Aspen: My Neighborhood

Jonathan Fillman landed in Colorado 15 years ago to pursue his dream of becoming a luxury-hotel GM. When he heard that The Little Nell was in need of one, it sounded like a winning lottery ticket. “When it comes to the crème de la crème, The Little Nell is where it’s at if you’re a hotel nerd like I am,” says the Georgia native. And now—thanks to hard work and a little luck—the fabled Five Star, Five Diamond hotel is where Fillman is at.

He loves “living in a small town and going into places where I know people and can talk to people.” Equally appealing is the active lifestyle of the Roaring Fork Valley. “Almost every day I ride my bike from Basalt to Aspen. It’s 22 miles each way, and I’m on a bike path until I hit the side streets of Aspen.” Here Fillman shares a few other outtakes from his highlight reel. —Kate Meyers

Fresh Air

“If I’m in the mood to have some incredible boarding, I go hike the Highlands bowl. It sounds scary, but thousands of people have hiked the bowl and you can, too. When you get up there and you’re looking around, it’s like being on top of Mount Everest.”

“In the winter, I like to hike up Aspen Mountain before the lifts are running and snowboard down right before work. It’s a great way to start the day and get first tracks. I hike with Yaktrax on my sneakers, and in my backpack I carry collapsible poles, my board, boots, jacket, and ski pants. I strap my helmet on the outside.”


“I love coffee and I’m super-picky. I really like Victoria’s Espresso. Victoria herself is always there, and she knows how to make a latte or a flat white just right. I go there every Thursday at 7 a.m. and several other times during the week. They have a wonderful patio for people-watching.” 510 E. Durant Ave., Aspen, 970.920.3001

Sweet Tooth


“My wife and I love Heather’s. Its official name is Heather’s Savory Pies & Tapas Bar, but everyone just calls it Heather’s. They always have live music. We come in, eat our vegetables and protein, and then just ogle the rack of desserts. I usually go for something chocolate or dark chocolate, and she usually goes for apple pie or cheesecake.” 166 Midland Ave., Basalt, 970.927.0151

“I love the J Bar at the Hotel Jerome. They have a Bourbon milkshake called Aspen Crud. It’s soo good. The bar is in one of Aspen’s iconic buildings, so going in makes you feel like you’re stepping back in history. The vibe is super-authentic and fun.” 330 E. Main St., Aspen, 970.429.7674

Top Secret


“It’s not a secret that we have an amazing wine program at The Little Nell. But a lot of people don’t know that we host events and parties in our cellar. You have to walk through a dusty concrete garage to get there. There are red lights, so we call it ‘the red light lounge.’ When you walk in, you see walls covered with signatures where people have Sharpied their names.” 675 E. Durant Ave., Aspen, 970.920.4600

“Steakhouse No. 316 feels like an old, upscale cowboy bar, and the cuts of meat are wonderful. If I’m ordering off the menu, I always have the prime bone-in filet, but I’ve gotten to know the GM, Roy, so he’ll call me when they have a special cut. The Steakhouse makes you feel like you’re coming home.” E. Hopkins Ave., Aspen, 970.920.1893

 Find your new home in Aspen, today.

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