Perched at the intersection of Highway 13 and Lake Superior, Bayfield began as a 19th-century fishing and brownstone shipping port; today it’s the launch point for the Apostle Islands — 22 islands known for red sandstone sea caves, historic lighthouses, and shipwrecks resting in startlingly clear water. But it’s also a destination in itself and an excellent base for exploring this region. So stay maybe four days here.
Your lodging choice depends on how in the mix you want to be. St. James Social, a tight eight-room inn with Nordic vibes — pale wood, clean lines, and even a Scandinavian-style sauna — sits in the heart of town. Tuesday pizza-and-vinyl nights in the lounge draw as many locals as guests, which tells you everything. For those who prioritize isolation and a wellness regimen: Wild Rice Retreat and its cabins spread across 100 wooded acres about 10 minutes south of downtown along the lake. On offer here are a cedar sauna, cold plunges, yoga, guided hikes, and meals built from regional produce and fish. For 360-degree forest views, book the retreat’s Treehaus suite.

There are no gaudy souvenir shops here — Bayfield’s retail skews thoughtful and local. Good Flower Farm produces small-batch botanical balms and serums using regionally grown herbs, while Honest Dog Books is the intellectual anchor, known for its focus on Great Lakes history and field guides. It’s also a community hub: A tiny back-of-house theater hosts readings, one- and two-person performances, DJ sets, and film nights. For picnic provisions, Juneberry Corner Store functions like a curated co-op, offering daily soups, jams, wines, and snacks. (Show up early to get the focaccia before it disappears.)
Late afternoon is Bayfield at its best. The newest hot spot, Bates Art Bar, layers rotating artwork, moody lighting, live music, and well-built cocktails with housemade breads and charcuterie boards. Copper Crow Distillery, founded by Red Cliff Band of Lake Superior Chippewa members Curtis and Linda Basina, is the first Indigenous-owned distillery in the country. Order an apple brandy old-fashioned made with fruit from nearby orchards.
The main reason, though, to travel to this part of the state is the access to the Apostle Islands, which lie just offshore. On a kayak trip to the Devils Island sea caves, you’ll see red sandstone cliffs carved by wind, ice, and Lake Superior’s force. It’s the best way to explore the island’s natural arches and narrow chambers, which glow copper against the blue water. To check out the best sea caves, we suggest a five-hour guided tour from Apostle Islands Kayaking Express.

The only inhabited island among the Apostles is Madeline Island, a 25-minute car ferry ride from Bayfield — and where you should stay for the remainder of your trip. A few minutes from the ferry landing spot in La Pointe, the Lazy Feather, a rental cottage from Madeline Island Cabins, is a haven that combines the rustic (outdoor shower) with the luxurious (clawfoot bathtub) and offers woodland views through the dining room windows.
The big draw on the island: Big Bay State Park, known for its stunning vistas of Lake Superior and its sandstone bluffs. A boardwalk trail cuts through lagoon and forest before opening to a wide, sandy shoreline, and the Bay View Trail delivers stellar lake views. It’s a great spot for mushroom foraging — and the occasional black bear sighting.
But Madeline Island isn’t just a hiker’s paradise. In La Pointe, the center of commerce on the island, you can take in some art. Bell Street Gallery & Artbar pairs regionally crafted ceramics, paintings, and jewelry with wine and encourages lingering with live music in the summer. For gifts, Woods Hall Gallery & Studios keeps its edit Scandinavian clean, with wood, linens, and small-batch provisions, along with work from artisans like Kristin M. Carey, a former children’s clothing designer who remade herself as a weaver of colorful rugs with geometric patterns.
The counter window at the Beach Club, on the harbor, is the place for fish tacos, fish sandwiches, fish everything. For something not quite so casual, the Pub Restaurant & Wine Bar, at the Inn on Madeline Island, is a charming spot to watch the sun set while relishing Lake Superior whitefish. Finish the night at the literally named Tom’s Burned Down Cafe, a local treasure. Rebuilt after a 1992 fire from driftwood and found objects (the roof is made of ripped tarp, the floor is tilted), it’s part folk art installation, part bar. There is often live music, and the mood is unapologetically quirky, especially on karaoke night.
[My Perfect Day]
Julie Buckles
The owner of Honest Dog Books is a former sled dog racer who has lived in Bayfield for more than 30 years.
“It begins with a walk on the beach with the dogs. The long, wild stretches of white sand are what sold my husband and me on this region. If I have a morning meeting, it’s going to be at one of the picnic tables at Howl Adventure Center, an outfitter and café. The food is good, but the staff is even better — the best source for all things outdoor. Lunch is at Juneberry Corner Store, Bayfield’s newest restaurant and market — ideal for reading a book or playing Scrabble. For dinner, I’m meeting friends at Hoop’s Fish Dockside for fresh-caught whitefish from Lake Superior. With its simple menu and casual atmosphere — it’s at the end of a pier — this is the place for seeing people you haven’t seen in a while, and there’s live music many nights. Last stop is a show at the Big Top Chautauqua, which could be anything from Trampled by Turtles to Bonnie Raitt, or free live music at Memorial Park, with the sun setting and sailboats bobbing near shore to catch the music.”

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