Summer is NOT over. This guide is good for this weekend but also other weekends this fall!
Labor Day weekend is the unofficial end of summer, and there is no better place to spend it than New York City. Get out on the water, explore Lower Manhattan, walk the High Line, discover waterfront parks and restaurants, take a ferry across the East River, explore DUMBO or Governors Island, and finish the weekend with some of the city’s best skyline views. Here is a three-day itinerary that takes you from the southern tip of Manhattan to Hudson Yards, across the East River and into some of New York’s most memorable neighborhoods. It’s everything that I do but spread over a few days!
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Start your weekend at the southern tip of Manhattan, where New York Harbor, the Hudson River and East River all come together. This day combines some of the city’s most important landmarks with waterfront parks, restaurants and opportunities to get out on the water.
Begin at Battery Park, one of Manhattan’s oldest public parks. Walk through the gardens, see the historic monuments and look across New York Harbor toward the Statue of Liberty.Battery Park is also the departure point for boats to the Statue of Liberty and Ellis Island, making it an easy place to begin a day focused on the harbor.
Walk north from Battery Park to the 9/11 Memorial, where two enormous reflecting pools occupy the footprints of the original Twin Towers. The names of those who died in the September 11, 2001 and February 26, 1993 attacks are inscribed around the pools. The memorial is a quiet and moving place to stop and reflect amid the energy of Lower Manhattan. The 9/11 Memorial & Museum tells the story of the attacks, the people who were lost, the rescue and recovery efforts and the events that followed.
Pro Tip: If you visit the museum, plan enough time to experience it rather than trying to squeeze it into a quick stop. **Might be overwhelming for children. Visit One World Trade Center instead!
Look up and you’ll see One World Trade Center, rising 1,776 feet above Lower Manhattan. The building is a defining part of the New York skyline and a powerful symbol of the rebuilding of the World Trade Center site.For sweeping views of the city, One World Observatory occupies floors 100 through 102, with views across Manhattan, Brooklyn, New York Harbor and beyond. Use Groupon for Super Savers
Next, walk through the spectacular Oculus, Santiago Calatrava’s soaring white transportation hub. The dramatic interior has become one of Lower Manhattan’s most recognizable architectural spaces. Even if you’re not catching a train, it’s worth walking inside.
From the World Trade Center, head west into Battery Park City and begin following the Hudson River north. The waterfront esplanade takes you through gardens, lawns, playgrounds and public spaces while skyscrapers rise behind you and the Hudson stretches out in front of you.
Continue north to Grand Banks, the floating oyster bar aboard a historic schooner at Pier 25. Have oysters, seafood or a drink while sitting directly on the Hudson. The combination of the historic boat, river views and Lower Manhattan skyline makes this one of New York’s most distinctive waterfront stops OR,
Stop at City Vineyard at Pier 26 for lunch, wine, cocktails or a break beside the Hudson. The restaurant has indoor and outdoor dining, a wine garden and rooftop spaces overlooking the river. It’s an ideal place to sit for a while and watch the boats passing along the Hudson before continuing north.
You can make the water the centerpiece of Day 1 with a ferry, sightseeing cruise or sailing excursion. New York offers everything from the Staten Island Ferry and NYC Ferry to sightseeing cruises and sailing trips along the Hudson. Sunset is particularly beautiful, when the skyline begins to glow and the Statue of Liberty and Lower Manhattan become silhouettes against the evening sky.
Day two heads north along Manhattan’s West Side, combining one of New York’s most famous parks with waterfront dining, public art, sailing and the dramatic architecture of Hudson Yards.
Begin your morning on the High Line, the elevated park created from a former freight rail line. Walk north through gardens, public art and constantly changing views of Chelsea and the surrounding architecture. The High Line gives you a completely different perspective on Manhattan—you are walking above the city rather than through it.
Make your way from the High Line toward the Hudson River and Little Island. The unusual park rises from the river on sculptural concrete columns. Wander through its gardens and paths, find a place to sit and enjoy the views of the Hudson and Manhattan. Little Island is especially easy to combine with the High Line because the two experiences are only a short walk apart.
Continue north to Pier 57, located at 15th Street between Little Island and Chelsea Piers. The reimagined pier combines food, public spaces and a large rooftop park overlooking the Hudson.
Leave Pier 57 and continue north along the Hudson. Check out Chelsea Piers, one of my favorite playgrounds in Manhattan, From the park with the gorgeous views, to my best ever place to go, SAILING
Chelsea Piers is home to several sailing and boat excursions. You can choose from traditional schooner sails, sunset cruises, harbor cruises and other ways to experience the Hudson from the water. A sunset sail is particularly memorable as the sun disappears behind New Jersey while Manhattan’s skyline begins to sparkle.
If you stay on land, continue north along the West Side and make your way to Hudson Yards:
For the third day, head to the East River. The ferry makes getting around part of the experience, and you can choose between historic Lower Manhattan, DUMBO or a day on Governors Island.
Head to Pier 11/Wall Street and take the ferry. The short ride gives you a completely different perspective of Lower Manhattan, the Brooklyn Bridge and the East River. From here, choose one of three main options:
Get off at Pier 11 and walk into historic South Street Seaport, one of the oldest parts of Manhattan with cobblestone streets, restored 19th-century buildings and a waterfront promenade.
For one of the most recognizable New York City experiences, take the ferry across the East River to DUMBO: Things to do in Dumbo, Dumbo Insider’s Guide
The ferry to Governors Island departs from the Battery Maritime Building at 10 South Street (with seasonal weekend Brooklyn ferry service). Once there, explore expansive parks, historic buildings, walking and biking paths and waterfront views overlooking Manhattan and New York Harbor. Click here for our full Governor’s guide.
If your Labor Day weekend needs a little sand, here are the top beaches within reach of the city:
DAY 1: Battery Park → 9/11 Memorial → One World Trade Center → Oculus → Battery Park City → City Vineyard → Grand Banks → Hudson River
DAY 2: High Line → Little Island → Pier 57 → Market 57 → Rooftop Park → Chelsea Piers → Sailing → Hudson Yards → Vessel → Edge → Peak
DAY 3: Ferry → South Street Seaport OR DUMBO → Waterfront → Governors Island (Or spend the day at the beach!)
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