1 follower

Follow

Follow

Follow

1/11

3 saved

10

Places to visit in October: Sleepy Hollow, NY

This is your sign: visit Sleepy Hollow & Tarrytown, NY

1 day Free itinerary

🎃👻Sleepy hollow is only 45 minutes from NYC and 1 hour from New Jersey, perfect por a day trip during fall🍂🚗

From historic mansions, cozy cafes to spooky legends at Sleepy Hollow Cemetery

Free spots, cozy streets, and the best autumn photo ops📸✨

Save this for your next weekend getaway!🤎

Tips: get there early, bring cozy layers, and don't miss the Hudson views at sunset.

#sleepyhollow #halloweentown #headlesshorseman #spookyseason #falltravel

2025/10/24 Edited to

Related posts

A person in a brown coat stands amidst fall decorations including hay bales, pumpkins, and mums, next to a large metal sculpture. The image is titled 'NYC Day Trip to Sleepy Hollow in October'.

The ornate ceiling and arched windows of Grand Central Station are visible, with text indicating the start of a day trip to Tarrytown via Metro North train.

NYC to Sleepy Hollow Day Trip

The name of the town Sleepy Hollow all started from a book by Washington Irving called “The Legend of Sleepy Hollow”. The book tells the story of the ghost of the Headless Horseman, a soldier who lost his head to a cannon ball during the Revolutionary War. Since Washington Irving and The Legend of

39 likes

How to Spend a Day in Sleepy Hollow, NY

These are just a FEW of the many cool things to do and see in Sleepy Hollow ! 🐴🎃🏰 Philipsburg Manor 🏡: a living history museum, where visitors enter the year 1750, when the Manor was a thriving milling and trading complex that was home to 23 enslaved people. Headless Horseman Statue 🐎: one

486 likes

A woman with an umbrella stands next to a 'Welcome to Historic Sleepy Hollow Settled in 1640' sign, decorated with pumpkins and corn stalks on a rainy day.

A street corner features a large clock tower adorned with pumpkins, hay bales, and autumn flowers, with cars on the wet street in Sleepy Hollow.

A path covered in red fallen leaves leads through a cemetery with old gravestones and trees displaying autumn colors under an overcast sky.

Sleepy Hollow NY

In the quiet village of Sleepy Hollow, schoolteacher Ichabod Crane became enchanted by local ghost tales, especially the legend of the Headless Horseman. As he longed for the affection of the beautiful Katrina Van Tassel, he earned the envy of rival Brom Bones. One eerie night, Ichabod encountered

551 likes

🎃Sleepy Hollow, NY - Spooky Season Getaway🕯️

If fall had a hometown, it would be Sleepy Hollow 🍁✨ This little village is packed with history, haunted legends, and just the right amount of spooky fun! 🕯️ Our favorite stops: • Sleepy Hollow Cemetery — where Washington Irving rests 🪦 • Old Dutch Church — straight out of The Legend of Sleep

45 likes

in Sleepy Hollow

weekend trip to Sleepy Hollow was a success 😁 next time we will explore cemetery as this time we didn't have time left and needed to get food in our stomachs 😂 #sleepyhollow #halloweentown #cemetery #trip

12 likes

A street clock post in Sleepy Hollow decorated for fall with a pumpkin man scarecrow, hay bales, and pumpkins, with the text 'CHARMING TOWNS to visit in New York IN THE FALL'.

An old stone church with a bell tower, surrounded by numerous weathered gravestones in Sleepy Hollow Cemetery, with text about the town's connection to 'The Legend of Sleepy Hollow'.

The Sleepy Hollow Lighthouse, a white and red structure, standing in the Hudson River connected by a walkway, with a list of 'Things to see' in Sleepy Hollow.

Charming New York towns in the fall: Sleepy Hollow

When traveling to New York, don’t miss one of the most charming towns located in the Hudson Valley just north of NYC! Sleepy Hollow is especially popular in the fall due to the lore around this famously fabled town in Washington Irving’s “The Legend of Sleepy Hollow” Things to do: Wander

59 likes

Sleepy Hollow series part 1: Events + Activities:

Sleepy Hollow Part 1 of this Sleepy Hollow Tips & Tricks series to help you plan your next spooky adventure🎃👻 This ones all about the events, how to find them and where to go. Love this tradition we have started and so excited for this spooky season🖤 #sleepyhollow #sleepyhollowce

25 likes

A woman walks towards the Beekman Ale House, which is decorated for fall with pumpkins and autumn foliage. The building features a prominent sign for the ale house.

