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Mark your calendar: May events from Visit Annapolis

Annapolis Capital Dome

Annapolis Capital DomeVisit Annapolis & Anne Arundel County (VAAAC) wants to make it easy for individuals to enjoy the many exciting events and activities that will be taking place in Annapolis and Anne Arundel County, Maryland in May 2016. To assist individuals who are making advance plans for business or vacation travel, VAAAC has put together a May 2016 Major Events Calendar. For a more comprehensive overview of events large and small, visit

60th Annual May Day Basket Competition
Sunday, May 1

Downtown Annapolis

Considered to be one of the most beautiful days in historic downtown Annapolis, May Day greets visitors and area residents with door after door of baskets filled with beautiful spring flowers. Come with camera in hand to capture the handiwork of downtown Annapolis residents and merchants who welcome spring by decorating their doorways with baskets of blooming flowers. Some 20 volunteers from the Garden Club of Old Annapolis Towne judge the entries and invite winners to join them at an annual Garden Club Tea.

Maryland Avenue/State Circle Spring Festival “May Day, May Day”
Sunday, May 1

10:00 a.m. to 5:00 p.m.

Maryland Avenue and State Circle, Annapolis

Admission: Free   

Enjoy an old-fashioned street festival with merchants and vendors offering art, antiques, jewelry, fashion, home décor, crafts, food and activities for the entire family. Galway Bay and Harry Browne’s offer bistro dining, and Galway Bay provides outdoor live music from noon until 5:00 p.m. Take advantage of free parking at the state garage located at Calvert and St. John’s Streets.

First Sunday Arts Festival
Sunday, May 1 (and every first Sunday through November)

Noon to 5:00 p.m.

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 and Calvert Streets 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.

The Big Read
Sunday, May 1 to Saturday, May 21

Chesapeake Children’s Museum, 25 Silopanna Road, Annapolis and other Anne Arundel County locations

Various times

Admission: Free and fee events 


A program of the National Endowment for the Arts, The Big Read broadens our understanding of our world, our communities, and ourselves through the joy of sharing a good book. The Big Read supports organizations across the country in developing community-wide reading programs which encourage reading and participation by diverse audiences.

Classics in the Courtyard
Sunday, May 1, and every Sunday through October


Reynolds Tavern, 7 Church Circle, Annapolis

Admission: Free

Enjoy free classic outdoor movie screenings in Reynolds Tavern’s courtyard. All films begin at dusk. Full menu is available during the screening. Event is dog and family friendly.

Wednesday, May 4

2:30 p.m. gaming; 6:00 p.m. costume contest; 7:00 p.m. performance with the Baltimore Gamer Symphony Orchestra

Chesapeake Arts Center, Hammonds Lane Theatre, 194 Hammonds Lane, Brooklyn Park

Admission: Free to the first 10 guests who provide a gaming console; $5 gaming access and concert

[email protected]

A long time ago, in a galaxy far, far away… turmoil engulfed the Galactic Republic and a legend was born. Every generation has a legend… every journey has a first step… every saga has a beginning. Join us for a special MAY THE 4TH BE WITH YOU event with video gaming, Star Wars Costume Contest and a special performance by the Baltimore Gamer Symphony Orchestra.

Wednesday Night Sailboat Races
Wednesday evenings, May 4 through August 31

First Gun: Approximately 6:10 p.m.

Annapolis Harbor  


Grab your favorite dockside seat in America’s Sailing Capital to watch some 130 crews compete in midweek races that involve sailing around several marks in the Chesapeake Bay before heading back to Spa Creek for a finish in front of the Annapolis Yacht Club. For many, the post-race party is the official beginning of the weekend.

Aerial Tours of Wednesday Night Sailboat Races
Wednesdays, May 4 through August 24

Monumental Helicopters, Tipton Airport, 7505 General Aviation Drive, Hangar 84, Ft. Meade, MD 20755

Admission: Visit website

Take in the bustle of City Dock and Ego Alley and get a grand view of historic Annapolis and the Wednesday Night Sailboat Races. Catch a “quick look” at Annapolis attractions and the beauty of Chesapeake Bay sailing, while you admire boats, marinas and stunning waterfront estates.

16th Annual Tee Up for a Child Golf Tournament
Thursday, May 5

Registration: 8:00 a.m.; Shotgun Start: 9:00 a.m.

Eisenhower Golf Course, 1576 Generals Highway, Crownsville

Admission: $175 per golfer; $700 for foursome
410-267-7877 ext. 6

Interested individuals are invited to participate in a golfing event to raise money for Anne Arundel County Court Appointed Special Advocates (CASA) for children.  

