usa · December — March · July (Music Festival)
The Little Nell at four. the long table at the Hotel Jerome under the lights. Cloud Nine for the chukkers in the snow. Aspen is the winter equivalent of the Hamptons — the same families, the same hosts, three thousand metres higher. The summer Aspen, quieter and arguably better, is the secret.
Where to begin
The addresses I would send to a friend on the first visit. The full guide is below.
Five-Star · 5★Aspen's only Five-Star, Five-Diamond, ski-in/ski-out hotel — 92 rooms at the base of the gondola, opened 1989.
Contemporary · Michelin GuideThe Little Nell's flagship dining room — Michelin Guide-recommended Colorado contemporary, and the most serious wine cellar in the Rockies.
On-mountain · Aspen HighlandsThe mid-mountain alpine cabin on Aspen Highlands — fondue and raclette for lunch, champagne-spraying dance party at two o'clock.
Historic · 5★The 1889 silver-mining-era landmark on Main Street, run by Auberge, with the J-Bar that has been the town's living room for a hundred and thirty-five years.
Slope-side · Aspen MountainThe 1960s cabin off Tourtelotte Park — the slope-side lunch that has fed Aspen Mountain for sixty years.
Mountain · Sardy FieldThe 8,000-foot strip at 7,838 feet elevation — the only sensible way into Aspen in a winter storm.
5★ ResortThe 179-room St. Regis at the base of Aspen Mountain, the most reliably American five-star in town.
Italian · 1994The 1994 Italian on Mill Street — voted Aspen Times Best Italian 2025 and 2026, and the regulars' table for thirty winters.
Ski school · PrivateThe Aspen Snowmass Ski & Snowboard School private instructors — priority lift access, four mountains, one card.
Hotels
Book the room.
Design · 4★The 88-room W on Wagner Park, with the rooftop pool that is the town's loudest après-ski deck.
Festive · clubs, line-ups, long lunches
Reserve the table for the night out.
Japanese · NobuThe 1998 Aspen Nobu — the first Matsuhisa outside Beverly Hills, in a Victorian house on Main Street, and still the festive dinner of every ski week.
Sport · tennis, padel, polo, golf
Book the court · the green · the chukkers.
Public · 18 holesThe Frank Hummel championship course two miles from town — ranked among Golfweek's 50 best municipal courses in America.