ANNAPOLIS, MARYLAND—Visit 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 June 2016. To assist individuals who are making advance plans for business or vacation travel, VAAAC has put together a June 2016 Major Events Calendar. For a more comprehensive overview of events large and small, visit

Paint Annapolis Wednesday, June 1 to Sunday, June 12 Streets and countryside of Annapolis and Anne Arundel County 410-268-4566

Peek over the shoulders of artists from around the world 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 May 30 to June 5. Thirty juried artists will paint in Annapolis’s Historic District and the surrounding countryside from May 31 to June 3. 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. Paint Annapolis is designed to explore in paint the colonial architecture, marine atmosphere, and overall energy of Maryland’s capital city. Plein air is painting outside – rather than in a studio. The term comes from the French ‘en plein air’, meaning ‘in the open air’. Popularized by Impressionists who were interested in the influence of changing light and the effects of light on color when outdoors, plein air painting now flourishes as its own art form.

Wednesday Night Sailboat Races Wednesdays, June 1 through August 31 First Gun: Approximately 6:10 p.m. Annapolis Harbor 410-263-9279

Grab your favorite dockside seat in America’s Sailing Capital to watch some 150 crews compete in midweek races that involve sailing around several marks in the 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, June 1 through August 24 Monumental Helicopters, Tipton Airport, 7505 General Aviation Drive, Hangar 84, Ft. Meade, MD 20755 Admission: Visit website 410-491-4354

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.

The Wedding Singer Thursdays-Sundays, June 2-18, plus Wednesday June 15, 8:30 p.m. Annapolis Summer Garden Theatre, 143 Compromise Street, Annapolis Admission: $22 410-268-9212

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.

Roar of the Greasepaint, Smell of the Crowd – A Musical Thursday-Sunday, June 2-5 Thursday, 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, $23 410-980-6662

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.

Annapolis Greek Festival Thursday-Sunday, June 2-5 Thursday, 4:00 p.m. to 10:00 p.m.; Friday-Saturday, 11:00 a.m. to 11:00 p.m.; Sunday, 11:00 a.m. to 7:00 p.m. Admission: Free Saints Constantine & Helen Greek Orthodox Church, 2747 Riva Road, Annapolis 410-573-2072 or

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.

Annapolis Towne Centre Free Friday Concerts Every Friday – June 3 to August 26 7:00 p.m. to 8:30 p.m. Annapolis Towne Centre at Parole, 1906 Towne Centre Blvd., Annapolis

Every Friday night, the area's best talent will take the stage on Towne Centre Boulevard to deliver a rockin' performance. Enjoy local music, including classic rock, jazz, 80's, blues, swing and Motown. Event includes a beer garden hosted by Towne Centre restaurants. Bring your own lawn chair or blanket.

Music on the Lawn Saturday, June 4 4:00 p.m. to 6:00 p.m. Captain Avery Museum, 1418 East West Shady Side Road, Shady Side Admission: Free 410-867-4486

Maryland boasts some truly gifted musicians, and Music on the Lawn showcases some exciting native talent. Come and enjoy regional food and drink. Bring your own blankets and lawn chairs.

24th Annual Annapolis Leukemia Cup Saturday, June 4 Eastport Yacht Club, 317 First Street, Eastport 410-267-9549

Join us for an exciting Regatta weekend while we help raise money to benefit the Leukemia and Lymphoma Society and the fight against blood cancers. Our Regatta Weekend includes four on- and off-water events, giving Maryland boaters and residents a wonderful chance to support the 24th Annual Annapolis Leukemia Cup. Weekend events include: the Summer Gala, Off the Water Races, Regatta Cup and our Rock the Dock for a Cure Party.

7th Annual Annapolis Arts, Crafts and Wine Festival Saturday-Sunday, June 4-5 Saturday, 10:00 a.m. to 6:00 p.m.; Sunday, 10:00 a.m. to 5:00 p.m. 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. 410-263-4012

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.

