There’s something about hitting the open road on a Harley-Davidson that feeds the soul. On Sunday, August 11, 2024, I set out from Milwaukee on my 2023 Harley-Davidson Pan America Special, ready for a journey that would take me through the Upper Peninsula, across Ontario, into Upstate New York, and back home. By the time I rolled back into Milwaukee on Friday, August 16, I had covered 2,350.9 miles, explored some of the most breathtaking landscapes, and created memories that will last a lifetime.
Day 1: Milwaukee to Thessalon, Ontario
My journey began with a ride through Peshtigo, WI, Escanaba, MI, and the unspoiled beauty of Michigan's Upper Peninsula before crossing the border at Sault Ste. Marie—a quick three-minute affair—and heading into Ontario. The ride was smooth, the weather was perfect, and I soon found myself cruising along the north shore of Lake Huron. I ended the day in Thessalon, a charming little community where I spent the night, anticipating the miles ahead.
Day 2: Thessalon to Sudbury – A Mechanical Glitch with a Silver Lining
The second day took me from Thessalon to Sudbury. It was here that I encountered my only mechanical issue of the trip. Thankfully, I was just blocks away from The Rock Harley-Davidson. Derek and his team were open, ready, and able to get me back on the road by noon the following day. A big shoutout to them for their incredible service! After Sudbury, I had a quick lunch stop in Espanola, but the highlight of the day was definitely the Serpent River area. The crystal-clear waters exposed a dark riverbed, making the river appear as though it runs like ink. The native pines and glorious blue skies added to the tranquility and undisturbed natural beauty of the region.
Day 3: Sudbury to Ogdensburg, NY – Nature’s Grandeur
Day three saw me traveling from Sudbury all the way to Ogdensburg, NY. Along the way, I passed through Meadowside, North Bay, Deux-Rivières, and Deep River, a town steeped in mid-20th century American history. The ride through Algonquin Provincial Park was nothing short of spectacular. The park is the crowing jewel of the region; combined with the sight of White Lake and its surrounding community, it made for a perfect day on the road. I arrived in Ogdensburg just after sunset and found a quaint lodge right on the banks of the Saint Lawrence River, ready to take on the Adirondacks the next day.
Day 4: The Adirondacks – A Day in the Mountains
Leaving Ogdensburg, I headed into the Adirondack Mountains, a region that never fails to impress. I rode through the Raquette Boreal Wild Forest, passed Tupper Lake and Long Lake, and even saw the fabled Gore Mountain with a midday stopover in Saratoga Springs. The day ended in Little Falls, where I spent the night. The Adirondacks are more than just mountains—they’re a place where nature’s grandeur is on full display, and I was lucky enough to witness it all from the seat of my Harley.
Day 5: Little Falls to Adams Center – Forests and Wind Farms
Day five took me from Little Falls to Adams Center, riding through or near no fewer than a dozen state forests, including Penn Mountain and Tug Hill. The Maple Ridge Wind Farm, with its 195 wind turbines, was an impressive sight. After a brief stop at FX Caprara Harley-Davidson to see an old friend and colleague, I jumped on the interstate for the first time since I left Milwaukee, making my way westward. I passed through Syracuse and Buffalo, stopping briefly for an early dinner at Old Man River Doghouse and Seafood Shack—a true dining destination in Western New York. I made short work of Pennsylvania and crossed into Ohio with about an hour of daylight to spare, finally setting up camp for the night at the Thompson / Grand River Valley KOA Holiday as the sun was setting.
Day 6: The Final Stretch – Back to Milwaukee
My final day on the road began with a lazy start. I broke camp, packed the bike, and faced the most grueling part of the trip: the Ohio Turnpike, Indiana, and Illinois Tollways. A quick detour through Sandusky allowed me to meet some industry friends and take a short drive along the shores of Lake Erie, passing directly by the Davis-Besse Nuclear Power Station before returning to the turnpike. The day was marked by on-and-off rain, but as I made my final fuel stop in the northern suburbs of Chicago, I knew I was in the home stretch. The last 90 minutes flew by as I took advantage of a break in the rain to ditch the interstate for some two-lane backroads.
This trip was incredible in every sense of the word. For those who have never been to the Upper Peninsula or Ontario, I encourage you to go—don’t put it off until next year. You’re missing some incredible scenery nearly in your own backyard. And for those looking for a longer adventure, the Adirondacks are a must-visit. The mountains are breathtaking, but it’s the glass-like lakes that’ll take your breath away. This ride was a 10/10, and I would definitely do it all over again.
I am looking forward to more rides and sharing more journeys. Until next time, ride safe and ride free.
If you're planning a similar trip or need any tips, please stop by House of Harley-Davidson. We're always here to help fellow riders get the most out of their adventures.
