Explore New York City

History Lessons: 5 NYC Walking Tours for Time Travelers

The Revolutionary War, the Roaring Twenties and other exciting eras live again on these tours.

NEW YORK CITY is a walking town, and one of the best ways to take in its historical sites is on foot. Even in winter, guided walking tours abound—and not just of the usual landmarks. Many head off the beaten paths to explore intimate neighborhoods and easily overlooked treasures, like Brooklyn’s DUMBO or Harlem’s Strivers’ Row. So bundle up and prepare to stride into the city’s past.

Those interested in Colonial America will be intrigued by Patriot Tours, which specializes in the Revolutionary War and the early days of the republic. Limited to 15-20 guests, its groups trod the twisting streets of the southern tip of Manhattan—what’s now the Financial District (or, for those in the know, FiDi). One tour visits the haunts of a spy ring that passed intel on the British to George Washington’s army. Another walk pays homage to Alexander Hamilton, along with his nemesis Aaron Burr, visiting the places where he studied, worked and is buried. Tour guide Karen Quinones punctuates her narratives with historic quotes from first-person accounts and facsimiles of period documents.

While Patriot Tours focuses on a particular era, ProwlerNYC takes a more offbeat approach to its two- and three-hour walks. Many are organized around an individual, tracing the milestones of his or her life through architecture and the “social, religious and technological forces that shape a style and a building’s appearance,” says founder Deborah Zelcer. The Little Pillbox Hat Tour, for example, uses Jacqueline Kennedy Onassis and her lifelong interest in historic preservation as the common link for a variety of Midtown structures, from Grand Central Terminal to the Olympic Tower. The life and times of Nikola Tesla are the theme of another tour; the electrical inventor—a rival of Thomas Edison’s—spent much of his life in the 20-block span of current-day NoMad, Murray Hill and Bryant Park.

Other groups pride themselves on offering tours that’ll surprise and delight even native New Yorkers (let alone visitors). That’s the unofficial motto for Untapped Cities, whose specialty is arranging access to places that are usually off-limits to the public. Intimate groups of up to 10 or 18 can get a behind-the-scenes look at an Ellis Island hospital or the fabulously ornate Woolworth Building, one of New York’s first skyscrapers. Or they can literally head underground, exploring the oldest sections of the subway system.

Nor will visitors hear the same old, same old on a tour by the Municipal Art Society of New York (MAS), whose guides often have degrees in history, art, architecture or other relevant fields, and whose narratives are filled with rich and well-researched detail. January tours include Edith Wharton's New York and a tour of subway art.

All this walking can work up an appetite. To the rescue: Foods of New York Tours, whose gastronomically themed walks include tastings. In particular, its Greenwich Village tours combine historical culture and cuisine in an enriching way; not only will visitors feast their eyes on the quaint houses, winding streets and architectural oddities of the area, they’ll snack in generations-old restaurants and food shops, learning how delicacies from the Old World were adapted for the New.