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 uninhabited logging roads that haven’t 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 Shackleton, who saved his entire team, or Sir John Franklin, whose crew resorted to cannibalism before perishing?
This adventure started with my idea to do a road trip with my son Ben, before his planned move south later this year. Since my client, Vredestein Tire was looking to promote their new Pinza all-terrain, go-anywhere tire, an idea was hatched; 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.
After the last two years, a road adventure was just what we both needed. While I handled the logistics, 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. Monica and Todd Brown of 109 Cheese and Wine in Ridgefield put together a hefty cooler bag of gourmet sandwiches and enough 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. His pitch, a 1,700-mile five-day journey all the way around New England on roads less traveled, ticked all the boxes, at least on paper.
At the outset, I didn’t grasp the scope or ambition of the trip. 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 of the Boston area.
Roger: In Westerly, Rhode Island we pull onto the sands of East Beach in front of the swanky Ocean House resort for some photos. All is well until I venture from the soft sand onto the wet sand and the car grinds to a halt. Utilizing my recovery boards, 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 sustainably designed building which has a LEED Platinum Certification. We finally hit Boston, pick up Ben and enjoy 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.
Roger: Coming from Connecticut, it’s HOT coffee for me. Arriving at Bar Harbor, the tide table is in our favor as the sandbar is fully exposed, a perfect setting for 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 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, 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 at the Swamp Buck, I venture out into Fort Kent to take some night photos. I love small towns and I love understanding the minutiae that makes one small town different than all the others. Fort Kent is small, with most buildings hugging Route 1 up to the border crossing. 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 scenic Park Loop Road in Acadia. 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 has 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. Keeping up a fairly high pace to avoid getting stranded, it’s simultaneously exciting and a bit terrifying. To the credit of the Vredestein tires, my Crosstrek is a champ and rips through the snow.
Ben: I really want to emphasize how intense those 80 miles got. We were totally isolated with nobody to be seen. A foot of snow had dropped a few days earlier 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, eyes peeled and ears perked for logging trucks and hazards around every blind corner. For 80 miles.
It was like we were on an off-road rally, except we had completely made up the route for ourselves, we weren’t competing with anyone 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. Seems Vermont likes to service all of its roads at once. We experienced: Construction equipment on multiple bridges, a tractor, excavation equipment placing a new drain pipe, and a truck repainting the double yellow line.
For me, running into multiple roadblocks on the final day of our trip 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 Food and Interesting People
Ben: The Brown Cow in Newport, VT. It’d been a long time since I’d been to a local diner, one with 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. Dinner was excellent with a wide variety of New England’s best brews on tap.
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 Antarctica!
Ben: Wild Blueberry Land calls to me. The geodesic dome. The mini golf course. The ominous gift shop in the distance with a mannequin torso in the window wearing a shirt that I 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”. I’m heartbroken it wasn’t open.
Roger: After dropping off Ben, and saying goodbye to the Morningstar clan, I had a few miles alone to reflect. 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. •