Art Under the Oaks returns to Islamorada, boosts Upper Keys nonprofits

The 42nd annual Art Under the Oaks filled the shaded gardens of San Pedro Catholic Church in Islamorada on Jan. 16, drawing a mix of residents and visitors as the Upper Keys opened its winter event season. The one-day arts-and-crafts fair showcased vetted artisans selling original work, a lineup of food vendors, family-friendly activities and live local music that began at noon.

Organizers emphasized a selective vendor approval process aimed at keeping offerings high quality and protecting the market value of local makers. That curation matters in a county where seasonal festivals are a core revenue stream for small creative businesses and where reputational quality can determine whether events bring repeat customers or casual foot traffic. Participating vendors also donated items for a raffle, and proceeds from the festival were earmarked for parish ministries and community programs, creating a measurable transfer of festival sales into local social services.

Community groups invited to participate included the Florida Keys Children’s Shelter and coral-restoration organizations, tying the fair’s cultural economy to social and environmental causes. For nonprofits that rely on unpredictable funding streams, the festival’s proceeds and donated goods provide both immediate dollars and visibility. For artisans, the event offered direct retail sales and marketing exposure at the start of a busy tourist season that runs through spring.

From an economic standpoint, Art Under the Oaks is more than a weekend activity. It functions as a marketplace that reduces transaction costs for consumers seeking handmade goods and for artists seeking customers, while concentrating visitor spending in Islamorada before it diffuses across the Lower Keys. The festival’s fundraising role also supplements local community programs without relying entirely on public budgets, an important dynamic given Monroe County’s constrained tax base and heavy dependence on tourism-related revenue.

Beyond the immediate sales and donations, the festival supports longer-term resilience for the Upper Keys by reinforcing networks among artisans, nonprofits and parish institutions. Maintaining a selective vendor roster helps protect producers’ margins and preserves the event’s reputation as a destination offering authentic, original work rather than mass-produced items.

For Monroe County residents, the practical takeaway is twofold: attending events like Art Under the Oaks directly channels consumer dollars to local creators and community services, and the festival calendar that follows will shape seasonal traffic and spending patterns across the Keys. Organizers plan to keep the curated approach for future fairs as the community looks to balance economic benefits with sustaining the area’s cultural and environmental priorities.