An outdoor clock tower is adorned with Halloween decorations, including a jack-o'-lantern scarecrow, hay bales, and pumpkins, set against a backdrop of colorful fall trees.

The historic Old Dutch Church of Sleepy Hollow, a stone building with a bell tower, stands beside a cemetery filled with numerous old gravestones and vibrant fall trees.

fall day trips from NYC: Sleepy Hollow

One of my favorite places to visit in the fall from New York is the magical little town of Sleepy Hollow just north of the city in the Hudson Valley . During the fall is the best time to visit as this is a true Halloween town and it really leans into its ties to the legendary tale of the Le

104 likes

Fall Day in Sleepy Hollow, NY

Spend a Fall day in Sleepy Hollow (and Tarrytown) 🥯 Grab a festive bagel from Horseman Bagels. ☠️ Visit Old Dutch Church & Burial Ground and Sleepy Hollow Cemetery 👻 Walk down Beekman Avenue to see all the Halloween decor 🍕 Enjoy lunch at Beekman Ale House 🌊 Take a walk alon

8 likes

Must visit place in October in NY 🎃

Sleepy Hollow Tarrytown #sleepyhollow #tarrytownny #ThingsToDo #placestogo #lemon8challenge

7 likes

Sights to see in Sleepy Hollow

Here are some spots to check out when visiting Sleepy Hollow, NY! I had the pleasure of living in Sleepy Hollow for one year, and it was definitely fun to be so close to so many great attractions! The town is a mix of historical and spooky during October, and it is fun to enjoy the history all year

26 likes

If you’re a Halloween fan, you need to visit Sleepy Hollow at least once! Home of the iconic headless horseman! Add this destination to your fall bucket list! #halloween #sleepyhollowny #sleepyhollow #newyork #fallaesthetic

0 likes

Things to do in NY for the fall🍂🎃🍎

#fallinny #fall #applecider #appleorchard #sleepyhollow

23 likes

Small towns I want to visitSleepy hollow New York

#forgottenplaces #towns #sleepyhollow #newyork #travel

1432 likes

Sleepy Hollow/NYC Weekend Trip

Pack with me for a weekend girls trip to Sleepy Hollow and NYC Tarrytown New York #ootd #falloutfitideas #halloween #girlstravel

1 like

The grand, ivy-covered facade of Kykuit, the Rockefeller Estate, a Gilded Era mansion in Sleepy Hollow, NY, featuring classical architectural details and a statue on the roof under a clear blue sky.

A formal garden at Kykuit with bare trees, a large fountain featuring a central statue, and a distant view of the Hudson Valley, highlighting the estate's historical significance.

A bronze sculpture of a crouching figure on a stone wall at Kykuit, with potted plants in the foreground and a scenic view of the Hudson River and surrounding hills in the background.

Let’s Explore Kykuit Estate in Sleepy Hollow, NY

Kykuit, the Rockefeller Estate is a historic hilltop mansion turned museum in the Hudson Valley. This gilded era vacation home of the Rockefeller family offers stunning views of the Hudson River. All tours of Kykuit leave from Philipsburg Manor near the Sleepy Hollow Cemetery, and the shuttl

658 likes

Perfect Fall Day in Sleepy Hollow! Sleepy Hollow 1 Day Itinerary (9AM-7PM) #terrytown #sleepyhollow #halloweentown #itinerary #thingstodoinsleepyhollow

6 likes

Sleepy hollow New York

#ThingsToDo #lemon8challenge Sleepy Hollow A stroll around the town of sleepy hollow New York during the spooky season We went during the sleepy hollow fall festival weekend and it was kinda packed but so worth it. Can not wait to go back ! #sleepyhollow #halloween #newyork

26 likes

Add Sleepy Hollow to your list of places to see! 🎃

We got to see Sleepy Hollow and it was definitely a cool experience in the Fall! #sleepyhollow #newyork #thelegend #fall

184 likes

SLEEPY HOLLOW PT. 2👻🧡: Transportation & Parking🚂

Part 2 of this Sleepy Hollow Tips & Tricks series to help you plan your spooky visit👻🧡 This ones all about the transportation, parking, and how to get around! With pumpkin spice filling our cups and the cozy weather around the corner, it warms my heart and makes me so happy to be able to hel

34 likes

Weekend Trip to Sleepy Hollow

Sleepy Hollow #sleepyhollow #tarrytown #weekendtrip #halloween #fall

4 likes

A highway sign indicating the exit for Tarrytown and Sleepy Hollow, with the text 'A DAY IN SLEEPY HOLLOW' overlaid.

