May at Holiday Music Motel: Kicking Off a Season of Art, Music & Community
As the chill of winter fully fades, May brings new energy and excitement to Sturgeon Bay and Door County. With festivals, art fairs, farmers markets, and live music filling the calendar, there’s no better time to stay at the Holiday Music Motel and experience the lively spirit of the season. From our weekly WRiTERS NiGHTs to major community celebrations, May is a month of creativity, connection, and fresh beginnings.
Celebrating Music and Creativity
The heartbeat of Door County’s artistic scene comes alive in May, offering countless opportunities to immerse yourself in the creativity that defines our community. From the soulful sounds of live music and original songwriting performances to the unveiling of vibrant public art installations, the month is a celebration of local talent in every form.
Every Thursday evening, Holiday Music Motel’s Tambourine Lounge hosts the beloved WRiTERS NiGHT, where songwriters, poets, and storytellers gather to share original works from 7–9 PM. Listeners are always appreciated, making this one of the most intimate and inspiring nights of the week.
This year, Steel Bridge Day marks the beginning of an exciting new tradition in Sturgeon Bay! Celebrated on June 14, 2025, the day honors 20 years of Steel Bridge Songfest and over 1,000 songs written in its name. Enjoy a free outdoor concert from noon to 5 PM at Martin Park featuring local favorites and Steel Bridge artists. In case of rain, the event will move indoors to MUSE, where a Steel Bridge 20th Anniversary Pass is required for entry. Later that evening, MUSE will also host a live Steel Bridge Radio listening party and a sold-out 20th Anniversary Showcase, celebrating two decades of unforgettable music and community spirit. Visit SteelBridgeDay.org for more information!
Art & Markets in Full Bloom
May marks the beginning of outdoor festivals and markets, showcasing the creativity and talent that Door County is known for. As the weather warms, parks and streets across the peninsula come alive with colorful art fairs, vibrant farmers markets, and lively celebrations that highlight the spirit of the community. It’s the perfect time to explore local craftsmanship, enjoy fresh produce, and experience the welcoming energy that defines Door County’s spring season.
Celebrate fine art over Memorial Day Weekend at the Sturgeon Bay Fine Art Fair on May 24–25 at Martin Park. Featuring dozens of artists from around the Midwest, this juried art show includes paintings, photography, jewelry, sculptures, and more. Enjoy live music, children’s activities, food, and beverages while strolling through a colorful sea of creativity.
Starting in May and running through September, you’ll find stunning public art displays throughout Sturgeon Bay with the Set Sail street art project. This initiative is a unique collaboration of art and community that has been developed to add beauty to the streets of Sturgeon Bay. All 25 pieces of art will eventually be auctioned off in the fall, but May is the perfect time to see them fresh on display.
On Saturday, May 31, the beloved Sturgeon Bay Farmers Market officially opens for the season! Held at Market Square every Saturday from 8:30 AM–12 PM, the market offers fresh produce, baked goods, handmade crafts, and locally sourced products. It’s the perfect Saturday morning tradition to kick off a day of exploring Door County.
Celebrating Community Traditions
As the peninsula comes back to life, May is filled with opportunities to join in some of Door County’s oldest and most beloved celebrations. From small-town parades to community fairs, these time-honored events capture the spirit and tradition that make the region so special.
Welcome summer a little early at Jacksonport Maifest, held May 24–25. This family-friendly festival includes a colorful parade, an art fair, live music, horse-drawn wagon rides, and the annual Footrace along beautiful Lake Michigan. Maifest is a true Door County tradition, offering a charming small-town experience just a short drive from the Holiday Music Motel.
Make the Most of May in Sturgeon Bay
May in Sturgeon Bay is a celebration of everything that makes Door County special: creativity, community, and the beauty of a new season. From WRiTERS NiGHT at the Tambourine Lounge to street art, farmers markets, and festive parades, there’s something for every visitor to enjoy. Book your stay with us this May and experience the vibrant heart of Door County as it comes alive!
