Our story begins with two Midwest natives who met shortly after moving to Los Angeles in 1990. After enduring years filled with earthquakes, riots, wildfires, and relentless traffic, my now-husband Michael and I sought a more peaceful life by relocating to Madison in 1997 with retirement in mind. In the summer of 2003, we embarked on a week-long getaway with friends from Madison to Madeline Island—a destination none of us had known about, let alone explored, until then.

What we discovered is that Madeline Island is a sanctuary of inclusivity and respect nestled within one of Wisconsin’s most stunning natural landscapes. The island’s splendor is celebrated, and its conservation is owed to its isolation and the dedicated guardianship of Indigenous communities, particularly the Ojibwe. For them, the island holds profound spiritual meaning, partly as the culmination of their ancestral journey. Even today, the ethos of conservation thrives. Thanks to mostly private initiatives, more than one-third of the island remains safeguarded from development.

Madeline Island is the largest and only inhabited island among the 22 that form the Apostle Islands archipelago, with about 428 year-round residents. When the Apostle Islands National Lakeshore was created in 1970, Madeline already had an established permanent community and significant private holdings. Since purchasing and depopulating the island wasn’t practical, Madeline Island lies just beyond the boundaries of the designated area.

The archipelago acts as a natural barrier against Lake Superior’s fiercest weather. During intense storms, enormous ore ships seek shelter within Madeline Island’s protected channels. In tranquil conditions, the Apostle Islands’ sea caves, coves, and beaches offer a haven for avid kayakers, sailors, and boaters.

Geographically, Madeline Island is elongated and narrow, reminiscent of Manhattan Island, though it is accessible only by ferry or small aircraft due to the absence of bridges or tunnels. With 27 miles of relatively flat paved roads, it’s a favorite among bicyclists. The state park, celebrated for its scenic trails along rugged bluffs, is an easy seven-mile ride from the ferry dock. Adjacent to it lies Big Bay Town Park, the island’s crowning jewel, featuring a pristine sandy beach, nature trails, and campsites. The island’s isolation and proximity to the Apostle Islands National Lakeshore contribute to some of Wisconsin’s darkest skies, making it perfect for stargazing, marveling at the Milky Way, and occasionally witnessing the mesmerizing Northern Lights.

Less commonly known is the authentic spirit of hospitality and courtesy that permeates the island’s community, making it remarkable.

Like many visitors, our group arrived on Madeline Island via a brief 20-minute ferry ride from Bayfield. Situated roughly 320 miles north of Madison and 80 miles east of Superior, Bayfield serves as the gateway to the island. The ferry crossing itself feels transformative, offering a sense of serenity as sailboats drift by and bald eagles soar overhead.

Upon reaching the town dock in La Pointe on Madeline Island, we took a short walk to our rental. After settling in, we eagerly set out to discover the island’s captivating charm.

Madeline Island’s warmth was evident from the moment we entered Tom’s Burned Down Café, a globally recognized seasonal bar affectionately called “The Burned Down.” Though it doesn’t serve food, this open-air establishment, built atop an old car, is renowned for its vibrant live music, whimsical signage, and inclusive vibe. I fondly remember spending several evenings there, immersed in the music and the unique energy.

On a whim the day before we departed, we toured the island with a local real estate agent. As destiny would have it, Michael was enchanted by an untouched parcel perched on a rocky bluff overlooking Lake Superior. By the time we returned home, we had convinced ourselves to pursue its purchase. I suggested building a modest log cabin there in a few years. Eventually, we constructed an architect-designed “retreat” in 2006, which was featured in Our Lives in 2019.

Just as we were finishing our new home, Wisconsin voted on a constitutional amendment to ban gay marriage. We actively participated in the Fair Wisconsin campaign and found that the welcoming atmosphere we experienced at The Burned Down wasn’t an anomaly. The island voted 74% against the ban, closely mirroring Madison’s 76% opposition.

After selling our Madison home and relocating to the island, Michael and I became deeply engaged in local organizations. Together, we’ve served on at least a dozen local boards. Grassroots activism thrives here. Since 2021, I’ve chaired the Town Board of La Pointe, which administers Madeline Island, running unopposed in each term. In 2022, Michael served as president of the newly formed Harbor Commission, leading successful negotiations to purchase the Madeline Island Ferry Line, the island’s essential connection to the mainland.

The Chequamegon Bay region is known for its progressive values. Angela Stroud, our dynamic, out-and-proud lesbian, State Representative, secured 56% of the district-wide vote in her first election in 2024, with an astonishing 78% support from Madeline Island. The area hosts active groups like the Neighbors Union and the Washburn/Chequamegon PFLAG chapter. Additionally, key businesses, including the island’s top vacation rental agency and a popular eatery, are LGBTQ+ owned.

However, it’s important to recognize that not all residents share the same political views. About 20–25% lean conservative, with some Trump supporters among them. Despite differing opinions on national and state issues, the island maintains a remarkable sense of harmony. The key to this coexistence is both simple and profound.

After all, Madeline Island is an island, and a strong sense of “we’re all in this together” unites its residents.

For example, nearly everyone relies on the ferry for daily necessities. The ferry schedule dictates routines. After Halloween, the community speculates when the ferry might cease operations due to thick ice—a famously unpredictable event. If the ice doesn’t support an ice road, people leave cars on both sides and use a “windsled”—an airplane-propeller-driven craft resembling a covered flat-bottomed boat—for crossings. These shared experiences build a sense of camaraderie, reinforcing the idea that we’re all in the same boat. Notably, residents unanimously supported the town’s purchase of the ferry line.

