It was early December and the dread was upon us… NYE plans. The night that everyone has set, super fun, Instagram-able plans. Of course, the obvious answer to escaping this pressure is to travel, but travel conveniently because airfare is typically astronomical. So we compromised by escaping the bar lines, cover fees and outrageous Uber surges for a two hour drive to a magical place where parking is mostly free and getting around is easy as can be – 5 minutes or less to your next destination.
We settled on Madison, WI and quickly discovered it as one of the most underrated cities in the US.
A short 45 minutes north of Madison, we arrived at Devil’s Head Ski Resort, where the fake snow wasn’t as bad as our prior expectations. With minimal lines, we accomplished just over two straight hours of skiing and heavy windburn as Allison didn’t have ski goggles π

We headed back to the city for the rest of the trip, Saturday through Tuesday. Days followed with brewery trips, bar Yahtzee, vegan menus (almost everywhere) and funky haircuts (everywhere). The culture of Madison is vibrant and its openness and acceptance towards all walks of life was obvious. We checked out many of the top restaurants, breweries and city sites… listed are a few of our favorites:
- Natt Spil, a sign-less spot for dim sum & brick oven pizza
- The Merchant – craft cocktails & trendy dining
- Short Stack Eatery – brunch spot, right downtown
- Breweries: One Barrel, Working Draft (favorite), Next Door
- Museum of Contemporary Art
- and of course, the magnificent Capitol Building

We rang in the New Year celebrating a Rock n Roll themed party hosted by Dillon & Kelly Olson. Fun times were had catching up with high school friends, snapping polaroid pictures and jamming to some AC/DC, Aerosmith and many classic oldies. All in all – Madison is a city where you can spend a long weekend, see and experience just about everything the city has to offer from the food to the breweries to the various city sites.
