Gansevoort Street Entrance, Meatpacking District
Lush greenery above gives way to cobblestone streets, Italian fare and shopping below the High Line's first entrance.
Dining: Catch 
After working up an appetite in the fresh air, head to this small-plate-focused seafood restaurant in the Meatpacking District that features a menu dotted with inventive dishes like crab spaghetti and scallop dumplings. The sleek, open space and shareable food create the perfect setting for a memorable meal with friends.
Shopping: Zadig & Voltaire 
Outfit yourself at the NYC flagship of this Parisian rock 'n' roll–inspired label. Inside, find delicate cashmere pieces, customized studded knitwear, washed-silk camisoles and hip-hugging denim.
Sightseeing
After a filling meal and some retail therapy, head back to the park and continue your stroll. The stretch of the High Line near the Gansevoort Street entrance is known as the Gansevoort Woodland. It's the ideal place to feel miles away from Manhattan, thanks to large trees like colorful redbuds and Whitespire grey birch. (All you have to do is ignore the sounds of honking taxicabs below.)
Coming Attraction: Whitney Museum of American Art's Future Building
Though the downtown outpost of this venerable Upper East Side institution won't open for another two or three years, construction is under way on the museum's new building—the work of architect Renzo Piano. To see how plans are progressing, look west toward the Hudson River from the High Line's Gansevoort Street entrance.