There are four major, can’t-miss festivals happening during this year’s Annapolis Arts Week: The Annapolis Arts & Wine Festival, Paint Annapolis, First Sundays Arts Festival, and the Annapolis Irish Festival. Each offers attendees a different experience – live music, painting, food and drinks, crafts, and live art demonstrations. Browse below to learn more about these great festivals and decide which ones you’d like to enjoy while you're in town for Arts Week

Arts & Wine Festival

June 10-11

It’s a celebration of the area’s local artists and Maryland wines! Join Annapolis for a weekend filled with local artists demonstrating their talents live on-site; sample over 25 Maryland wineries; enjoy dishes from 14 food trucks; browse over 200 artisan tents selling a wide range of arts and crafts; and live music!


Paint Annapolis

June 4-11

Paint Annapolis is a week-long juried plein air painting competition held each year that brings plein air painters to Annapolis from around the world. The event is designed to explore in paint the special colonial architecture, marine atmosphere and overall energy of Maryland’s capital city.


First Sunday Arts

June 4

The First Sunday Arts Festivals brings in thousands of locals and visitors to enjoy shopping directly from artisans during each first Sunday on West and Calvert Streets in downtown Annapolis. The festival provides shopping opportunities from over 130 local and regional artists and crafters selling their artwork from 11 am to 5 pm.


Irish Festival

June 2-3

Celebrate everything Irish at the only festival of its kind in the region: The Annapolis Irish Festival provides the opportunity to enjoy traditional Celtic music, Emerald Isle food, Irish rock bands on two different stages along with workshops and exhibits.