Good Times Squared
If you look past the bustling crowds and bright commercial displays, you'll see Times Square's less-corporate, colorful, seedy past. Every Friday at noon, the Times Square Alliance offers free "Times Square Expose" tours, offering a behind-the-scenes look at Times Square then and now. You'll see historic theaters, up-and-coming projects, as well as the sights and sounds of the modern Times Square.
http://www.timessquarenyc.org/about_us/info_center.html
Beat and Bohemia
Explore a vivid center of modern American art, music, literature, and cinema on the Edgar Allen Poe Greenwich Village Tour. During the 1960s, the Village nurtured the careers of many artists like Simon and Garfunkel, the Velvet Underground, Barbara Streisand, and Bob Dylan. On this tour, you can visit the coffee shops, nightclubs, and theaters where many influential cultural icons got their start (from the Beat Poets to Jimi Hendrix). The tour covers the home of Edgar Allen Poe, Bleeker Street, Cafe Wha?, New York University, and more.
http://www.unclesamsnewyork.com/
Eat the Big Apple
On the Foods of New York Tour, experience New York's edible culture whether it be from a local "mom and pop" shop or a historic "speakeasy." Choose between SoHo, Chelsea, Greenwich, Chinatown, and a Japanese specialty tour. While on tour, enjoy the area's history, architecture, and every tasty morsel.
http://www.foodsofny.com/
Patch of Green
Rain or shine, the Central Park Conservancy offers a number of free tours giving insight into this iconic landmark. View the Belvedere Castle or Bethesda fountain, discover a hidden bench that tells time, and learn how the park was key in the American Revolution. From its beautiful woodlands, maze-like pathways, and characteristic history, you'll learn the inside scoop on Central Park history.
http://www.centralparknyc.org/
Head to the Fed
Get a glimpse of the heart of the United State's monetary system on this free tour. Travel 50 feet below sea level to see the billions of dollars in gold hidden in the vaults of the Fed. The educational exhibit Fedworks will test you on Fed facts while bringing you up to speed on the bank's function in the economy. You'll learn about history of money and receive a some at the end of the tour--shredded, that is. Call at least a week in advance to make reservations, because security clearance procedures can be long and tedious.
http://www.newyorkfed.org/aboutthefed/visiting.html
Fashionable Excursions
Shop Gothem offers insider information on the bargain hunter's paradise hidden in New York City. This company will take you on a shopping spree tour through the chic hot spots while filling you in on celebrity trivia, fashion history, and more. Tours are held in SoHo and Nolita or at private Wholesale Showrooms and Sample Sales.
http://www.shopgotham.com/daily-new-york-shopping-tours.php
Grand Central Tours
The Whispering Gallery, the Chrysler Building, and the original Lincoln Memorial are all stops on this engaging, free tour sponsored by the Grand Central Partnership. Full of fun facts and trivia, the tours are given by Justin Ferate, a historian and narrator of the changing events in the Grand Central neighborhood.
http://www.grandcentralpartnership.org/
Pub Crawl Your Way through Literature
This tour may give you flashbacks to your college days but literature and beer can be a surprisingly good combination. All tours are given by enthusiastic, local actors with the Bakerloo Theatre Project. At each stop, you can unwind, have a drink, and give an ear to tales about the great authors who frequented or wrote at the very same bar. Authors mentioned include Kerouac, Thomas Paine, Dyan Thomas, Edgar Allen Poe, and more.
http://bakerloo.org/
Tour Rockefeller Center
Along with highlighting Rockefeller Center's indoor skating rink, famously large Christmas tree, and Radio City Music Hall, the tour allows you to get a real feel for this beloved historic landmark. The Center architecture and design are merged with public art, and gardens are cultivated on the roof. It hosts the Today Show and Saturday Night Live while displaying artwork by Mexican socialist Diego Rivera. It is truly a fascinating part of New York. As an added bonus, the tour provides headphones so you can hear the tour guide uninterrupted--a pleasant relief.
Ghostly Treks
Some say that New York is America's most haunted city. On the Ghosts of New York tours, you can listen to New York's myths, legends, and scandals as told by the costumed Edith Warton or O. Henry. Directed by CUNY Professor Phil Schoenberg, this tour company will spin tales about the ghosts of Mark Twain, Harry Houdini, and even Eleanor Roosevelt's dog. These night-time romps are not for the meek of heart.
http://www.ghostsofny.com/
General Tours
If you are interested in something a little more touristy or more individualized, these tour companies come highly recommended:
NYC Discovery Walking Tours
Joyce Gold History Tours
Big Onion Walking Tours
Adventure on a Shoe String