First Sunday Arts Festival Sunday, June 5 (and every first Sunday through November) Noon to 5:00 p.m. First block of West and Calvert Streets, Annapolis Admission: Free 410-263-4012

Enjoy live entertainment and the works of 100 local and regional artists as you stroll along the first block of West Street 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.

Mr. Paca’s Backyard Pre-School Program Tuesday-Wednesday, June 7-8 10:00 a.m. to 11:15 a.m. William Paca House and Garden, 186 Prince George Street, Annapolis Admission: $7 general admission; $5 for HA members and volunteers; free for active military families

From ancient Greece until today, people love sports! This summer the Olympics will be held in Brazil. We will focus on different events and the countries that will be participating. Can you run, jump and throw? In After School Sports Club we learn about sportsmanship and working together as a team. We will play games in the garden and go home with a medal! Let the games begin! Please note: Only purchase a ticket for the children who are attending the program. Chaperones do not need a ticket.

The Complete Works of William Shakespeare – Abridged! Tuesdays, June 7, 14, 21, and 28 (and every Tuesday through September 27) 7:30 p.m. Reynolds Tavern Courtyard, 7 Church Circle, Annapolis Admission: $30 410-415-3513

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. Written by Adam Long, Daniel Singer and Jess Winfield. Directed by ASC Artistic Director Sally Boyett.

Latitude Adjustment Party Thursday, June 9 5:00 p.m. to 10:00 p.m. Eastport Yacht Club, 317 First Street, Eastport Admission: Advance ticket price: $10; $15 at the gate 410-267-9549

Live island-themed music and menu, raffle, photo booth, rum punch and more help kick off the Annapolis to Bermuda Ocean Race. Dance the night away at the premier Eastport block party with music by the Tiki Barbarians. All proceeds of the Latitude Adjustment Party benefit the Eastport Yacht Club Foundation’s Marine Skills Training Scholarship Fund. The Foundation promotes participation in boating, education in the marine industry and environmental awareness through collaborative programming, fundraising and community partnerships.

Annapolis Tango Friday, June 10 and every second Friday through September 7:00 p.m. to 10:00 p.m. Susan Campbell Park, Annapolis City Dock Admission: Free 410-263-7958

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

11th Annual Bands in the Sand Saturday, June 11 5:00 p.m. to 10:30 p.m. Chesapeake Bay Foundation’s Philip Merrill Environmental Center, 6 Herndon Avenue, Annapolis Admission: $100 per person or limited VIP tickets 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.

25th Annual Strawberry Festival Saturday, June 11 10:00 a.m. to 4:00 p.m. Historic Benson-Hammond House, 7101 Aviation Blvd., Linthicum 410-626-1437

Celebrate all things strawberry at this festival honoring Anne Arundel County’s agricultural heritage. Event features craft vendors, demonstrations of traditional crafts and skills, entertainment for the entire family, and delicious strawberry treats. The U.S. Navy Band Country Current will return for an encore performance.

Kids’ Fishing Day Saturday, June 11 8:30 a.m. to 12:00 p.m. Patuxent National Wildlife Visitor Center, 10901 Scarlet Tanager Loop, Laurel Admission: FREE; Pre-registration required. Check website for details. 301-497-5887

Kids ages 15 and under are invited to learn to fish with live demonstrations and instructions. Catch and release fishing only.

Sundae Sunday Sunday, June 12 1:00 p.m. to 4:00 p.m. Captain Avery Museum, 1418 East West Shady Side Road, Shady Side Admission: Free; small sundaes $2.50 410-867-4486

This summer tradition on the lawn attracts kids of all ages: teenagers playing music and singing on the front porch, families playing croquet and other games on the lawn, artists with easels in the raingarden, couples dangling their toes in the water off the pier, and even folks napping in the shade.

Maryland Avenue/State Circle Summer Festival Sunday, June 12 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.