A collage showcasing various uniquely styled scarecrows displayed around Sleepy Hollow, with the text 'so many scarecrows!' overlaid.

A person pointing at a map on an informational sign at Scenic Hudson RiverWalk Park, with the text 'planning what to do' overlaid.

A DAY IN SLEEPY HOLLOW 👻

Sleepy Hollow We took a day trip from NJ to Sleepy Hollow🩶 The first thing we noticed was how there was a scarecrow in every block and they were all uniquely styled and even had their own name which i personally would’ve taken the whole day just looking at all of them. Our first stop was

26 likes

A person stands in front of the stone entrance wall of Sleepy Hollow Cemetery, featuring the cemetery's name on a prominent plaque.

A rustic wooden bench with 'THE LEGEND OF Sleepy Hollow' carved into its backrest, positioned against a stone building.

A large, historic stone building with arched entrances and a prominent tower, set within the Sleepy Hollow Cemetery grounds.

Sleepy Hollow Cemetery

Strangers Journey into SLEEPY HOLLOWS CEMETERY #paranormal #explore #urbex #haunted #creepy

3 likes

Halloween Town in real life🎃

took a day trip to Sleepy Hollow and it honestly felt like stepping into a Halloween movie 👻🍂 if you’re obsessed with fall, add this town to your list ASAP. #foryoupage #sleepyhollow #halloweentown #daytrip #fall

11 likes

An aerial view of a waterfall cascading into a blue lake, surrounded by vibrant orange and yellow autumn trees. The image has a text overlay that reads "Best places to visit in October."

A snowy landscape featuring mountains, pine trees, and houses under a sky illuminated by the green and purple hues of the Northern Lights. Text describes October as ideal for seeing the Northern Lights in Iceland.

Numerous colorful hot air balloons ascend into a clear blue sky over a city or landscape. Text highlights the Albuquerque International Balloon Fiesta, manageable heat, and peak fall foliage in New Mexico during October.

Best Places to Visit in October🛩️🎧🍸

Here are the top 5 recommended places to visit in the month of October! Most of these locations have special festivals occurring during the month, which is why they are perfect for any fall break trips!🛩️ • Iceland🇮🇸🗻 • New Mexico🏜️🌵 • Mexico City 🇲🇽💀 • Munich🍺🇩🇪 • Mauritius🏝️🇲🇺 Have you

220 likes

Spend the Day with me in Sleepy Hollow, NY

A little Halloween magic in Sleepy Hollow 🎃👻 From train rides to spooky parades — it was a vibe! 🍂 #Halloween2025 #SleepyHollow #NewYork #WestchesterCounty

0 likes

Sleepy Hollow Stole Our Hearts and Our Heads 🐎🎃🪦💀🍁👻

Our sleepy hallow day in pictures. This was by far our best day on our third year visiting our favorite spooky Halloween town. Vlog ging next follow for more!

1 like

Sleepy Hollow NY in Fall!

#bucketlisttrip #sleepyhollow #newyork #halloween #travel #headlesshorseman

245 likes

Take is a sign to go to Sleepy Hollow NY this fall

One of my favorite weekend getaways! Sleepy Hollow #sleepyhollow #headlesshorseman #weekendgetaways #fallplaces #halloween

1 like

Sleepy hollow New York 🐴🎃🪦 Take me back 😩

#sleepyhollow #spookyplaces #halloween #roadtrip

67 likes

My trip to Sleepy Hollow Cemetery!

⭐️Overall rating: 10/10:I went with family since we had to get a car fixed, it was a bunch of walking, but beautiful views and history! Definitely a place I’d love to visit again someday❤️ Sleepy Hollow #sleepyhollow #cemetery #ghost #history #newyork

9 likes

An aerial view of the New York City skyline at sunset, featuring the Empire State Building, with text 'Fall in NYC 5 things to do this fall' and bat icons.

Carved jack-o'-lanterns with glowing lights floating on a body of water, reflecting the lights. Text describes the 'Halloween Pumpkin Flotilla in Central Park' on October 31st.

