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Message
My 5 Day hiking trip through NYC.
Posted on 10/5/25 at 9:34 pm
Posted on 10/5/25 at 9:34 pm
This is more of a solo trip itinerary for someone who wants to get all over the city and see a ton in a short period of time. I will list my days there and you can take from it what you can. I will say first, in order to prepare I made a list of everything i wanted to see or looked interesting to get pics of and i cut lower manhattan island into 3 sectors that i zoomed into on google maps and printed, then highlighted the parts of interest and made notes which helped me visualize and make an efficient plan for each day.
Day1: Flew into Laguardia got in around 1030, 1 hour commute into Manhattan via bus/subway. Used stasher to find place near station to hold my suitcase for rest of day since hotel was far away and didnt let me check in until later.
1) Went to Roosevelt Isle Tram...a cable car ride across to the isle where you can get view of the city to/from/ and on the isle.
2) Walked from Tram to 5th Ave around 58th street and walked that street looking at Trump Tower and luxury shopping stores until i reached Rockefeller Plaza and St. Patricks Cathedral where i got pics and looked around.
3) I also did the Top of Rock observatory here for city views.
4) Then went on a walking pic tour seeing Radio City Hall, Carnegie Hall, Petrossian building, and the bar from How I Met Your Mother since it was nearby (could easily skip this one). A restaurant/bar called Beast and Butterflies was also on my list around this area but i didnt end up going. Suppose to be nice with great views.
5) Did a day walk through Times Square. You dont have to spend a lot of time here but i still think its fun to visit for the spectacle.
6) Visited Bryant Park... one of the nice parks in the city with clean public restrooms.
7) Then went up Empire State Building and did my 2nd observatory. This building has a bit more of a production before it and in riding the elevator.
8) Walked over to Grand Central Station and got some quick pics inside and out and enjoyed the architecture.
Then walked over to pick up my luggage and took a subway to my cheap (for NYC standards) hotel/crash pad in Chinatown.
Day2:
Took Subway up close to Central Park. Had breakfast at a nice cafe on 57th and 6th called Mangia where you can sit outside. Then walked into Central Park and did the following sites inside; Gapstrow Bridge, Mall and Lit walk, Bethesda Terrace, Bows Bridge, then finally Belvedere Castle. You could also see the Sail Central Park pond but i would do that another day.
I proceeded over to the American History Museum nearby and spent 5 hours there touring all the floors. So much to see that i only chose a few things to read here and there as i moved and walked and saw all of the exhibits. You could easily spend a week here.
After the museum i walked over to Sheep Meadow in C.P. chilled for a bit then walked over to Hells Kitchen and had some drinks at a local bar called Daltons watching the Yankees play game 1. Then after dark i strolled through Times Square for a night time walk through it where the lights are brighter and its more energetic.
Day 3:
Took subway over to the Vessel and just took a pic before heading over to the Highline, but you could also add in another observatory called the Edge here. I walked the Highline which was a bit more crowded then i was hoping, but still a great walk seeing how they transferred an old rail line on the west side of the city into an elevated pedestrian path and garden which then became a catalyst for new building and investment projects.
I walked over to Little Island which in my mind could easily be skipped but is a nice park they built over the water and does have one good view/pic of the financial district. I think i meant to see Chelsea Market but forgot all about it.
I then walked through West Village through iconic neighborhoods. Seeing the Liv Tyler house, Friends Apt, brownstones, "narrowest" apartment, ate at L'Industrie Pizzaria, before heading over to Washington Park. Wash Park could easily be skipped but i did like seeing the chess hustlers i had always heard about. I took a subway over to The Ghostbusters fire house and got a pic there and of the Jenga building.
From here it was a short walk to the Financial district where i saw the 911 memorial pools, the new building, and the museum along with a mall called the Occulus. Then over to wallstreet and the stock exchange where theres a nice church along the route before going over to the very crowded Bull to fight for a good pic.
After this i took an ebike to save time over to Pier 11/ Wall St. jumped on a ferry across to Dumbo Park in Brooklyn and was able to get great views of the city at Sunset. There is also an iconic photo shot around here of the manhattan bridge.
I then took an ebike over to Domino Park in the Williamsburgh area where i got some nice night shots of the city. (i had brought a phone holder that attaches to bikes and this was helpful here as i had to go a roundabout route here. But the rides themselves are very fun way to get around city. I got some great night shots then headed over to Radegast Hall & Biergarten for some yummy german food and beer. Really cool bar area and they had live music. When leaving i used the ebike to ride across Williamsburg bridge at night (back to chinatown) which was very thrilling and something i can def suggest. The Williamsburgh area is a very nice part of Brooklyn with a lot of shops, restaurants, and bars. Seems like a young professional area of the metro.
