For the last 7 years I’ve organized an annual trip to Killington, VT. Last month, 27 friends came together for a weekend chock full of activities and antics. This trip is a chance for us to escape the city, participate in fun activities, and bond – over group dinners, in the hot tub, and at the foot of an ice luge. Every year the accommodations improve, and this year we stayed at the Hideaway Chalet. The Chalet slept 24, had three kitchens, an outdoor hot tub, and a foosball table to boot.

Some of the lessons I’ve learned from organizing these trips:

• Start early: I booked the house in November and sent invites to 32 people. 18 committed immediately and another 9 eventually trickled in.
• Get people to commit (read: pay) immediately
• Collect more than is required: It can always go towards food and drink (and damage deposit).
• Assume 20% default rate: As expected, 4 people bailed within the last two weeks. I was prepared for this and had others ready to step into their place.
• Costco is amazing: I must have saved $150 by buying all my groceries there.

Though all of my pictures are on Flickr, here’s a snapshot of the trip:

Coffee, check – bread,check – chicken poppers, check – 4-pack of spicy mustard, WTF?

Sharon and Jocelyn meet us in Ramsey, NJ for the road trip to VT

Jack, Maker’s, more Jack…that seems about right

Sharon christens the hot tub toting a pack of Newports and a glass of Franzia. My friends be classy!

Lauren arrives and rubs my lucky helmet. Little does she know that it leads to…

spontaneous combustion of ones clothes and an unrivaled state of arousal

Luciano, the house mascot

When you google “Ian Springer” I hope this is the first thing that comes up. It will also be the last thing you see once you turn to stone. Fortunately, all the house members saw this move coming and scurried to there rooms for a good night’s rest.

Many of us actually managed to ski all three days despite our typical 4:00am curfew.

By Friday evening just about everyone had arrived at the house. Since there were many groups of people meeting for the first time, Arlyn had the (brilliant and equally nerdy) idea to develop an organizational chart of the house. Leave it to a Columbia MBA student to break out a flow chart between games of asshole…

How else would people get to know one another but play ‘Never Have I Ever.’ Please appreciate the box of Franzia in the foreground

Friday night’s dinner included such delights as Arlyn’s spaghetti and meat sauce served with a healthy side of love and regret

Shortly after dinner, the 90s dance party commenced. As I was setting up the camera to take a cute picture of Pawel and Luci dancing together, Sharon burst on the scene to show us all the true meaning of doggy style. In so many ways she lives up to the expectations of a Jersey girl. And that’s why I love her. Drinking + dancing + a house on the Killington Access Road = a night at the Wobbly Barn…

Jad and I perfecting the skill of alienating any woman within a 5-foot radius

The charm of Ian Kaplan is irresistible across the nation. Friday was a relatively slow night at the Wobbly, so we called our driver to take us back to the house at 2:00 and what followed was a pretty natural progression of the evening…

Shots of Jack as Jocelyn cringes in disbelief. This was followed up by a continuation of our 90s dance party (and some not-so-discrete-intimate-encounters…as per usual).

By Saturday evening, everyone had become acquainted, new relationships were budding, and therefore more drinking was to be done. I felt like a proud father when I took this picture. Speaking of relationships budding…

I’m as surprised as you are Ruth Ann

Saturday night Ian Kaplan whipped up some chicken curry and rice…which Danielle seemed to enjoyed

Vishal shows off the skills he learned at his mixology class. There’s nothing more natural than a man in camo overalls drinking a cosmo.

Nominee for most industrious use of cleavage in Killington

Onlookers gather for the first Killington ice luge

And if you start the night with shots from an ice luge, you’re likely to end up at…

The Wobbly Barn…that’s right

Killington – bringing people together since 1999. For your last Killington moment, I leave you with Ian Kaplan covering the Styxx at The Wobbly. Simply Glorious!

Come celebrate Halloween in costume at the Wobbly Barn and compete for a chance to win a Killington Resort 2007-2008 Season Pass…

The Wobbly Barn Steakhouse opens for its 44th season with the annual Halloween Costume Party on Wednesday, October 31, 2007 at 8 p.m., featuring the high-energy rock and roll sounds of Joey Leone’s Chop Shop. Costume prizes in various categories will be awarded by The Wobbly Barn judges, with a grand prize of one Killington/Pico 2007-2008 Season Pass awarded to the individual with the most creative costume.

www.wobblybarn.com