Up on the Rooftop: Two 360 Experiences, One Spectacular St. Louis Holiday Season

From the Glittering Downtown Skyline to the Panoramic Views of Westport, St. Louis' Favorite Rooftop Destinations Are Turning Holiday Celebrations Into Something Extraordinary

By Grayling Holmes

BABY, IT'S COLD OUTSIDE. BUT THE HOLIDAY SCENE AT 360 IS HEATING UP!

There's something magical about St. Louis during the holidays.

The twinkling lights. The festive decorations. The beautifully dressed partygoers. The familiar Christmas melodies floating through the air. And, of course, the wonderful excuse to gather with friends, raise a glass, and celebrate another year of memories.

As someone who loves a great party, a spectacular view, and an evening spent enjoying everything our city has to offer, I've already started making holiday plans with my bestie, Mary Wimbley, and several of our friends.

And this year, we've decided that one holiday outing simply won't be enough.

Not even close!

Our plans include exploring downtown St. Louis, taking in the holiday lights, enjoying some of the region's most beloved seasonal attractions, and ending our adventures high above the city at the original 360 Rooftop Bar.

Then, on another evening, we'll head west to discover the equally festive—and wonderfully expansive—360 Westport.

Both locations have transformed themselves into glittering holiday destinations with their seasonal Up on the Rooftop cocktail experiences, running November 6 through December 29.

And from everything I've seen and heard, these are two holiday celebrations that deserve a prominent place on everyone's social calendar.

TWO ROOFTOPS. TWO DISTINCT EXPERIENCES. ONE FABULOUS HOLIDAY SEASON!

Downtown St. Louis: A Holiday Wonderland Worth Rediscovering

Let me say something that deserves repeating.

DOWNTOWN ST. LOUIS DOES THE HOLIDAYS RIGHT!

There's no reason to travel to Chicago or New York to experience the excitement of a beautifully illuminated city during the Christmas season.

We have our own magnificent skyline, our own cherished traditions, and an abundance of attractions that make downtown St. Louis a wonderful destination for holiday entertaining.

Mary, our friends, and I are planning to make the most of it.

I can already imagine an evening that begins with a carriage ride through downtown, taking in the city's architecture and sparkling seasonal decorations.

There's something wonderfully nostalgic about experiencing a city from a horse-drawn carriage, especially when the streets are dressed for the holidays.

Of course, we'll want to spend time around Kiener Plaza, where the annual Winterfest celebration brings skating, seasonal activities, and festive energy to the heart of downtown.

The Gateway Arch provides an unforgettable backdrop, reminding us just how beautiful our city can be when its landmarks and public spaces come alive.

And we'll certainly want to take in the spectacular holiday lights associated with Anheuser-Busch, one of St. Louis' most iconic institutions.

Those magnificent illuminated displays have long been part of the city's holiday identity.

But why stop there?

As the old holiday song reminds us, over the river and through the woods we go!

Our plans also include venturing across the Mississippi River to explore the holiday light displays and seasonal attractions on the Illinois side of the metropolitan area.

Way of Lights at the National Shrine of Our Lady of the Snows across the river to Illinois

There are so many wonderful opportunities for holiday sightseeing throughout the region that trying to squeeze everything into a single evening would be an exercise in futility.

AND THAT'S WHEN IT HIT ME: WHY NOT MAKE 360 DOWNTOWN OUR HOLIDAY HEADQUARTERS?

Instead of racing from attraction to attraction, we can enjoy several outings throughout the season, each culminating in cocktails, conversation, and perhaps dinner at one of the most spectacular rooftop destinations in the Midwest.

Now that's my idea of holiday planning!

360 Downtown: The City Becomes the Centerpiece

Perched approximately 400 feet above downtown St. Louis, the original 360 Rooftop Bar atop the Hilton St. Louis at the Ballpark offers a perspective of the city that never gets old.

From its lofty perch, guests can admire the illuminated Gateway Arch, the Mississippi River, Busch Stadium, and Kiener Plaza.

And during the holiday season, the view becomes even more extraordinary.

