Halloween in the Hudson Valley is something special. It is spectacular, spooky and outrageous! Each town is better than the next on some level. Perhaps if you live right in Woodstock, Saugerties, Kingston or New Paltz you feel there is no competition. Your town does it better than any other. and you won’t hear otherwise. If you live in the smaller towns in between these destinations, you get to decide which place to go, and even have the luxury of changing destination each year if you so desire.
I grew up in Woodstock. Woodstock was it. I couldn’t imagine a town doing Halloween the way we did. The main street gets shut down to vehicles and the crowds take over. All the stores literally buy garbage bags full of candy to hand out to the revelers.
The costumes are outrageous. The young folks look adorable clad as superheroes, princesses, clowns and creatures. Yet it is often the grownups’ costumery that take the cake – inventive handmade costumes with fully painted faces in different shapes and sizes,
The costumes sometimes make sly political commentary, including thoughtfully designed couple costumes that are a play on words or a cluster of people portraying a group from a movie or show, with every individual playing a role. These costumes have been planned down to the tee.
There is a certain glee in the eyes of the costume-wearer when someone shoots out, “Hey, you are (so and so).” Ha ha, someone has figured out an obscure costume choice.
Naturally, when I had my child and Halloween came, we headed to Woodstock, even though I now lived in Stone Ridge. When your kid is small, you can head to Woodstock early, and your kid can take their time toddling from store to store trick-or-treating. There was time to get distracted and wander about. It was fun to be first.
Then the streets would begin to fill and fill and fill. And right at that moment your child would be tired. She had had enough candy, and it was a good time to go home. You have seen just enough imaginative costumes to feel you got to appreciate Woodstock at its best!
Once my kid was school-aged, we attempted for a few years to get to Woodstock after school as quickly as possible. When we arrived, we saw that the streets were already overrun. The candy had run out at half the stores. Fighting through the crowds became tiresome.
My kid wasn’t interested in seeing the costumes and commotion. Candy was key, and it just could not be gotten at the necessary pace to satisfy the lust for this as the one day for free candy!
So we changed our routine. After school, we would get into our costumes at a slower pace. We would go get some pizza. Then we would head into the Kingston neighborhoods.
Our favorite spot was behind the McDonald’s in the Armory neighborhood. The houses are spaced perfectly. There are blocks and blocks of houses, one after the other.
Kingston neighborhood trick-or-treating predictably starts at about 5:30 and runs until curfew. There is little to no traffic on these streets, so kids are free to dash from door to door. The faster they go, the more candy they get.
Parents can walk leisurely on the streets while their kids run maniacally to both sides of the street and on and on and on. Usually slightly before curfew, my kid’s energy would wane. The bag she was thrusting at the beginning of the night was dragging behind by the end.
I don’t remember many costumes or a particular group vibe in these neighborhoods, but if candy is your game this is the place for you.
At the end of the evening we would get in our car while our child happily chattered in back seat about how much fun that was. At home candy was dumped in a giant pile, sorted and counted: 100… 101… 102…103. Colorful piles and piles of Starburst, Smarties, Milky Ways, Laffy Taffy.
In other places, my kid would have possibly aged out of Halloween during the pandemic. High school in other areas declares kids too old for playtime. The Hudson Valley will not hear of that! There are as many teens and adults out on the street enjoying Halloween as there are little ones. With Halloween returning last year, we again decided to try a new town. Maturing does perhaps take away the desire for hundreds of pieces of candy. But Halloween is something to behold.
Still wanting to wear costumes, we headed to New Paltz. New Paltz has a very long Main Street, and we had heard that it had the biggest, most impressive parade. That sounded about right for a 15-year-old.
The parade indeed did go on and on. It started up at the high school and headed down the hill. The people kept coming, all ages from little kids to teenagers to college students to adults. Some had coordinated outfits, others had coordinated dances. There were costumes that lit up, there were handmade costumes of every variety.
We walked down the hill at the beginning of the parade, and we just sat and watched. The parade went on for what seemed like hours, but in reality was probably a good 45 minutes.
I have heard rumors of other places boasting of being the best. Perhaps they are all the best. Each place holds a special mood, a special scene.
Halloween is fun. You can’t go wrong. My advice: Get a costume on and just go, you can’t go wrong.
Join the family! 
