Digs in Vermont – Travel Blog

Digs in Vermont

Every year over MLK weekend, we take a road trip and head to Vermont. We rent a big house near Okemo Mountain with lots of beds and get a great group of friends together for a long weekend of skiing, snowball fights, food, wine and hot tubbing.

This year in Vermont

We were supposed to be 5 families, with 9 little boys and 2 little girls. We ended up with 4 families, 8 boys and 1 lone girl (GIRL POWER!). One family got sick the day before we were supposed to leave, and ended up bailing. The rest of us got sick pretty quickly thereafter, with most people only getting on the mountain a day or two to ski before falling victim to the flu.

Vermont Accomplishments

Despite the sickness, the kids had a great time playing together and enjoyed the extra time with their iPads. Some of the highlights:

  • We made home cooked meals every breakfast and dinner (and most lunches)!
  • We still managed to drink a lot, despite the children around us keeping us up all hours of the night.
  • I learned to play the Scrabble app, and Rachael taught me the hard way all the nonsensical two letter words that Scrabble considers words like “qi”), even though they don’t consider “vape” or “zen” to be words!
  • We talked politics, which I will not share here.
  • Jessica rode the chairlift for the first time.
  • Owen and Ezra skied with Dan and did awesome! The only fail was Owen being too short to get on the chairlift once. Of course, Dan wasn’t next to him to help him (way to look after his 5 year old!), and the woman who came to help Owen after stopping the lift couldn’t pick him up! Yes, he is that sturdy.
  • Both drives were a success with very little traffic, and we only stopped once each way for a pit stop – we made record time.
  • Best of all, nobody came home with any injuries!

Vermont Real Estate

We rent a large house every year. It costs about $1,000 a night for all of us. The house is nice and does the trick, but it’s certainly not new or fancy. Sometimes we contemplate buying a house in Vermont for $250,000 and renting it out. It would pay for itself pretty quickly. But, then, we’d be stuck managing a property from 4+ hours away and stuck holding a relatively illiquid asset. Homes tend to sit on the market for a long time. For now, we’ll still with renting once a year.



Digs Realty is a residential real estate brokerage in NYC that provides full service at a discount. The Digs Mission: Saving you money without compromising service. We give our home buyers up to 67% of our commission and charge our sellers up to 4% less than traditional brokerages.


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