Large illuminated figures of Jack Skellington and Sally from 'The Nightmare Before Christmas' in a dark, outdoor setting. Text promotes 'The Nightmare Before Christmas Light Trail' at NYBG.

5 Things to do this fall in NYC 🍂🎃👻🌇

23 likes

Sleepy Hollow, New York

Sleepy Hollow #sleepyhollow #ThingsToDo #placestogo #lemon8challenge #ny

5 likes

A person sits at the edge of an infinity pool overlooking the ocean and a lush green cliff, with text overlay "Best Destinations to VISIT IN OCTOBER Part 4."

A scenic view of a rocky coastline with natural pools and people, under a blue sky with clouds. Text overlay indicates Portugal's average temperature is 73-77 degrees.

A mountainous landscape with two smaller images below: a volcanic lake in Azores and a beach with rock formations in Algarve. Text lists best cities to visit in Portugal.

Best Destinations to Visit in October: Part 4🍂

October is the month to escape the large crowds of tourists and experience a destination almost to yourself. Here is my series of the best places to visit during this month! 👇🏽 Part 4: 📍Portugal Portugal 🇵🇹Best Cities to Visit: Madeira Madeira , Azores Azores , Porto Porto , Lisb

317 likes

A trip to sleepy hollow is a must 🎃

4 likes

Sleepy Hollow, NY 🍂

#lemon8diarychallenge

3 likes

The Halloween capital of New York: Sleepy Hollow. 🎃 It’s one of the best fall day trips from NYC. 👻 When you arrive, you’ll tour haunted mansions and cemeteries, see 7000+ hand carved jack-o-lanterns, and visit the real life places from The Legend of Sleepy Hollow. 🚆 Sleepy Hollow is less

1 like

A yellow building with decorative trim and storefronts, featuring signs for 'ENDERLIN.' and 'Roxbury,' representing a cool town to visit in October.

A scenic waterfall cascading over rocks into a stream, with a stone arch bridge and autumn foliage in the background, depicting a cool sleepy town in the Catskills.

A woman sitting on a bed in a themed room with a large yellow gown hanging above, highlighting a themed room at The Roxbury Motel and other attractions.

Places to visit in October: Roxbury, NY

When looking for places to travel in the fall or the month of October, one of my favorite places to visit is the town of Roxbury in the Catskill Mountains , NY. Eat at The Fierce Grizzly ! Shop at the Roxbury General . See the Jay Gould Memorial Reformed . Take a scenic train ride on the

32 likes

My Spooky trip to sleepy Hollow

#halloween2024 #lemon8contest #spookywalk #spookyearrings #hauntedhues #spookyspring Throwback Thursday to my trip to Sleepy Hollow last year! Wear comfortable shoes because you can take a beautiful hike through the cemetery, which is gorgeous.

15 likes

UPSTATE NY FALL BUCKET LIST !

there is nothing like an upstate autumn. fresh crisp air and foliage that is truly breathtaking while divulging in history, nature, and a whole lot of fun. what is your fav place in upstate ny to celebrate fall ?! take a little look in the LTK link. link in bio (link in bio.) 🪾✨ https://liketk

1 like

A dark, eerie image with silhouettes of people and a large, ghostly hand-like shape, featuring the title "A HALLOWEEN LOVER'S Guide to NYC" in prominent white and green text.

A dog wearing a hat, sitting in a "This is Fine" dumpster fire wagon costume at a dog costume contest, with spectators in the background. The event is for Fort Green Park and Washington Square Park.

A creepy clown-like figure in a hallway lined with numerous skulls, depicting the Blood Manor haunted house attraction. It's a $45 attraction featured on Jimmy Fallon.

SPOOKY SPOTS TO SPEND HALLOWEEN IN NYC

Dog Costume Contests Fort Green Park - October 26, 12pm Washington Square Park - October 26, 12:30pm Cityside Pumpkin Patch Summer Club, LIC 25,000 square foot space with 10,000+ pumpkins from upstate, plus food and drinks, photo opps, face painting and tarot card readings for $20. Blood

24 likes

Exterior view of Lyndhurst Mansion, a Gothic Revival stone building with arched entrances, a green lawn, and a sundial in the foreground on a cloudy day.

