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Heartbreak Hill may refer to:
- Heartbreak Hill refers to several ascents in footraces considered difficult for the runners:
- in the Boston Marathon, Heartbreak Hill is an ascent about 20 miles from the start
- in the City2Surf (Sydney), Heartbreak Hill is a 2km incline on New South Head Road starting about 6km into the race
- a steep sand dune located at Cable Beach in Broome, Western Australia, popular with tourists and locals for walking.
- Heartbreak Hill, a set of locks more formally known as the Cheshire Locks on the Trent and Mersey Canal
- Heartbreak Hill, local name for a work program operational in Redcar and Cleveland from 1932–1938, officially known as the Cleveland Work Camps