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York is supposedly the most haunted city in Europe, so there are many attractions that are a bit on the shady side. Start with York Dungeon, where live actors re-enact scenes of torture, plague and execution in grisly detail. Then, there is the Micklegate Bar Museum, which stands at the main gateway of the city, where the heads of executed traitors were once displayed to encourage citizens to abide by the law. During the summer, Yorkboat also offers a 90-minute ghost cruise, complete with costumed storyteller. If that is not enough excitement, take an evening Ghost Walk. Tour guides will escort you through the narrow alleys of York, recounting tales of York’s haunted past.
For interesting dining options, there’s Plunkets on Petersgate, which offers fine dining against a backdrop of hippie décor from the 60’s.
York has a few gay-friendly bars. The York Arms at 26 High Petergate is an open-minded bed & breakfast whose rooms are also reasonably priced. There is also the Pink Pony on Gillygate and Thomas's Bar is gay friendly but without being an overtly gay-specific establishment.
If you really want to get out of the tourist zone, you could try to book in for a meal at the excellent Meltons restaurant on Scarcroft Road. Premium prices, but premium quality.
There is a pleasant 1.5 mile walk down one side of the river, across the pedestrian + cyclist only Millennium Bridge and back up the other side. Start at Skeldergate Bridge and head out of town on the west (=south) bank, and the return journey will reward you with a leafy path. At night the bridge has a stunning lights display which is worth seeing. When you get half way back, a short detour down Alma Terrace will take you to a real local English pub, The Wellington Arms, with tiny original rooms and Sam Smith's beer. If you get in the mood for exploring further, another 200yards to the end of the road on the opposite side of the busy Fulford Rd will bring you to the Fulford Arms, which often hosts local bands. Retrace your steps along Alma Terrace, or catch the no7 or 416 bus into town if you have walked far enough, alighting by York Dungeon.
Where the Minster is York's "big church" there is also the "Secret Church" (Holy Trinity) tucked away at the crook of Goodramgate and Low Petergate. You will really have to look for the entrance, just a little way into Goodramgate on the left. This is a beautifully tranquil ancient church where you can be transported back in time only yards from the bustle of the city.
The Golden Fleece pub opposite the outer end of the Shambles has the most gloriously crooked corridor from the front to the back bar. Get your friends to stand at one end and amaze them as you appear to shrink before their very eyes as the corridor messes up their sense of perspective. The Olde Starre is a nice pub down a long corridor and Trembling Madness is a well hidden delight - upstairs above "The Bottle" in Stonegate.