Our Story
A live-work creative space in historic Bayfield, Wisconsin.
Why Island Gateway
Island Gateway Gallery & Gathering grew out of a shared belief that creativity thrives when people feel welcome, unhurried, and connected — to art, to place, and to one another.
Founded by Mary and Dale Whittaker, Island Gateway is a true live–work creative space. We live in the building and work here every day. The gallery, retreat space, and gathering areas are extensions of our interests, passions, and the life we’ve built together.
Island Gateway is intentionally personal, intentionally calm, and intentionally centered on people.

Educators Who Create and Host
We are educators at heart, and you will feel that the moment you walk through the door.
Mary and Dale approach Island Gateway the way educators approach a classroom or studio: with care, curiosity, and attention to how people learn best together. Dale worked in higher education for his entire career, and Mary brings her educator’s training to breaking down tasks, preparation, and creating environments where people can learn and gain confidence.
At Island Gateway, education doesn’t feel formal. It shows up as encouragement, conversation, shared discovery, and learning by doing — whether that’s through a gallery talk, a quilting retreat, or a small hands-on workshop.
The Gallery
The gallery at Island Gateway is curated as a series of month-long exhibitions, each focused on a theme or an individual artist. This format allows time — time to look closely, return, ask questions, and build conversations around the work.
Dale is deeply interested in supporting artists and helping people new to collecting experience the joy of owning original art. Exhibitions are designed to tell stories and spark dialogue, with artist talks, demonstrations, and openings as a regular part of gallery life.
We believe a vibrant arts community grows through shared energy. Bayfield’s evolving gallery scene excites us, and we see Island Gateway as part of a larger creative ecosystem — one that gives people more reasons to visit, stay, and return.
Retreats: A Place to Be Together
The retreat space at Island Gateway is just as central to our vision as the gallery.
Mary hosts small retreats — typically up to eight people — designed for those who want time away from daily routines to be together, laugh, work on projects, quilt, stitch, and enjoy one another’s company. These retreats are as much about connection as they are about making.
The space itself is bright, light-filled, and thoughtfully equipped, with large work tables, cutting and ironing stations, comfortable seating, and lunch.
Everything is set up so guests can arrive, settle in, and focus on what matters — creativity, conversation, and rest.
Retreats take place in the heart of downtown Bayfield, where shops, restaurants, and unique lodging are just steps away, yet the space itself remains calm and quiet. Lake Superior’s shoreline, wooded trails, and places to wander are close at hand, offering balance between making and being outdoors.
Learning, Lightly Held
In addition to retreats, Island Gateway offers short workshops — opportunities to learn new skills, try something playful, or make a small project alongside others. These sessions are designed to feel approachable and joyful, not intimidating or high-pressure.
Whether you are experienced or just beginning, the goal is the same: to learn together in a supportive, welcoming environment.
How We Got Here
Before moving to Bayfield, Mary and Dale lived year-round on Madeline Island, where they began imagining a place that could bring together living, making, hosting, and community.
When a beautiful red brick building in Bayfield’s commercial district — part of Bayfield’s National Register Historic District — became available after years of sitting unused, it felt like the right home for that vision. Though just steps from Rittenhouse Avenue, the building offers a surprising sense of quiet and calm.
With Mary’s background in historic preservation, the building was restored to National Park Service Historic Preservation Standards, honoring its past while opening it to new life as a creative gathering place.
A Place to Gather
Island Gateway is, above all, a place to gather — around art, around tables, around shared curiosity.
It is a gallery where art sparks conversation and a retreat space where creativity unfolds in good company. We invite you to step inside, slow down, and be part of what’s growing here.
