Exploring the Charm of Westchester County
As a native New Yorker, I feel well-qualified as Exhibit A in an analysis of the dynamic, the bond, the fabric that will forever link New York City to its northern neighbors.
With so much to see, there is a shared culture, regional economy, and family and friends who bounce between the two destinations to visit each other.
A Journey Through Westchester’s Cozy Communities
There is also Amtrak, the nation’s railroad, that runs trains multiple times a day, north from Moynihan Train Hall in Manhattan to Westchester County stations. On a recent Friday, I indulged my passion for train travel by boarding an Amtrak train in New York City bound for Croton-on-Hudson, an expansive yet cozy community in Westchester County, 38 miles north of the Big Apple.
As I answered the timeless bellow of “All Aboard,” I began a 36-hour adventure, along the idyllic Rivertowns, that would take me from Croton and Ossining to Tarrytown, Sleepy Hollow and White Plains. A music festival, cemetery tour, Hudson River sunset and plenty of fine dining made this trip most compelling—and unforgettable.
Play: Unforgettable Experiences in Westchester
Sleepy Hollow Music Festival: A Top-Tier Event
Bravo to the organizers of the Sleepy Hollow Music Festival held on June 8. I’ve attended many, many music festivals, from the top tier to the bush league, and I would rank the Sleepy Hollow Music Festival among the best.
The performers, the location, the staff and the security generated a vibe of top-tier professionalism and left us attendees feeling like we were part of something special—because we were.
The location—Kingsland Point Park on the Hudson, accessible by Metro-North and Uber—was itself a star of the day. Sweeping views of the river consumed us all. A wide expanse of land provided plenty of space for concert-goers, families, children’s activities, vendors, and food trucks—Wanna Empanada was especially popular with the crowd. And parking was a breeze.
Croton Gorge Park: A Natural Wonder
An eight-minute Uber ride from Croton-Harmon Station, Croton Gorge Park is home to the stunning and grand Croton Dam, which I’d call an honorary wonder of the world and a work of art that illustrates the human spirit.
A 97-acre property at the base of the dam, Croton Gorge Park delivers eye-popping views of the dam and spillway. On weekends you can expect folks playing frisbee or lounging out on blankets. The park is a popular spot for fishing, picnicking and hiking. Also, the bridge that spans the Croton River features a compelling view of the spillway.
The Old Croton Dam, built to supply New York City with water, was completed in 1842 and was the first large masonry dam in the nation. But as New York City’s needs outgrew the Croton Dam water supply, work began on the New Croton Dam in 1893. Finished in 1907, the second incarnation of the dam stands more than 200 feet high.
Discovering Croton-on-Hudson, Ossining, and Tarrytown
Each of these communities boasts a charming downtown with a buzz.
Croton-on-Hudson: The Black Cow Coffee Co.
The staff was super friendly, and I’ve got to give a special shout-out to Black Cow Manager Agyei Encarnacion. I don’t know that I’ve ever felt so welcome at a coffee shop as I did at The Black Cow. Everyone there truly knew how to make someone feel welcome.
Ossining: A Hidden Gem
Ossining, without a doubt, blew my mind.
I have driven through Ossining on Route 9, and taken Metro-North and Amtrak through Ossining, many, many times. But now, I’m kicking myself because I never checked out Main Street.
From Route 9, Main Street in Ossining slopes and curves its way downward to the Hudson River. Delicately preserved buildings showcase this village’s rich history, and architecture from long ago maintains its luster and highlights the vibrant community spirit. And please take my word for it when I say that Ossining’s Louis Engel Waterfront Park is the place to be in Westchester for the sunset. When I was there, Ossining’s Hudson River shore was ensconced in a certain stillness. The receding sun surrendered its oranges and yellows to the Hudson Valley and the waves on the river, a deep blue, rocked oh-so-gently back and forth.
I consider myself a person who is constantly on the go, always racing against deadlines and constantly playing beat-the-clock. Thank you, Ossining, for demanding I slow down for what turned out to be the most serene 20 minutes I’ve enjoyed in quite some time.