Spring Member Show
Thursday, May 5 to Friday, May 27

11:00 a.m. to 5:00 p.m. daily

Maryland Federation of Art’s Circle Gallery, 18 State Circle, Annapolis

Admission: Free   


The annual Spring Member Show is an all-media, juried exhibit featuring the work of Maryland Federation of Art members. Reception: May 15.

6th Annual Naptown barBAYq
Friday-Saturday, May 6-7

Friday, 4:00 p.m. to 10:00 p.m.; Saturday, noon to 10:00 p.m.  

Anne Arundel County Fairgrounds, 1450 Generals Highway, Crownsville, MD

Admission: $15; kids 12 and under, free  

Enjoy the live music of more than 40 bands performing on three stages, abundant food, cooking demonstrations, a barbeque competition, arts and crafts vendors and more during the family event sponsored by Parole (Annapolis) Rotary Foundation. The barbeque cooking contest is sanctioned by the Kansas City Barbeque Society and is expected to attract more than 60 competitor teams.

Orchestral Brilliance
Friday-Saturday, May 6-7

8:00 p.m.

Maryland Hall for the Creative Arts, 801 Chase Street, Annapolis

Tickets: $38 to $58; students, $13 


Britten’s “Young Person’s Guide to the Orchestra” is a vivid example of the virtuosic capabilities of an orchestra, even using a simple theme by British Baroque composer Henry Purcell. But Smetana, Fung and Franck are highly original composers in the way they treat the orchestra as an instrument. Smetana accomplishes a vibrant depiction of a major Central European river with “The Moldau”; Fung presents an interesting essay in orchestral colors and textures with her “Dust Devils”; and Franck’s “Symphony in D Minor” shows he was a pioneer developing a concept of cyclic music.

Romeo and Juliet
Friday, May 6 to Sunday, May 29

Friday-Saturday, 8:00 p.m.; Sunday, 3:00 p.m.; Friday, May 27, 2:00 p.m. and 8:00 p.m.

Annapolis Shakespeare Company, 111 Chinquapin Round Road, Suite 114 Annapolis Admission: $25-$55    


The Annapolis Shakespeare Company gives a command performance of Shakespeare’s classic play about two star-struck lovers determined to be together in life and death.

Roar of the Greasepaint, Smell of the Crowd – A Musical
Friday, May 6 to Sunday, June 5

Thursdays, 7:00 p.m.; Friday-Saturday, 8:00 p.m.; Saturday-Sunday 2:00 p.m.

Compass Rose Theater, 49 Spa Road, Annapolis

Admission: Adults, $38; Seniors (65 and older) and Military, $33; Students (with ID) and Children, $23  


An upper class gent and a lower class commoner compete for the top of the heap in this play about a contest of wills. Add a band of rowdy urchins and this un-story dances into our hearts. Running on Broadway in the late 1960s, the musical is more of an allegory than a story. Featuring hit songs, including “Who Can I Turn to” and “Feeling Good”, the show is a circus romp of good and bad, up and down. 

Maritime Republic of Eastport’s 16th Annual .05K Bridge Run
Saturday, May 7

Crack o’ noon

Spa Creek Bridge, Eastport

Admission: $20 for runners; free for spectators

Described as “the least challenging athletic event ever conceived” by Runner’s World magazine, the .05K (yes, point-zero-5K) extreme sports event is a grueling test of mental and physical toughness. Some competitors have taken as long as five minutes to complete the course that begins on the Annapolis side of the Spa Creek Bridge. Registration begins at 11:00 a.m. in the parking lot of Fleet Feet at 318 6th Street in Eastport. The awards ceremony and trophy presentation take place around 12:10 p.m. Proceeds benefit local charitable organizations.

Chelsey Green
Saturday, May 7

6:00 p.m. VIP reception; 8:00 p.m. performance

Chesapeake Arts Center, Hammonds Lane Theatre, 194 Hammonds Lane, Brooklyn Park

Tickets: visit

Described as “passionate, electrifying, and innovative,” Billboard charting recording artist Chelsey Green tears down all stereotypes of the violin by fusing traditional classical technique with popular songs and enticing original pieces in various genres. Her ensemble, The Green Project, recently released their highly anticipated second CD and first full length album, The Green Room, which debuted on the Billboard Contemporary Jazz Chart at #22 and iTunes Jazz Chart at #7 within the first week of its release.

William Paca Garden Plant Sale
Saturday-Sunday, May 7-8

Saturday, 10:00 a.m. to 4:00 p.m.; Sunday, noon to 4:00 p.m. Historic Annapolis members will be admitted at 9:30 a.m. on Saturday.

