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Hellingly sits just north of Hailsham, where the landscape begins to roll toward the Low Weald. At its heart is a rare and ancient "church cirque," where the village houses and the 13th-century church of St Peter and St Paul are arranged in a defensive circular layout that predates the Norman conquest. The Cuckoo Trail, a popular 14-mile surfaced path following the route of the defunct "Cuckoo Line" railway, cuts right through the parish, providing a direct, off-road link for walkers and cyclists heading toward Heathfield or Polegate. While the village has grown significantly in recent years with the redevelopment of the former hospital site at Roebuck Park, it manages to keep its distinct identity apart from Hailsham. The Upper Horsebridge area serves as the practical hub of the parish, where the River Cuckmere passes under the road and the local secondary school is located, making the village a functional base for daily life rather than just a historic curiosity.