5 Romantic Places to Propose in Westchester County

We’ll do the legwork. You bring the ring.

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We pick some of our favorite romantic county destinations to pop the question. All you have to do is bring the ring.

When surrounded by Westchester’s stunning scenery, are you feeling inspired to buy a ring and ask for your true love’s hand? Finding someone to marry is the hard part—proposing should be easy. And, now, it’s even easier with our helpful list of five perfect places to pop the question and propose in a way your loved one will never forget. Take your pick from our à la carte menu of proposals.

1. The RiverWalk at Croton Landing Park

If your sweetie is a nature lover, it’s hard to go wrong with a proposal at The RiverWalk at Croton Landing Park (unless, of course, it’s raining…we 100% recommend waiting for a sunny day). Plus, your one-and-only will be dazzled by the gorgeous, up-close-and-personal view of the Hudson River and its accompanying little sandy beach when you propose.

Afterward: Celebrate your engagement with a romantic seafood dinner at the Ocean House Oyster Bar & Grill in Croton-on-Hudson. (You know what they say about oysters.)

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propose in croton
Photo by Doug Schneider

2. Purdy’s Farmer & The Fish

If there’s one bad thing about proposing outdoors, it’s that you can’t control the weather. At this homey North Salem farmhouse, you’ll be cozying up in front of a warming fire in one of the restaurant’s several stately fireplaces (or, if the weather is warmer, lounging at one of the outdoor tables) before you can even slip the ring out of your pocket to propose.

Afterward: What better proposal-topper than dessert? Choose one of the restaurant’s decadent desserts, or pick something up in advance from the farm store to take home.

3. Playland

You’d have to plan this one for summer, but Playland is full of picture-worthy backdrops for a proposal: the 1920s-era carousel, the art deco tower, the top of the Ferris wheel, etc. If your future-betrothed isn’t one for amusement parks, go for a long walk on the nearby beach and take in the view of the Long Island Sound.

Afterward: Isn’t it obvious? A turn on the Dragon Coaster! Buy the cheesy, mid-drop photo at the end of the ride as a souvenir of your engagement day.

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propose at playland
Photo by J.J. Cady

4. The Neuberger Museum of Art

Show your intended that you appreciate the finer things—your relationship included—by surrounding yourselves with a collection of world-class art when you propose. If the weather is nice, you might also want to take a stroll on the grounds of PepsiCo, which conveniently has works of art by internationally renowned sculptors next to grassy areas perfect for kneeling down on.

Afterward: In addition to the ring, hand your beloved tickets to whatever is going on at the Performing Arts Center for an all-inclusive night out.

5. Anthony’s Nose

Jane Daniels, author of Walkable Westchester, says she personally knows two couples who got engaged there—the views are so fantastic. Your sweetheart will be so wowed by the panoramic vista of the Hudson River and Bear Mountain Bridge—and so pumped with endorphins—that you’ll be guaranteed a yes when you propose.

Afterward: Hike on down and head over to Peekskill Brewery to hoist a Captain Lawrence in your honor.


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Bonus for the Brave: The Metro-North Railroad

Sure, the Metro-North’s ultra-bright lighting and cars full of strangers don’t scream “romance,” but, for a certain type of couple looking for an offbeat, unique engagement story, it just might be the place to get down on one knee (that is, if you can snag an aisle seat). What better way to brighten up a dreary commute than with a sweeping romantic gesture? Plus, the Hudson Line offers the pretty backdrop of the River—we recommend doing the deed at the southbound Dobbs Ferry stop for a nice, uninterrupted view.

Afterward: Stop in for celebratory drinks at Grand Central Terminal’s Oyster Bar.

Related: Where to Eat in Westchester Before Heading to Rockefeller Center