It’s that time of year again—when New Yorkers shed their winter layers, embrace the sun, and search for the city’s best spots to eat and drink outdoors. And right now, there’s one area that’s stealing the al fresco spotlight: THE PENN DISTRICT. This buzzing corner of Manhattan’s West Side has transformed into an unexpected paradise for those who love their pizza with a view, their gelato in the sun, and their bar bites with a breeze. Check it out on Instagram!
Watch this video to get a glimpse:
Is Rooftop Pizza in THE PENN DISTRICT Worth It?
Imagine this: You’ve just survived a chaotic day at Penn Station (no small feat), and you’re starving. What’s your reward? A slice of Roberta’s Pizza on their brand-new rooftop terrace. Yes, you heard that right—rooftop pizza. Roberta’s is already famous for its crispy, cheesy perfection, but eating it while soaking in a panoramic city view? That’s next-level bliss. It’s like combining two iconic New York experiences in one bite.
I tried it myself last weekend, and let me tell you, it’s worth the hype. The pizzas are just as good as you’d expect from Roberta’s—charred, flavorful, with that ideal sauce-to-cheese ratio. But the rooftop vibe? It makes you forget you’re in the middle of Manhattan’s most chaotic intersection. Instead, you feel like you’ve snuck away to a secret spot only locals know about.
Pro Tip: Go for the Bee Sting—the spicy honey drizzle with soppressata hits all the right notes. Oh, and grab a craft beer to complete the rooftop dream.
What’s the Deal with Anita Gelato and Why Should You Care?
You can’t just leave THE PENN DISTRICT without something sweet to balance out all that savory goodness. Lucky for you, Anita Gelato has set up shop right downstairs. Originating from Tel Aviv, Anita’s gelato is basically the definition of indulgence. Creamy, rich, and bursting with flavor, it’s the perfect cooldown after a pizza feast.
The open-air setting adds to the charm—nothing like strolling around Plaza33 with a cone in hand, debating whether cookies & cream or pistachio wins the flavor battle. Honestly, why choose? Get both.
If you’re feeling extra adventurous, time your visit around sunset. The way the light hits the cobblestones while you’re digging into your gelato? It’s an Instagram story waiting to happen.
Can You Still Find the Classics Here?
Yes! Bar Primi is holding strong, continuing to serve Italian comfort food on its cobblestone terrace. Picture this: Aperol spritz in hand, a plate of cacio e pepe in front of you, and the hum of the city in the background. The terrace itself feels like a mini vacation from Midtown madness.
Is it a bit cliché to order a spritz in the spring? Sure. But there’s a reason clichés exist—they just work. The contrast of the bitter, bubbly cocktail with the creamy pasta is everything your taste buds didn’t know they needed.
If you’re more in the mood for sports bar vibes, The Rutherford offers rooftop energy with plenty of space to spread out and unwind. Ideal for gathering the crew before catching a game at MSG—or just pretending you care about sports while secretly focusing on the elevated bar bites.
Are There Any Hidden Gems Worth Finding?
Just when you think you’ve seen it all, THE PENN DISTRICT keeps surprising you. Across the way, Avenida’s tropical rooftop and Blue Ribbon Sushi & Steak make you feel like you’ve stumbled into a little escape. Avenida’s cocktail menu leans tropical, which makes it the perfect spot for after-work drinks when you just need a mental break. Think pineapple-infused creations and breezy seating—it’s almost enough to trick your brain into vacation mode.
Meanwhile, Blue Ribbon balances things out with sushi that’s as fresh as it gets and steak that melts in your mouth. It’s upscale without feeling pretentious—exactly the kind of place you’d take someone you’re trying to impress.
What’s New and Worth Looking Out For?
Here’s a little insider scoop: Dynamo Room is coming soon, courtesy of Sunday Hospitality Group (the folks behind Café Chelsea). Expect creative drinks and a relaxed vibe that makes lingering way too easy. Also, keep an eye out for Avra Estiatorio later this year—a Mediterranean gem with an expansive patio that’s practically begging for a leisurely lunch.
The great thing about THE PENN DISTRICT is that it’s evolving (but not in that overhyped, painfully trendy way). It’s just becoming cooler, little by little, and I’m totally here for it.
What’s the Real Draw of THE PENN DISTRICT?
You could argue it’s the location—right in the heart of Manhattan with easy access to trains and arenas. You could say it’s the diversity of dining options—from classic pizza to tropical cocktails. But for me, it’s the mix of everything. It’s the feeling of stumbling into a neighborhood that’s redefining itself right before your eyes.
As someone who’s seen Penn Station at its most chaotic (think pre-pandemic rush hour), this new version of THE PENN DISTRICT feels like redemption. It’s proof that even the most hectic corners of the city can evolve into something vibrant and, dare I say, enjoyable.
People Also Ask
Is THE PENN DISTRICT good for outdoor dining?
Absolutely. With rooftop spots like Roberta’s and Avenida, plus open-air spaces like Anita Gelato, it’s perfect for soaking up the sun while eating well.What’s the best place for drinks near MSG?
The Rutherford is a great option, especially for pre-game meetups. For something more refined, try Avenida’s rooftop.Where can I find the best dessert in THE PENN DISTRICT?
Anita Gelato, hands down. The creamy, flavorful scoops are worth every calorie.
Final Thoughts
If you’ve written off THE PENN DISTRICT as just another chaotic hub, it’s time to give it a second chance. The area’s new wave of al fresco dining brings a fresh, lively atmosphere, making it one of my favorite hangouts this spring. Whether you’re grabbing a pizza on the roof or savoring gelato under the open sky, it’s a food lover’s dream with a Midtown twist.
So, are you ready to explore THE PENN DISTRICT? Your taste buds—and your Instagram feed—will thank you.
Sarah Knapp is a Brooklyn based entrepreneur whose love for the outdoors and community building led her to the October 2013 creation of OutdoorFest. She has a BA in History, is a Wilderness First Responder and a NY state hiking, camp and boating guide. Her proudest achievement to date is reading the Aeneid in Latin. 
Allison was one of our first top writers and Chief Editor but is no longer working with offMetro. Allison is a native New Yorker, who has lived in Rome, Tuscany, Melbourne, Toronto and Los Angeles. She frequently contributed travel pieces to Family Travel Forum, using her own children as guinea pigs as they travel the globe. She never missed a chance to sample local delicacies, as her love for travel goes hand-in-hand with her love for food and wine. 
Josh Laskin is a freelance travel writer and photographer based in the White Mountains of New Hampshire. When he is not at work or on the road, you can find him in the mountains snowboarding, climbing, hiking, fly fishing, mountain biking, and eating bagel bites.
Annie is a travel writer, environmentalist, and surfer based in Venice, CA. She heads up our West Coast team, keeps our grammatical errors in check, and makes sure our California writers always have a plan for their next adventure. Follow Annie’s travels @annelisemcb.
Carly Pifer is a freelance writer who has been known to follow whims inspired by romantic movie scenes or colorful street style shots to India, Japan, Tunisia and Argentina. After stints living in Seoul, Boston, Paris and Los Angeles, writing and searching for something intangible, she landed somewhat steadily in Brooklyn and has begun to find inspiration in her more immediate surroundings. 
Kate E. O’Hara is a New York based freelance writer and photographer who loves all things food—especially the people who make it and market it. Her writing aims to capture the essence of the food experience; the stories that go well beyond a plate of ingredients. In addition to her love of food, Kate is also known to have a hankering for red wine and craft beer. You can also find Kate on Instagram