William Paca Garden, 1 Martin Street, Annapolis

Admission: Free

Take a piece of the William Paca Garden home with you! Choose from among more than 300 varieties of perennials, annuals, vegetables, herbs, trees and shrubs – including heirloom and “cutting-edge”, native and exotic – that have been raised by Paca Garden volunteers. Gardeners on hand to answer questions. Information-packed catalog available online or for purchase. Free admission includes free tours of the Paca Garden. Proceeds support the William Paca Garden and its programs.

Annapolis Tango
Friday, May 13 and every second Friday through September

7:00 p.m. to 10:00 p.m.

Susan Campbell Park at Annapolis City Dock

Admission: Free


Watch and join in the dance while the moon rises over the Annapolis Harbor.

First Annual Bay Bridge Paddle
Saturday, May 14

8:30 a.m.

Sandy Point State Park, 1100 East College Parkway, Annapolis

Admission: Elite race, $75; Intermediate, $55; Beginners, $35

Watersports enthusiasts of all ages and expertise are invited to join in the inaugural Bay Bridge Paddle, open to stand-up paddleboards, kayaks and other paddle craft. Each race will present a different experience and challenge. The Elite 8.4-mile crossing is designed for racers with a high level of fitness and paddling experience. It will take paddlers underneath the Bay Bridge. Less experienced racers can enjoy the 5K paddle or the 1.5K novice slalom course closer to the beach. After participants have conquered their courses and refueled with lunch, they’ll celebrate with live music and an awards ceremony that includes more than $7,000 in cash and prizes. The event will benefit local charities, including the Foundation for Community Betterment and Maryland Special Olympics.

Anne Arundel County Public Library’s Comic Con
Saturday, May 14

10:00 a.m. to 3:00 p.m.

Odenton Library, 1270 Odenton Road, Odenton, MD 21113

Admission: Free

Phone: 410-222-6277

Join in the first ever Comic-Con at the library! Spend the afternoon exploring comic books and literacy through panel discussions, interactive workshops, crafts for kids and a costume contest.

ASO Family Concerts
Saturday, May 14

2:00 p.m. and 3:30 p.m.

Maryland Hall for the Creative Arts, 801 Chase Street, Annapolis

Admission: $12.00

Squeaks, tweets, rattles and honks!! Michael Boudewyns and Sara Valentine of Really Inventive Stuff bring you The Professor, a whimsical Austrian sound scientist who travels the world with his amazing acoustical laboratory, but needs the audience’s help to complete the melody of Mozart’s “The Toy Symphony”. Come prepared to play along – as the audience is the missing instrument.

The Complete Works of William Shakespeare – Abridged!
Tuesdays, May 17, 24 and 31 (and every Tuesday through September 27)

7:30 p.m.

Reynolds Tavern Courtyard, 7 Church Circle, Annapolis

Admission: $30; $55 on opening night which includes a cocktail reception with cast and artistic team  


It’s Shakespeare like you’ve never experienced it! Come prepared for a lighthearted evening when three talented members of the Annapolis Shakespeare Company team perform lighthearted parodies of the bard’s most well-known plays. They wrap up the bard’s outsized oeuvre in 90 roller-coaster, rib-tickling minutes. Written by Adam Long, Daniel Singer and Jess Winfield. Directed by ASC Artistic Director Sally Boyett.

Rock-Able Concert
Friday, May 20

10:00 a.m.

Chesapeake Arts Center, Studio 194,194 Hammonds Lane, Brooklyn Park

Admission: $10

Jesse Magee of Eldersburg, MD is the leader of the Rock-Able program, singer/songwriter of his own rock band, Leftstronger, and a professional drum instructor. He accomplishes all this and more despite being legally blind and having cerebral palsy on his right side. His talent speaks for itself and nothing will stand in the way of his success and being a role model for others. Jesse will inspire parents of children with disabilities. He’ll also inspire children with disabilities to strive to accomplish anything they want to do in life. Jesse has over 100 original catchy songs and a 4+ octave vocal range. He shares his personal disabilities’ story, shows the audience how he plays guitar upside down (and backwards), plays keyboards with one hand, performs an amazing drum solo and fronts his amazing rock band with four of his original songs.

USNA Commissioning Week
Tentatively scheduled for May 20-27

U.S. Naval Academy, Annapolis

Each year, approximately 1,000 midshipmen graduate from the U.S. Naval Academy and receive their commissions as officers in the U.S. Navy or Marine Corps. On Monday, cheer on members of the class of 2018 as they attempt to climb the Herndon Monument. Traditionally, the Blue Angels’ flight rehearsal is on Tuesday and the Blue Angels’ flight demonstration is on Wednesday. On Thursday, catch the Color Parade at Worden field. For more information, visit the U.S.N.A. website.

