Spotlight On Westchester: Tarrytown & Sleepy Hollow


 We all love our own little cozy corners of Westchester. There are so many things to do and see, places to eat, parks to visit. Who doesn’t love exploring the county and “finding” the kid-friendly gems! It is our mom-bloggin’ duty to highlight some of those awesome places so that other moms can take advantage too! With each installment one or two new towns/cities will be highlighted to give you a glimpse into the awesomeness that is Westchester! Read all posts in our Spotlight on Westchester Series.

From the listless repose of the place, and the peculiar character of its inhabitants, who are descendants from the original Dutch settlers, this sequestered glen has long been known by name of Sleepy Hollow…A drowsy, dreamy influence seems to hang over the land, and to pervade the very atmosphere. — Washington Irving, “The Legend of Sleepy Hollow”

I am a lifelong resident of our fair county (save for a few years I spent hiding out in Jersey – a sordid tale for another day). And though I spent my formative years introducing myself at college orientations and job interviews alike with the factoid that both DMX and I hail from Yonkers, I have left the southernmost city for a northern Westchester retreat. A retreat more befitting my goth-y aesthetics and love of horror movies – Halloweentown itself, Sleepy Hollow. 

Our school district may be home to the scariest school mascot – Headless Horseman, who else? – and the streets certainly get creepy and kooky when October rolls around – but I absolutely love raising my kiddos here. Community programs are countless, (I’ve talked about my daughter’s great experience with the town peewee football cheer team) and the stuff to do – especially as we approach the warmer months – is endless. 

Tarrytown & Sleepy Hollow

We may be the Hudson Valley’s favorite haunted hideaway, but here’s a few of my personal favorite local haunts.

What to Do:

Tarrytown Music Hall: At the time of writing this I am fresh off my most recent visit to Main Street’s historic theater. The theater plays host to a vast variety of performances – from stand-up comedy, to battle of the bands, to Shopkins Live. Snacks are offered along with beer and wine for the Mom and Dad night out shows. But besides a convenient location to catch a performance of any sort, the theater regularly plays host to free family events. For example, me and my kiddos caught a free showing of the Lego Movie complete with lego-tivities before the show. 

Philipsburg Manor: Fans of the Halloween time favorite “Horseman’s Hollow” will recognize the location name. But Philipsburg has happenings long after the Horseman has taken his last ride of the season. Step back to the 1800s to experience what the Philips’s estate would’ve been like at the turn of the 19th century. 

Sleepy Hollow Cemetery: I promise I’m not just leaning in to my creepy with this suggestion. Hear me out! With famous residents including a Rockefeller, Elizabeth Arden and Washington Irving himself, the cemetery is one steeped in history. The grounds are beautiful and historical landmarks abound. 

Head Outside:

No shortage of parks in our tandem towns. Hard to narrow it down but here are a few must sees.

Pierson Park: This is the money maker right here, it’s why you came for the show! Nestled practically underneath the new Tappan Zee, this expansive space has river views, playgrounds, and a nice splash pad for the summer time. 

Patriot’s Park: You’d be hard pressed to find a weekend without a community event going on. Located right as Tarrytown becomes Sleepy, this spot is home to the likes of the town Rubber Duck Derby, Christmas tree lighting, and in the warmer months  – our beloved TaSH farmer’s market. 

Douglas Park: Located in a woodland clearing it is spacious and peaceful. Let the kiddos hang out on the nature inspired playground and take it in.

Where to Eat:

Little B’s: Absolute no brainer, this is my town fave. Located right on Main Street in Tarrytown, expect good brews on tap and and even better selection of burgers ripe for the DIY-ing. Brown paper tablecloths keep the kids occupied while you steal a fry or twenty. 

Muddy Water: After Little B’s dart across the street for some coffee, dessert and a side of atmosphere. With couches and seats aplenty, it’s the perfect spot to zone out with a cup or get a bit of work done. Soups, salads, and options galore for a vast array of dietary restrictions speckle the menu. 

The Taco Project: A spot so good, a second location recently opened back in my home city of Yonkers. Your (anything but) run-of-the-mill taco joint bringing street tacos to the streets of Tarrytown. 

Horsefeathers: This is a personal fave and a neighborhood standard for over 35 years. A traditional pub feel, Horsefeathers’ claim to fame is that it’s where all the locals hang out. The menu is pretty vast but oh boy – a burger with some soft cheddar and a side of fried potatoes. All. The. Yes. 

Bridgeview Tavern: With a spectacular view of the (yep) bridge, cozy up in the homey vibe and order from a splendid and diverse beer menu. Or post up out back in the beer garden, which boasts heaters for an (almost) all-weather good time. 

Tarrytown & Sleepy Hollow is a wonderful place to live with  fun for the whole family during any season. What’s your favorite place to visit?