We took 2015 off and we visited Salem on Halloween. I will say this: it is absolutely an EXPERIENCE. The amount of people in the streets on Halloween is in the thousands. There were people throwing candy from buildings, a beer garden, the shops along Essex street were open and later on throughout the night there was a DJ set up that played really funky mashups with a Halloween twist. The real fun is just walking around and enjoying the atmosphere. If you want to sightsee, you need to do that before Halloween. So this past year, we went up Thursday -Sunday. Thursday we went around and visited Hocus Pocus locations, Friday we did some sightseeing and then that evening went to the Hawthorne Hotel's annual Halloween party and then Saturday we went out and enjoyed Halloween.
NOW, I will also say this--PARKING IS ATROCIOUS. There will be nowhere to park, so just plan that now. There are a handful of parking garages in downtown Salem and they WILL all be full. At least the day of and before Halloween. Parking garages go up to $20 on Halloween and there will be parking areas that the locals set up for people to park...also for $20....and they also will be full. NOW, we found a parking garage RIGHT on the very outskirt of downtown that NEVER filled up...mostly because people didn't know about it I expect. If you want, I can give you the info on it's location BUT the good thing is in Salem everything is so close together that it was literally a 5 minute walk from the garage and you were at the intersection of Essex street where everything happens. ALSO that parking garage's rates never went above 5 dollars...even ON Halloween. The only caveat is that they close early on Halloween(I think by 8p.m.) so if you don't get your car out by 8 you're gonna be stuck until 1 a.m. or so. BUT the festivities are shut down at 10 p.m. anyway with the fireworks show...so you're only cutting it out early by 2 hours.
We also chose to stay at the Mariott in nearby Peabody which is a 15 minute drive...they were very reasonable and the only place that had anything open. (rooms book a year in advance in a lot of places)
The locals were VERY nice, the witch shops are fun to peruse and pick up some odds and ends, the cemeteries were my favorite part, though. And everything is condensed into downtown Salem so once you park you can walk everywhere. You do get local conservative groups that preach some very ignorant hate speech in the days leading up to Halloween. (One guy was going on about how God hates Dracula, which I thought was kind of funny.)
I will say the Hawthorne Hotel party was...not so great. There were beautiful costumes and it was fun but...WAY too many tickets were sold and it was very crowded and the DJ's weren't hitting on much. The Salem Witches host a costume ball at the Hawthorne too...not sure about that one but the tickets for that are very pricey.
Overall, it was something that I believe EVERY true Halloween fan needs to experience at least once but we definitely missed OUR party and OUR people so we're excited to get back to it this year! Feel free to message me about any questions whatsoever.