Old Town Scottsdale: The Weekend Edit

Ask ten people what Old Town Scottsdale means to them and you may get ten completely different answers. Someone will immediately tell you about the nightlife, someone else will start talking about the restaurant where they celebrated an anniversary, and another knows exactly which Arizona wine tasting room pours their favorite Syrah, which gallery they wander into on Thursday nights or where to grab pizza when getting dressed up for dinner has completely lost its appeal.

That range may be what makes Old Town so much fun right now. There is not one Scottsdale experience hiding inside these few walkable neighborhoods, but dozens of them.

You can check into a midcentury icon or disappear into a tiny boutique inn tucked behind the Arts District. Dinner can mean a multi-course tasting menu, omakase, wood-fired Latin food, pizza with the locals or a margarita and tacos at a place that has been doing Old Town long before Scottsdale became quite so shiny.

You can taste Arizona wine without driving to wine country, spend an afternoon shopping labels that would feel perfectly at home on Rodeo Drive, wander through Western art, discover a restaurant inside a century-old house and end the evening with Italian wine, Japanese whisky or a very good Negroni.

Old Town has a party reputation, and it has certainly earned it, but the clubs are only one version of the neighborhood. This is the Old Town I want visitors to discover, and perhaps the one those of us who live here occasionally need to rediscover ourselves.

Stay: When the Hotel Is Part of the Trip

One of the easiest ways to stop treating Old Town as somewhere you drive for dinner and start experiencing it as a destination is to book the room. Better yet, choose a hotel where checking in gives you much more than somewhere to sleep. Old Town has become particularly good at this, with hotel restaurants worth visiting even when you are not staying upstairs, pools that can consume an afternoon and enough personality that choosing where to stay can completely change the weekend.

Hotel Valley Ho + ZuZu

Before Scottsdale became Scottsdale, Hotel Valley Ho was already here looking impossibly cool. The midcentury-modern icon opened in December 1956, and its colorful architecture, palm trees and pool scene still deliver exactly the retro desert fantasy you want from a Valley Ho stay.

It feels cool rather than preserved. That distinction matters. You are not checking into a museum. The hotel continues to evolve while holding tightly to the personality that made it special in the first place.

Then there is ZuZu, which makes a very good case for staying put. Breakfast can turn into a long brunch, an afternoon at the pool can become cocktails, and dinner can happen downstairs without ever retrieving the car. For someone visiting Scottsdale for the first time, this remains one of my favorite recommendations because you are not simply sleeping in Old Town. You are staying in a piece of it.

Bespoke Inn + Virtù Honest Craft

Bespoke Inn offers almost the opposite experience. Small, intimate and tucked into the Arts District, it feels as though someone dropped a lovely little European hideaway into the middle of Scottsdale. Borrow a bike, wander the neighborhood, spend an afternoon gallery hopping and return without ever feeling like you are navigating a sprawling resort.

When dinner rolls around, Virtù Honest Craft is right there, and Chef Gio Osso’s Mediterranean-inspired restaurant has long been one of my favorite Old Town reservations. Add the courtyard, a menu that changes often enough to keep returning interesting, a bottle of wine and nowhere you need to drive afterward, and suddenly staying twenty minutes from home feels like an actual getaway.

The REMI + Kauboi + F/Sixteen

If Bespoke whispers, The REMI has no intention of doing so. One of Old Town’s newest hotel personalities sits directly in the Entertainment District and leans into the energy around it.

At Kauboi, Japanese-American steakhouse influences meet robata, sushi, steaks, Japanese whisky and highballs. F/Sixteen heads in an entirely different direction with diner nostalgia, all-day breakfast, burgers and the sort of food that suddenly sounds brilliant after a night out. You can have the polished Scottsdale dinner and the slightly less polished next-morning recovery meal without changing addresses.

Senna House + CALA

Senna House occupies a lovely middle ground. It is stylish without requiring the weekend to become a scene, central enough to make exploring Old Town easy and polished enough that returning to the hotel still feels like part of the vacation.