Day4. I took a subway up to 86th and hit up Broad Nosh Bagels where i tried one of their Lox Bagels. I walked across Central Park to the Metro Museum of Art. You could def spend some time here if you like art. But for me after seeing the 45 min line and realizing how beautiful and cool it was outside, i decided instead to leave take a stroll through Park Place/Madison area and then back into Central Park by the picturesque pond where they sail the small boats around. Then walked through the city one more time along 5th and Rockefeller Plaza one last time seeing some sites again and enjoying the weather before heading back to my hotel to change into some nice clothes to go to a broadway show that night.
I had some extra time so i hit up a bar (Irons Bar and Grill) around 8th ave before walking over to see The Book of Mormon. I really enjoyed the show, and if i had known that before i probably would have done 1 more show on this trip. I then walked back through Times Square one more time later at night before catching a subway.
Day 5 final day. Had a late flight and one more possible excursion left on my MyCityPass pick 5. I decided to go on a water cruise where i saw the city line and went by Statue of Liberty for a good close up view. After the boat tour i rode an ebike up the west side of Manhattan to the Seinfeld Deli called Toms and got a pic then ate a few doors down at a really nice legit deli.I then hopped on another ebike and rode over to central pack and through it, down broadway through times square close to Bryant Park where i had stored my suitcase using stasher and hopped on a subway back out to the airport.
Apps used: Todaytix for broadway shows, nyc ferry to book across to brooklyn, mycitypass to get a discount on booking 5 events, stasher to find a place to hold my suitcase while i made most of day.
Select pics:
Day1: Flew into Laguardia got in around 1030, 1 hour commute into Manhattan via bus/subway. Used stasher to find place near station to hold my suitcase for rest of day since hotel was far away and didnt let me check in until later.
1) Went to Roosevelt Isle Tram...a cable car ride across to the isle where you can get view of the city to/from/ and on the isle.
2) Walked from Tram to 5th Ave around 58th street and walked that street looking at Trump Tower and luxury shopping stores until i reached Rockefeller Plaza and St. Patricks Cathedral where i got pics and looked around.
3) I also did the Top of Rock observatory here for city views.
4) Then went on a walking pic tour seeing Radio City Hall, Carnegie Hall, Petrossian building, and the bar from How I Met Your Mother since it was nearby (could easily skip this one). A restaurant/bar called Beast and Butterflies was also on my list around this area but i didnt end up going. Suppose to be nice with great views.
5) Did a day walk through Times Square. You dont have to spend a lot of time here but i still think its fun to visit for the spectacle.
6) Visited Bryant Park... one of the nice parks in the city with clean public restrooms.
7) Then went up Empire State Building and did my 2nd observatory. This building has a bit more of a production before it and in riding the elevator.
8) Walked over to Grand Central Station and got some quick pics inside and out and enjoyed the architecture.
Then walked over to pick up my luggage and took a subway to my cheap (for NYC standards) hotel/crash pad in Chinatown.
Day2:
Took Subway up close to Central Park. Had breakfast at a nice cafe on 57th and 6th called Mangia where you can sit outside. Then walked into Central Park and did the following sites inside; Gapstrow Bridge, Mall and Lit walk, Bethesda Terrace, Bows Bridge, then finally Belvedere Castle. You could also see the Sail Central Park pond but i would do that another day.
I proceeded over to the American History Museum nearby and spent 5 hours there touring all the floors. So much to see that i only chose a few things to read here and there as i moved and walked and saw all of the exhibits. You could easily spend a week here.
After the museum i walked over to Sheep Meadow in C.P. chilled for a bit then walked over to Hells Kitchen and had some drinks at a local bar called Daltons watching the Yankees play game 1. Then after dark i strolled through Times Square for a night time walk through it where the lights are brighter and its more energetic.
Day 3:
Took subway over to the Vessel and just took a pic before heading over to the Highline, but you could also add in another observatory called the Edge here. I walked the Highline which was a bit more crowded then i was hoping, but still a great walk seeing how they transferred an old rail line on the west side of the city into an elevated pedestrian path and garden which then became a catalyst for new building and investment projects.
I walked over to Little Island which in my mind could easily be skipped but is a nice park they built over the water and does have one good view/pic of the financial district. I think i meant to see Chelsea Market but forgot all about it.
I then walked through West Village through iconic neighborhoods. Seeing the Liv Tyler house, Friends Apt, brownstones, "narrowest" apartment, ate at L'Industrie Pizzaria, before heading over to Washington Park. Wash Park could easily be skipped but i did like seeing the chess hustlers i had always heard about. I took a subway over to The Ghostbusters fire house and got a pic there and of the Jenga building.
From here it was a short walk to the Financial district where i saw the 911 memorial pools, the new building, and the museum along with a mall called the Occulus. Then over to wallstreet and the stock exchange where theres a nice church along the route before going over to the very crowded Bull to fight for a good pic.
After this i took an ebike to save time over to Pier 11/ Wall St. jumped on a ferry across to Dumbo Park in Brooklyn and was able to get great views of the city at Sunset. There is also an iconic photo shot around here of the manhattan bridge.
