By Roger Garbow and Ben Garbow

Roger: As my four companions and I struggled to free Jack’s car from the heavy spring snow, I considered our options. We were traveling through the uninhabited Maine North Woods on logging roads that appeared to not have seen another vehicle in days. With no cell service or satellite phone, we were on our own—which left me, as the team leader, with a decision to make. Do we press on into the unknown like the great explorers of the past, or turn back? Am I Sir Ernest Shackleton, who saved his entire team, or Sir John Franklin, whose crew resorted to cannibalism before perishing?

All this meant we were bombing through gravel roads as fast as we reasonably could, with threadbare maps and navigational references, no cell service and no satellite phone, eyes peeled and ears perked for logging trucks and snow hazards around every blind corner. For 80 miles.

This adventure started with my idea to do a road trip with my adult son Ben, before his planned move out of New England later this year. Since my client Vredestein Tire was looking to promote their new Pinza all-terrain, go-anywhere tire, an idea was hatched. Let’s outfit my Subaru Crosstrek with some rugged off-road gear, fit it with the Pinzas, and do something memorable: a complete circumnavigation of New England.

Travel by plane is tolerable at best, but travel by car can be a joy. And after the last two years, a road adventure was just what we both needed.

While I planned the route, made lodging reservations, and sourced the necessary equipment, some local companies stepped up to assist. Colonial Subaru of Danbury offered to prep the car and install the tires and LP Aventure off-road gear (wheels, skid plate, rock sliders and bumper guard). Monica and Todd Brown of 109 Cheese and Wine in Ridgefield put together a hefty cooler bag of gourmet sandwiches and enough delicious snacks to last us for days. After installing a Thule roof box with survival gear, and covering the car with stickers to ensure other travelers were aware of how epic our journey was, we were ready.

DAY 1. RIDGEFIELD, CT to BOSTON, MA

Roger: Since Ben currently lives in Boston, I am picking him up en route. With the cinematography brother team of Tom and Jack Morningstar following along (in another Cool Gray Khaki Crosstrek) to document the escapades, and their father Joe joining them since it seemed like a fun idea, we head off. The first stop is Stamford’s Lakeside Diner for a breakfast of warm cinnamon sugar donuts.

Ben: My dad and I have wanted to do a big dumb car-related adventure for a while now. Maybe a road rally, maybe an endurance race, maybe a crazy road trip. His pitch, a 1,700-mile five-day journey all the way around New England, traversing all six states and taking roads less traveled, ticked all the boxes, at least on paper.

But at the outset, I didn’t really grasp the scope or ambition of what we had planned. I’ve lived my whole life here, gone to each state many times, driven everywhere. How would this trip be any different? That’s what I was asking myself as we had dinner and drinks at one of my favorite local haunts, the Publick House in Brookline.

Roger: In Westerly Rhode Island we pull onto the sands of East Beach in front of the swanky Ocean House resort. The plan was to drive the car on the beach for some photos and drone footage. All is well until I venture from the soft sand onto the wet sand where the car grinds to a halt. Fortunately, I had packed recovery boards in the roof box. With the guys pushing, we quickly extricate the Subie and we’re back on the road. After a tour of the spectacular Audrain Auto Museum collection in Newport, we head north to Subaru of New England headquarters in Norwood, Mass. The execs give us a full tour of this striking, sustainably designed building which has a LEED Platinum Certification. We finally hit Boston, pick up Ben and enjoy a well-earned dinner.

DAY 2. BOSTON, MA to BAR HARBOR, ME

Ben: Morning starts bright and early with the traditional Boston breakfast: iced coffee at Dunkin. I drive the first leg from Revere Beach up to Portland, Maine. Because of the nature of the trip, hugging coastlines and borders, we pass through New Hampshire in the blink of an eye. I’ve driven this chunk of highway, the main route north from Boston up to Maine, more times than I can count.

Roger:  Coming from Connecticut, it’s HOT coffee for me, as the bean roasters intended. Arriving at Bar Harbor, the tide table is in our favor as the sandbar is fully exposed, affording us the optimum setting to get some wonderful late afternoon photos. Finally, we savor lobster rolls and beer at my favorite local watering hole, the Thirsty Whale.

DAY 3. BAR HARBOR, ME to FORT KENT, ME

Ben: We keep traveling east, until there’s no more east to travel to. We reach West Quoddyhead Lighthouse, the easternmost point in the continental United States. For about ten minutes, there are no humans or cars farther east in the US than us.

We drive north. Maine has an abundance of space that the rest of New England lacks, and in this part of the state you really feel a sense of distance between things, wide-open fields dotted with farmhouses and silos, mountains far in the distance.