Aerial Tours of U.S. Naval Academy
Friday-Friday, May 20-27

Monumental Helicopters, Tipton Airport, 7505 General Aviation Drive, Hangar 84, Ft. Meade, MD 20755

Admission: Visit website

You’re sure to see a special sight during Monumental Helicopters’ Commissioning Week U.S. Naval Academy tours – from a parade of plebes to midshipmen racing sailboats in the Bay. If you’re in town for a U.S. Naval Academy event, you haven’t seen it all until you’ve seen it from our point of view! We welcome U.S. Naval Academy families from all over the country for these special tours.  

Chesapeake Bay Blues Festival
Saturday-Sunday, May 21-22

Gates open at 10:30 a.m.; Music from 11:00 a.m. to 9:00 p.m. Saturday; Music from 11:00 a.m. to 8:00 p.m. Sunday

Admission: Advanced Pricing: Saturday only, $65; Sunday only, $75; Regular pricing, TBA; Children under 12, free, with paying adult.

Sandy Point State Park, 1100 East College Parkway, Annapolis

Enjoy John Mayall, Sonny Landreth, Mud Morganfield, Danielle Nicole, Canned Heat, Tab Benoit, Heritage Blues Orchestra, Dan Fuchs, Ronnie Baker Brooks, Michael McHenry Tribe and more in concert. Event includes a large crafter village and a wide variety of food and drink. Bring your own chair for the lawn seating.

Combined Choirs Commissioning Week Concert
Tuesday, May 24

8:30 p.m.

Admission: $16 and $19  

U.S.N.A. Chapel, Annapolis

The Naval Academy Men’s Glee Club, Women’s Glee Club, and Gospel Choir join forces to present a special performance in honor of the Class of 2016! Join us for this memorable 90-minute concert featuring patriotic favorites, sea chanties, Broadway, and sacred songs in the beautiful setting of the Naval Academy Chapel.

Blue Angels’ Flight Demonstration Cruises
Practice Day, Tuesday, May 24; Air Show Day, Wednesday, May 25

1:00 p.m. to 3:00 p.m.

Admission: Adults, $53; Children under 12, $27    


Watch the Navy’s Blue Angels practice and perform aerial demonstrations over the Severn River from a comfortable seat aboard a Watermark yacht.

Commissioning Week Organ Concert
Wednesday, May 25

4:00 p.m.

Admission: $16

U.S.N.A. Chapel, Annapolis 


Immediately following the Blue Angels, join us in the beautiful Naval Academy Chapel as world-class organist, Mr. Monte Maxwell, demonstrates the incredible power and sound of one of the finest organs in the world. Ample air-conditioning included!

Hugo Kauder Trio from Slovakia
Thursday, May 26

7:00 p.m.

Maryland Hall for the Creative Arts, 801 Chase Street, Annapolis

Admission: Free

Playing the piano, oboe and viola, the instrumentalist trio will perform with an Austrian vocalist. Presented by World Artists Experiences Ambassador Series.

The Wedding Singer
Thursdays – Sundays, May 26 through June 18, plus Wednesday June 15

8:30 p.m.

Annapolis Summer Garden Theatre, 143 Compromise Street, Annapolis

Admission: $22

Join Annapolis Summer Garden Theatre for the first production of its 50th Anniversary season of “Music Under the Stars”. Based on the hit New Line Cinema film starring Adam Sandler, The Wedding Singer’s hilarious book and sparkling new score do for the ’80s what Hairspray did for the ’60s. Just say yes to the most romantic musical in 20 years.

Annapolis Memorial Day Parade
Monday, May 30

10:00 a.m.

Parade kicks off at Amos Garrett Boulevard and West Street, Annapolis

The parade will follow the traditional route with staging at Amos Garrett Blvd. It will process down West Street to Church Circle and down Main Street to City Dock. It will be followed by an annual Memorial Day Ceremony at Susan Campbell Park. It’s an excellent opportunity to pay our respects to the men and women who made the ultimate sacrifice for our country.

Paint Annapolis
Monday, May 30 to Sunday, June 5

Streets and countryside of Annapolis and Anne Arundel County  


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 May 31 to June 3. On May 31, all interested artists are invited to participate in painting along Main and West Street after sunset in a Nocturne painting event. An optional Paint Out for artists will take place on June 4th at a location to be determined. Back by popular demand, the Dueling Brushes painting event will take place in Annapolis’s Historic District on Sunday, June 5, from 8:00 a.m. until 11:00 a.m. All interested artists are invited to participate. Jurying and awards for the Dueling Brushes creations takes place at noon. The Maryland Federation of Art will exhibit the work of Paint Annapolis’s professional artists at its Circle Gallery from Saturday, June 4, (opening reception) through Sunday, June 12.

VAAAC is a nonprofit, membership-based destination marketing organization that generates revenues for the local economy by promoting Annapolis and the Chesapeake Bay to leisure and business travelers across the country and around the world.

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