Given the hoopla of planning/throwing Jay's retirement we didn't think we'd get away on a trip for Halloween. As things worked out, the four of us (Jay, Jude, Dee and myself) decided to clear our calendars and catch our breaths on a Halloween trip to Sleepy Hollow, New York - a mere hour away.
Very little planning went into this trip so we developed a new strategy that I'll share with you. Even in the little village of Sleepy Hollow things book up fast for the spooky season, many months in advance. So it was a challenge getting tickets to everything we wanted to see and do.
There are no accommodations in the village of Sleepy Hollow itself. Tarrytown is the village adjacent to Sleepy Hollow. (At one time it was part of Sleepy Hollow then was annexed, it's within walking distance of Sleepy Hollow).
Accommodations are in Tarrytown.
We lucked out and found an Executive Room with 2 beds at the SpringHill Suites by Marriott Tarrytown. We didn't mind sharing a room at all. $230 per night.
Because the guys are Bonvoy Members breakfast in the Club Lounge was included in our stay. The hotel also has the Toasted Barrel Restaurant, a Starbucks and Bar/Lounge. And a heated indoor pool.
We took advantage of a Stay 5 Nights offer which reduced our $230 per night cost even more.
Other local recommended Tarrytown accommodations:
Tarrytown House Estate on the Hudson
A historic 19th-century estate with Georgian mansions, cottages, and guest rooms, just 3 miles from Sleepy Hollow. Known for its romantic setting, Hudson River views, and romantic atmosphere. Amenities include two pools, fitness center, tennis courts, and a restaurant (Goosefeather) serving Cantonese cuisine.
Courtyard by Marriott Tarrytown Westchester County
A clean, quiet, and recently renovated option with spacious rooms, bar/food options, and a peaceful, woodsy atmosphere. It’s a popular choice for repeat visitors seeking a reliable, comfortable stay.
Sleepy Hollow Hotel
Located in the actual town of Sleepy Hollow, this 246-room property offers free self-parking, a heated indoor pool, and some rooms with terraces or balconies. It’s a short walk to Tarrytown and is noted for its affordable price and pleasant grounds.
Armour-Stiner Octagon House
A boutique, historic property offering unique accommodations with a local charm, ideal for those seeking a more intimate stay.
For a “spooky” or themed stay, Tarrytown House Estate offers the most authentic Sleepy Hollow vibe, while Sheraton, Courtyard, and Marriott provide modern comfort. If you want to be in the village itself, Sleepy Hollow Hotel is the closest option.
October in Sleepy Hollow is gloriously, almost impossibly busy. On a single autumn Saturday there can be two or three dozen things happening within a few miles of one another. It is a wonderful problem to have. It is also, if you're visiting for the first time, a slightly overwhelming one.
This is just a sensible way to string a few things together so you're not driving back and forth, doubling up on tours, or arriving somewhere starving only to wait in a long line.. And if you planned spur of the moment like we did and couldn't get tickets to everything you wanted to, it's a way to compensate for that and still have plenty to see and do. Think of it as one good plan you can adjust, rather than the only plan.
Mornings are the calm before the village fills up, the calm before the storm when the village fills up. Start your mornings slow. Make your first stop the Sleepy Hollow Tarrytown Chamber of Commerce.
1 Neperan Rd, Tarrytown, NY
FYI - Tarrytown and Sleepy Hollow are adjoining villages, within walking distance of one another.
The good folks at the Chamber can advise you as to which attractions and events tend to be the most popular and therefore, have the longest lines and at what time of day those lines are the longest.
They can advise you as to which restaurants you won't get into without a prior reservation or will have a long waiting line.
Simply put, they can help you save a whole lot of time not wasted standing in long lines and help you more efficiently plan your Sleepy Hollow/Tarrytown visit.
We played it smart and arrived on a weekday.
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Sleepy Hollow Tarrytown Chamber of Commerce
On weekends the village gets jammed because that's when most of the attractions are held. Arriving on a weekday allowed us to get the lay of the land so we weren't wasting valuable time getting lost trying to find this attraction and accommodations prices per night are less expensive on weekdays.
What we learned visiting Sleepy Hollow/Tarrytown for the first time we learned by trial and error:
Especially on weekends, earlier morning is the calm before the storm, when the village is relatively quiet before the hordes of visitors descend on the village.
If you have a morning ticketed event scheduled, do it as early as possible before the long lines start forming. Then fill in the rest of the morning with freebie attractions there are no lines for. Don't do more than 2 ticketed events per day or you'll feel overwhelmed and rushed.
Dining: Most restaurants do not take reservations during spooky season so expect to encounter lines. We found that by dining before or after the expected meal rush meant shorter lines or no lines at all. And depending on the crowds, avoid downtown village restaurants. There are plenty of other good options if you get further away from the village downtown areas.
