Where Should This Reader Propose To His Girlfriend?

Quick note: A reader wrote me asking for a good place to propose to his girlfriend. Rather than limit it to my locations knowledge, I asked my readers, and was inundated with lots of great ideas. If you’re looking for a good place to propose in NYC, just check through the comments.

A Scouting NY reader is planning on proposing to his girlfriend, and needs your help!!

Central Park - Wedding

I recently got a letter from a fan of the site telling me that he is planning on proposing to his girlfriend, and is looking for the perfect NYC location to do it. Both he and his girlfriend are huge fans of NY history and enjoy exploring the city together, and he really wants to choose a location that ties the city into his proposal in a unique, intimate and historical way, a locale they will remember for the rest of their lives.

His first thought was Gramercy Park – neither of them has ever been inside, and his hope was to work something out with the Gramercy Park Hotel for access, take her on a tour, then ask the big question when she was least expecting it. Great idea, right?

Of course, it comes as no surprise that the douchiest park in NYC is bordered by the douchiest hotel in NYC. They said the rules are very strict, and that he could only gain access by paying the $500/night room fee, which he can’t afford.

Coming up short on ideas, he wrote me a very thoughtful letter asking if I could suggest any other locations. His only requests were that it be somewhat off the beaten path, pretty, intimate, and historical. My first thought was Bannerman’s Castle, an incredible abandoned castle-like structure located on an island in the the Hudson. Then again, perhaps visiting decrepit ruins on an island in the middle of the freezing winter doesn’t exactly scream romance. Other ideas include Staten Island’s Snug Harbor, Governor’s Island…Bethesda Fountain is probably too cliched, no? Perhaps he could gain access to Grove Court by talking with a neighbor? Gantry State Park in Queens is a pretty amazing location.

Rather than limit the options to my knowledge of the city, I promised I’d turn it over to SNY readers: where should this guy propose?? Historical, intimate, off the beaten path, and New York-centric. Hell, if one of you comes up with something that he uses, maybe I’ll come up with a cool Scouting NY prize for you. Just post your ideas in the comments.

Ready? Go!


PS – “The park was at one time opened to the public on Gramercy Day (which changed yearly, but was often the first Saturday in May). In 2007, the Trustees of Gramercy Park announced that it would no longer open the park on that day.” Fuck you, Gramercy Park. Seriously, go fuck yourself.

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  1. my fav place, is the spot in grand central station,(its near juniors) where one person stands on one side of a wall under an arc across from the other and can whisper to another by talking to the wall. SO CUTE. pop the question and then the person hears it and has to turn away from the wall with all these strangers walking by, and they realizes the rest of their life has been answered for.

  2. Let’s see. There’s a very romantic park on 5 Ave and maybe 103 St. There’s an arbor there overlooking a garden. It probably doesn’t look like much in the winter. How about one of the glass houses at either the Bklyn or Bx Botanic Gardens? Beautiful, inside/outside vibe, some privacy could probably be arranged. Congrats!

    • I used to pass by this park all the time. I always thought it was really cool. What’s the name of this park, do you know? I always assumed it was private. Is it public?

  3. How about at the Temple of Dendur at the Met? Cleopatra’s Needle?

  4. I was going to say Grand Central Station too. Campbell’s Apartment has always had a cool history of NYC vide to it.

    I’ve also always loved the piers over in LIC which look over the whole city. Kind of cold this time of year but on a clear night it’s the best.

    Brooklyn Bridge, just don’t be this dude: http://gothamist.com/2009/04/02/brooklyn_bridge_proposal_nearly_end.php

    How about set up a personal walking tour for them of historical NYC locations then pick a romantic last stop and he can propose then. If they’re a fan of SNY that would be pretty awesome.

  5. I’m going to suggest either Astoria Park, Roosevelt Island, City Island or Governor’s Island.

  6. theonewhoknowstorock

    i’d go for D.U.M.B.O.

  7. Retro Roadhusband and I had our first date in NYC as it was half way between Boston and Delaware. We stumbled upon Bethesda Fountain while trying to find Strawberry Fields (we’re both rabid Beatles fans) and spent most of that first date talking while sitting there watching brides getting their photos taken at the fountain (talk about first date pressure!)

