New York City
New York City Fall Trip: My 9-Day Itinerary
New York always delivers. The energy, the food, the views, it's all top tier. Whether it's rooftop drinks, catching a show, or just walking through the city at night, it always feels alive. I put together my full NYC itinerary so you can experience it the right way. Go have fun and tag me when you do!
Trip Snapshot
Where: New York City
Trip style: Fall trip
When we went: Late October into early November
Weather when we visited: 51°F to 64°F, mornings start crisp and the temp drops fast after sunset
What to pack: Light jacket, hoodie, sweater, long sleeves, jeans, sneakers, and an umbrella
Affiliate Disclosure: Some links on this page are affiliate links, which means I may earn a commission if you book through them, at no additional cost to you. I only share experiences I’ve actually done and would recommend.
Day 1 | Arrival
Landed and kicked things off with taco Tuesday. Easy first night, just settling in.
Day 2 | Soul Food + Rooftop Movies
BLVD Bistro for soul food, walked through Little Island, then caught the Yotel rooftop movie experience.
Day 3 | Uptown
5th Avenue, Central Park, then Tao Uptown for their $1 happy hour, 4 to 7 PM. Night ended at Somewhere Nowhere.
💡 SHANE'S TIP
If you're doing Tao Uptown, time it for happy hour. $1 specials from 4 to 7 PM is one of the better deals in the city for a spot that nice.
Day 4 | Halloween
Blend on the Water, then Bryant Park Winter Village, then the Village Halloween Parade that night. If you can time a trip around Halloween in New York, do it, the city goes all the way in.
Day 5 | Governors Island
Ferried out to Governors Island, then hit the Brooklyn Museum for their First Saturdays event, free admission.
Day 6 | Views + Soho
Top of the Rock for the skyline, then walked through Soho. Later, we made the trip out to the Great Jack O'Lantern Blaze.
💡 SHANE'S TIP
The Blaze isn't in the city, it's out in Croton-on-Hudson, about 45 minutes to an hour from Manhattan by car or Metro-North. Worth it if you love Halloween, just don't plan it as a quick after-dinner stop.
BOOK TOP OF THE ROCK TICKETS →
Day 7 | Midtown
Summit One Vanderbilt in the morning, then Times Square.
BOOK SUMMIT ONE VANDERBILT TICKETS →
Day 8 | Hudson Yards
The Edge observation deck, then walked around Hudson Yards.
Day 9 | Departure
Sugar Hill Creamery before heading out. Simple last day.
Getting Around
Which airport you fly into depends on where you're staying. LaGuardia is best if you're in Manhattan, JFK works well for Brooklyn or Lower Manhattan via the AirTrain and subway, and Newark is the move if you're in the Tri-State area or flying United. Around the city, you've got trains, Uber, the Long Island Railroad, biking, or just walking.
Good to Know: Prices
Top of the Rock runs anywhere from about $47 on lighter days up to $60 on peak days, it's dynamic pricing. Summit One Vanderbilt starts around $44 on weekdays and climbs to $57 to $63 for sunset slots. The Edge starts around $42. The Jack O'Lantern Blaze runs $24 to $52 depending on the date. These move around based on demand and season, so treat them as a ballpark, not exact.
Would I Do This Trip Again?
Definitely. Timing it around Halloween made the whole trip, the parade, the Blaze, Bryant Park lighting up for winter, it's a completely different city than a summer visit.
Want Help Planning Your Own Trip?
Tell me where you're going, your dates, your budget, and what kind of trip you want.
I'll help you find options for places to stay, things to do, restaurants, and experiences.
You handle the booking and coordination.
Go somewhere. Make it worth it.