After dinner and drinks at the Swamp Buck, I venture out into Fort Kent to take some photos at night. I love small towns, and I love understanding the specificities and minutiae that makes one small down different than all the others. Fort Kent is small, with most businesses and buildings hugging Route 1 up to the border crossing. There’s a surprising variety of restaurants, and a pile of rubble blocked off with orange cones. It’s quiet and wonderful.

Roger: We start the day with an excellent breakfast at Two Cats— I recommend the blueberry pancakes—and then a peaceful drive along the Park Loop Road in Acadia. I’ve driven this road countless times, yet the views of Maine’s rocky coastline never get tiring. A quick detour up to the top of Cadillac Mountain afford us a chance to take in the spectacular vistas before getting back on the road.

DAY 4. FORT KENT, ME to NEWPORT, VT

Roger: This is where our story began: the logging roads. My ambitious plan had us navigating these gravel roads all the way to the remote border crossing at St. Pamphile, Canada. After getting Jack’s car unstuck—with the help of the recovery boards and manpower—we decide to press on. But we need to keep a fairly high pace up to avoid getting stuck, potentially for days. It is simultaneously exciting and a bit terrifying. To the credit of the Vredestein tires, my car is a champ and rips through the snow.

Ben: I really want to emphasize how intense those 80 miles got. We were totally isolated. Not a logging truck to be seen, roads that had clearly not been traversed in days. Ten inches of snow had dropped a few days earlier which had mostly dissipated on wider routes. The narrower tree-lined roads, however, got much less sunlight, and as a result still had a shocking amount of snow for early May. And because it had been slightly melting for days, it had the consistency of wet cement.

All this meant we were bombing through gravel roads as fast as we reasonably could, with threadbare maps and navigational references, no cell service and no satellite phone, eyes peeled and ears perked for logging trucks and snow hazards around every blind corner. For 80 miles.

It was like we were on a true point-to-point off-road rally, except we had completely made up the route for ourselves, we weren’t competing with anyone, no one knew where we were, and there was no prize waiting for us at the end. Our prize was crossing into Canada.

DAY 5. NEWPORT, VT to RIDGEFIELD, CT

Ben: Today was specifically designed to try our patience. I guess Vermont likes to service all of its roads at once on Tuesday mornings. Throughout the day we had to stop for, were held up by, or got stuck behind:

  • Construction equipment on multiple bridges
  • A tractor
  • Excavation equipment placing a new drain pipe (held us at a full stop for like 15 minutes)
  • A service truck repainting the double yellow line (so we couldn’t even pass!!)

For me, running into more roadblocks on the final day of our trip than we had this was extremely funny. Dad looked ready to jump out of the car and punch a tree.

We also did maybe the most Vermont thing I can think of: taking two Subarus to visit the Ben and Jerry’s factory.

Roger: Two thoughts from the day: (1) Ben and Jerry’s ice cream is always better at the factory and (2) road construction delays suck, no matter what state you are in.

Best dining experiences

Ben: The Brown Cow in Newport, VT. It had been a long time since I’d been to a local diner, the kind of place that has paper placemats filled with ads for local businesses. The bacon egg and cheese on an English muffin was killer, and not just because it was our last morning on the road and I could taste freedom.

Roger: The Swamp Buck. With every other Fort Kent dining establishment closed on Sunday night, this was it. In spite of our low expectations, dinner was excellent and there was a wide variety of New England’s best brews on tap. 

Most interesting people we met

Ben and Roger: Susanne Ottendorfer and Siegfried Weinert from Austria who we met at the West Quoddy Lighthouse in their overlanding RV as they began their 18-month journey traveling the entire North and South American continents—and Antartica!

Favorite roadside attraction

Ben: Wild Blueberry Land calls to me. The geodesic dome. The mini golf course. The slightly ominous gift shop in the distance with a mannequin torso in the window wearing a shirt that I can only assume says something like “I Went To Wild Blueberry Land on Historic Route 1 in Maine And All I Got Was This Stupid T-Shirt”. Actual blueberries, I assume. I’m heartbroken it wasn’t open.

Roger: I couldn’t agree more. 

Epilogue

Roger: After dropping off Ben, and saying goodbye to the Morningstar clan, I had a few miles alone to reflect on the trip. The sights, the roads, the food and the adventure were everything I could have hoped for. But spending those five days with Ben is something I will truly cherish. We talked about everything, we laughed until we could barely breathe, and we shared some kickass experiences. Pulling into my driveway, I ended up were I started. But this trip was never about the destination. It was all about the journey.

Watch the entire journey here.