For dinner refuel before any ticketed events, like in the late afternoon. Or grab a quick snack to hold you over and eat dinner later. Dining options at ticketed events are limited and a good number of evening events take place over the time span of a few hours so you won't miss anything by dining later.
Take advantage of the farmers markets to pick up picnic fare and skip the restaurant lines altogether. The TaSH is in Tarrytown's Patriots Park every Saturday from 8:30am to 1:30pm.
The Irvington Farmers Market is held on Main Street in Irvington on Sundays, 9 am to 1:30 pm.
Friday, October 23
We actually arrived on the 22nd in order to take advantage of the Stay 5 Days promo offered by the Springhill Suites and get rested up for the weekend.
We had a leisurely complimentary breakfast in the Club Lounge, then headed for downtown Tarrytown to stop at the Chamber of Commerce.
We'd brought our bicycles along so headed out to bike the Sleepy Hollow Riverwalk that runs along the Hudson River.
If you're walking it’s just a brief walk, less than 5 minutes, to reach historical gems like Sleepy Hollow Cemetery and Phillipsburg Manor. Additionally, you can stroll down to the waterfront, enjoy the scenic trail along the Hudson River, and explore the Sleepy Hollow Lighthouse.
Sleepy Hollow Cemetery
540 North Broadway, Sleepy Hollow
We had tickets for the 10 am daylight tour of the cemetery so tackled that first.
This Cemetery was established in 1849 and was originally named Tarrytown Cemetery but changed upon request to Sleepy Hollow Cemetery after Irving’s classic story.
You'll begin your tour in the "old section" of the cemetery. One of the most famous gravestones to visit is that of Washington Irving himself in his family plot located right next to the Old Dutch Reformed Church and burying ground in the Sleepy Hollow Cemetery.
From there you'll head to the section of the cemetery where Walter Chrysler, William Rockefeller, and Andrew Carnegie are interred.
The cemetery offers both daylight and night by lantern light tours. This tour includes a steep hill, some stairs and grassy, unpaved gravel roads. There is no place to sit down during the tour. Please consider your own abilities before purchasing tickets.
Sleepy Hollow Cemetery SOUTH GATE, 430 North Broadway. There is plenty of free parking inside the gate.
Saturdays and Sundays through Thanksgiving weekend from 1:00-2:00 p.m. and 3:00-4:00 p.m. Weekdays in October from 3:00 - 4:00 p.m. Weekends in October also 11:00 a.m. - 12 noon.
Sleepy Hollow Sculpture
420 North Broadway at Gordon Avenue, Sleepy Hollow
One of the best Sleepy Hollow attractions and quick photo stop is the Headless Horseman sculpture located just outside the Sleepy Hollow cemetery and next to the famous bridge where it all happened!
The 18-foot high sculpture is made out of metal and has a rusted appearance made by Miglo-Bufkin depicting the moment the Headless Horseman chased down Ichabod Crane on horseback and hurling a pumpkin at his head.
Headless Horseman Bridge
This always confuses people because the actual location and bridge that the Headless Horseman hurled a pumpkin at Ichabod Crane’s head over the Pocantico River is a modern-looking bridge that cars travel over on Broadway on Route 9.
There are actually 5 wooden bridges, none of which are the actual location and bridge.
if you want a more authentic looking wooden bridge to accompany the “Legend of Sleepy Hollow,” and the tale of the Headless Horseman, there’s a
popular wooden bridge often photographed in the Sleepy Hollow Cemetery nearby you can check out.
To find it, from the modern Headless Horseman Bridge you will drive into the Sleepy Hollow Cemetery and take the furthest right road along the Pocantico River. As you’re driving along the river, you will come across a little wooden bridge that’s perfect for photos directly parallel to Andrew Carnegie’s Grave. The drive will take less than 2 minutes and if you’re visiting by foot the walk is less than 15 minutes following this route.
Afternoon: Head down to the riverfront to Bridgeview Tavern & Biergarten, 226 Beekman Ave Sleepy Hollow.
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The vibe here was great, we sat in the beer garden in the back.
The service was quick and friendly. Made a point to highlight weekly specials and made recommendations with enthusiasm!
We didn't have to wait to be seated.
Much better than average bar food, bison, elk and boar on the specialty burgers menu. The portions were filling.
Having an amazing view of the Hudson didn't hurt!
Sleepy Hollow Lighthouse
Kingsland Point Park, Sleepy Hollow
As long as we were down by the waterfront we visited the Sleepy Hollow Lighthouse.
