The Brief The 2025 Windermere Cup returns to the Montlake Cut this weekend, with the highly-anticipated rowing event expected to draw hundreds of spectators. The 2025 Windermere Cup is happening in Seattle this weekend, with the highly-anticipated rowing event expected to draw hundreds of spectators. When is the 2025 Windermere Cup? The Windermere Cup is on Saturday, May 3, with the first race scheduled to begin at 10:15 a.m.Where is the 2025 Windermere Cup? Each race lasts just a few minutes except the later ones, which includes showdowns for the Erickson Cascade Cup and coveted Windermere Cup trophy.