[Updated July 19, 2023] This walking itinerary in Hudson River Park can, if you so desire, begin and end with a glass of wine at two different waterfront wineries.
In between the vino, you’ll encounter some of New York City‘s newest revitalized spaces and most spectacular photo ops. You’ll enjoy river views and skyline views from various vantage points and Manhattan’s most iconic landmarks will make appearances again and again.
The Hudson River walk takes you from the urban oasis of Little Island to the city’s newest and largest rooftop park at Pier 57 to beautifully restored Pier 26 and a Tribeca winery. If you love seeing New York City on foot, slip on your most comfortable walking shoes and take this scenic 1.7-mile walk along the Hudson River.
This is a great itinerary to connect to a walk on the High Line. From the 14th Street exit, it’s only a five-minute walk to Little Island. Alternatively, you begin at Pier 26 and walk north if your itinerary includes something like the Intrepid Sea, Air, & Space Museum or a sailing excursion on the Hudson River.
Note: I prefer starting this walk at Little Island, then going a few steps north to the rooftop park at Pier 57, then having a glass of wine at City Winery, before continuing my walk south down Hudson River Park. It would also make a lot of sense to kick off your walk at City Winery, then check out the view from the rooftop, then head to Little Island and beyond. It’s your choice!
Hudson River Walking Itinerary Map
See an interactive version of this map.
1. Explore the Winding Paths of Little Island
Clusters of white “tulip pots” rise out of the Hudson River at Pier 55, forming the foundation of Little Island. The structures, which really do resemble flowers, sit at varying heights, creating a unique undulating landscape to this public park.
One of the most impressive views is outside the entrance, where you get the full visual effect of those flower-like structures. But inside is pretty cool, too.
Since the day Little Island opened in May 2021, tourists and locals have flocked there to walk on windy garden paths, take in skyline and river views, and catch (seasonal) live music, dance, and comedy performances in the open-air amphitheater known as The Amph (ticket fees apply).
Compared to most New York City parks, which are designed for leisurely all-day blanket picnics, Little Island’s twisting paths, stairways, and various lookout points propel you to stay on the move and keep exploring.
You’ll also encounter lots of play items like music-making dance chimes which beg to be stomped, mesmerizing spinning discs, and dizzying spinning chairs. Refreshments are available at The Play Ground from May to September, including beer, wine, coffee, sandwiches, ice cream, salads, and more.
One point of interest about Little Island is that it was an initiative of The Diller-von Furstenberg Family Foundation (that’s fashion icon Diane von Furstenberg and media mogul husband Barry Diller). Another is that Heatherwick Studio was part of the design team, a team that also conceived of the Vessel at Hudson Yards, as well as a set of barrel-windowed apartment buildings along the High Line (at 18th Street).
Looking for more things to do at Little Island? A free 40-minute audio tour is available on their website for those wanting to know more about the history, design, and landscape of this quirky urban space.
Little Island is fully ADA compliant.
Pier 55 at Hudson River Park, Hudson River Greenway, NY
Visiting Little Island
- Entrance is FREE but timed reservations are required Thursday-Sunday (and holidays), from May 12-September 19, from noon to close.
- Fom September 20-May 11, no reservations are needed any day or time.
- Ticket prices vary for events in The Amph.
2. Take in Panoramic Views from the Rooftop Park at Pier 57
Pier 57 is just a 2-minute walk north of Little Island–that sprawling green building on the river is it. City Winery is located here, as is a Rooftop Park, which opened to the public in April 2022.
At 80,000 square feet, the rooftop is massive. There are two levels of walkways, benches, lookouts, and generally interesting spots to sit and gaze across the river to New Jersey and down to Little Island, a vantage point from which you can appreciate its waves and curves. There are also canopies that provide shade or, as when we visited, shelter from a spring downpour. 57 Hudson River Greenway, New York, NY. Entrance is FREE.
3. Sample Locally Produced Wine at City Winery at Pier 57
Are you ready for a glass of wine? If so, you’re in luck.
City Winery, located at Pier 57 in the same building as the Rooftop Park, is the ideal waterfront location to sit down to a glass of wine and perhaps a bite to eat. While their grapes are sourced from more than 30 vineyards around the world, the wine is made on-site, making them the largest winery in New York City.
Their on-site production allows them to serve wine on tap; without bottling, labeling, and shipping costs, prices are a bit lower than the NYC norm. Wine tastings are available if you’re interested. Reservations are recommended.