At CALA, Mediterranean-inspired food, cocktails and a lively brunch give you another example of why Old Town’s hotel restaurants should not be treated as backup plans. This is where I would point someone who wants to be close to everything, have somewhere beautiful to return to and also fully intends to sleep. A surprisingly important vacation category.

W Scottsdale + Sexy Roman

W Scottsdale has never really understood the idea of a hotel lobby being somewhere you simply walk through. The pool, music, crowd and location make the property part of Old Town nightlife before you ever step outside.

Downstairs, Sexy Roman gives you a reason to start the evening at the hotel rather than simply return to it afterward. Handmade pastas, Italian wines and a cocktail program with a little theatrical flair make it more than the obligatory hotel restaurant. And if someone wants to put a strawberry Negroni in front of you, just say yes, please and thank you.

Caesars Republic + Luna by Giada + Wolf by Vanderpump

Caesars Republic feels built for someone who wants the full production. Its location beside Scottsdale Fashion Square puts shopping, restaurants and nightlife within easy reach, but you could also make a perfectly respectable argument for barely leaving the hotel.

Luna by Giada brings Giada De Laurentiis’ California-meets-Italian style to Scottsdale, while Wolf by Vanderpump delivers drama, design, cocktails and a room that understands people will absolutely be taking pictures in it. This is the heels-are-coming-out-of-the-suitcase Scottsdale getaway, and sometimes that is exactly the assignment.

Eat: Choose the Kind of Night You Want

Trying to create a definitive guide to Old Town dining is an excellent way to accidentally write another magazine, so rather than pretending there is one best restaurant list, choose according to the kind of night you want. Old Town can do elegant, neighborhood casual, longstanding local favorites and shiny new things particularly well.

When Dinner Is the Destination

Cafe Monarch has become almost synonymous with special-occasion Scottsdale dining. There is romance built into the room before the first course even arrives, and the prix-fixe format makes the experience feel more like an evening than simply dinner. For something even more intimate, The Reserve takes that idea further. This is anniversary territory, birthday territory, proposal territory, or Tuesday if Tuesday has been particularly trying.

House Brasserie brings a different kind of romance. Set inside a historic Old Town house with a garden patio, it feels tucked away despite being right in the middle of things. And sometimes the answer is simply a really good steak. Mastro’s City Hall and Ocean 44 are martini-and-a-good-outfit restaurants, and there should always be room in a travel guide for those.

At Uchi, Chef Tyson Cole’s Japanese concept brings sushi, sashimi, hot and cold tastings and an ever-changing omakase experience into Old Town. Anhelo is quieter about what it does, which may be part of why I like it. The intimate space and tasting-menu approach turn dinner into something deliberate rather than rushed. Courses arrive, conversation stretches and suddenly much more time has passed than expected, exactly what a great dinner should do.

The Old-School Heroes

New restaurants are exciting, but neighborhoods are built by places that stay. The Mission Old Town is one of those restaurants that feels inseparable from this part of Scottsdale. Chef Matt Carter’s modern Latin cooking, freshly made tortillas, wood-fired flavors and candlelit space have been part of the Old Town dining conversation for years.

Then there is Cien Agaves, with tacos, tequila, margaritas and a patio full of people having a very good time. It has been part of the Old Town landscape since 2007, and the original remains exactly the kind of place visitors imagine finding in Scottsdale.

Pizza With the Locals

Not every meal needs to involve a tasting menu and a reservation made weeks in advance. Sometimes you need pizza and a beer. Pizzeria Virtù brings Gio Osso’s approach to the neighborhood pizzeria, while Craft 64 pairs wood-fired pizza with local beer and the sort of neighborhood energy that makes ordering one more round seem completely reasonable.

Meet the New Kids

Ponderosa is particularly interesting because the setting already has a story. A restored century-old house becomes part restaurant, part cantina and part patio, giving the Arts District another reason to linger.

Wayward adds another personality with globally influenced cooking, live-fire elements, cocktails and a room that feels very aware of what is cool without appearing to work particularly hard at it. These are the places that give locals an excuse to come back, because the easiest mistake to make with somewhere close to home is assuming you already know it.