    2 years later we were at the fountain after he played a gig in the city, and he popped the question on that very same spot where we sat on our first date!

    Bethesda Fountain worked for me! I do have a soft spot for Grand Central as well, and told the husband if they ever make a movie of our courtship I’m going to pretend that I got off the train at GC on the way to our date instead of getting off the bus at Port Authority like I really did 😉

  8. Bear Mountain State Park – from wikipedia: Bear Mountain State Park is located on the west side of the Hudson River in Orange and Rockland counties of New York. The 5,067-acre park offers biking, hiking, boating, picnicking, swimming, cross-country skiing, cross-country running, sledding and ice skating as well as a zoo, trailside museums, a hotel called Bear Mountain Inn, a carousel (!!!!!) and a dining facility. You could really just go exploring, and propose when the moment struck you – making the spot truly and uniquely yours!

    p.s. from the NYSP website: The Merry-Go-Round at Bear Mountain State Park features hand painted scenes of the park and 42 hand carved seats of native animals including black bear, wild turkey, deer, raccoon, skunk, Canada goose, fox, swan, bobcat, rabbit and more.

  9. Brendan’s idea is the best idea anyone could think of, in my opinion. That spot in Grand Central where you can talk to each other across the room is an amazing place to do it!

    If the guy doesn’t know how to do it, he should ask someone there so everything goes perfectly. It may not be intimate, but there’s something special about the thought of a proposal in a busy place like that. It won’t matter, in a way, because they’ll feel like they’re the only people there. 🙂

  10. Oh, to expand on the Grand Central idea, they have guided tours every Wednesday and Friday at 12:30. Maybe he could call ahead of time and set it up where that one spot is the last stop on the tour.

  11. Probably not the most romantic, but maybe Castle Clinton in Battery Park? http://nyharborparks.org/visit/cacl.html

  12. There’s no better place than Hunters Point South – especially since it’s going to be a generic high-rise neighborhood in just a few months.

    For now, however, it’s unbelievably gorgeous:


  13. By the Gowanas canal. Very romantic, especially on a warm spring day.

  14. I’m not sure how these locations would play out in winter, but…

    * The Chinese Scholar’s Garden at the Staten Island Botanical Garden is amazing: http://media.timeoutnewyork.com/resizeImage/htdocs/export_images/sg08/Sg08.x600.Seek.17.jpg?

    * The abandoned Fort Tilden in the Rockaways is very historical, pretty (in a desolate kind of way!) and definitely “off the beaten path”: http://www.nytimes.com/2006/07/21/arts/21tild.html

    * The Shakespeare Garden and Belvedere Castle in Central Park are not so out of the way, but very pretty and intimate (and probably not as crowded with tourists in the winter)

    * On Barrow Street in front of “NYC’s narrowest house” http://www.nyc-architecture.com/GV/GV043NarrowestHouse.htm or on any of the surrounding cobblestoned, adorable streets in the Village, many of which have rich architectural and cultural histories, like Grove Court, which was the setting for an O. Henry story. The alley of Patchin Place has the only original gas streetlamp left in Manhattan and was once home to the poet e.e. cummings and actor Marlon Brando. See http://www.forgotten-ny.com/Alleys/GREENWICH%20VILLAGE/green.html

    * The Unisphere in Flushing-Meadows Corona Park — it’s not exactly romantic, but it’s definitely different.

    * My husband proposed to me on a walk in Forest Hills Gardens. We happen to live in Forest Hills, but it’s absolutely a picturesque neighborhood that’s intimate (no throngs of tourists or commuters like you’d find in Grand Central) and historic. Here are some pictures from flickr: http://www.flickr.com/groups/fhg/pool/

    Best of luck to the happy couple — please keep us updated on what happens!

  15. The Cloisters and the surrounding park is pretty epic, as long as you don’t mind the tourists, all the religious art, and the 92839 other people taking wedding photos there!

  16. I’ve always been partial to the tobacco warehouse in DUMBO. It feels very historical and has great views of the bridges and lower Manhattan.