I then took an ebike over to Domino Park in the Williamsburgh area where i got some nice night shots of the city. (i had brought a phone holder that attaches to bikes and this was helpful here as i had to go a roundabout route here. But the rides themselves are very fun way to get around city. I got some great night shots then headed over to Radegast Hall & Biergarten for some yummy german food and beer. Really cool bar area and they had live music. When leaving i used the ebike to ride across Williamsburg bridge at night (back to chinatown) which was very thrilling and something i can def suggest. The Williamsburgh area is a very nice part of Brooklyn with a lot of shops, restaurants, and bars. Seems like a young professional area of the metro.
Day4. I took a subway up to 86th and hit up Broad Nosh Bagels where i tried one of their Lox Bagels. I walked across Central Park to the Metro Museum of Art. You could def spend some time here if you like art. But for me after seeing the 45 min line and realizing how beautiful and cool it was outside, i decided instead to leave take a stroll through Park Place/Madison area and then back into Central Park by the picturesque pond where they sail the small boats around. Then walked through the city one more time along 5th and Rockefeller Plaza one last time seeing some sites again and enjoying the weather before heading back to my hotel to change into some nice clothes to go to a broadway show that night.
I had some extra time so i hit up a bar (Irons Bar and Grill) around 8th ave before walking over to see The Book of Mormon. I really enjoyed the show, and if i had known that before i probably would have done 1 more show on this trip. I then walked back through Times Square one more time later at night before catching a subway.
Day 5 final day. Had a late flight and one more possible excursion left on my MyCityPass pick 5. I decided to go on a water cruise where i saw the city line and went by Statue of Liberty for a good close up view. After the boat tour i rode an ebike up the west side of Manhattan to the Seinfeld Deli called Toms and got a pic then ate a few doors down at a really nice legit deli.I then hopped on another ebike and rode over to central pack and through it, down broadway through times square close to Bryant Park where i had stored my suitcase using stasher and hopped on a subway back out to the airport.
Apps used: Todaytix for broadway shows, nyc ferry to book across to brooklyn, mycitypass to get a discount on booking 5 events, stasher to find a place to hold my suitcase while i made most of day.
Select pics:
This post was edited on 10/6/25 at 1:44 am
Posted on 10/5/25 at 9:34 pm to BlackPawnMartyr

This post was edited on 10/5/25 at 9:37 pm
Posted on 10/5/25 at 9:34 pm to BlackPawnMartyr

This post was edited on 10/5/25 at 9:38 pm
Posted on 10/5/25 at 9:53 pm to LemmyLives
Thanks, these were all from my phone. I did take my Nikon and got some good pics as well. Here are a couple from it.


Posted on 10/6/25 at 4:31 am to BlackPawnMartyr
Thanks for the inspiration. I'm going to NYC in two weeks (just for three nights, though), and I will do a few of the same things. I've previously spent 5 days in NYC, but I've never been to Brooklyn, so I'm definitely going to replicate that part of your trip.
I also appreciate hearing that Stasher worked well. I've previously used Luggage Hero with good results.
Posted on 10/6/25 at 8:37 am to BlackPawnMartyr
Thanks for the review. NYC can be big and scary to some, but I find with a little bit of planning and willingness to walk, take transit, and bike its a city where you can do/see some many awesome things in a short period of time and still just barely scratch the surface of what it offers.
Question, how many total steps and miles on bike did you get in?
Question, how many total steps and miles on bike did you get in?
Posted on 10/6/25 at 10:00 am to NOLALGD
I didnt track any of that as i dont own a smart watch. Usually id never care, but for this trip i did sorta wish i had one because i know i walked a frick ton which is why i called it a hiking trip. But that was by choice, someone less willing to do all the walking could easily still have a nice trip by pacing themself the first day where most of the sites were fairly concentrated. Pacing themself on the highline and through west village, skipping Wash park. And knowing how far they have to go other times and really utilizing the ebikes which are everywhere and a lot of fun to ride. Just be careful with them, they get up to speed very quickly so easy on that first pedal rotation.
Posted on 10/6/25 at 10:10 am to BlackPawnMartyr
Also, it can be a bit of a hassle finding a place to use the restroom in the city. The biggest hack i found was buying a drink from starbucks and asking for the code. They were very willing and there are starbucks everywhere! The bathrooms in Bryant Park are very clean and monitored. Bars were pretty easy for me as they didnt seem to really monitor walkins. Holding it until you reach a museum/observatory or making sure to go before you leave is always smart. Its really the restaurants and stores thats its difficult. I was able to use Raising Canes in times square without a hassle.
Posted on 10/8/25 at 8:03 am to BlackPawnMartyr
Awesome pics, thank you for sharing
We were up there last year and we also did the cable car over to Roosevelt Island, we had brunch at panorama room… which is the top floor restaurant of the graduate hotel, unbelievable views!
We were up there last year and we also did the cable car over to Roosevelt Island, we had brunch at panorama room… which is the top floor restaurant of the graduate hotel, unbelievable views!
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