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Aspen is a magical place.  There aren't many places where you get world class skiing, sunshine, a happening town, and top notch food all within walking distance.  Here are a few spots you can't miss:

Hands down, Matsuhisa is one of the best sushi restaurants I've been to.  It's truly a special place.  Located in a Victorian House on Aspen's Main Street, you'll walk downstairs to find a walnut cocktail bar and sushi bar spanning the majority of the restaurant.  The fish is incredibly fresh, and the cocktails equally as delicious.  Open since 1998, Matsuhisa has consistently been a top Aspen restaurant.  Matsuhisa has since expanded to Vail and Denver, which are also delicious-- but there's something unique about the Aspen location that makes it my favorite.
This mountain contemporary upstairs restaurant is where it's at.  With wall to wall windows, you'll enjoy the view from the beautifully designed restaurant with a fun vibe. During the summer, you can have a cocktail al fresco on the wraparound balcony.  Not only is the atmosphere a ten, but the food and cocktails are top notch.  The menu has so many enticing options it's tough to choose-- but you can't go wrong.  Highlights include the octopus appetizer, the chicken ravioli, and -- if you're feeling rowdy-- the bone marrow bourbon shots. 
Hotel Jerome is the iconic Aspen hotel on Main Street where you'll be greeted by mountain men in cowboy hats.  J Bar is a casual restaurant with a Western vibe, and perfect for a midday meal.  Hunter S. Thompson was known to hang out here in his day.  Try the "locally famous" burger or the lobster cobb salad.  For a more classic brunch experience, Prospect is another good option in the hotel.
Lovely Northern Italian restaurant near the base of the mountain.  The wooden walls juxtaposed with white table cloths give the restaurant a warm feel with classic elegance.  Casa Tua is a bit more formal than many other Aspen restaurants, so expect fine dining.
One of Aspen's few hole in the wall restaurants.  You'll have to walk through the plastic ribbons hanging from the doorway and head to the basement, but don't worry- keep going.  The food is authentic, and damn good.  Try the grilled stuffed calamari and rellenos.
Intimate restaurant in-- you guessed it-- a white house.  I would recommend this spot for lunch.  There are some heartier options, which is perfect after a day on the mountains.  I'm a sucker for the Macho Salad-- it's so good!  White House Tavern is best for small parties due to limited seating.  Snag a seat outside if you can!
If I lived anywhere near Peaches, I would get their coffee and breakfast every day.  This is the best coffee shop in Aspen.  There is nothing better than sipping a nitro brew on their patio on a sunny day.  Their breakfast menu is no joke.  Try the Farm Table (sunny side up eggs, sautéed spinach and crimini mushrooms over rosemary olive bread topped with goat cheese) or their French Toast Waffle if you're feeling naughty.  I drink out of my oversized Peaches mug daily at home to imagine I'm back there! 
If you're looking to detox after a weekend of fun, the Pyramid Bistro is as healthy as it gets.  You'll walk through a bookstore to get to the restaurant.  Pyramid Bistro is named the first "nutritarian" restaurant, so healthy food and clean preparation is the focus.  I recommend for lunch-- it's delicious.  
Located in the historic Wheeler Opera House in the center of downtown, Justice Snows is one spot I always hit when I'm in town-- at least for a cocktail (or four).  Sit at the bar and choose from one of their beautifully crafted cocktails, or have the bartender whip up their choice.  I typically do the latter, and have never been disappointed!
Hooch is a sexy underground cocktail bar.  Enter the inconspicuous door and follow the music downstairs, and you'll find a seductive lounge with dozens of chandeliers.  The cocktails and ambience are both a 10!
I could go on and on about the Belly Up, which is my favorite music venue of all time.  The word that best sums up this magical place: legendary.  With a capacity of 450 people, it is extremely intimate and you'll feel like you're part of the band.  I've personally experienced Calvin Harris, Thievery Corporation, and Phoenix here which were incredible.  But imagine seeing John Legend, The Flaming Lips, or Jimmy Buffet-- just a few bands who have performed here.  My advice: go.  Just make sure you're ready for a wild dance party and the show of your life. 
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