Want more than wine? City Winery’s Barrel Room Restaurant & Wine Bar serves plates just right for sharing. Try the whipped feta, raspberry chipotle chicken wings, or Kung Pao cauliflower. Flatbreads and entrees are on the menu, too, if you’re looking for a full meal.
There’s indoor and outdoor seating, both of which offer views across the Hudson River. It’s also a concert space, featuring such performers as Melissa Etheridge and Lyle Lovett. City Winery serves lunch and dinner, and the recurring Sunday event: Strawberry Fields: Ultimate Beatles Brunch, with live music and an unlimited buffet brunch. (Reservations required)
While this Chelsea location opened in the Fall of 2020, City Winery first opened in New York City in 2008 and has since become a nationwide chain. Additional NYC locations include City Vineyard at Pier 26 (see #6 below) and City Winery Rockefeller Center.
25 11th Avenue at 15th Street, New York, NY
4. Fill up on Fantastic Local Cuisine at Market 57
The newest and very welcome addition to Pier 57 is Market 57, an indoor food hall that highlights local eats made by a mix of women- and minority-owned businesses. More than a dozen vendors, curated by The James Beard Foundation, have gathered under one roof to satisfy all your food cravings. Feast on everything from Mexican, Indian, and Japanese dishes to oysters, lobster rolls, and Island Style BBQ.
Well-known and beloved local restaurants like Nom Wah, Zaab Zaab, and Mothershuckers are there to serve up their specialties. Harlem Hops is on-site with small-batch beer and wine is served at Due Madri. You’ll also find vendors with pastries, cookies, ice cream, and more to satisfy your sweet tooth! 25 11th Ave., New York, NY. See business hours.
5. Take a Leisurely Walk on a Pleasant Riverfront Path
Once you leave City Winery (or Little Island if you skipped the vino and rooftop park), you’ll embark on the longest stretch of your Hudson River Park walking itinerary. At a regular pace without stopping, this would probably take around 30 minutes.
This is a pleasant walk where you’ll pass lots of revitalized spaces offering benches, tennis courts, playgrounds, and a riverfront reprieve from city life. And while it’s not exactly a non-touristy destination, it is a place where local New Yorkers come to picnic, jog, and walk their dogs, or maybe just catch those cool river breezes.
Pier 40 is the largest pier on the Hudson River and a port for City Cruises and other excursion vessels. The Trapeze School of New York is also located here, as is the Village Community Boathouse, which offers free rowing sessions from April through October.
6. Enjoy an Ecological Marvel at Pier 26
This 2.5-acre pier is another example of New York City’s newer revitalized outdoor spaces. Opened in September 2020, it provides the opportunity to walk through an urban ecological wonderland.
Walk on the Tide Deck above a cultivated salt marsh or through five different ecological zones (woodland forest, coastal grassland, maritime scrub, rocky tidal zone, and the Hudson River) on the Tribeca Native Boardwalk. There are also lots of seating areas to relax while also appreciating more skyline and river views.
If you’re interested in kayaking at Pier 26, the Downtown Community Boathouse is located here, offering free kayaking on the Hudson River on weekends and holidays from May to October (10:00 a.m.-4:30 p.m.). No reservations are necessary.
7. Toast Your Achievement at City Vineyard
This is a City Winery (see #3 above) property so it’s the same deal: locally made wine on tap and a menu that serves cuisine similar to City Winery, though the dishes are not exactly the same.
The vibe is a bit more casual here, which has been at this Tribeca location since 2016. When the outdoor seating area gets busy, it feels like a backyard party on a warm summer day. They have indoor and outdoor seating and a fabulous large rooftop with more of those incredible river views.
City Vineyard serves lunch, dinner, and weekend brunch. Reservations are not accepted May through October; seating is first-come first-served during that time. 233 West Street, New York, NY
Now that you’ve completed your Hudson River walk, clocked a good number of steps, and taken a zillion photos of the Manhattan skyline, sit back, relax and clink your glass to a day well spent!
Like this post? Pin and save for future reference!
Getting There and Away
- To Little Island – Take the A, C, E, L, 1, 2, or 3 train to 14th Street. Walk approximately 12-15 minutes.
- From Pier 26 – Walk about ten minutes to the 1 train at Franklin Street Station in Tribeca.
Restrooms in Hudson River Park
One awesome aspect of this walking itinerary is that there are bathrooms the entire way. You’ll find plenty of well-maintained restrooms at Little Island and Pier 57. On your walk, there are public restrooms at Piers 51, 45, and 40, and of course at City Vineyard at Pier 26.