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.

2020 Secret Garden Tour
When: Saturday-Sunday, June 6th-7th (12pm-5pm)
Admission: $30 in advance, $35 on June 1 and 2, 10% discount for groups of 10 or more purchased in advance

The Hammond-Harwood House 2019 Secret Garden Tour (SGT), continues an Annapolis tradition and a treasured annual event. It will take guests through one of Annapolis’ most historic areas: Charles, Cathedral, Conduit and Franklin Streets and Acton Landing (the old Anne Arundel Medical Center), all just a minute’s walk from some of the state’s most historic areas; State and Church Circles and City Dock. Guests to the SGT will enjoy going beyond the gates of beautiful and lovingly tended private gardens not normally seen from the sidewalk, each displaying the tastes and lifestyle of the homeowners. Tour goers will enjoy the beauty, quiet and tranquility of the gardens they visit as well as discover ideas suitable for their own plantings and outdoor living areas.

First Sunday Arts Festival
When: Sunday, June 6th (and every first Sunday through November 7th) 11:00 a.m. 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 for more information.

Annual Dinner Under the Stars
When: Wednesdays, June 3rd through September 16th)
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 each Wednesday evening 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 for more information. 

Paint AnnapolisPaint Annapolis
When: June 7tht-14th
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 1st-8th. Visit for more information.

15th Annual Bands in the Sand 
When: June 13th, 2020
Where: Chesapeake Bay Foundation’s Philip Merrill Environmental Center (6 Herndon Avenue, Annapolis, Md) 
Admission: $175 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! 2018’s headliner, Cowboy Mouth, 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 for more information.

Bands in the Sand

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