Predicting how food webs will respond to global environmental change is difficult because of the complex interplay between the abiotic forcing and biotic interactions. Mechanistic models of species interactions in seasonal environments can help understand the effects of global change in different ecosystems. Seasonally ice-covered lakes are warming faster than many other ecosystems and undergoing pronounced food web changes, making the need to forecast those changes especially urgent. Using a seasonally forced food web model with a generalist zooplankton grazer and competing cold-adapted winter and warm-adapted summer phytoplankton, we show that with declining ice cover, the food web moves through different dynamic regimes, from annual to biennial cycles, with decreasing and then disappearing winter phytoplankton blooms and a shift of maximum biomass to summer season. Interestingly, when predator-prey interactions were not included, a declining ice cover did not cause regime shifts, suggesting that both are needed for regime transitions. A cluster analysis of long-term data from Lake Baikal, Siberia, supports the model results, revealing a change from regularly occurring winter blooms of endemic diatoms to less frequent winter bloom years with decreasing ice cover. Together, the results show that even gradual environmental change, such as declining ice cover duration, may cause discontinuous or abrupt transitions between dynamic regimes in food webs.