Historic NYC Tours

At first glance, NYC's Foley Square paints an uneventful scene: a few trees, concrete civic buildings and men and women in suits clutching coffee on their lunch break. But this isn’t the whole story, not if you hear it from a NYC tour guide.

"You're standing in the middle of what was [once] the most densely packed urban slum in the world," says Megan Doherty, a tour guide with Big Onion Walking Tours. During the 1800s, she adds, this section of Lower Manhattan, once known as the Five Points neighborhood, was crowded with 6-story tenement buildings.

This story of extremes comes alive on a NYC tour. "New York is such a complex place that it lends itself to being evaluated through a lot of lenses," says Seth Kamil, Big Onion's founder. Exploring the city also takes a bit of "urban detective work," he adds. Check out these NYC tips to explore the city that never sleeps.

The Gangs of New York
NYC’s steely edge was forged in part by gangs, and immortalized in Martin Scorsese’s Gangs of New York. Explore the city’s violent 19th-century underbelly with a walk through the Five Points neighborhood, so named because of a 5-pointed intersection created by the crossing of several streets. Swing by Foley Square (also known as Thomas Paine Park) for a glimpse of where many gang members once lived and “worked.” Visit Bayard Street, where, in 1857, more than 1,000 gangsters duked it out in "the city's most epic gang battle," says Doherty. At 1 Pace Plaza, near City Hall, see the site of the 1863 Draft Riots, sparked by anger over the Civil War draft. Stroll down the Bowery, an avenue where a rowdy bar culture thrived during the 1860s -- at least 6 bars per city block -- and fueled a few barroom and street brawls.

Eat Like an Immigrant
As a point of arrival for many early immigrants, NYC became home to colorful neighborhoods. Sample traditional cured meats and cheeses at Di Palo's Fine Foods, an iconic fixture of Little Italy since 1925, and spicy tofu from assorted street vendors and noodles from Tasty Hand-Pulled Noodles in Chinatown. Finally, for a taste of the Jewish world that once inhabited the Lower East Side, stop by Pickle Guys for a mouth-puckering sour pickle. Kamil notes that even the Pickle Guys have changed with the neighborhood; they now offer Asian specialties such as spicy, pickled pineapple. Delicious!

Brooklyn Bound
Remember when Brooklyn got an uncool rap, unlike Manhattan? How times have changed. Today, Brooklyn is a thriving center for commerce, food and culture, with an interesting history of its own. The borough is so captivating that it merits 6 separate Big Onion walking tours.

"Few people understand Brooklyn," says Kamil. "It's geographically and numerically 3 times larger than Manhattan; it's huge." It’s best to explore Brooklyn’s many different neighborhoods one by one, says Kamil. In Park Slope, the largest landmark district in NYC, take time to appreciate the brownstone architecture throughout the neighborhood, says Kamil. Make stops at the Montauk Club, a ritzy private social club founded in 1889, and Grand Army Plaza, an 11-acre plaza at the entrance to Prospect Park. The Brooklyn neighborhood of Williamsburg is currently the center of NYC's hipster music scene. Wander along Bedford Avenue, the longest street in Brooklyn, which is home to trendy bars and galleries.

Armed with an insider's edge, plan to take on the Big Apple one bite -- or neighborhood -- at a time, and unravel the rich history of the city's immigrant past.

Valerie Conners is a freelance writer and editor and has worked for media outlets such as the Travel Channel, Discovery Channel, Animal Planet, Boston Globe, Philadelphia Inquirer and Frommer's Travel Guides.