Fun, outdoor festivals and events dominate the entertainment landscape of Annapolis in June. Aside from all the great tours, on the water activities, and outdoor dining options, this June welcomes a new, annual arts event as well as a revamped local favorite in the Annapolis Arts & Wine Festival. There’s live music, art, food, and so much more happening throughout the month. Here is a taste of what you can expect in Annapolis this June.

1st Annual Arts Week

Newly added in 2017, the annual Annapolis Arts Week (June 3 - 11) is a celebration of Annapolis and Anne Arundel County’s talented and diverse local arts community. The week-long event encompasses all the wide ranging artistic creativity that has made the area a haven for art lovers with its many art galleries, performance arts studios, musicians, and all around artistic talent.

With block parties, classes and workshops, four major events/festivals, live music, art exhibits, and much more, Annapolis Arts Week is the perfect way to get a sense of all the amazing art available to visitors and locals alike. Here’s a few of the events happening during the week:

First Sunday Arts Festival

Every first Sunday of the month (May – December), from 11 am to 5 pm, the first block of West Street and Church Circle are closed to traffic and opened to hundreds of arts and crafts vendors selling all kinds of local art. Grab some food, enjoy live music, and shop for a new piece of artwork. It’s the perfect way to spend an afternoon with the whole family. Click here for more information.

Paint Annapolis

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. You’ll see dozens of artists spread across the city painting right on the street demonstrating their talents. Visit the Maryland Federation of Art online to learn more about this countywide event.

The Annapolis Arts & Wine Festival

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; over 25 Maryland wineries to sample; dishes from 14 food trucks; over 200 artisan tents selling a wide range of arts and crafts; and live music! As one of the most anticipated events of the summer, it’s a great way to enjoy a sun-filled weekend. Visit our page on the Annapolis Arts & Wine Festival for more information and to purchase tickets today.

Tides & Tunes: Free Summer Concert Series

On Thursday nights this summer (July 15 – Aug 17), bring the family to the Annapolis Maritime Museum to enjoy live music by local bands against the scenic backdrop of the Chesapeake Bay. Each week features a different style of music; there's a little something for everyone. Admission is FREE; however, a $10 donation per person is appreciated. Beer, wine, signature cocktails, and food will be available for purchase. (Please refrain from bringing your own beverages as proceeds support environmental education programs at the Museum.)

Bring a blanket or lawn chairs for seating during the concert. In case of inclement weather, the concerts will be held under the tent on the Museum back deck. Click here for more information.

Eastport A Rockin’

One day, three stages, more than 25 bands. Recognized as the local music festival of the summer, Eastport A Rockin' was created to expose local music to a larger audience. From rock, to folk, to roots, to jazz, to bluegrass, to funk, the breadth of music is designed to please a wide range of audiences. Streets and sidewalks are filled with music and lined with local artisans and entertainers. A kids' area includes a moon bounce, face painters, tattoo artists, laser tag and cotton candy. Click here for more information and to purchase tickets.


Photos courtesy of VisitAnnapolis