My friend and I met in an online coaching program a few years ago, when we were placed in a cohort together to practice delivering the material we were learning. After the program wrapped up, we decided to continue our Friday meetings to refine our skills. Over time, those sessions gradually morphed into social check-ins, allowing us to bond beyond the coursework. In 2023, we decided to meet in person and booked a trip to Salem, planning our adventure for mid-August. It turned out to be a fantastic experience filled with tours, learning, and some absolutely delicious food.

Embracing the idea of an annual adventure to towns known for their witchy, spooky, and historical vibes, we set our sights on Sleepy Hollow for October 2024. Based on Instagram and Pinterest posts, we quickly booked a stay at a castle nearby, dreaming of a whimsical escape into the world of Washington Irving's haunting tales, complete with picturesque autumn scenery and perhaps a few spooky encounters.

However, what we envisioned as an amazing weekend getaway soon turned into a trip that fell short of our expectations.

First Impressions Gone Awry

When the trip was first booked, the reviews for the Castle were absolutely amazing. All the blogs I read stated that this was the place to stay if you wanted to splurge, and that the grounds and amenities were fantastic. Posts about all of the spooky tours and things to do in the area made it sound like it was a location with a lot to offer.

However, about a week before our trip, I received an email from the hotel stating that the restaurant and spa would be closed during our stay. I didn’t think much of it, assuming based on reviews that everything would be close by and there would be plenty of other options for food and things to do. If only I had taken the time to read the reviews more carefully before we arrived; I might have had a clearer picture of what to expect.

Day 1: Tarrytown

I arrived in Tarrytown about an hour before my friend, anticipating that I wouldn’t be able to check in early. The friendly staff member at the front desk took my luggage and informed me about the hotel closures. No big deal, I thought—until he mentioned that we’d need to Uber to get anywhere since there was no walkway from the castle down to the road and no sidewalk leading into town.

Once my friend arrived, we hopped into an Uber and headed to Horsefeathers. Based on the reviews, I knew this spot would be tough to get into, and I really wanted to try it. I will tell you that based on all of the meals and restaurants we ate at, this was absolutely one of my favorites. It was decorated to perfection, had a special list of their fall drinks, and a surprisingly big menu to choose from. I had the butternut squash soup and chicken cutlet wedge (based on our server’s recommendation), and both were delicious. My only regret was not hanging around longer; the International Film Festival was coming to town, and we missed spotting some celebrities, including Evan Peters, by just a hair.

After our late lunch, we explored Tarrytown, and I must say, it’s an adorable town filled with shops and restaurants. We wandered through the boutiques, scoped out dining options, and I picked up a few books and a postcard from Transom Bookshop on Main Street. Once we finished exploring, we decided to stop into The Taco Project to regroup and figure out our next move.

That’s probably about when we realized that Sleepy Hollow and Tarrytown weren’t the same—and that they weren’t particularly close, either. It’s doable to walk, but it would require a 30-40 minute trek, depending on your destination. So, back into an Uber we went.

We aimed for the Bridgeview Tavern, thinking it would be close enough to “Sleepy Hollow” for dinner and a bit of exploration. Unfortunately, we were mistaken. After a 30-minute wait outside, we were finally seated—mostly because there were just two of us, unlike the larger groups waiting ahead of us.

For dinner, we shared the Belgian Curry Mussels and the Fig and Goat Cheese Flatbread. While the mussels were decent, I prefer them in a white wine and garlic sauce. However, the flatbread was fantastic—and I’d come to find out, a staple on many local menus.

This is where we ended our night. The margaritas and pumpkin beer were flowing, and we met a fantastic couple sitting at the bar. We ended up sitting with them for quite some time, talking about life and reading astrology charts.

The Castle Hotel and Spa and Horsefeathers

Day 2: Sleepy Hollow and Hudson Valley

We woke up a bit sluggish on our second day. After realizing I had left my bag of books at the Tavern, we made that our first stop before heading to Sleepy Hollow. Once we retrieved my belongings, we set off to explore more of the town, which was about a ten-minute walk down Beekman Avenue.

