As Petula Clark sang, “When you’re alone and life is making you lonely, you can always go downtown.” But when you’re not exactly alone (say, with a couple of miniature people and a yacht-sized stroller in tow), you can still go downtown. While it’s a natural pedestrian traffic hub that makes it a bit of a mob scene (a less child-friendly term for it would be a compound word beginning with “cluster” and ending with a colorful expletive you probably had to retire as soon as your kids learned to speak), the shopping, restaurants, and people-watching make Union Square the hippest square of them all.

photo courtesy of Orin Zebest

When to go: Union Square is always busy, but try to go on a weekday either between 9:00 am and noon or 2:00-5:00 pm for the best chance of having some personal space.

Approximate travel time: With 8 subway lines servicing its labyrinthian train station, getting there should be a snap, even from far-flung outer boroughs. If you’re traveling from Park Slope, Williamsburg, or points in Manhattan, the trip can take as few as 10-15 minutes–not counting the time spent wrangling small bodies and/or strollers down steps and through turnstiles.

What to do: People-watching on the expansive steps leading to Union Square Park (14th Street between Broadway and University Place) is better–and cheaper–than any fashion magazine. While you take in the camera-ready crowd, the kids will love watching nearby musicians, skateboarders, and local artists selling their wares. On Saturdays at 2:00 pm you can take a free tour of the square, and Thursdays at 10:00 am and noon there’s free entertainment for children. A highlight of the park is its colorful Dr. Seussian playground (17th Street between Broadway and Park Avenue S.), which features an area for bigger kids with fun, sculptural play structures as well as a baby and toddler enclave. Even the most committed literary aficionados will appreciate the awesome scope of The Strand Bookstore’s (12th Street and Broadway) 18 miles of books, stacked high on seemingly endless shelves, but if they get bored, send them on a scavenger hunt. Union Square is also home to an impressive number of statues. See if the kids can find inanimate versions of icons like Abraham Lincoln, Gandhi, and Andy Warhol.

photo courtesy of HBarrison

Where to eat: Start the day off with The City Bakery’s (3 W. 18th Street at 5th Avenue) famous pretzel croissants, or, if you visit Union Square between 8:00 am and 6:00 pm on a Monday, Wednesday, Friday or Saturday, pick up fruit, breads, baked goods and even fresh yogurt from farmers at the Greenmarket on the north and west sides of Union Square Park to snack on throughout the day (there’s also a cavernous Whole Foods on 14th between Broadway and University, if you prefer a middleman between you and your farmer). And little ones will love the menu at Chat ‘n Chew (10 E. 16th Street between Broadway and 5th Avenue), a kitschy comfort food diner that serves up slightly trashy, stick-to-your-ribs classics like gooey mac n’ cheese, hearty “sammies,” and the irresistibly retro “TV dinner” of chicken fried steak, green beans, and mashed potatoes.

photo courtesy of Barbara L. Hanson

How to dress: You can’t go wrong with casual, well-tailored clothes in a neutral palette, and comfortable but stylish footwear is a must. The downtown crowd may seem impossibly chic, but you still need to be able to walk.

Bonus: In November and December, a maze of festive holiday pop-up shops invades the square. Stock up on one-of-a-kind gifts, or just hit up the food carts selling hot chocolate and seasonal treats.

Cost of trip: Varies, but since so many activities are cheap or free, this is an extremely affordable day trip.

What’s your favorite thing to do in Union Square? 

— Una LaMarche