  17. Carl Schurz Park … in the circular sunken garden, past the footbridge.

  18. I like the idea of Grammercy park. If you’re only getting in once, make it the most important “once” in your life. I bet the readers of this fund could pool enough change together to get the kid access to the park.

  19. I just did a post on this: “If You Like It, Here’s Where to Put a Ring On It” – http://kreyrecommends.com/9948786. My third suggestion is definitely off the beaten path but is still in NYC. Good luck with the proposal! 🙂

  20. Fort Washington Park, at the foot of the majestic George Washington Bridge and right next to the cute Little Red Light House. That spot can be reached by a wild and romantic trail through an abandoned part of the park. It has a sweet little beach area – where the Hudson ‘waves’ come crashing in -, splendid views of the New Jersey Pallisades and the Hudson Valley and there are hardly ever any people there. Far away Downtown, the skyscrapers loom in the distance, as well as the tower of the Riverside Church. My vote!

  21. If he can wait until springtime, the Cherry Walk at the Brooklyn Botanical Garden is absolutely incredible!
    A more quirky one that would definitely require lots of permission is to set up a private tour of the Intrepid and ask her there.
    Another one that would require some careful planning is finding an old theater and getting a tour of that-he could have it set up to walk on stage and have a spotlight hit them and then ask.
    I’ve gotta say, though, the Grand Central idea is pretty awesome!
    Oh, who am I kidding, this is a list of places I’d like to get proposed to!

  22. Was the CCNY campus already mentioned, in Hamilton Heights? Gothic and romantic and I’m sure a tour of the beautiful Sheppard Hall can be arranged for a stained glass surrounded proposal.

  23. can anyone recommend a restaurant or venue? something like the defunct Rainbow Room?

  24. Being a Jersey guy, I think the city always looks best from the Jersey side, so I would go with Hamilton Park in Weehawken. On top of the cliff, the city makes an incredible backdrop.

  25. The Champagne Room at Rick’s Cabaret!

  26. Yeah, it’s pretty common, but I proposed at the top of the Empire State building. Born and raised in Manhattan, it was my first and only visit. My wife couldn’t understand why – out of the blue – I wanted her to meet me for a ride to the observation deck. The coolest part was that EVERYONE in the Houlihans in the lobby where I waited for my wife-to-be knew my story. When she showed up a hush fell across the entire restaurant. At the time I was living across from Gramercy Park and had a key. Duh!

  27. I proposed to my wife while walking down 10th street on our way to a birthday party at Cowgirls. Sounds tacky? It wasn’t. It was December, the street dark, lit only by twinkle lights that were strung across the sidewalk. They created a great canopy of starlight against a background of fantastic NY architecture. I paused, bent on one knee and proposed as other couples walked by.

    The truth is that anywhere in New York can be the perfect background for your life. It’s a city full of magic 🙂

  28. What about this little secret garden which was the backdrop of a gorgeous wedding? http://www.maxwangerblog.com/?p=1797

  29. Wikipedia claims that residents of the buildings looking onto Gramercy Park along with Calvary Church have access to the keys for the park. I think, if anything, you should swing by the church and have a chat with someone. I doubt you’d be turned town access for a day considering your story.


  30. Being a huge fan of NYC history, I would say St. Paul’s chapel. I could be wrong but I think it is the oldest building in Manhattan dated 1764.

    Perhaps something along the lines of – May our love last like this church has, through good times and challenging ones.

    Whatever you decide, congrats!!!

  31. Once upon a time, I had an amazingly romantic dinner at Terrace in the Sky: http://www.terraceinthesky.com. Wonderful views.

  32. that is the most beautiful proposal I have ever seen. You are both so very lucky!!! Bless you both.

  33. If he needs a photographer to hide and take pictures when he proposes let me know! I’d love to do it!

  34. Since it’s winter and perhaps too cold to be outside, what about a little excursion to Roosevelt Island then popping the question in the Tramway while on the way back into Manhattan? You can’t beat that view.