Tarrytown: A Vibrant Community
Tarrytown, oh Tarrytown, let me count the ways I love thee.
My Saturday morning in Tarrytown was filled with young families and couples making their way through a community that was buzzing so loudly you’d think it was plugged into an electric socket. I bopped around town to a few shops that were most engaging and compelling, to say the least.
Bella’s Boutique illustrated through merchandise—including books and mugs—just how large a role Washington Irving’s short story, The Legend of Sleepy Hollow, with its Headless Horseman, plays in the community. The Village of Sleepy Hollow, formerly North Tarrytown, sits due north of Tarrytown.
ShayLuLa Jewelry & Gifts offered a wide range of eclectic items, including beaded purses, candles, bracelets and earrings.
Pretty Funny Vintage gave me a solid laugh with a sign on its front door that read, “No Solicitors: Unless you are wrapped in bacon.” Who doesn’t love bacon? Vintage snapshots for only $2 a pop, wood carvings and yes, more Sleepy Hollow merch, were among the items to choose from Pretty Funny Vintage.
Sleepy Hollow Cemetery: A Lantern Tour to Remember
Notable Names and Spooky Atmosphere
Going from the sights, sounds, feels and tastes of the raucous Sleepy Hollow Music Festival, to an Ossining sunset, to a lantern tour of the Sleepy Hollow Cemetery offered contrasts that illustrate just how much Westchester County has to offer over the stretch of just a few hours.
The cemetery tour offered a very different lens on the county. It included a two-hour, nighttime stroll through a final resting place that boasted such notable names as:
- Washington Irving (1783–1859), a lawyer, diplomat and internationally famous author of essays, short stories, histories and biographies. His short stories, The Legend of Sleepy Hollow and Rip Van Winkle, are longtime regional favorites
- Andrew Carnegie (1835–1919), a Scottish-American industrialist, steel magnate and philanthropist
- Walter Chrysler (1875–1940), the businessman and founder of the Chrysler automobile company; commissioned New York City’s iconic Chrysler Building
- Samuel Gompers (1850–1924), an American labor leader; the first and longest-serving president of the American Federation of Labor
But far beyond these famous people, the cemetery tour offered plenty of atmosphere. The tour kicked off at 9 p.m. on Saturday, and as we climbed a hill the last traces of that Ossining sunset could be seen across the Hudson River, juxtaposed with a crescent moon. Later in the evening, the lit-up Governor Mario M. Cuomo Bridge could be seen, as well as New York City skyscrapers. Very cool, I say. Very cool.
The stars of this show were the kerosene lanterns that lit our way as they generated the spooky atmosphere; and our host, John Camilleri, who shared his generous spirit, his wealth of knowledge, and his expertise as someone with strong local connections. John wove all these things together with the nuts-and-bolts of the cemetery facts, stories of growing up in the community and a commanding authority that left my tour group dazzled. Bravo, John.
Eat: Culinary Delights in Westchester
When it comes to the food I ate during my 36 hours in Westchester, I’m mostly conflicted. Can there even be a “best” thing that I ate? Cue thinking emoji.
OK, maybe if I spell it out here in print I can make sense of it all.
Capriccio Pizzeria & Restaurant: Italian Excellence
The team at Capriccio Pizzeria & Restaurant in Croton-on-Hudson wowed me with their warm hospitality, banter and friendly conversation. I know I left an impression on them by ordering a good bit of food. Hey, what can I say? I may be Irish, but I was born in the Bronx and take my Italian food seriously.
Thank you, Capriccio, for the Barbecue Chicken and Penne a la Vodka slices, the Veal Cutlet Parmesan Sandwich and the Mozzarella Sticks. The food at this joint was great. The atmosphere was great. The whole experience was great. And the leftovers were great. Yes, oh yes, I’ll be back.
Baked by Susan: Sweet Treats
Baked by Susan in Croton-on-Hudson was ideal for a mid-afternoon snack. The rainbow and chocolate cupcakes I ate hit the spot perfectly. The display cases with cakes, cookies, empanadas and paninis left my mouth watering, even though my belly was content a la Capriccio.