A person with an umbrella stands under a Halloween-decorated archway with a "BEWARE" sign, flanked by a ghost figure and pumpkins in a grassy park.

Two horse skeleton figures, adorned with autumn wreaths and pumpkins, stand in a grassy outdoor setting under weeping trees.

Lyndhurst mansion - sleepy hollow

#ThingsToDo #lemon8challenge Tarrytown Lyndhurst Mansion Lyndhurst, also known as the Jay Gould estate, is a Gothic Revival country house that sits in its own 67-acre park beside the Hudson River in Tarrytown, New York, about a half mile south of the Tappan Zee Bridge on US 9. The house

210 likes

Unreal places in upstate New York in the fall

When planning a New York road trip this fall, don’t miss these gorgeous places to visit during fall foliage. Finger Lakes There are so many breathtaking places to visit in the Finger Lakes in the fall, plus there are tons of farms to enjoy things like apple cider donuts, pumpkin picking,

131 likes

Rainy Sunday stroll around Sleepy Hollow🍂☔️

Rainy days call for a cozy stroll through Sleepy Hollow and Tarrytown🍂🍄🪵 I was so excited to get home and start decorating the new apartment for alllill the fall vibes, but jokes on us since we never brought our autumn trinkets and decor over from storage (realized it when we got back home)🥲 We&

5 likes

Sleepy Hollow State Park

Sleepy Hollow State Park is an absolute dream for family sessions. Between the peaceful trails, wildflower fields, and that stunning dock over the water — it’s the kind of place where memories feel a little extra magical. The natural light filters through the trees just right, and every spot fee

0 likes

NYC✨ Spooky Halloween Night in Sleepy Hollow 👻

👻 Step into a haunted colonial manor and enjoy an immersive Halloween experience~ 📍 381 N Broadway @

0 likes

🍋5 Cheapest Places to Travel in October🍋

Fall glow-up mode: activated 🍂✨ Here are the Top 5 Cheapest Places to Visit in October if you want cozy, cinematic travel on a budget: 🇬🇷 Greece — half-price hotels, full-sunset energy 🇦🇷 Argentina — springtime charm + wine for days 🇹🇷 Turkey — hot air balloons & budget luxury 🇮🇩 Bali —

716 likes

Best USA Cities to Visit in November: Part 1🍂✨

November is a great month to enjoy fall and explore new places. There are so many incredible destinations within the country that offer great views and great time! Here is my series of the BEST USA Cities to visit in November 👇🏽 Part 1: 📍Sedona, Arizona 🇺🇸 Sedona Average Hotel Cost: $112

81 likes

#sleepyhollow #headlesshorseman #roadtripmemories #spookyseason🎃 #hauntedtravel

55 likes

A person walks towards the pink, octagonal Armour-Stiner Octagon House with a domed roof, set on a green lawn. The image highlights fairytale places in Upstate New York, featuring this unique architectural gem in Tarrytown.

Bannerman Castle, a stone fortress with 'BANNERMAN'S ISLAND ARSENAL' inscribed, stands on an island in the Hudson River, backed by a forested mountain. It's described as a fairytale destination accessible by boat tour from Beacon, NY.

The ornate pink and red Armour-Stiner Octagon House, with its distinctive domed roof and intricate details, is nestled among lush green trees. Located in Tarrytown, NY, it is available for tour visits only.

3 Fairytale Places in Upstate New York

Check out these fairytale places in Upstate New York and save them for New York road trip inspiration! Bannerman Castle Visit by boat tour from Beacon, NY The Armour-Stiner Octagon House In Tarrytown, NY visit by tour only Montour Falls In the Finger Lakes region You don’t ev

504 likes

weekend trip to Sleepy Hollow

spooky weekend trips are always a delight

1 like

Sleepy Hollow🪦💀

This Halloween, we had to stop by the historic town of Sleepy Hollow👻 First we stopped by the legendary Sleepy Hollow Cemetery🪦💀 As we strolled among centuries-old tombstones and mausoleums, the atmosphere was nothing short of chilling🪦 After that we ventured to the Old Dutch Church, where the Hea

2 likes

Add these activities to your NY Fall Bucket List 🍁

There’s nothing like autumn in New York! I always try to make a trip upstate every year to really take in the beautiful leaves and scenery. These are a few of my favorite places 👇 🍂 Storm King Art Center : This art park is open year round, but fall is the peak time to visit! I would recommend bo

87 likes

See more