Fun, outdoor festivals and events dominate the entertainment landscape in June. The First Sunday Arts Festival, in downtown Annapolis every first Sunday, May through October, is in full swing. This free street festival-slash-art market-slash-entertainment venue is not to be missed. Another fun arts festival in June? Paint Annapolis, a five-day juried plein air painting competition in which artists from across the country descend on Annapolis, set up their easels outdoors, and invite passersby to look over their shoulders while they work (there's also a competition component at the end of the festival). In keeping with June's festive nature, there's Eastport-a-Rockin', featuring a day of home-grown local music in a relaxed atmosphere on the grounds of Annapolis Maritime Museum, on the banks of Eastport's Back Creek.

Irish Festival Live Music

Annapolis Irish Festival
When: Friday-Saturday, June 2-3
Where: Where: Anne Arundel County Fairgrounds, 1450 General’s Highway, Crownsville

Celebrate everything Irish at the only festival of its kind in the region. Enjoy traditional Celtic music and Irish rock bands on three different stages, along with workshops and exhibits. When you get hungry, try some delicious Irish beef stew and other Irish favorites. Little Leprechaun Land provides crafts, face painting and other free activities for the kids. As in past years, the festival will benefit local charities. Visit www.annapolisirishfestival.com for more information.

First Sunday Arts Festival
When: Sunday, June 4 (and every first Sunday through November) Noon to 5:00 p.m.
Where: First block of West and Calvert Streets, Annapolis
Admission: Free

Enjoy live entertainment and the works of 100 local and regional artists as you stroll along the first block of West Street (the Arts District) and Calvert Street next to Whitmore parking garage. Local restaurants set up outside cafes that are perfect for people watching and an afternoon bite to eat. Free parking for the family-friendly event is available at the state parking garage on the corner of Calvert and Bladen Streets. Visit www.firstsundayarts.com for more information.

Dinner Under the Stars
When: Wednesdays, May 31 through Mid-September (Tentative dates)
Where: 6pm - 10pm, West Street, Annapolis

The first block of West Street (from Church Circle to Calvert Street), located in the heart of the Arts District, will be closed to traffic on Wednesday evenings and filled with café tables reminiscent of the open air cafés in France, Spain, and Italy. Visitors and area residents are invited to dine, stroll and shop along West Street while enjoying live music beneath a canopy of lights. Visit http://www.annapolisartsdistrict.org/ for more information. 

Paint AnnapolisPaint Annapolis
When: June 4-11
Where: Streets and countryside of Annapolis and Anne Arundel County
Admission: Free

Peek over the shoulders of artists capturing the beauty of light and shadow on canvass during a five-day juried plein air painting competition hosted by the Maryland Federation of Art. Thirty juried artists from across the country will paint in Annapolis’s Historic District and the surrounding countryside from June 4-11. Visit www.mdfedart.com for more information.

Annapolis Greek Festival
When: June 1-4;
Where: Saints Constantine & Helen Greek Orthodox Church (2747 Riva Road, Annapolis)
Admission: Free

Capture a taste of Athens right here in Annapolis when you join in the fun at this annual family-friendly event. Enjoy Greek dance performances, sample Greek cuisine, savor Greek music, tour the beautiful Greek Orthodox Church and more. Visit www.annapolisgreekfestival.org for more information.

Annapolis Greek Festival

Annual Annapolis Arts and Wine Festival
When: Saturday-Sunday, June 10-11; Saturday, 10:00 a.m. to 6:00 p.m.; Sunday, 10:00 am to 5:00
Where: Navy-Marine Corps Memorial Stadium, 550 Taylor Avenue, Annapolis
Admission: Adult (age 21 and up) wine sampling kit, $30.00; General admission and children, $12.00. Prices subject to change.

One of Annapolis’ largest and most popular events, the weekend arts and wine festival features samplings of more than 100 Maryland wines, 150 arts and crafts displays, food, kids’ activities, entertainment and live music. Visit Arts and Wine Festival online for more information.

Arts, Crafts, and Wine Festival

12th Annual Bands in the Sand 
When: Saturday, June 10; 5:00 p.m. to 10:30 p.m.
Where: Chesapeake Bay Foundation’s Philip Merrill Environmental Center (6 Herndon Avenue, Annapolis, Md) 
Admission: $100 per person or limited VIP tickets
Contact: 410-268-8816

Featured bands are destined to have you dancing in the sand. Check your shoes at the optional “shoe dock” and enjoy an evening of cool drinks, groovin’ live music, tasty food, and to-die-for raffle items on the beach. It’s a party to save the Bay, a natural treasure! 2015’s headliner, the Bacon Brothers, entertained 1500 guests, with Misspent Youth closing out the night. Founding event sponsor, Boatyard Bar and Grill, will provide food & beverages throughout the evening. Visit www.cbf.org/bandsinthesand for more information.

Bands in the Sand