As we ventured into Sleepy Hollow, it became clear that the town wasn’t as bustling as we’d hoped. The main strip featured a few restaurants, mostly pizza places, with a handful of others scattered about. It quickly dawned on us that the number of dining options would likely struggle to accommodate the number of visitors expected that Friday evening.

We chose to eat at J.P. Doyle’s Restaurant and Public House for lunch. While the menu was a bit underwhelming, we weren’t in the mood for pizza, so we decided to make the best of it. We split a goat cheese salad, and I ordered fish and chips. The fish was decent, but the breading left a lot to be desired.

After lunch, we headed toward the famous Sleepy Hollow Cemetery, which is truly the highlight of the area. After a 20-minute walk, passing by Philipsburg Manor and crossing the Headless Horseman Bridge (which wasn’t much to see beyond its sign), we finally arrived at the cemetery. I’ve never experienced such a large and peaceful resting place. After wandering for over an hour, we realized we hadn’t even scratched the surface. The numerous mausoleums were impressive, and I kind of wished we had opted for a tour. Just a heads up: the ground can be uneven, so you’ll want to watch your step, especially if you visit at night.

Philipsburg Manor during the day and Sleepy Hollow Signs

After exploring the cemetery, we made our way back to Tarrytown, stopping at a pizza place for a soda about halfway through our 35-minute walk. Once we arrived, we debated whether we were hungry and ended up at Mint, where we ordered a bowl of fruit. It turned out to be the prettiest and most varied fruit bowl I’ve ever had in a restaurant!

Post-refreshment, we called an Uber to return to the hotel. We spent the afternoon relaxing, unsure if we wanted to make another trip into town since we had a tour booked for the evening—the Great Jack O’Lantern Blaze. A quick note: while it’s featured on all the Sleepy Hollow websites, it’s actually located in Hudson Valley, about a 20-25 minute drive away, and walking there is definitely not an option.

Despite its distance, the Great Jack O’Lantern Blaze was impressive. Over 7,000 carved pumpkins were displayed in stunning arrangements, featuring massive spiderwebs, fields of sunflowers, zodiac signs, a trio of witches with a cauldron, and even a large, moving windmill. Upon entering, you pass through a small shop and there are a few stalls with fall drinks and snacks, but we opted to skip those due to long lines. Keep in mind that getting an Uber to this event can be tricky due to traffic, and it can be quite chilly because of its proximity to the water.

After the Blaze, we returned to our hotel rather than deal with parking or another Uber trip back into town late at night. Thankfully, we discovered that DoorDash was available! We decided to order from The Taco Project and got our order just in time for the 9:40 cutoff. The chips and salsa (which was more like pico) and veggie tacos made for the perfect late-night snack.

The Great Jack O’Lantern Blaze: Hudson Valley

Day 3: White Plains & A Little Bit of Everything Else

On Friday evening, we decided to research the best brunch spots in White Plains, as we had already explored most of what Sleepy Hollow and Tarrytown had to offer. Many of the ticketed activities were already sold out - even weeks prior, we barely managed to secure the few spots we did.

We chose The Blind Pig of Westchester for brunch, and it was fantastic. It’s described as a dark, intimate saloon with a 1930s vibe, and it definitely lived up to that. I ordered the Purple Panties cocktail, made with Prosecco, and the smoked salmon eggs benedict—both of which were a solid 10/10. After brunch, we were unsure what else to do, so we wandered over to the mall. While it wasn’t the most exciting way to spend a Saturday, there weren’t many other obvious options. I did find some Halloween-themed shorts at Victoria’s Secret, which was a fun little win. Afterward, we grabbed a coffee, strolled around town a bit more, and then headed back to the hotel.

For dinner, we had reservations at The Sailhouse, near the Riverwalk in Tarrytown. The outdoor area seemed lively, with lots of tables, music, a food truck, and a patio. But knowing we had an outdoor tour planned later, we opted for indoor seating. The meal started off strong with delicious mussels in white sauce, but everything went downhill from there. It took nearly an hour for our entrees to arrive, and when they finally did, the food was somehow both cold and undercooked, outside of my soup which was scalding hot. My friend’s tacos and fries were practically cold, and my macaroni was undercooked, and the sauce wasn’t even warm. Our server disappeared after dropping off our meals, and by the time he returned, we didn’t have enough time to ask for a replacement before our 8:30 tour. In the end, only the fries were comped.

