Coming February 9, 2020. Meet you mate on the mountain! If you’re looking for someone special to spend Valentine’s Day with, check out Chairlift Speed Dating at Wilmot Mountain. This Wisconsin ski resort is a short drive away from Chicago and Milwaukee with nearly 120 skiable acres and 23 trails. A matchmaking service pairs singles up based on their interests and compatibility (a survey is sent ahead of time) and then couples head to the lifts. After a quick 3 minutes or so riding to the top of the slopes, couples decide whether to spend more time together or head their separate ways to be pair up again. After an hour, there’s a party at the ski lodge bar with après-ski giveaways.This year, find love on the lift at Wilmot Mountain’s Chairlift Speed Dating!