Imagine looking out over a city sparkling with thousands of lights while surrounded by lavish Christmas decorations, shimmering ornaments, and festive displays.

That's the magic of Up on the Rooftop at 360 Downtown.

The venue has been transformed into a glittering, sky-high holiday wonderland, complete with whimsical décor, specialty cocktails, and countless opportunities for memorable photographs.

Inside, guests can settle into the festive atmosphere and enjoy cocktails and conversation.

Outside, the wraparound patios offer spectacular views, with warming fire pits providing a welcome refuge from the chilly winter air.

And for those who prefer something more substantial than cocktails and hors d'oeuvres, 360 offers its full menu of elevated dining until 10 p.m. daily.

I can already picture Mary and our friends gathered around a table, recounting our adventures while the city's holiday lights sparkle below us.

Perhaps we'll begin with shared appetizers, move on to dinner, and linger over cocktails as the evening unfolds.

Because the beauty of 360 is that there's no need to rush.

THE VIEW IS THE ENTERTAINMENT. THE CITY IS THE BACKDROP. AND THE COMPANY MAKES THE EVENING COMPLETE.

Best of all, there's no cover charge before 10 p.m., and the holiday experience operates on a first-come, first-served basis without reservations.

For those planning a gathering of 10 or more, group arrangements are available.

360 Downtown
1 S. Broadway, atop Hilton St. Louis at the Ballpark
Open daily beginning at 4 p.m.
www.360-stl.com

360 Westport: Bigger, Bolder, and Ready for a Holiday Celebration

360 Westport rooftop bar St Louis Christmas holiday pop up decorated interior. 360 Westport rooftop restaurant Gold Tower Westport Plaza panoramic views patio.

While downtown 360 offers one of the city's most iconic skyline experiences, its sister location at 360 Westport brings an entirely different personality to the rooftop scene.

And if you haven't visited yet, here's your invitation to discover it.

Located atop the Gold Tower at Westport Plaza, this spacious destination offers expansive panoramic views, generous room to socialize, and a sophisticated atmosphere that lends itself beautifully to everything from an intimate evening for two to a lively celebration with a crowd of friends.

The additional space provides more opportunities to find your perfect spot.

Perhaps you prefer being in the center of the action, surrounded by lively conversations and holiday revelers.

Maybe you'd rather enjoy a quieter corner where you can catch up with friends over a beautifully crafted cocktail.

Or perhaps the outdoor patio and its welcoming fire pits are calling your name.

AT 360 WESTPORT, THERE'S ROOM FOR EVERY KIND OF HOLIDAY CELEBRATION.

The seasonal Up on the Rooftop experience transforms the space into a dazzling, oversized snow globe, complete with glittering decorations and an unmistakable sense of holiday magic.

And the menu makes it easy to turn a casual cocktail outing into an entire evening.

Guests can enjoy shareable small plates, beautifully prepared entrées, and tempting desserts, making the experience equally appealing for cocktail enthusiasts and serious diners.

I'm particularly drawn to the idea of gathering with friends, sampling several appetizers, ordering dinner, and letting the evening unfold naturally.

No rushing from one reservation to the next.

No elaborate itinerary.

Just good food, festive cocktails, wonderful company, and a spectacular setting.

THAT'S THE KIND OF EVENING THAT MAKES THE HOLIDAYS MEMORABLE.

360 Westport
111 Westport Plaza, Gold Tower
Open daily beginning at 4 p.m.
21 and older
www.360-stl.com/westport

Holiday Cocktails With Personality—and Plenty of Christmas Spirit!

Of course, no holiday pop-up would be complete without an imaginative cocktail menu.

And the creative minds behind 360 have developed a seasonal collection that is every bit as festive as the decorations.

The names alone are enough to put you in the holiday spirit!

You're a Mean One, Mr. Spritz brings a sparkling, citrus-forward interpretation of a French 75, blending vermouth, apple, warm spices, lemon, and sparkling wine.

Peppermint Condition sounds like Christmas in a cup—a warm, indulgent mint-chocolate mocha with vodka, coffee liqueur, hot chocolate, peppermint whipped cream, and peppermint crunch.

