What it’s actually like
The Civic Center mall is the pedestrian spine that runs east from Brown Avenue past the library, the museums and the lawns of the Civic Center park, and Trailside Galleries sits on it at 7330 East Scottsdale Mall — away from the Main Street gallery row, on the quieter, more institutional side of Old Town. That location tells you what kind of gallery it is. Trailside is not a boutique. It is one of the pre-eminent dealers in American representational art in the country, and its Scottsdale rooms are the winter counterpart to a Jackson, Wyoming flagship that has anchored that town’s art scene since 1963.
The art is the serious end of the Western tradition and its neighbors: Western and wildlife painting, figurative work, impressionism and landscape, by nationally established names, hung with museum spacing and priced for collectors who know the artists’ auction records. It is the kind of gallery where a single canvas can be the most expensive object sold in Old Town that week, and the staff carry that knowledge lightly; a curious visitor is welcome to walk the rooms, and a collector will get a conversation about a specific painter’s market in detail.
Trailside also presents the Jackson Hole Art Auction, one of the major sales in the Western art calendar, which means the gallery is plugged into the national market in a way most Scottsdale galleries are not. Come here to see what the top of the category looks like, even if you are buying at the bottom of it somewhere else.
What to buy
A major representational painting. Western, wildlife, figurative or landscape by an established name — this is a gallery for the piece a collection is built around, and the staff will discuss an artist’s history and market with precision.
Wildlife art. A Trailside specialty since its Jackson origins, and a category few Scottsdale galleries handle at this level.
Impressionist and figurative work. The non-Western side of the roster, for the buyer who wants the quality without the cowboys.
A conversation about the auction. If the Jackson Hole Art Auction is on your horizon, this is where to ask how it works and what to watch.
Parking, timing and the practical stuff
Trailside is the easiest gallery in Old Town to park for. The free Civic Center garage off Drinkwater Boulevard is a two-minute walk, and the Scottsdale Civic Center park’s lawns and fountains make the approach the most pleasant in the district. The Old Town on foot note connects the mall to Main Street and Brown Avenue, both under five minutes west, and the Old Town guide covers the whole.
The gallery keeps daytime hours; it is off the Main Street and Marshall Way ArtWalk route, so do not expect it to be part of Thursday night, though the walk over is short. High season is January through April, when the Western art collectors are in town and the Scottsdale Arts Festival fills the Civic Center in March; that is also when the mall is busiest with events. Summer weekday mornings are quiet and cool enough for the walk from the garage, and the museums on the mall make a natural pairing.
Eat while you’re there
AZ88 is right on the Civic Center mall, the glass-walled room for a martini and a burger after the gallery — the natural pairing. West on Brown Avenue, The Mission beside the Old Adobe Mission is the modern Latin dinner. On Main Street the Rusty Spur Saloon pours in a 1921 bank, and the Sugar Bowl at Scottsdale Road and First Avenue, pink since 1958, is dessert.
How it got here
Trailside began in Jackson, Wyoming in 1963 as the first gallery in a town that had none, and by most accounts it is the foundation of the Jackson art scene that now rivals Santa Fe and Scottsdale as a Western art capital. Over the following decades it became one of the pre-eminent dealers in American representational art, with a ten-thousand-square-foot flagship on East Broadway in Jackson and a roster of nationally established painters and sculptors across Western, wildlife, figurative, impressionist and landscape work.
Scottsdale was the logical second home. The Western art market has always run on a seasonal circuit — the Rockies in summer, the Southwest in winter — and by the 1970s and 1980s Scottsdale had become the winter capital of the trade, with Main Street’s galleries selling to the collectors who wintered in the resorts. A Jackson gallery of Trailside’s standing needed a Scottsdale presence for the months its own town was under snow. Accounts vary on exactly when the Scottsdale gallery opened, and this page does not guess; what matters is that it has been a fixture of the Civic Center mall through the district’s modern era.
Its address is a choice. Rather than the Main Street row, Trailside sits on the Civic Center mall, the pedestrian spine the city built in the 1960s and 1970s as its cultural heart, beside the library and the museums. That places the gallery in an institutional setting that suits its scale and separates it from the Thursday-night browse; collectors come here on purpose, and the room is built for the long look rather than the passing one.
Trailside also presents the Jackson Hole Art Auction, one of the major sales on the Western art calendar, which ties both galleries into the national market. In Scottsdale its closest peers are The Legacy Gallery at Scottsdale Road and Main, which has its own Jackson sister space and hosts the Scottsdale Art Auction, and Altamira Fine Art on Main Street, another Jackson Hole gallery with a Scottsdale room. Between the three, the Jackson–Scottsdale axis of the Western art trade is fully represented in Old Town, and the Main Street Arts District is a five-minute walk west.