What are some great free things to do in or around Times Square?
The New York Public Library - Mid-Manhattan Library is at 42nd and 5th -- a couple of blocks east of Times Square. That's the main branch, the one with the big lions out front. They frequently have exhibits and events. The front steps are great for people-watching and there are often street performers.
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I recommend people to subscribe to the skint prior to visiting, a site that provides an agenda of free or cheap things to do in the city. While events may not center around Times Square, it is a centralized hub of most subway lines and will help you gain access to the whole city.
Honestly, the best and free thing to do in NYC is to walk around, absorb the energy and look up! NYC is unique, because distinct historical and cultural periods is evident in its architecture and amazing to see how the city has evolved.
Bryant Park has tons of free activities from free fencing lessons to juggling, language class, dance classes, and summer movies. Check out more here: http://www.bryantpark.org/plan-your-visit/calendar.html
if dad's a runner, there's a 10K in Queens http://www.nyrr.org/races-and-events/2015/nyrr-five-borough-series-queens-10k.
But, OK, you say you want to stay around Times Square. I assume you want to talk, and not just go to a show. I'm not a big fan of Times Square, so let me think of some answers that are left of center:
Take a walk along the Hudson. It's really pretty.
Go to the USS Intrepid.
Head down to the High Line Park - and walk there.
Of course, there are restaurants galore. I recommend going to the ones on 9th or 10th avenue. They are more original, more memorable, and less expensive.
there are two street fares, if you want some fried oreos or other street fare standard fare:
Walk around the Apple Store
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Hi Cathy! Sometimes there are free outdoors concerts on Broadway plaza , walking around or sitting for a few hours just watching the illuminated signs. I read on a magazine a few days ago that the city has been renovating some pedestrian plazas of the area, so this will add an extra bonus to your stay. I love to watch those who wear costumes (like the man wearing the cowboy hat and underpants, playing the guitar) or the many Elmos or Iron Men that can be seen all over Times Square. This is part of the NYC culture that makes me feel a little bit New Yorker. The above picture was taken by my daughter while simply watching the crowd.
Simple but not ordinary.