Sip: Walk Through Arizona Wine Country

One of my favorite Old Town surprises has nothing to do with tequila. Arizona wine has quietly become part of the neighborhood. The Scottsdale Wine Trail brings several Arizona producers into tasting rooms scattered around Old Town, giving visitors an introduction to the state’s wine industry without requiring a drive to Sonoita, Willcox or the Verde Valley.

The trail includes LDV Winery, Aridus, Carlson Creek, Los Milics, Salvatore and The Wine Collective, making it easy to turn an afternoon into a walkable wine tasting. LDV is especially fun because the tasting room acts like a neighborhood gathering place as much as a wine stop. Tastings may turn into winemaker events, cheese pairings or trivia nights, which is exactly the kind of experience that makes wandering fun.

When Wine Isn’t the Mood

Old Town certainly has other ideas. There are agave cocktails at The Mission and Cien Agaves, Italian wine and that strawberry Negroni at Sexy Roman, and Mai Tais at HULA’S Modern Tiki. Add Japanese whisky and highballs at Kauboi, rooftop cocktails, hotel bars and whatever catches your attention while walking between them, and the bigger problem becomes deciding where to stop. A respectable vacation problem.

Shop: Luxury Labels and Local Finds

There are people who travel and buy refrigerator magnets, and there are people who travel and buy shoes. Old Town is very accommodating to both.

Scottsdale Fashion Square has evolved far beyond simply being the really nice mall next to Old Town. Luxury designers make it one of the strongest retail destinations in the Southwest, and increasingly the restaurants have become attractions themselves. Catch, Din Tai Fung, Élephante, Nobu and Toca Madera can turn shopping into dinner, while Maple & Ash just outside the mall gives you one more reason not to call the rideshare home quite yet.

The other side of Old Town shopping deserves just as much attention. Walk away from the luxury storefronts and you find galleries, Southwestern art, Native-made goods, vintage fashion and independently owned boutiques tucked throughout the district. Sometimes it is art, sometimes jewelry and sometimes something you absolutely did not need until you saw it. Those are usually the best souvenirs.

Play: Leave a Little Room in the Schedule

A good Old Town itinerary should contain at least one block of time with nothing planned. That may sound irresponsible to anyone who travels with a spreadsheet, but try it anyway.

Western Spirit

At Western Spirit: Scottsdale’s Museum of the West, the mythology of the American West gets a little more texture. Art, artifacts, history and culture help tell a broader story than the cowboy version of Arizona visitors may arrive expecting. It is also conveniently positioned in Old Town, which means visiting does not need to become an all-day museum expedition. Spend a few hours, then go wander.

Thursday Night ArtWalk

Scottsdale ArtWalk has been giving people an excuse to wander the galleries along Main Street and Marshall Way on Thursday evenings for decades, and it remains wonderfully uncomplicated. Walk, step into whatever gallery catches your eye, talk to artists, find something you love and debate whether your house actually has wall space left. Then go to dinner.

Follow the Architecture

Historic buildings sit beside midcentury architecture and shiny new hotels, while the Arts District looks completely different from the Entertainment District despite the two being an easy walk apart. Sometimes exploring a destination is less about checking things off and more about noticing how the pieces fit together.

A Scoop of Old Town History

Not every piece of Old Town history comes with a museum ticket. Sometimes it comes in a pink booth with a sundae on the table.

The unmistakably bubblegum-pink Sugar Bowl has been serving ice cream in Old Town since 1958, and remarkably, much of the experience still feels like stepping into another era. Pink booths, an original soda fountain and ice cream creations that do not particularly care about restraint have made it a Scottsdale tradition for generations. For a neighborhood that seems to reinvent itself every few months, there is something wonderfully charming about walking into a place that has spent nearly seven decades being exactly what it is.

Build Your Own Old Town Weekend

Check into the hotel that matches your version of Scottsdale. Give one dinner the time to become the destination. Taste a little Arizona wine, leave space for a cocktail and walk into the gallery or shop that catches your eye.

Most importantly, leave a little room for Old Town to surprise you.

The neighborhood is too layered for one version of the perfect weekend, which is exactly why it is worth returning to.