A Sleepy Hollow-een!

For the last several years, Lewie and his friends have gone on Halloween trips. First, it was the Jack-O-Lantern Spectacular at the Roger Williams Zoo in RI, then it was Salem, MA, and this year it was Sleepy Hollow.

Years ago, we took Lewie to Sleepy Hollow, to see The Great Jack O'Lantern Blaze (similar to the Jack-O-Lantern Spectacular) and tour the Sleepy Hollow Cemetery, which included the Old Dutch Church.  I knew this trip might be less exciting than our trip to Salem last year, but my good friend, Sue, and I decided to give it a try. As on past trips, it would be Little Lewie and her son, Ryan, their friend Noah, and Big Lew, Sue, and me. 

Our trip started with a stop at the Captain Lawrence Brewing Company for lunch. Then, we were off to explore downtown Sleepy Hollow.  In short, the trip was okay, but it didn't keep the boys' interest. First, we quickly discovered there were not as many interesting shops as in Salem. Instead, there are more historic things to do — such as tours of the cemetery, the Old Dutch Church, and Philipsburg Manor. Unfortunately, unlike my husband and me, Sue and the boys were uninterested in the tours, explaining that they didn't believe in spending money for information they would soon forget.

We walked around the historic landmarks, but again, without a ghost tour or something to make them entertaining, they didn't spark much interest. In the end, the boys walked back to the car while Sue and I walked around the Old Dutch Church before retreating to the Extended Stay American Suites in Elmsford--a moderately priced, no thrills hotel. (In other words, the hotel was just as blah as the trip.)

The two "events" we were most looking forward to were that night and the next morning. For example, we bought 10 p.m. tickets for the Haunted Hayride. The event is so popular, those were the only tickets I could secure!  The next morning, we would head to the SUP Witches Festival at Kingsland Point Park in Sleepy Hollow, NY — a craft fair and music festival with an interesting twist. Here is the newyorkcity.explore Instagram post:

Hundreds of witches are taking over the Hudson River this weekend! 🌊

Join the SUP Witches Festival as costumed paddlers glide across the river, transforming SUP boards into floating spells, and bringing legendary Halloween vibes to the waterfront. Expect:
✨ A wicked paddle parade
🎶 Live music & DJ sets
🍂 Food trucks & “witchy” treats
🛍️ Vendors, spooky goods & more
🎭 Appearances by the Headless Horseman

Before the hayride, a block party kicked off at 5 p.m. (We arrived around 7:30.) The block party featured all kinds of food, craft vendors, and two music stages--one for a heavy metal cover band and one for a "pop-music" DJ.  Lew and I enjoyed the block party — even dancing to a song or two. The boys walked through it and plopped themselves down on the sidewalk. All I could do was hope they would, at the very least, enjoy the hayride.

Around 9:30ish, we walked to the fire station to find out about our tickets. Should we stand in line now? They suggested we should, but I almost fainted when I saw the line stretch a pure mile down the road. "This is the line?" I asked, hoping I was wrong.  I wasn't. To make matters worse, there was some type of problem during the hayride. (We learned that some local teenagers were causing problems on the trail.) This backed up the event for TWO HOURS!  So, we didn't stand in line for 30 minutes to go on our 10 p.m. hayride. We stood in line for TWO HOURS, getting on the hayride at midnight!!!!

The Haunted Hayride's advertisement reads...

"Climb aboard the Sleepy Hollow Haunted Hayride and hold on to your head! All seems well when you board your hay wagon in the brightly lit streets of downtown Sleepy Hollow. The journey begins innocently enough. Rumbling off into the dark, you realize too late you are heading down the Albany Road past the Old Dutch Church, following exactly Ichabod Crane's flight from the Headless Horseman. Then you're through a set of iron gates, and the wagon slips into the dark woods of the hollow. Clatterin across a wooden bridge, you start to hear shrieks and the sound of hoofbeats...[when the Headless Horseman makes his appearance]."

The hayride itself was cool. We rode right through the Sleepy Hollow Cemetery and heard shrieks until we came to nearly a mile of ghoulish, creepy costumed characters and scenes. Before getting to the scary part of the hayride, I enjoyed the trip through the city and up through the cemetery. The sky was super clear, and I pointed out a shooting star (meteor) to Lew and Lewie. We watched for more and saw others...

Unfortunately, the two-hour wait on our feet ruined it for the boys. If the trip had left on time, I think they would have liked it. Instead, they were irritated by the wait and thought the ride was too expensive. They were right; each ticket cost $50! However, none of them had to pay for their own tickets — Sue and I bought them! With the ride lasting nearly an hour, we didn't arrive at the hotel until well after 1 a.m. We were exhausted!

The next morning, we ate breakfast at a diner across the street from the hotel and headed out to the SUP Witches Festival. The location, skirting the Hudson River, was absolutely beautiful, and we arrived right on time to watch 100+ witches "take flight" on their paddleboards. Off to the lighthouse, they went! Unfortunately, from our vantage point, they looked more like black dots on the water, but there are some great pictures of the witches up close online.

Photo by Chris Mantz / Photos on the Fly, Courtesy of Rivertowns SUP & Yoga

We had a beautiful day for the festival, and while I enjoyed checking out the craft vendors the most, it was also cool to "people watch." There were families there for a Sunday afternoon outing and tons of people dressed up as witches. Some dogs were dressed up, too!

After 40+ minutes (maybe less), the boys were bored and wanted to go home. I suggested we take a walk to the lighthouse and back, but I was outnumbered. We walked back to our car, ready for the quick 1-hour-and-15-minute ride home.  

There was much hope for this trip, but it was not a favorite. In the end, it made me leave, wondering if the boys are just getting too old for excursions like this. I hope that's not the case, but with Lew's two friends going to college next year, this will be, more than likely, our last Halloween boys' trip.