A Toast Above Times Square: Old Fashioneds, Cosmopolitans, and a Perfect NYC Night

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Courtesy photo.

Some weekends just feel extra special, and this New York trip had that sparkle. My bestie Sharma and I made our way to Highball, perched above the buzz of Times Square, and it instantly felt like the kind of place where memories are made between sips. With our shared love for classic cocktails (especially a good Old Fashioned and a perfectly balanced Cosmopolitan), we were ready for a night that felt both elevated and completely us.

Located inside Tempo by Hilton New York Times Square, the space feels modern and polished but still welcoming, the kind of atmosphere where you can dress up a little, laugh a lot, and take in those iconic city views without feeling rushed. From the moment we stepped in, the energy felt celebratory but relaxed, like the start of one of those perfect NYC evenings that just unfolds naturally, and it was a great start to our weekend stay at the hotel.

Cocktails First, Always

We went straight for what we love most: classic cocktails done right. There is something about ordering an Old Fashioned that feels like a quiet test of a bar’s personality, and Highball absolutely delivered. Smooth, aromatic, and beautifully presented, it felt like the perfect start to the evening. And of course, I could not resist a Cosmopolitan moment, light, citrusy, and just indulgent enough to feel like a little celebration in a glass. Sitting there, catching up, laughing, and people-watching from above, it felt like one of those simple but meaningful reminders that slowing down with someone you love is always worth it.

One of the things I appreciated most is that nothing felt overly complicated or pretentious. The cocktails are thoughtful and creative but still rooted in flavors you recognize and crave. It feels elevated, but approachable, which honestly is my favorite kind of luxury.

Shareable Plates that Keep the Night Going

As much as we love cocktails, great drinks deserve great food, and the menu made it easy to turn the night into a full experience. We leaned into the shareable plates (because sharing with your best friend is always more fun), enjoying bites that felt both comforting and just a little refined. Think flavorful small plates that pair perfectly with a second round, encouraging you to stay a little longer, talk a little more, and order just one more thing.

There is something about that rhythm of conversation, cocktails, and small plates that makes a night feel complete, that is not rushed, not overly formal and just genuinely enjoyable.

From Morning Coffee to Evening Cocktails

What makes this spot even more appealing is that the experience carries into the daytime. And this is thanks to their own breakfast and bakery.

There, Highball also offers breakfast options that feel just as thoughtfully curated as the evening menu. It is easy to imagine starting the day with coffee and something light, then returning later for cocktails as the city begins to glow. That day-to-night versatility gives the space a welcoming personality that feels very New York, which is busy and stylish, but always ready to help you pause for a moment.

A Perfect NYC Memory

Spending the evening here with Sharma felt like one of those small but meaningful travel highlights that stays with you long after the trip ends. Great cocktails, delicious bites, and the kind of easy conversation that reminds you why these moments matter so much.

Highball captures that ideal balance of energy and comfort. It feels lively without being overwhelming, polished without being stiff, and celebratory without trying too hard.

If you love classic cocktails, a beautiful setting, and those effortless nights that turn into favorite memories, this is one to add to your list.

Because sometimes the best part of travel is simply sitting across from a dear friend, raising a glass, and realizing the moment feels exactly right.

Highball is located at 1568 Broadway at the 11th Floor of the Tempo by Hilton New York Times Square, New York, NY. For more information, visit highball.nyc or call 212-703-8600.

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