Places

• Heartbreak Hill refers to several ascents in footraces perceived as difficult for the runners:
  • in the Boston Marathon
    Boston Marathon
    The Boston Marathon is an annual marathon hosted by the U.S. city of Boston, Massachusetts, on Patriots' Day, the third Monday of April. Begun in 1897 and inspired by the success of the first modern-day marathon competition in the 1896 Summer Olympics, the Boston Marathon is the world's oldest...
    
    , Heartbreak Hill is an ascent about 20 miles from the start
  • in the City2Surf (Sydney) Heartbreak Hill is a 2km long winding ascent starting about 6km into the race
  • a steep sand dune located at Cable Beach
    Cable Beach
    Cable Beach is a stretch of beach near Broome, Western Australia. Cable Beach was named after the telegraph cable laid between Broome and Java in 1889....
    
     in Broome
    Broome, Western Australia
    Broome is a pearling and tourist town in the Kimberley region of Western Australia, north of Perth. The year round population is approximately 14,436, growing to more than 45,000 per month during the tourist season...
    
    , Western Australia
    Western Australia
    Western Australia is a state of Australia, occupying the entire western third of the Australian continent. It is bounded by the Indian Ocean to the north and west, the Great Australian Bight and Indian Ocean to the south, the Northern Territory to the north-east and South Australia to the south-east...
    
    , 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
  Trent and Mersey Canal
  The Trent and Mersey Canal is a in the East Midlands, West Midlands, and North West of England. It is a "narrow canal" for the vast majority of its length, but at the extremities—east of Burton upon Trent and west of Middlewich—it is a wide canal....
  
  

Music

• Heartbreak Hill (album)
  Heartbreak Hill (album)
  Heartbreak Hill is a studio album by English band Strawbs. The album was recorded in 1978 but, due to record deal and management difficulties, was not released until 1995...
  
  – an album by English band Strawbs

• Heartbreak Hill – an album by English guitarist Albert Lee
  Albert Lee
  Albert William Lee, born 21 December 1943 in Leominster, Herefordshire, England, is an English guitarist known for his fingerstyle and hybrid picking technique. Lee has worked both in the studio and on tour with some of the most famous musicians which stretch through a very wide of genres...
  
  

• Heartbreak Hill (band) – a Canadian country music band

• Heartbreak Hill (song)
  Heartbreak Hill (song)
  "Heartbreak Hill" is a single by American country music artist Emmylou Harris. Released in 1989, it was the first single from the album Bluebird. The song reached #8 on the Billboard Hot Country Singles & Tracks chart.-Chart performance:...
  
  " – a country music song appearing on the Emmylou Harris
  Emmylou Harris
  Emmylou Harris is an American singer-songwriter and musician. In addition to her work as a solo artist and bandleader, both as an interpreter of other composers' works and as a singer-songwriter, she is a sought-after backing vocalist and duet partner, working with numerous other artists including...
  
   album Bluebird
  Bluebird (Emmylou Harris album)
  Bluebird was an Emmylou Harris album from 1989, which merged a number of eclectic songs with polished, country-music production. It included her most recent top-ten country-charting single, "Heartbreak Hill"...