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The Best of the Flatiron District

April 2, 2016 | by
Reviewed by real estate expert Michael Colacino

The Flatiron District, which some have been known to call Silicon Alley, has become a hub for tech startups in Manhattan. The increase in companies choosing to call the area home means that more employees are looking to take advantage of everything the Flatiron district has to offer. If that sounds like you, we’ve done the research already and have created a list of our Flatiron favorites for you to check out!

Best Lunch – Shake Shack

We’d be remiss if we failed to list Shake Shack as a Flatiron favorite for lunch. The original location of this uber-popular burger chain is located in the heart of Madison Square Park. You can’t go wrong with the traditional Shack Burger, but Shake Shack has also scored major points with their crinkle fries, chicken sandwich, and frozen-custard concretes. Beyond the delicious food, Shake Shack’s location in Madison Square Park will give you the perfect backdrop to get some fresh air and clear your head. Beware of long lines during the height of the lunch hour rush, but a quick check of their live stream before heading out of the office could help you avoid this problem!* For more Flatiron lunch recommendations, check out our ‘Best in NYC Lunch: Flatiron’ post.

Best Company Outing – Flatiron Hall

If you’re looking for a place where you can kick back with some coworkers and have a great time, look no further than Flatiron Hall. The beer hall features a 25ft bar that was crafted in 1870 with antique leaded glass arches. The bar, which was originally located in the Commodore Hotel in downtown Manhattan, serves as the centerpiece for the hall, which has a Victorian feel. Companies have the option of reserving long, picnic-bench-like tables, which can sit large parties. With 12 specialty beers on tap at all times and carefully crafted cocktails, Flatiron Hall provides the perfect atmosphere for employees to cut loose and get to know each other in a casual setting.

Location: 38 West 26th Street

Best Coffee – Toby’s Estate

Even if Toby’s Estate didn’t have great coffee, it would still be a coffee shop to visit for the ambiance alone. The clean, all-white, trendy interior reminds you of a cafe plucked straight from the streets of Paris and looks great in photos. Luckily for customers, however, the drinks are as great as the atmosphere. The standouts include the cold brew, the macchiato, and their soy lattes. While there isn’t a ton of seating options in the coffee shop itself, we suggest taking your drink with you to peruse the Club Monaco clothing store or Strand bookshop with which Toby’s Estate shares a space. Coffee and a new book? What could be better than that?* For more Flatiron coffee recommendations, check out our ‘Best in NYC Coffee: Flatiron’ post. 

Location: 160 5th Avenue

Best Workout – Flywheel

In a time when boutique cycling studios such as Soul Cycle and Cyc are wildly popular, the studio that’s caught our eye the most is Flywheel. What sets Flywheel apart from the other studios is their ‘Torque Board’. Gone are the days when you’re trying to guess what exactly your instructor means when tell you to “turn your resistance a full turn to the right”. At Flywheel, the personal Torque Board attached to your bike allows you to monitor stats such as resistance, RPM, and total power in real time. You can then use those numbers to adjust to your trainer’s instructions, ensuring that your workout stays on track. Another plus is that your won’t feel nickel-and-dimed at Flywheel, with perks such as water, shoes, towels, and snacks offered free of charge. Your first class is also free, so there’s no reason for you not to stop into a Flywheel studio, listen to awesome music, meet the incredibly friendly instructors, and break into an honest sweat.

Location: 39 West 21st Street

Best Event Space – Flatiron Penthouse

The Flatiron Penthouse, located steps away from iconic NYC landmarks such as the Flatiron building and Madison Square Park, is a two-story private loft space with an outdoor balcony, terrace, and a rooftop. With the capacity to hold up to 80 guests, the fully-furnished space comes with state-of-the-art features including top-notch audio and video equipment, lounge seating, a conference table, full kitchen, built-in bar, and a passenger elevator. The penthouse also offers a range of in-house services ranging from catering and bar packages to audio and visual crews to ensure that your event runs as smoothly as possible. The homey feel of the venue makes it a perfect location for PR events, intimate social gatherings, cocktail parties, and corporate meetings.

Location: 18 West 23rd Street

Best Happy Hour – The Headless Horseman

Even from the outside, The Headless Horseman has a medieval air about it. The entrance is defined by grey stone, and an equally distinctive archway with the words Headless Horseman inscribed above the doorway. Once inside, the dimly-lit bar feels almost like a dungeon, but in the most charming of ways, with exposed brick walls and dark wood floors and accents adding to the atmosphere. Happy hour at this haunt lasts from 4pm until 8pm on weekdays and features $5 wells and draft beers, making it the perfect stop for drinks with coworkers, even if (and maybe especially if) you had to stay at the office a bit late for the day.

Location: 119 East 15th Street

Best Place to Relax – Madison Square Park

Madison Square Park is an urban oasis situated in the Flatiron district. While the area surrounding the park is a bustling entertainment hub, the park itself offers a nice respite from the stereotypical New York City hustle. The 6.2 acre park is a popular lunch hour destination, frequented by many employees of companies that call the Flatiron district home. This should come as no surprise since the aforementioned Shack Shack sits in the heart of the area. Whether you want to sit on a bench and catch up on some reading, take a leisurely stroll, or enjoy an outdoor lunch with coworkers, Madison Square Park can be your perfect escape.

Location: Madison Square Park

Best-Kept Secret – The Cellar

The Cellar is, quite literally, a hidden gem. Tucked away below Beecher’s Handmade Cheese (an artisan cheese shop) is the dimly-lit subterranean hideout that serves up a range of cheese-focused food (and even drinks). The entrance, just a flight of stairs in the back of the cheese shop, is so unassuming that we wouldn’t be surprised if you missed it completely. The decor of the restaurant stays in theme with pictures of animals such as cows, goats, and sheep lining the walls. The restaurant also doubles as Beechers’ actual cheese cellar, and patrons are able to see wheels of cheese being aged behind one of the restaurant’s glass walls. Standouts on the menu include the phenomenal cheese plates (obviously) as well as the “World’s Best” Mac & Cheese, which certainly lives up to its name! Pair any of the cheese offerings with a glass of wine and you’re in for a delicious treat!

Location: 900 Broadway

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