Ajax Tavern - The best place for lunch in Aspen, right next to the gondola. It's run by The Little Nell hotel. After hiking or skiing, you'll want their famous double cheeseburger (it will remind you of In-N-Out's version if you've had that) or tomato soup and grilled cheese.
J-Bar at Hotel Jerome - They have another famous Aspen burger here, but it's the laidback vibe and imposing, gorgeous bar (with the roomiest bar seats ever!) that I love. The Hotel Jerome, built in the 1880s, has the coolest lobby - it melds that time in Aspen with a fresh, Ralph Lauren-y feel. The newly renovated rooms are great too.
Paradise Bakery - This is a chain I love - I go to them in Scottsdale all the time. It's grab-and-go & they have their insanely addicting mini chocolate chippers.
Explore Booksellers - The perfect small bookstore, located in an older Victorian home. You'll leave with stacks of books!
Pitkin County Dry Goods - If I had thousands of dollars to spend on clothes, I'd spend it all here. They carry such a great selection of brands for men & women.
Silver Queen Gondola on Aspen Mountain - A must for amazing views and fresh mountain air at 11,200 feet high.
Maroon Bells - One of the most photographed spots in Aspen - it is simply gorgeous. Easy to access by car.
Aspen Square Hotel/Condos - This is sort of my "secret" in Aspen. Even though it's right in the middle of town, it's never written about. These are all privately owned condos and the ones I've stayed in have been gorgeous. They also have full kitchens and I've loved shopping at the (1990's-style) City Market grocery store and cooking dinner here instead of going out. Best of all, you can get really great rates - especially in the shoulder seasons. Aspen is so beautiful in the fall!
The Little Nell - The chicest, most serene and scene-y hotel in Aspen, right on the mountain. There's no grand lobby - it's all very quiet and sophisticated.
The Aspen Institute - An institute for lifelong learning, the institute brings in incredible speakers and offers programs on leadership, education, the arts, politics, and more. I would love to attend The Aspen Seminar one summer. Located at The Aspen Meadows Resort just outside of the town center.