As is the case with most great things, one of my favorite traditions happened by accident. I wish I could claim brilliance here, but we tripped over it and immediately knew it was worth its weight in gold. My dad, my brother and I had booked tickets to visit my grandfather one more time before he passed away, but his health faded more quickly than we anticipated. In just two weeks we had planned and performed his funeral ceremony, and we were all back in our own towns grieving his loss.
Due to the nightmare of dealing with airlines we were stuck with our tickets to a very normal midwest city we had all been to before. Instead of changing the tickets we decided to keep our flights, fly to that city and make a weekend of it. We would treat it as an urban retreat and city immersion. If I’m honest, part of me wondered, “Is this place worth our time?”
We found ourselves wandering the city with no real plan, strolling through city blocks and discovering local hangouts. We stopped at unique places and talked with strangers. Locals were thrilled to recommend their favorite spots. We found amazing things we didn’t know existed. A very ordinary city came alive to us. It was an amazing few days that would mark us forever.
This has turned into an annual tradition we call “City a Year.” Each year we pick a different under-rated city and immerse ourselves in it. When I tell people where I am visiting they usually say something like, “If you’re looking for an adventure why would you go THERE?” Much of our trip is aimed at finding the extraordinary in ordinary places. Here’s an overview of last year’s trip to Pittsburgh from my brother’s vantage. I also share more about “City A Year” in my new book Staying is the new Going.
Our trips won’t include world class cities like New York, San Francisco or Chicago, but we will find places teeming with life— great people who have decided to make it their home and celebrate its uniqueness. In order to immerse ourselves in the story of our chosen city that year we read a book about its history and sit with a church planter asking questions about the realities of the city. We listen to stories from the locals, travel by foot and two wheels, and choose our food based on local recommendations.
Every “City A Year” immersion has reminded me of the undercurrent of urban recovery on the rise everywhere. It has helped me to be more present and aware of both cultural advance and God’s work in my own underrated city. We have to slow down long enough to see the beauty of our places instead of just a dot on a map or a tourist destination.
So, where are we heading this year? Portland, Maine. If you have any recommendations of things to do, people to meet or food to consume leave a comment.