After dinner, we headed to the Twilight Village at Sleepy Hollow. Given our general disappointment with the hotel and town, we had checked the reviews for this event beforehand (something we probably should’ve done before buying tickets). It was a total letdown. I read one review on the Sleepy Hollow Facebook page that praised the event, but based on the post the post, they were mostly drinking and hanging out.

If you can fit in the parking lot that’s a plus, if not they have overflow just around the corner and up the hill. You once again walk through a store to enter and then head towards the bridge to wait in line to get in. Once you cross the bridge, you’re given the option to grab a cinnamon sugar donut upon entry. If you like ice cold donuts, they weren’t bad.

For $30 per ticket, the event was a waste of money. It promised vendors and activities, but there were only about four vendors—one of which sold items that could easily be found on Amazon. They had a s’mores station and a few other snack booths, but the rest was underwhelming. There was a storyteller in a barn, a fortune teller, a ghost on stilts, someone juggling fire, and a few cheesy games. Essentially, you pay $30 to wait in line, buy more food, look at a handful of vendors, and play cornhole. Kids seemed to enjoy it, but we were in and out in 15 minutes.

Afterward, we drove back to the hotel. The number of cars parked along the road between Sleepy Hollow and Tarrytown made it clear that parking was going to be a challenge, so we didn’t bother stopping again.

Last Day: Riverwalk

We initially had reservations at The Sailhouse but, after Saturday night’s disappointing dinner, decided to cancel. Instead, we booked a table at RiverMarket Bar & Kitchen. With checkout at 11 AM, we headed straight to the Riverwalk, and I’m glad we did—it wasn’t long before the parking lot started to fill up. We spent about an hour strolling along the river, enjoying the beautiful views, which made for a peaceful morning before lunch.

Lunch at RiverMarket was decent, but the restaurant was freezing, which altered the experience. The highlights of the day were spotting Steve Martin dining at the restaurant and enjoying some incredible ice cream from a small shop right outside the restaurant. It’s an unassuming little place, but the ice cream was absolutely fantastic!

We spent the rest of the early afternoon sitting on a bench by the river, taking in the scenery before it was time for me to head to the airport.

My Overall Impression on the Area

Sleepy Hollow is not quite what social media or bloggers make it out to be. If you’re familiar with New York, you probably know that Sleepy Hollow and Tarrytown are two distinct places, but for outsiders, they often seem interchangeable online (or at least extremely close to each other). If you don’t want to walk long distances or rely on Uber, this is important to know. Sleepy Hollow itself doesn’t have much going on.

The town is cute, but feels like it’s trying to live up to a reputation that’s not quite yet deserved. Yes, Washington Irving lived here and based The Legend of Sleepy Hollow on the area, but beyond that, there’s little to do. The town is charming enough but lacks both food options and attractions. In hindsight, I’d suggest spending no more than a day in Sleepy Hollow and focusing on Tarrytown. Tarrytown has a better selection of restaurants, more variety, and some cute shops to explore. However, even combining both, a day or two is more than enough—any longer and you’ll likely run out of things to do, apart from trying more restaurants.

As for events, they’re limited and often scheduled for specific weekends. If you’re visiting when something special isn’t happening, you’ll miss out, and the few events that are available need to be booked well in advance. Having visited Salem in October, I understand the demand, but the issue in Sleepy Hollow isn’t just ticket availability—it’s the underwhelming experience.

In summary, it’s worth seeing, but not for more than a day or two, unless you’re a big foodie. Sure, the fall colors were beautiful, but depending on where you live, you can experience that for a lot less money and with less crowds. Accommodations are limited, parking is scarce, and walking or Ubering is almost essential. Even if you have a car, parking on weekends can be a nightmare, with cars lining the streets and creating a bit of a sketchy driving experience.

I found that Sleepy Hollow had some nice fall vibes, but it didn’t quite capture the Halloween magic I was expecting. As I explored the area, I couldn’t shake the feeling of disappointment, hoping for memorable photo ops and unique experiences that, frankly, just weren’t there.

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