From the AI Proving Grounds to Pavement: A Four-Day New England Motorcycle Tour
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This post is part of our Everyday AI series crafted by WWT AI experts to enhance awareness and comfort with Generative AI (GenAI). Our goal is to empower you to harness GenAI's diverse capabilities and benefits, both professionally and personally.
We set out to let AI plan a four-day motorcycle ride through New England, and what followed was a mix of structure, spontaneity, and the kind of stories you only get from the road. Over 1,000 miles across nine states — Pennsylvania, New Jersey, New York, Vermont, New Hampshire, Maine, Massachusetts, Rhode Island, and Connecticut. We found ourselves balancing AI's precision with the unpredictability of real travel. The iron horses carried us through mountain passes, coastal roads, historic cities, and endless backroads, but the real journey was everything that happened along the way.
Day 0 — Philadelphia Kickoff
The adventure started before the motorcycles. I flew early out of Phoenix landing in Philadelphia early afternoon, and wasted no time: a cheesesteak from Jim's South Street, a stop at the Liberty Bell, and ran the steps of the Philadelphia Museum of Art like Rocky and caught a Phillies game before heading out to Leesport. It was the perfect prelude: baseball, food, and history in a single day.
Day 1 — Leesport to Jersey City
Morning came with a rental pick-up at the Harley-Davidson dealer. Amanda from EagleRider handed over a Heritage Classic Softail, saddlebags ready for my gear, while Jeff rolled up on his BMW. We strapped in cameras, mounted phones, and hit the road.
As with any trip you'd take with me, coffee ranks high on the list of priorities. Our first stop was Gems & Joe a coffee shop in Allentown run by my friend "F." I had met him when he was just opening the shop earlier this year, and now it was thriving. He poured a perfect cortado (Onyx beans, dialed-in), and it felt like catching up with an old friend.
From there, it was on to Jersey City's Empty Sky 9/11 Memorial. On September 11, standing across the river from Manhattan, we joined crowds of visitors and police officers under clear blue skies. The Freedom Tower rose in the background — a powerful moment of remembrance and perspective for both of us.
After wrestling with New Jersey traffic and debating the pros and cons of lane filtering — Legal in Arizona, not in the New England States, we enjoyed some evening backroad riding and finished the day in Kingston.
Day 2 — Albany, Route 100, and Into New England
This was the day we'd been waiting for: backroads, mountain passes, and Vermont's famous Route 100. Obviously, we had to start with coffee, so we ventured over to Alias Coffee in Albany, where Andrew served up what might have been the fastest-consumed oat latte in history (Jeff's). Then it was all curves, rolling hills, and the first signs of fall foliage.
We stopped at a roadside Vermont country store for maple syrup and souvenirs before continuing north into New Hampshire. For me, it was a first — leaning a Harley into true switchbacks, learning the rhythm of curves, and doing it all with Jeff coaching along the way. With ten hours of riding in total, we rolled into Manchester, NH, exhausted but …
Day 3 — Coastal Riding
We hit the road at 6:30 AM and headed straight for Kittery, Maine. The reward? Exceptional coffee and baked goods at Lil's Café — sailors, locals, tourists, and bikers all lined up for the same thing.
From there we traced Route 1A along the Atlantic. This stretch is pure motorcycle magic: crashing waves, sandy beaches, and seaside towns rolling by under a perfect September sky. We stopped often for photos, soaking in the smell of salt air and the sound of gulls.
By afternoon we were in Salem, Massachusetts, weaving through waves of tourists. Salem felt like a mix of history and carnival — markets, parks, and tour buses dropping off crowds.
That evening, we swung by to see my cousin, just three weeks into his first semester of college. A quick hug and a check-in meant a lot to both of us. From there, we pressed on to New Haven, Connecticut, where Jeff shared a favorite Indian restaurant, Mamoun's Falafel. Dinner never tasted better after rain jackets, wet highways, and hours in the saddle.
Day 4 — Connecticut Backroads and the Final Push
Coffee first, as always. In Bridgeport, Hannah at Sound Coffee poured me a perfect cortado. That's when disaster struck: I dropped my iPhone onto the hot exhaust pipe, melting the case and shutting it down. A refrigerator, some patience, and a lot of luck brought it back to life.
We rode through switchbacks, across rivers, and over the Hudson on a sun-drenched Sunday, surrounded by other riders making the most of the weather. Jeff peeled off near his hometown, while I continued alone toward Leesport. Those final backroads — Amish farms, cornfields, open stretches with no traffic — gave me space to reflect on the whole ride.
AI's Role
AI was our co-pilot in planning, not the star of the ride. It built the packing lists (yes, zip ties really do solve everything), guided gear purchases, and found coffee shops and restaurants that matched our tastes. It even surfaced historical context about places we visited. AI handled logistics and the road gave us the experience.
Closing Thoughts
Over 1,000 miles and nine states, we covered some of the best roads in New England. We drank too much coffee, ate great food, and saw everything from baseball stadiums to mountain passes to seaside towns.
This trip proved that AI can take the stress out of planning — but it's the unexpected, the human moments, that make the journey unforgettable.
For us, AI was a useful assistant. The open road and camaraderie was what made it all worth it.
If you're interested in connecting with fellow riders, we've also started a WWT Nexus Group, "Two Wheels, One WWT" where employees can share stories, plan rides, and keep the spirit of the road alive together.