Cycling Madeline Island

I woke to the sound of a car driving by. I was parked in the woods at a pull-off, near a snowmobile trailhead. Being mid-July, I had the place to myself. I made a hearty oatmeal breakfast with berries, omega-3 mix, protein powder, almond milk — and probably too much maple syrup. I’d need the fuel for today’s trip.

I drove to the ferry in Bayfield and found a long line of cars and trucks already waiting to board. I parked in a $10 all-day lot near the public library, changed into riding clothes, loaded up with everything I thought I’d need, and coasted down the hill to the ferry landing.

I passed the line of cars and was greeted by a woman near the gate. She had a card reader and sold me a round-trip ticket for Madeline Island. She pointed out where to wait for boarding. I stood by for about 20 minutes, watching them load cars, a cement truck, passengers, and finally me — the lone cyclist — tucked into the back corner behind still-running vehicles with their windows down (urgh).

I had a map of the island and planned to ride the outer loop, estimated at 24 miles it turned into 33 miles. I stopped early at Q & Z’s Bakery & Café, tucked in at the end of a blue building on Middle Road. They only had brewed coffee, and the pastries weren’t especially flaky.

Next door was a cycle rental shop with mopeds, e-bikes, and regular bikes. I watched as they explained moped operations to a family. Once they rode off, I asked the staff about biking the island loop. He gave me a detailed breakdown and mentioned that the west side was gravel. I said I should be fine — I’m riding a gravel bike.

There were a lot of people out riding, and for the first few miles, I passed quite a few. I turned toward the state park, keeping a pace around 15–16 mph. I finally caught up to a couple just before the park entrance — he was on a Trek, and she was riding a new e-bike. I said, “You had a really good pace there.” We started chatting and it turns out they’re from Connecticut. I said, “Simsbury,” and we laughed.

As I reached the north side of the island, I stopped seeing other cyclists. The road turned to gravel — washboard on the sides, but perfectly smooth in the center if I stayed right on the ridge. I rode about five quiet miles without seeing a car. There were homes tucked into the woods and quite a few "for sale" signs from the local realtor. At one point, an older couple walking on the roadside called out, “Have a great day!”

The west side had more ups and downs than I expected. I’d assumed it would be mostly downhill, but it wasn’t. About six miles in, the road had just been graded, and now both sides had about an inch of loose, sand-like gravel. There were two wide tire tracks I could ride in, and I tried to stay in one for better traction. It was definitely more of a workout than I’d planned.

Eventually, I caught up to the big yellow grader responsible for the new surface. Honestly, I preferred the old washboards to this soft gravel. I dismounted, lifted my bike over the 15-inch mound the grader had left in the center of the road, passed it, and popped back to the ungrated side. I finally understood why I hadn’t seen a single car on that stretch.

When the gravel ended, I was back on paved road heading into La Pointe. To my left, I heard the low hum of a twin-engine plane. I spotted a runway ahead and figured the plane would be landing soon. A few minutes later, it passed low overhead and landed right in front of me. I rode into the small airport, watched the plane taxi to one of several hangars, and noticed a group of old cars nearby. One had a Cuban license plate in the window — something I’d never seen before.

Grampa Tony’s

I wrapped up my trip into La Pointe late in the afternoon and started hunting for something to eat. It was close to 4 p.m., and most of the coffee shops and restaurants had already closed for the day. I ended up at Grampa Tony’s, a casual spot right on Main Street — easy to find thanks to the giant ice cream cone out front. I grabbed a black-bean burger with fries and a side salad. The burger really hit the spot — hot, flavorful, and just what I needed after a long day. The salad was basic, and the much-hyped house dressing didn’t live up to the buzz, but honestly, I didn’t care. I was hungry, and it all tasted good. Grampa Tony’s won’t change your life, but it definitely filled the gap.

After eating, I explored the rest of La Pointe. It’s not a big town. I cruised through the main streets and then rode into the Capser Trails, which cut through the forest and into a marshy area north of town. I didn’t see another soul. The bikes were mostly parked for the day.

I stopped by the old La Pointe Indian Cemetery, also known as St. Joseph Mission Cemetery, and spent a quiet moment taking it in from outside the fence. This sacred ground dates back to the 1830s and holds the remains of both Ojibwe (Chippewa) leaders — including Chief Buffalo — and early European settlers. What caught my eye were the small offerings tucked along the fence line: coins, beads, feathers, even little ghost-like figurines. These aren’t just decorations — they’re tributes. In Ojibwe tradition, items like these are left to honor the spirits and support the journey of those who’ve passed on. The coins are a way to leave behind prayers or respects, and the other objects serve as spiritual gestures rooted in a deep connection to the land, the people, and their stories. It’s a powerful place, and even though the cemetery is closed to the public now due to past vandalism, you can still feel its presence from just beyond the gate.

Across the street from the cemetery is another quiet but powerful tribute to the Ojibwe people. I wandered over and took a few photos of the site, which was dedicated on May 30, 1987, in memory of the Ojibwe ancestors buried beneath the ground. What struck me most was the story behind it — in 1989, this land was proposed for development, but thanks to the joint efforts of tribal members and supporters, those plans were stopped. The site now stands as a permanent memorial, honoring those who came before and protecting the resting place of generations past. It’s a reminder that history isn’t just something we read — it’s something people still fight to preserve.

After another six-mile ride, I figured I’d earned an ice cream. I went back to Grampa Tony’s for a double scoop and an espresso — served in a real porcelain cup. Honestly, it was better than the meal.

Live Music

Around 6 p.m., I headed up the street for some live music. There were empty benches, and I grabbed a spot at the end of one. Most people avoided me at first, but eventually Barbara (from Minneapolis) and Ann joined me. Ann told me there are about 250 year-round residents on the island, which swells to several thousand in the summer. Everyone seemed to know each other — including the band members. It was a cover band playing hits from the ’60s through the ’90s, with a few originals thrown in.

At 7:25, I hopped on the bike and made it to the ferry just as they were raising the ramp. They lowered it and let me roll on. The ride across the lake was gorgeous, with the setting sun casting soft golden light across Madeline Island.

The climb back up the hill in Bayfield nearly knocked the breath out of me, but I made it. As I was packing up the van, Jeff and Denise walked by and we started chatting. I gave them a tour of the van and told them about my trip. I plan to stop in and see them when I make it to Minnesota.

I drove back to my quiet little spot in the woods. It was after 10 p.m., and another van had parked nearby. I cleaned up, crawled into bed, and was instantly asleep. It had been a full and memorable day exploring Madeline Island.