Old Town Scottsdale is small — a dozen blocks, give or take — and it rewards being walked slowly and in order. Most visitors wander into it from the wrong end, hit the bars, and leave thinking it’s a themed strip. It’s a real place with a real history, and the route below is how I show it to people. Park once, near the Civic Center, and don’t get back in the car.
Start: the Civic Center and the Old Adobe Mission
Begin on the lawn at Scottsdale Civic Center, the white-walled city hall and library complex with the fountains and Robert Indiana’s LOVE sculpture. It’s the city’s front room and the easiest place to orient: Old Town proper is directly west of you.
Walk west toward Brown Avenue and you’ll hit the Old Adobe Mission, the whitewashed adobe church that the town’s Mexican and Yaqui families built by hand in the early 1930s. It’s the most photographed building in Old Town, and the one that says most clearly that this was a farming town before it was anything else.
Brown Avenue: the Western storefronts
Turn north on Brown. This is the block that gives Old Town its “West’s Most Western Town” reputation: false-front storefronts, wooden sidewalks in places, hitching posts that are mostly decorative now. The Mission sits right here beside the church, if you’re planning dinner.
Cut over a block to Main Street for the Rusty Spur Saloon, Scottsdale’s oldest bar, pouring in the 1921 Farmers State Bank building; the vault holds the liquor now. Live country music, no cover, and a wall of memorabilia going back to the days when Western movie stars drank here between shoots.
The Sugar Bowl and the schoolhouse
Continue to Scottsdale Road and the Sugar Bowl, the shocking-pink ice cream parlor that has been on the corner since 1958 and shows up in decades of Family Circus cartoons. A hot fudge sundae here is a rite of passage.
Back toward the Civic Center is the Little Red Schoolhouse, the 1909 grammar school that is now the Scottsdale Historical Society’s museum. It’s tiny, it’s free most of the time, and it’s the best fifteen minutes of context you’ll get: the town was founded when Army chaplain Winfield Scott bought land here in 1888 (the 1880s page has that story), and the schoolhouse is what the settlement looked like twenty years later, when it was still a 1900s farm village of a few hundred people.
Fifth Avenue and the shops
Head north a few blocks to Fifth Avenue, the curving street of boutiques, jewelers, Native American art dealers, and the restaurants that made this stretch a dining destination. The Fifth Avenue & downtown page has the neighborhood in detail. This is the block for turquoise, for a proper coffee, and for the kind of shop where the owner is behind the counter. Craftsman Court, the little courtyard off Fifth, is where FnB lives.
Marshall Way: the galleries
Marshall Way and Main Street between them form the Arts District, and the galleries here are the real thing — Western and contemporary art, sculpture, Native jewelry, and the occasional bronze horse the size of a car out on the sidewalk. Wander in. On Thursday evenings the whole district opens its doors for the Scottsdale ArtWalk, the longest-running gallery walk in the country, and it’s the single best time to do this section of the route.
The Waterfront, the canal, and Soleri Bridge
Marshall Way delivers you north to the Arizona Canal and the Scottsdale Waterfront: the mixed-use stretch along the water with restaurants, public art, and the walkway that follows the canal both directions. The canal itself is over a century old and still moves irrigation water; the Waterfront is the newest part of Old Town, built around it.
Cross on the Soleri Bridge, the pedestrian bridge designed by architect Paolo Soleri, with its pair of tall pylons that work as a solar calendar — a sliver of light falls between them at noon on the solstice. Every November the canal fills with light art for Canal Convergence, and this is the spot to see it from.
After dark: the Entertainment District
Just east of the Waterfront, the bars and clubs around Saddlebag Trail and Indian Plaza make up what the city calls the Entertainment District. It’s loud, it’s young, and on a Saturday night it’s exactly what you’d expect from a town with a lot of resorts and a lot of bachelor parties. If that isn’t your night, the quieter end of the evening is back on Fifth Avenue or at a hotel bar, and both are a ten-minute walk from where you started.
Timing
Mornings are best. Nine to eleven, the light is soft, the sidewalks are empty, the shops are opening, and you can walk into the Rusty Spur and the Sugar Bowl without a line. Thursday evening is the alternative, for the ArtWalk and the galleries lit up. Weekend afternoons are the crowd.
In summer, the whole walk is a morning-only activity, finished by ten. The blocks between Brown Avenue and the canal have real shade in places and none in others, and the pavement radiates. Water in hand, hat on, and every air-conditioned gallery is a rest stop. Come back after sunset for the canal and the patios.