What better way to lead into Halloween weekend than with a photo recap of my recent trip to Sleepy Hollow?

Sleepy Hollow is a village near Tarrytown, New York. About 30 miles north of Manhattan along the Hudson River, it’s easily reached by Metro North trains from Grand Central. It takes less than an hour to get there and costs around $20 round-trip.

In what has become my default mode of travel, I didn’t do any research before getting on the train. On the ride out I Google “Sleep Hollow travel blog” to see what pops up (that’s my new favorite way to research an area — I add ‘travel blog’ and no matter how obscure the location, at least one person has put together a detailed write-up with photos, suggestions, and tips).

But it turns out that Tarrytown has my back. They’ve posted this handy guide and map right outside the train station:

I decide on my route and walk maybe a half-mile or so to the heart of Main Street in search of lunch, pausing along the way to snap photos of the New England-y exteriors. (I know, New York isn’t technically New England. Tell that to this bucolic Main Street.)

I grab a bite at Sweetgrass Grill, a seasonal restaurant with an ever-evolving menu. The quinoa, kale, and sweet potato burger is delicious.

I would return to Muddy Water coffee shop later that afternoon…

And if I wasn’t already pumped full of caffeine, I would have stopped at this place too:

After lunch I turn left off of Main Street and continue on Broadway for a half mile before officially entering Sleepy Hollow. I’m so pleased this is walkable from the train; I’m keeping pace with the steady car traffic.

I was listening to the Hamilton soundtrack and then Dear Sugar podcasts, because I have good taste. (Kidding / not kidding.)

Cute park along the route, right across from the Sleepy Hollow road sign:

Even emergency vehicles here depict images of the Sleepy Hollow headless horseman legend.

So do the street signs:

This place is drowning in Halloween decor. Perfect place to visit this time of year, though I can imagine it might get old for residents.

I walk further along Broadway to the Philipsburg Manor, one of several historic mansions in this part of New York. Tours are all booked up for the day, but I wander the grounds and snap photos of the pretty pond, bridge, and structures across the water.

Stunning landscape:

There’s something called Horseman’s Hollow that takes place on this property at night. Perhaps it’s a variation on a haunted house, maybe outside on the property?

The last stop before I turn around is the Sleepy Hollow Cemetery at Old Dutch Church. This cemetery figures prominently into Washington Irving’s The Legend of Sleepy Hollow.

Greeters hand out maps of gravesites so that visitors can find where the prominent people are buried. I actually don’t recognize anyone on the list but simply wander and snap photos. The cemetery is enormous and sprawling, and the mood is anything but somber — there is a tent for beer and cider, which guests may sip as they walk the premises. Many people (and a few dogs) are in costume.

Look, it’s the headless horseman!

Next I walk to the Old Croton Aqueduct Trail since it’s listed on the map of highlights at the train station. It’s just a simple path that runs behind houses but the foliage is lovely.

View of the Tappan Zee Bridge in the distance:

Heading back towards the center of Tarrytown, I pass by busy Beekman Ave. as townspeople set up for tonight’s Halloween block party.

I’m curious what occupied this space before it was torn down — a factory? A mall?

Views along the water are divine.

I spy Manhattan WAY in the distance:

What a view… fall has arrived like a tidal wave, sweeping over the hills and turning them red and orange:

I pass by the train station and walk back up to Main Street just before the town-wide Halloween parade begins. I grab a warm beverage at Muddy Water coffeehouse and pick a spot along the parade route.

Afterwards the whole place turns into a giant Halloween party with music and dancing. I’m so pleased to have stumbled into the festivities.

It’s time for dinner but all of the restaurants are unsurprisingly crowded. This must be one of the biggest nights of the year for them. But I spy this variation of a food truck serving pizza baked in this oven-on-wheels:

Twelve bucks and ten minutes later, I’m burning the roof of my mouth on the first slice since I don’t understand the concept of delayed gratification. And little do I know it would be the last time I enjoyed pepperoni pizza before this week’s news that processed meat is strongly linked to certain cancers.

If you’re in New York City during the month of October, hop on the train to Sleepy Hollow for a fun day trip! In total I walked maybe four or five miles, so it’s totally doable on foot. The major attraction I missed was The Great Jack O’Lantern Blaze, a display of over 7,000 hand-carved illuminated jack o’lanterns at a historic 18th century riverside estate. I wanted to go but was deterred by three factors: 1) it’s sold out for the night I’m there, 2) it’s 10 miles from the train station and I don’t have a car, and 3) admission on Saturdays is $25 which seems kinda pricey to me. BUT I’d love to come back someday and photograph it.

Speaking of photographs, I left my heavy DSLR camera at home and brought along my tiny point-and-shoot. While these images aren’t of the same quality as my DSLR pics, I’m happy with how they turned out.

Thanks for the taste of fall, Tarrytown and Sleepy Hollow!