3 Westerly Bar & Grill: Waterfront Dining
3 Westerly Bar & Grill, in my newest favorite community, Ossining, really stole the show with its Hudson River waterfront location and the hot lobster roll. Served with house lobster butter, lobster bisque, slaw and old bay frites. The hot lobster roll was divine.
I can say the same for the lawn and alternate access to Louis Engel Waterfront Park, which reveals a huge arch and pier with stunning views of the river.
Hudson Farmer & the Fish: Hearty Meals
Hudson Farmer & the Fish in Sleepy Hollow also offers views of the Hudson, but it’s this eatery’s proximity to the Westchester RiverWalk Park at Sleepy Hollow that truly stands out. Perfect for working up an appetite or walking off a hearty meal, the RiverWalk provides more great views of the river and the bridge, but everything is more immediate.
As for hearty meals, I can’t recommend the beer-battered fish and chips at Hudson Farmer & the Fish strongly enough. Served with vinegary slaw and tartar sauce, I was duly impressed with a meal that I eat often, but rarely rave about. And for the record, I’m raving. That fish was a slab-o-fish, hearty and robust, that left me wanting for nothing upon my last bite.
Drink: Refreshing Beverages and Cozy Cafes
The Perfect Mocha at Black Cow Coffee Co.
When it comes to mid-afternoon pick-me-ups, I’m a hot mocha man—no whip—through and through.
Regardless of how hot it may be outside, there’s nothing like the mocha-espresso-steamed milk fusion to re-spark my ignition.
The aforementioned Black Cow Coffee Co. in Croton-on-Hudson delivered big time for this emboldened traveler. The same can be said for Coffee Labs Roasters in Tarrytown, which was a 2024 participant in the Grand Tasting Village at Westchester Magazine’s Wine & Food Festival at Kensico Dam. It’s worth mentioning that the staff at both locations handled a robust flow of customers with patience and grace, which gave all of us waiting plenty of patience and grace to share.
Sing Sing Kill Brewery: Local Craft Beers
The Sing Sing Kill Brewery in Ossining revels in an industrial setting that manages to evoke the utilitarian and the familiar while offering “New York Farm Beer: Local Ingredients, Short Supply Chain, Low Carbon Footprint.” “Citrus Sucker Punch” and “Mind the Gap” are just two of the many beers served at the brewery.
At my lodging for the evening, the Cambria Hotel White Plains, I enjoyed several seltzer and cranberries at a cozy bar with a friendly bartender.
Stay: Comfortable Accommodations in Westchester
Cambria Hotel White Plains: A Grand Experience
And speaking of the Cambria, I’ve got nothing but grand things to say about this hotel.
The parking attendants were super friendly. The location was convenient for all my travels in and out of downtown White Plains. And the room was spacious and quite comfy—just what the doctor ordered following a nearly twelve-hour day on my feet.
But the real star of this show is the second floor, which is home to the lobby, gathering spaces, business center and bar and dining area. Real estate on this level is seemingly never-ending and all-consuming. The outside deck offers an opportunity to catch one’s breath while enjoying sites from high above downtown White Plains.
Conclusion: Westchester County’s Endless Appeal
I’d like to offer a round of applause for Westchester County and its cozy and charming communities, its endless array of captivating activities, its culture, cuisine and maneuverability.
That slab of fish in my fish and chips at Hudson & the Farmer.
That penne slice at Capriccio.
The colossal Croton Dam.
The Sleepy Hollow Music Festival, its vibe and its major-festival feel.
I loved it all. I won’t soon forget any of it. And to the fine folks of Ossining, please savor that sunset as I did. You’ve got a real gem of a spot on the Hudson River, there.
Until next time, Westchester.
Take Amtrak to Westchester County
Visit Westchester County and all the wonderful cities it has to offer via Amtrak to Croton-Harmon Station. Don’t forget to use Amtrak See New York and Save 15% discount! Amtrak also stops in Yonkers. Both stations offer Metro North service to Ossining and Tarrytown.