Madeline Island’s population swells tenfold during summer, as seasonal visitors join year-round residents, creating a vibrant mix of artistic, musical, outdoor, wellness, and community activities that nurture lasting friendships.

Beyond its appeal to tourists, Madeline Island is an exceptional place to live, especially for young families. This holds particularly true for parents with remote work flexibility. In 2013, the island gained gigabit-speed full-fiber broadband service.

The island’s public elementary school boasts a rich history, operating continuously since the late 1800s. With two multi-grade classrooms and a gym/cafeteria, the school typically enrolls 10–20 students, fostering close relationships and personalized attention. While it may not meet size criteria for a standard state report card, most island students excel academically and consistently make the Honor Roll throughout their middle and high school years on the mainland.

St. John’s United Church of Christ serves as the island’s spiritual heart, hosting activities including a vibrant food shelf, weekly winter community dinners, the Woods Hall Gallery and Studios, recovery meetings, a Little Learners group for preschoolers, and a Full Moon Circle for women. Last summer, the congregation unanimously voted to be designated as “open and affirming,” though this commitment was evident long before the official decision. I had the honor of serving as church council president for four years about a decade ago.

The island also proudly holds the highest per capita taxpayer support for a public library in Wisconsin. This cozy library acts as the island’s “living room,” offering diverse educational and recreational programs, including a makerspace and a popular summer children’s series.

The island is fortunate to have its own full-time police force, a dedicated volunteer fire department and EMS team, and a small clinic handling routine health care and vaccinations. In emergencies, a ferry remains docked to transport patients to mainland hospitals, primarily in Ashland, 20 miles away.

We continue to cherish our life here. We launched a small retail business across from the town dock, selling our handmade soy candles, premium fudge, apparel, gifts, and souvenirs. Michael works remotely as the Chief Financial Officer for Senator Tammy Baldwin’s campaign committees and is wrapping up a six-year term as a Sanitary District Commissioner. I continue to serve as Town Board Chair and a member of the Harbor Commission.

So much for retirement!

Island Essentials

Your guide to the beaches, trails, shops and creative spaces that define Madeline Island.

Set apart by water but connected by community, Madeline Island blends natural beauty, creative energy and small-town charm. From sandstone cliffs and quiet beaches to locally owned shops and galleries—including LGBTQ+-owned businesses—the Island invites you to slow down and experience a place where recreation, art, history and community intersect.

* denotes LGBTQ-owned/operated businesses

Recreation

• Swim and relax at Big Bay Town Park or Joni’s Beach.
• Hike the scenic boardwalk from Town Park to Big Bay State Park.
• Rent bicycles or mopeds from Motion to Go, located near the ferry.
• Experience guided kayak and boat tours at Adventure Vacations (adv-vac.com).
• Enjoy public tennis and paddleball courts, freshly paved and painted.
• Participate in annual competitive events, including a running marathon/half-marathon in May, an inline skate marathon in June, and a 2.2-mile open water swim race from Bayfield to the Island in early August.
• Madeline Island Trails maintains hiking and groomed cross-country ski trails, subject to snowfall.

Shopping

• Woods Hall Studios and Gallery operate as an artists’ cooperative beside St. John’s UCC, offering woven rugs, ceramics, and jewelry.
• Dockside Gifts* is a unique shop located at the ferry dock.
• Bell Street Gallery is located across from Tom’s Burned Down Café.
• La Pointe Center Arts Gallery is a nonprofit gallery adjacent to the Chamber of Commerce office.
• Adventure Vacations and La Pointe Provisions (Mission Hill Coffee) also sell apparel, gifts, and souvenirs.
• WOW Art Gallery & Studio, featuring abstract artist Steve McHugh, is open daily from May to October on Benjamin Boulevard, seven miles from downtown, and offers live music on Monday evenings during the season.
• Ricky Rocks and JEM showcase a collection of stones, rocks, and jewelry.
• Madeline Island Yacht Club Marina Store provides marine supplies, hardware, clothing, and refrigerated goods for sailors.
• Madeline Island Candles* creates and sells soy candles, premium fudge, apparel, local preserves, and distinctive souvenirs.
• History
• Madeline Island Historical Museum is a recommended first stop. The museum presents an engaging 20-minute film about the Island’s history.
• Madeline Island Historical Preservation Association has assembled several historic buildings near the museum.
• Madeline Island Wilderness Preserve maintains trails throughout the Island and hosts educational lectures at the museum and other locations.
• The Flicker House is an emerging Indigenous cultural center on Main Street and hosts cross-cultural events year-round.

Music/Island Vibe

• Tom’s Burned Down Café is an iconic spot on Madeline Island, renowned for its live music evenings and summer fun atmosphere.
• The La Pointe Center for the Arts hosts live music on Thursdays during the summer at the Harry Nelson Recreation Center.
• Madeline Island Music Camp attracts many of the country’s most talented, classically trained young musicians for spring and early summer concerts. Its scheduled and pop-up performances are just another facet of the Island’s plentiful and deeply creative culture.

General Information

• The Madeline Island Chamber of Commerce website provides links to Chamber member businesses and request forms for Visitors Guides to help plan your visit.
• The Island Gazette has been published by the same Island family for over sixty years and serves as an invaluable resource for visitors. Free copies are widely available at the post office and around town.
• Lakeview Laundromat is the only public laundromat, offering 24/7 access.