Killington Files...Open with Caution!

CJM
Jan 28, 2025
6 min read

Updated: Nov 17, 2025

A while back I talked about my love for skiing and mentioned Killington. And the fun [trouble] I get into while I’m there. My cousin Kerry, is my partner in crime on and off skis and we end up at Killington a lot each season. To the point where the locals are asking us if we’re local. It’s been like Vegas—what happens in Killington, stays in Killington. But now, I need to share the tales we’ve lived to tell from our time spent there.

While Killington is expensive, it feels fully accessible, whereas some mountains are In the middle of nowhere. Killington Road has a 1+ mile stretch on it of hotels, bars, restaurants, ski shops, and more. It feels like you’ve just arrived in Disney as a 5-year-old, and you’ve gotten a golden ticket. Kerry has been going to K town long before me; however, we’ve perfected our trips there together in the past few years. And a trip to K town isn’t complete until we’re driving back home in complete silence. Begging for lobotomies and perhaps a few days of sobriety.

Our first trip to Killington began in March 2023, and we had great weather for skiing all weekend. This trip we were simply amateurs. We skied until last chair and stayed at the Hilton by Killington (One of the best places to stay there! Just beware of Ash the flirty janitor). We got right into the hot tub after a long day of skiing and immediately were served Margaritas (Ummm was I in Heaven?) The hot tub was a sight to behold. Picture twenty full grown adults in a hot tub that is barely big enough to hold us, passing around bottles of Fireball while singing Pitbull. Maybe we were in Heaven.

Kerry and I ended up going out on the town that night, but unfortunately, we didn’t bring any suitable outfits. So, we dressed in our ski leggings, gross sweaters, and hats to tame our helmet hair. We were not a beautiful sight, but we were introduced to The Pickle Barrel, otherwise known as the best bar in Rutland.

Upon coming back to the hotel that night, we became closely acquainted with the lobby concierge. He was an 18-year-old who lived in the hotel, and let us take as many free snacks as we wanted. Score! We spent the night bothering this poor guy and oddly woke up in time for another full day of skiing. To say it was a great trip would be an understatement, however it was only the first one. We still had much to learn.

Coming up on the 23-24 season, we quickly planned our first trip back for right after New Year’s. I had just gotten my new Blizzard skis, and we were so excited to be back. The skiing was okay, considering we hadn’t gotten a real snowfall yet and the mountains were trying their hardest.

We arrived on a Friday night and as soon as we unpacked our 7 bags of food for the two of us, it was time to track Mr. Peacock down. Kerry and I went to the front desk and inquired about his whereabouts and ended up speaking to the Hilton manager (and her boyfriend in jail via FaceTime!) We were then informed he had been let go for undisclosed actions. But like all stories, the show must go on...

We ended up finding a local distillery at the edge of the mountain and fell in love. Still on The Mountain features locally distilled gin, vodka, wines, etc. and is a cozy atmosphere with great food. Of course, Kerry and I showed up and made our presence known. We quickly became friends with the bartender, the manager, and other employees in our typical fashion. A snowstorm hit at the end of the weekend, ‘forcing’ us to stay an extra night, this time at the Inn next to the distillery, which was the cherry on top. We met Nick, our singer pal and Pat and stayed up way too late. Another trip in the books!

Flash forwards a few weeks, and we were missing it. We were dying to attend Subaru Fest, aka party weekend in K town, hosted by their biggest sponsor, Subaru (and everyone knows what Charty thinks of Subarus). Kerry and I decided saddle up and tried to find a cheaper hotel for the first night. Enter Grey Bonnet Inn. We drove up at 4am on Saturday in February to chase powder- and man it was a beautiful ski day. Sunny skies, fair temperatures, and just one of those days you look up and say, “it’s a good day for living.”

We skied all day and showed up to the Grey Bonnet exhausted—ready for a hot shower and to make our way to dinner. But upon arriving, the lobby was full of people and an older French man told us we needed to sit down and wait. Uh what?

The clerk explained that he had overbooked people and needed to clean and flip 7+ rooms himself because his staff had gotten bird flu and left. He invited us to hang out in the lobby until then. It was absurd. We watched this process repeat with every newcomer inside and emotions rose higher and higher. The clock continued to click, and we continued to lose patience, until Kerry suggested we bring our hooch in from the car and bartend in the lobby. What a marvelous idea! I brought in tequila, lime juice concentrate, and Coronas to mix up ‘Margaronas’ for all our new friends. (Recipe attached)

It felt like we were Noah’s Ark saving our fellow people with our resources. Kerry and I acted like game show hosts in the lobby, asking people where they were from, explaining the situation, and dishing out booze. We should’ve been paid for our services! After a few hours, we finally got into a room and quickly changed to greet the night. And you know we told all our local friends about the terrors that happened at the GBI! (We did barricade the door all night in case the front desk clerk came back)

The next night we were thankfully at our trusty Mountain Inn and stayed until last call with our fave bartenders. Recalling our stories for our friends there and bugging everyone with our annoying jokes and same one-liners. It’s always heartbreaking for us to be asked when we’ll be back and not having a return date.

Sure enough, March rolled around, and Kerry and I found ourselves planning a final (her say not mine!) trip to our favorite place. The consensus of our trips to Killington are that if you have plans when we plan a trip- cancel them. So, Saint Patrick’s Day weekend, we trekked up to our mountain again. Now this trip was certainly the bellringer. We’re still not sure if we're welcome back! We arrived on Friday morning and this time stayed in the cutest Air BNB at a development. The skiing was tough—spring conditions with low visibility and mushy snow, but we persevered!

Friday night we went to the distillery and then ended up at Jax, one of the bars, to see our local friends. We rolled in Dukes of Hazard style, ready to raise hell! After being booted out of the bar at closing time, we haphazardly got ready for another day of skiing. We met a new buddy named Rob and spent the day skiing with him (Rob has since become one of my dear friends).

Hot toddies were had, along with $40 lunches, and nothing but good times. It’s not lunchtime at Killy until Kerry and I call out every person at the salad bar telling them they’re skinny! Saturday night we shut The Pickle Barrel down again, sponsored by green tea shots and misbehaving into all hours of the night.

Upon awakening the next morning, I was sure I was in purgatory. The hangover, the carpet nailed down in my mouth, I don’t even think my legs worked properly. Kerry insisted we skied though- so there I was on top of Killington Peak trying not to toss my cookies! We did a few runs, and I had to take a break for a Diet Coke...

We stumbled into one of the lodges and found a vending machine…only to realize we were out of money. Seriously. No money left in any of our pockets. Not even a credit card. It was then I pulled the plug and said we have to get the hell out of here. The show is over! Again, we drove home in silence and rounded another ski season off at our favorite place.

The summer was long, and we were constantly missing our favorite place. Thankfully I was able to get back up to Killy a few weeks ago, and of course it was nothing short of the best. I got to spend time with my buddy Rob, drink dark liquor, ski my favorite sunny trails, and just be. Put it in the meeting minutes that I was also called "mature" and "nonchalant!" Kiss! What a dream.

Until we see you soon, K town!

-Charty