From Kipling you can travel via Saskatchewan Snowmobile association trails via snowmobile to the US through the port of Carievale or from coast to coast once you go far enough north to access the Trans Canada Trail system. You can also access Windthorst, Corning, Stoughton, Estevan, Weyburn, Carlyle, Redvers, Oxbow, Carnduff, Arcola, Kenosee Lake, White Bear, Grenfell, Broadview, Yorkton, Hudson Bay, Nipawin, Prince Albert, and areas north to Candle Lake. Check out the local website:
sasksnow.com/trail-club-updates/zone3/moose-mountain-snowmobile-club-311/