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Gregg’s Insider Guide to Aspen

I’m basically a modern day nomad. I’m one of those strange individuals who get excited upon arriving to an airport. I spend much of my time exploring the world. But, there is one perfect spot that is always on top on my list. Aspen aka “my happy place”, is one of those incredible places where I can’t wait to return. I'm considered a local since we spend 3-4 months there each year (and it actually gets me a discount at Starbucks).

Aspen is small mountain city in Colorado that offers everything from world class skiing in the winter to one of the best food and wine festivals in the summer. “I came for the winter, but stayed for the summer” is a phrase you’ll often hear.

This is no ordinary ski destination. Unlike the Disney-like ski villages you may have visited, Aspen is an upscale hometown (boasting some of the best public schools in the country). It’s basically five square blocks complete with five star accommodations, restaurants and shopping. My favorite month is January where Aspen plays host to the original Gay Ski Week ( and X-Games as well as international tourists from Australia and Brazil.

But summer is just as good as winter! Food & Wine Classic, the Ideas Festival and the Music Festival are some don’t miss highlights, and the town offers a cool comfortable climate where you can hike like a local, spend the day shopping, or bike to Woody Creek Tavern for lunch.

But beyond the scenery, the skiing and the shopping, it's the people of Aspen that bring me back year after year. I think this might be the real “happiest place on earth” or at least the friendliest. I think I have more friends in Aspen than I do in NYC. I was even a “bridesman” in one of my favorite local couple’s recent wedding! (And Aspen is a perfect place to get married).

Join me at my 18th consecutive Aspen Gay Ski Week in January (or anytime over the winter) and let me plan your vacation to this spectacular town.


The Little Nell

Located just steps from the gondola, this is Aspen’s only five star, five diamond hotel!

Hotel Jerome

My favorite hotel bar in town straight out of a Ralph Lauren ad. Love this property.

St. Regis

Luxurious accommodations and home to Aspen’s best spa and one of the best restaurants (Chef’s Club).


Located in Snowmass (my favorite mountain for skiing)

**If you book any of these properties, we can offer you exclusive amenities including daily breakfast, bar credits and more!!


Matsuisha (Nobu): Simply one of the best Japanese restaurants in the world!

Steakhouse 319: My favorite steakhouse with great food, ambiance and service.

Cache Cache: An Aspen classic with consistently delicious food

Peach’s: Something healthy and casual and yummy


Cloud Nine:

“Where the Wildest Ski Party happens twice a day, Everyday!”

Caribou Club

Find a member (just ask me if I'm in town) to take you into Aspen’s most chic and exclusive club: created by members of our community of course! ;)

Belly Up

Renowned yet pint sized world class music venue. You won't believe their amazing calendar of events.

Woody Creek Tavern

Bike here (it’s almost all downhill) but get a ride home after some delicious food and margaritas

Shopping & Art Galleries

Aspen has incredible art galleries and world class shopping from Gucci to Prada but the local spots are the best:

Pitkin County Dry Goods (clothing)

Cos Bar (beauty and cosmetics)

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