Jeff the Planner

A smiling woman and man stand together in front of a scenic landscape of green hills, a small church, and tall mountains in the background.

Santa Maddalena, Dolomites, Italy

I have an MBA and a decade in manufacturing and operations planning, so I know how to build a plan, manage, and execute it. But my heart has always been in the wild.

I grew up in the southern Adirondacks. Okay, technically I was born in Ohio, but I moved to upstate New York when I was four. I grew up in a very small town about 20 miles west of Lake George. My family home was outside the town in the mountains on a large piece of land with a barn and miles of overgrown logging paths running through thick woods. We raised goats, chickens, ducks, and turkeys as a hobby, and I spent a lot of time exploring the woods with my dog. My school district was made up of four small neighboring towns, and even then my graduating class was only 70. Many of my friends lived in those neighboring towns, so when I biked to soccer practice or to a friend’s house, I was committing to at least a 26-mile round trip, which I did regularly in the summer. Growing up out in the mountains really made me earn my appreciation for distance and planning.

My love for travel started with family road trips across the United States. We explored Yellowstone, dug for fossils in South Dakota, camped in the Painted Desert, hiked in Glacier, and watched orcas hunt off the coast of British Columbia. I have taken a train from New York to Colorado to see the Rockies. I have hiked extensively in the Adirondacks and Berkshires, and have done trips to the White Mountains, the Smokies, and even chased two total solar eclipses. That early exposure gave me a deep appreciation for scenic beauty, regional character, and the experience of moving through different landscapes.

Winters in the Adirondacks were incredibly difficult, and by the time I left for college, my family had moved down to the Saratoga/Albany region of New York. I attended college in Plattsburgh, where I was able to explore more of the High Peaks, chasms, and rustic charm of the northern Adirondacks. International travel became a real passion when I studied abroad in Ningbo, China. Navigating an unfamiliar culture challenged me to grow and gave me a deep respect for the ways people live and connect around the world. I was also enough to travel outside of class. These moments still come back in full color, visiting a countryside Buddhist temple, taking the bullet train to Shanghai, even a hotel breakfast in Hangzhou, all visceral. I graduated college with a very clear desire to get out and see more of the world.

In 2021 my wife and I took our first trip to Europe. We hiked in the Swiss Alps, wandered Tuscan hill towns, explored Florence and Siena, and ended on Lake Como. In 2024 we returned for an adventure honeymoon through the Italian Dolomites, Slovenia, and Croatia’s Istrian Peninsula. We explored castles, alpine meadows, glacial lakes, Roman ruins, and medieval villages. We hiked, biked, kayaked, and made space to reflect and recharge. Those trips deepened my appreciation for the kind of travel that combines scenic beauty, culture, movement, and a real sense of place.

On the home front, I moved to the Berkshires in 2018 after taking a job with a distributor in southern Berkshire County. I live in Pittsfield now, but I have also lived in Great Barrington. I earned my MBA in North Adams, where I also met my wife. I proposed to her on Bartholomew’s Cobble in Sheffield. I married her on Lake Onota in Pittsfield. Today we live in the city’s Little Italy neighborhood in what we consider our forever home.

What I appreciate about the Berkshires is how naturally they fit into that larger story. I was drawn to the area right away because the scenic beauty is undeniable, but also because it offers the same kind of layered experience I have always valued. There is nature here, there is history here, and there is culture here. It is a place where mountains, lakes, small towns, museums, music, and local character all exist close together. For me, the Berkshires feel like a place where adventure at home and appreciation for the wider world meet in a very natural way.