  35. I’ll second the vote for Fort Tryon Park, although at this time of year something indoors might be nicer — how about the lobby stairs in Radio City? Maybe Scout could get them in.

  36. I suggest Straus Park at 106th St and West End. It is dedicated to Isidor and Ida Straus, the couple on the Titanic who preferred to die together than be split apart by lifeboats. The Strauses originally lived at 105th and West End, so there’s the local history. Their death is romantic and a testament to true love. They’re a real NY couple–Isidor Straus was a partner at Macy’s and the Straus in Abraham & Straus. And the park is lovely:


  37. Go to the Rose Hill Campus of Fordham University up in the Bronx. There’s a few spots too. One is in front of the main classroom building, Keating Hall, on the steps that commemorate visits from heads of state. Another is near the University Church and Queens’ Court dorms, dating back from 1841. Now with the construction of the new dorms there, I’m not sure how it will mess up the west portion of the campus, but on a nice spring day there are few areas of the city that are as beautiful, and the guards should let you in with a little prodding.

  38. How about some place that they have been to before, but was personally special to them rather than just being “Historical, intimate, off the beaten path, and New York-centric.” Having proposed twice in my life If the place has some special personal meaning to both of y’all that would be the first filter, Then I’d filter the decision through the rest of the criteriia. NYC has scads of historical places. This is one of the things that keeps me coming back to NYC. It like finding a bit of greenery that you like. Mine just happens to be Sheridan Square.

  39. SVA has a dorm in gramercy park. all the students who live there have access. bet you could arrange something with one of them.

  40. Fort Tryon Park/The Cloisters is lovely. I love the Little Red Lighthouse idea that someone suggested.

    Or what about the High Line?

  41. Ooh, great question & great suggestions so far!

    I would second Astoria Park and the tram, and add:
    – Socrates Sculpture Garden (on the water, beautiful views, sometimes some lovely art, rarely-to-never crowded)
    – Staten Island Ferry
    – Brooklyn Heights Promenade
    – Owl’s Head Park in Bay Ridge (http://www.flickr.com/photos/tomvu/4110422963/)
    – Jamaica Bay / Broad Channel

    Good luck!

  42. Gustad, that is just beautiful. Best wishes for your life together.

  43. Staten Island Ferry as they are passing Lady Liberty…or atop Lady Liberty…(I trade my “freedom” for a life forevermore interwoven with and in mutual submission to my love)…

    or Bklyn Bridge (no words necessary)…

    or in a very special spot inside the Met (our love will stand the test of time)…

  44. For a romantic adventure like no other in NYC; go underground.
    Beneath the streets of Brooklyn, the mysterious and beautiful Atlantic Avenue Tunnel awaits.

    Three great things to consider:

    1)The only way in is by climbing down through an actual manhole in the middle of Atlantic Avenue (a lane of traffic is closed when tours are given). – It’s a trip!

    2) Besides being one of the most faccinating, historic sites in the city, the tunnel is strangely warm in winter – its a constant 60 degrees – winter and summer and not damp. It’s bizarre; but it must have something with the tunnel being underground and sealed up tight.

    3) The next tour is on February 14th!

    By flashlight or flickering candle, no lover will be able to resist a sparkling diamond ring presented in such a velvety dark setting.

    Good luck!

    Hopefully, one day we’ll have marriage equality – so that I’ll be able to do this too –with my man!

  45. I guess it’s too cold for Coney Island. If you want a view that will take her breath away, how about the Smith/9th Street Station on the F/G line? On the Coney Island bound side in particular you get a spectacular panoramic view of Brooklyn-Staten Island-Verrazano Bridge-harbor-New Jersey-Statue of Liberty-lower Manhattan-Queens. At sunset on a clear day, truly amazing, especially if the reflection from the setting sun is blazing in the windows of nearby buildings. It’ll be cold, but the better for snuggling!

  46. Here are my suggestions:

    He could propose in front of Federal Hall, where George Washington was inaugurated as the first president of the United States. I can’t think of any place more historically significant in NYC than Federal Hall.

    Historical and NYC-centric
    He could propose at the Transit Museum in Brooklyn — in one of the old buses or subway cars. It sounds hokey, but those old relics are quite charming.

