Troy is a bit sketchy in certain areas.There's a lot of runned down neighborhoods. I try not to linger there too long, especially after dark. A group is probably a bit safer.

Troy, Schenectady, and Albany are the top ranked for (violent) crime rates in the region.

However, there are a few interesting things to see and do in each city. When visiting, just use common sense precautions like you would in any other city, and be aware of your surroundings.

Upstate NY has very little in terms of location pins, unfortunately.

Grew up there, and didn't even see a location pin till I was 12 :/

There is an Addams Family (3 games for a dollar) at McGeary's in Albany right near a Hampton Inn on Pearl Street. I think there is another pin in a bar across Pearl Street. Both Albany and Troy have universities, and as long as you stay out of the sketchier areas, you will be ok. I stayed at the Hampton Inn during Labor day.

I've played there many times and also at the Hangar across the street. Which venue and who's playing? Where the club is isn't bad, as others wrote there are bad 'hoods' around the area.

I used to work in Troy. Most of Troy is sketchy but I never had any major problems. I never saw a show the Ale House but I worked on River St. and went to the Ale House many times for lunch. It's located on the Hudson River in a so-so neighborhood. Parking sucks there. Try not to park on the street if you can. The building is pretty nice, good food, although it's been almost 10 years since I have been there.

I have been to McGeary's many times. It is close to the Palace Theatre so it's a good place to hang out before a show.

You would probably have to go to NYC for that.

There may be a few places in Rochester, NY, though.

There is the sanctum in Meriden, CT, but it's only open on Monday evenings.
https://www.facebook.com/thepinballsanctum/

No public places out here have more than two machines. Buffalo has Pocketeer with 40+ machines, and I've heard there'll be a place opening in Syracuse soon

A month earlier and Saratoga Springs would be the place to go with the racetrack open and lots of concerts at SPAC. Lot's of good golf courses in the highlighted area. If you want a touristy place to go there is Lake George. Lake Placidis cool, and preferable to Lake George IMO, but it is off the beaten track. Too early for skiing.

Be careful driving on the Northway. The troopers love giving tickets to Canadians.

There's a number of interesting non-pin related attractions, but if you're looking strictly for pins, there's very little in that area. A small handful of locations with one or two pins. Lake George might be your best bet, though the arcade with the largest number of pins have titles that are poorly maintained and heavily routed.