For those who appreciate a classic cocktail with a seasonal twist, the Sugarplum Old Fashioned combines bourbon, cognac, chai honey, and bitters into a sophisticated holiday indulgence.

Feeling adventurous? The Spiced Pumpkin Painkiller offers a tropical-meets-autumn combination of dark rum, pumpkin spice, coconut cream, citrus, and warming spices.

The Fruitcake Paloma delivers a playful blend of tequila, passion fruit, pomegranate, cinnamon, and citrus.

And for those who enjoy a little sparkle, Silver Bells is a frosty, glittering creation featuring vodka, spiced pear, almond, and lemon.

Even the smaller Stocking Stuffer cocktails embrace the spirit of the season.

Whether your preference is something warm and comforting, bright and bubbly, or bold and spirited, there's plenty to explore.

And, as always, a fabulous night out is even better when everyone makes arrangements for a safe ride home.

New Year's Eve at 360 Westport? Mary and I Are Making Plans!

Now, here's where our holiday plans get especially exciting.

MARY AND I HAVE OUR SIGHTS SET ON NEW YEAR'S EVE AT 360 WESTPORT!

We've heard wonderful things about its New Year's Eve celebrations, and the thought of welcoming 2027 surrounded by friends, spectacular views, and the energy of a festive rooftop party sounds absolutely irresistible.

After a year filled with galas, charitable celebrations, cultural events, and unforgettable evenings throughout St. Louis, what better way to bring 2026 to a close?

I can already imagine the glamorous attire, sparkling cocktails, festive atmosphere, and anticipation as midnight approaches.

And when the clock strikes twelve, we'll raise a glass to another year of friendship, opportunity, and adventures yet to come.

We're planning to book our celebration once the details are confirmed, and I encourage anyone considering the same to inquire early about New Year's Eve arrangements.

IF THE HOLIDAY POP-UP IS THE OPENING ACT, NEW YEAR'S EVE COULD BE THE GRAND FINALE!

A Holiday Season Worth Celebrating Right Here at Home

One of the things I love most about St. Louis is that we don't have to travel far to enjoy exceptional dining, beautiful surroundings, exciting entertainment, and memorable seasonal experiences.

Sometimes the best adventures are waiting right in our own backyard.

For Mary, our friends, and me, this holiday season is shaping up to be a wonderful combination of familiar traditions and new discoveries.

We'll explore downtown's holiday attractions, admire the festive lights, perhaps enjoy a carriage ride, and venture across the river to experience more of the region's seasonal magic.

We'll make 360 Downtown our gathering place in the sky, where the glittering city becomes part of the celebration.

And on another evening, we'll head to 360 Westport to discover its spacious rooftop setting, festive atmosphere, delicious food, and panoramic views.

Then, if everything comes together as planned, we'll return to Westport for a fabulous New Year's Eve celebration.

Because while the holidays are about decorations, gifts, and special occasions, the memories that endure are usually the simplest ones.

Laughter with friends.

A beautiful view.

A wonderful meal.

A toast to another year.

And the pleasure of celebrating the city we call home.

ST. LOUIS, YOU LOOK ABSOLUTELY FABULOUS FOR THE HOLIDAYS!

And from 360 feet—or even higher—the view is simply spectacular.

Plan Your Up on the Rooftop Holiday Experience

November 6–December 29, 2026

360 Downtown — 1 S. Broadway, atop Hilton St. Louis at the Ballpark. Opens at 4 p.m. daily. No cover before 10 p.m.; holiday seating is first-come, first-served. Full dining menu available until 10 p.m. Guests must be 21 or older after 7 p.m. 360-stl.com

360 Westport — 111 Westport Plaza, Gold Tower. Opens at 4 p.m. daily. A 21-and-over experience featuring festive cocktails, small plates, entrées, desserts, and panoramic views. 360-stl.com/westport

Both locations welcome walk-in guests, with arrangements available for groups of 10 or more.

TWO ROOFTOPS. ENDLESS HOLIDAY MAGIC. ONE BEAUTIFUL CITY TO CELEBRATE!