    He could propose on top of the Washington Arch at Washington Square Park. He’d have to talk the Parks Dept into giving him access. If denied access, he could propose under the arch.

    In Better Weather
    He could propose on the roof at the Metropolitan Museum. It offers nice views of Central Park. They even have a roof bar that serves champagne.

    In Better Weather
    He could propose on top of the Wonder Wheel at Coney Island.

    Other Ideas
    The reservoir at Central Park in April, when the cherry blossoms are in bloom, is incredibly romantic and beautiful. Another spot that is ultra-romantic is the pier near Empire-Fulton Ferry Park in Brooklyn at night. The view of Manhattan all lit up in bright lights is spectacular.

  47. In the parlour of the Merchant’s House museum, since Gertrude Tredwell never got to marry her beau.

  48. Re: the Merchant’s House Museum, maybe in the little pretty garden: http://farm4.static.flickr.com/3135/2748417920_023a2c482f.jpg?v=0

  49. And, sorry for commenting again (I wish there was an edit feature on this), not only is it pretty and intimate, but it’s uniquely historical – it’s a perfectly preserved NY house, with all the furnishings and belongings intact from the family that lived there from the 1800s for a hundred years, it has a romantic story attached to it (although one of thwarted love), and the people at the Museum are so nice, I bet they could help him to arrange something special. And though the garden is pretty, if it’s cold, he could do something inside. He just has to hope that none of the resident ghosts turn up to celebrate alongside them!

  50. The Conservatory Garden (around 105th and 5th Ave) in Central Park, the South Garden … as early as possible or before it closes when there are the least people around … romantic, intimate garden, small classical fountain, flowers, etc. (Spring is probably best … when the cherry blossoms are out). Good luck !

  51. The New York Public Library Schwarzman Building (5th Ave. and 42nd Street)is available for proposals. You and your fiance(e) can come in after hours and have our gorgeous Astor Hall all to yourselves for 45 minutes – or you can bring a photographer – or your Moms, etc.
    Contact our Special Events Department to discuss. 212.930.0730.

  52. Gustad,

    Granted I’m no alpha male, but the way you told your story and the photos made me shed a tear 🙂

    I think you exemplify the way to go about proposing: a bridge in Central Park sure is pretty, but by no means the most amazing/original/surprising location. What IS amazing/original/surprising is what you made of it and the sincerity with which you expressed your feelings, and I think that’s a good lesson for everyone.

    Sure, someone might propose on top of Mount Everest, but doesn’t the extravagance overshadow what really matters, ie. love for one another?

    Thank you for sharing your lovely story and pictures.

  53. How about one of the Tudor City parks on Tudor City Place and E42 or 43 St? Very NYC and like little brothers/sisters of Gramercy Park. But without the attitude.

  54. Dave,
    Yes, Tudor City is very romantic and a great spot to get engaged or married (you can rent the park for a reasonable fee). You will forget that you are in the heart of Manhattan. Check out their website at http://www.tudorcitygreens.org

  55. The top of the Beekman Tower at 49th & 1st. Worked for me.

  56. What about taking her on a private wine tasting or giving her the ultimate spa engagement. The website http://www.proposal-ideas.com/new-york-proposals/new-york-proposal-ideas.html has other great ideas you should check out! Good luck!

  57. That’s so sweet of you. I wish I could have the same proposal when my bf plans to do it.

  58. I liked the Bethesda Fountain idea. It’s romantic, picturesque and above all, free! I was having breakfast in the Palm Court restaurant of The Plaza Hotel when two 40-somethings came in to get married. I was surprised I wasn’t asked to be a witness, but they brought their own. However, for the actual proposal, I would prefer the after-theater desert and dancing in the Palm Court. And then there’s the Brooklyn Heights Promenade. And last December, everyone was proposing in the Channel Gardens, and they were asking me to take their pictures — even the ones from Korea and China! But I don’t suppose you can beat the top of the Empire State Building, which figured in 2 movies named, “Love Affair,” “An Affair to Remember” and “Sleepless in Seattle.”