The pub is known for being a destination for coast-to-coast walkers, for once being washed into the sea (then rebuilt), and also for having its windows wrecked by the bowsprit of ship during a heavy storm.

[5][6][7] A similar event occurred in 1878 when a ship wrecked in the bay smashed the building's windows due to the eastern frontage looking out immediately over the sea wall.

[8][9][10] The rebuilt 1860s building was said to have "throbbed throughout" when the high tide lashed against its walls, but it had some protection in the form of a buttress protruding out onto the beach.

[18][19] The Robin Hood's Bay Folk Club have a regular meet and performance in the Wainwright Bar each week.

[21][22][23] The Bay Hotel has also been host to the ancient Court leet of Fylingdales, which is still extant today and deals mostly with land enclosure issues.