The Tarrytown Lighthouse in Sleepy Hollow (also known as the Sleepy Hollow Lighthouse, Tarrytown Lighthouse, and Kingsland Point Lighthouse. It was built in 1883 in response to pleas from local steamship companies for help navigating those waters.
Eight keepers and their families occupied the five-story tower over its years of operation until it was taken out of service in 1961.
From land, the best views are from the Westchester RiverWalk at Edge-on-Hudson. Start either inside Kingsland Point Park or from the RiverWalk entrance at the foot of Beekman Avenue.
Take a 45-minute interpreter-led tour of the Tarrytown Lighthouse in Sleepy Hollow to learn about its history, its significance, and what daily life was like for its keepers.
Reservations are required. Book tours through Westchester County Parks on Eventbrite.
The tour is free; parking fees may apply. The front gate locks 15 minutes after the tour start time.
The five-story structure includes four narrow stairways. There are no restrooms in the lighthouse — restrooms are available at Kingsland Point Park.
We'd seen the inside of plenty of lighthouses so we skipped the tour and just visited the exterior so Dee could take some photos.
Glass Pumpkin Patch Fundraiser
Kingsland Point Park 299 Palmer Avenue, Sleepy Hollow
We saved the rest of our Riverwalk bike ride for another day. We try to support community charity events whenever possible during our travels so wanted to visit the Glass Pumpkin Patch Fundraiser that was donating its proceeds to the Make-A-Wish® Hudson Valley Chapter.
The event showcases hundreds of whimsical, vibrantly colored glass pumpkins crafted by the artists at the Adirondack Glassblowing Studio.
The glass pumpkins are for sale.
Food trucks will also be on site.
The event is FREE although a parking fee at Kingsland Point Park will apply. The event runs from 10 am to 5 pm.
For more information about the artists and the glass pumpkin patches visit https://www.tryglassblowing.com.
Evening: Dinner at Goosefeather, 49 E Sunnyside Ln, Tarrytown.
Goosefeather is a warm little restaurant in Tarrytown with excellent Cantonese-fusion food every night.
The place is by no means as expensive as you might fear, though. Goosefeather is a lovable neighborhood destination spot, and yet it’s not so fancy that you’d be second-guessing yourself by ordering a signature cocktail.
Goosefeather also features rotating seasonal specials.
Open for indoor and outdoor dining.
Dining Hours:
Monday-Thursday: 5PM-9PM
Friday: 5PM-10:30PM
Saturday: 11AM-2:30PM and 4PM-10:30PM
Sunday: 11AM-2:30PM and 4PM-8PM
For reservations call 914-829-5454
Twilight Village at Sleepy Hollow
As evening settles over Philipsburg Manor, channel the spirit of Irving’s famously creepy tale at this immersive outdoor experience with live storytellers, fire performers, and eerie encounters around every corner. Mingle with Legend icons Ichabod Crane and Katrina Van Tassel, wander through a pop-up market with curious goods, oddities, and handmade wares, and grab delicious bites from food trucks while sipping cocktails and mocktails.
Throughout the evening, a roving band fills the air with music, fortune tellers offer glimpses into your future, and the Headless Horseman makes a dramatic appearance in a sound-and-light spectacle that recreates his midnight ride.
Tarot readings are available in limited quantities on a first-come, first-served basis. Food and beverages available for additional purchase.
The Sleepy Hollow Twilight Village reminded me of an Edgar Allan Poe version of a Renaissance Faire - only more commercialized with its pop up market. Still, we had an enjoyable time. The Headless Horseman was pretty cool although I think people were more into petting the horse than paying attention to the Headless Horseman. But it was a nice way to end our evening.
Advance Tickets Only. Not Sold on Site. $25-$35
Saturday, October 24
Tarrytown Halloween Parate & Block Party
Over 15,000 people attend the Tarrytown/Sleepy Hollow Parade so you want to get there plenty early to get a good viewing spot. We brought portable camp stools along so we didn't have to stand the entire time.
Parking in the Villages of Tarrytown and Sleepy Hollow will be extremely limited on the night of the Halloween Parade due to road closures. The Halloween Parade urges you to use Metro-North Railroad to Tarrytown Station or Westchester County buses instead.
The annual Village of Tarrytown Halloween Parade steps off from Patriots Park at 5 pm and winds south along Broadway to Main Street, where the real party begins with DJs, live music, outdoor dining, performers, and more. Block party runs to 10 pm.
Want to march? Groups and floats can enter with a theme for a chance to win prizes. Registration is required to be eligible — register here.
We were all hyped up for the block party...but it was so packed you were shoulder-to-shoulder so we left and returned to the hotel where we had a quiet drink together and went for a swim in the pool. For us, it was the perfect end to the perfect day. At our age we'll leave the heavy duty partying to the kids.