R5 Five Places to Propose

3. Playland
You’d have to put this on hold until 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.

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. 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—the Purchase Symphony Orchestra performs on February 19, for example—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.

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

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.