If someone suggests going sailing to you in Aspen, they may be inviting you to boat on Ruedi Reservoir. Or they may be talking about garage “sale-ing,” an even more unique experience and better cultural bellwether, because in Aspen the accumulation of ridiculous amounts of stuff is nearly universal. Actual sailing, not so much.

Garage sales are especially popular in the Roaring Fork Valley because you can get killer deals on high-end pieces like Rolex, Louis Vuitton, Tiffany, “investment-quality Persian rugs,” and gold Dunhill lighters with the ex’s initials on them. It’s also possible to make awesome historical finds such as antique mining maps, vintage Aspen Music Festival posters, or even an aquamarine handblown glass Burnett’s “cocoaine” bottle from the 1880s. Or a vintage Deering cocaine grinder from the 1980s—possibly from its original owner. 

On a more mundane level, there are always steals on swag like skis, bicycles, stereos, unregistered guns, and other “shit that fell off a truck,” but also unique opportunities such as when the author Clifford Irving held a yard sale of books a few years ago at his home just up Independence Pass. It was as much fun talking to the man who wrote a fake biography of Howard Hughes as it was browsing his sprawling collection. His openness made for a good sales technique: some people took eight boxes of books back to homes already structurally weakened by truckloads of them. 

Once you’ve hit enough garage sales around Aspen, you start to recognize some distinct patterns. When the items for sale are lopsidedly male or female, it’s an obvious tell that you may be at a Divorce Sale, which can offer big bargains. That gold Dunhill lighter, for example, or anything inscribed to one or both of the couple, including sterling silver wedding gifts they never opened. Cheap sports gear, and all of it, is often the order of the day from whichever spouse has departed: those golf clubs he bought her that she never used because she didn’t play and didn’t want to; the skis she gave him that he didn’t like. 

The lofty-sounding Estate Sale tries to elevate the unloading of old hockey skates, cassette tape players, lamps with frayed cords, and “well-loved” chairs to a more formal and profitable status than a mere garage sale. Often they’re just depressing, but you can sometimes stumble across the real deal. After more than five decades here in the valley, Georgia Hanson, the longtime director of the Aspen Historical Society, and her husband, Andy, made a multiday bash of their Estate Sale last October before they moved to Mexico. They didn’t just place classified ads: they ran display ads and sent out email invitations for people to bring potluck dishes and to carpool due to limited parking.

The Hansons’ was a prime example of how a big sale can turn into a neighborhood event akin to a block party with lots of food, music, and drinking, which all help lubricate sales. It also demonstrated the impressive confidence some people have in the salability of their belongings, as well as the belief their friends and customers will turn out en masse deep in the off-season.

Longtime Aspen philanthropist and socialite Merrill Ford hosted an Estate Sale years ago at her Aspen Meadows townhome that was probably the only one ever in the tony neighborhood. As with Irving’s, the classified ad for Ford’s sale carried her name, and many people stopped by out of curiosity. Some of them doubtlessly ended up with bits of her jettisoned art—say, a LeRoy Neiman poster of an Ali–Spinks fight or some papier-mâché carnival masques—that they would later try to sell themselves. Along with some of Irving’s books.

Probably the best buying opportunities are at the regrettable Foreclosure Sales. Putting a positive spin on an otherwise negative situation—it’s an ill wind that blows no man any good!—it’s a shame your neighbor went under, but that doesn’t mean you should miss some smoking deals on the Hummer-styled golf cart, the Franklin Mint coin collection, the Bing and Grondahl plates, and other “shrewd” investments.

Foreclosure Sales are often characterized, late on Sunday, by the attitude of: “Screw it. Take whatever you want, and throw some money in the bucket; the bank’ll get it otherwise.” You can usually make an offer on the whole show, including the house. And the bucket.

Then there’s the Death Sale, kind of the ultimate sale off into the sunset, so to speak, and good for finding cheap sports gear left by whichever spouse has departed …. OK, maybe it isn’t all that different from the Divorce Sale, except that there are usually more goods available, because this departed wasn’t able to take any of it with them—just as the old saying warns. Which means that other old saying, “Whoever dies with the most toys wins,” isn’t really true. The actual winners are—garage-salers!

“Whoever dies with the most toys wins” isn’t really true. The actual winners are—garage-salers!

Where to find the rarity while in town: