason that you cannot ride through winter. Even if there is alot of snow, as long as you know that there is not ice underneath it. But perhaps 4 feet of snow isn't the best riding terrain, but about 1 foot would be fine. Trail riding is something your horse and you can enjoy, and you can fine tune some skills. Plus trekking through the snow is a work-out! It will definitely keep your horse in shape over winter.