11th Annual Eastport Home and Garden Tour Sunday, June 12 1:00 p.m. to 5:00 p.m., rain or shine Admission: $20 until June 5; $25 thereafter 410-271-3420

For the past 11 years, neighbors and out-of-towners mark their calendars for this annual event that provides for an entertaining walk through well-appointed, sometimes historic, and always lovely homes and gardens of Eastport. This year's tour will focus on the small gems tucked between Second and Third Streets on the Eastport peninsula. Eastport boasts a variety of home styles, including watermen’s cottages built in the 1930s when streets were paved with oyster shells. On the outer peninsula, you’ll also find traditional farmhouses next to renovated craftsman-style homes.

The highlight of the Home and Garden Tour is the beautiful Eastport gardens in full bloom. Be sure to catch the calming spaces, lattice trellises and unique yard art.

Corvettes on the Bay Show Sunday, June 12 1:00 p.m. to 5:00 p.m., rain or shine Admission: $20 until June 5; $25 thereafter 410-271-3420

Corvette Annapolis was founded in 1991, and is dedicated to the promotion of the Chevrolet Corvette, and camaraderie among Corvette owners in the greater Annapolis and Central Maryland area. Come join us for a celebration of America's Sports Car as we celebrate our 24th Anniversary. This Corvette-only Fun Show will occupy center stage at the historic Annapolis City Dock area. In 2011 this event was the first formal car show to be held in downtown Annapolis, and has repeated through 2014. These shows have been a great success and promises again this year to be an exciting event for participants and spectators.

Paca Girlfriends’ Flower Power Party Wednesday, June 15 6:00 p.m. to 9:00 p.m.; VIP admission at 5:00 p.m. William Paca House and Garden, 186 Prince George Street Admission: Cost TBD 410-626-1033

Join the Paca Girlfriends for the 8th Annual Paca Girlfriends’ Party, a night of food, fine

wine, friendship, flowers and fun you won't want to miss! Experience the charm of the William Paca House and indulge in culinary creations donated by the area's premier chefs while you stroll through the reconstructed 18th-century garden, filled with beautiful rose bushes, holly, summer blooms, an endearing fish-shaped pond and other garden features – all while you enjoy sipping a signature Pacatini. Proceeds benefit Historic Annapolis’s educational programs and activities.

Tides & Tunes Summer Concert Series Thursdays, June 16 through August 25 7:00 p.m. to 8:30 p.m. Annapolis Maritime Museum, 723 Second Street, Eastport, Annapolis Admission: Free, $10 donation suggested 410-295-1040, ext. 4

Ten weeks of folk, classic rock, soul, psychedelic funk, country, Hawaiian swing, Island music, boogie-woogie, and swing – all on the beach!

Midsummer Madness Wednesday, June 22 to Friday, July 8 11:00 a.m. to 5:00 p.m. daily Maryland Federation of Art’s Circle Gallery, 18 State Circle, Annapolis Admission: Free 410-268-4566

Reception: July 8.

2nd Annual Annapolis Italian Festival (Festa di Santa Madre Cabrini) Saturday and Sunday, June 25-26, rain or shine Saturday, 11:00 a.m. to 9:00 p.m.; Sunday, 9:00 a.m. mass until 3:00 p.m. Knights of Columbus Hall, 2590 Solomons Island Road, Edgewater Admission: $1 dollar charitable donation

Celebrate all things Italian at this two-day event of music, food and fun honoring Saint Mother Cabrini. Proceeds benefit local charities and Annapolis Sons of Italy Lodge 2225’s scholarship fund.

Rent Thursdays - Sundays, June 30 through July 20, plus Wednesday July 20, 8:30 p.m. Annapolis Summer Garden Theatre, 143 Compromise Street, Annapolis Admission: $22 410-268-9212

Exuberant, passionate, and joyous, Rent is a pop culture phenomenon that won the Tony Award for Best Musical and the Pulitzer Prize for Drama. On the 20th anniversary of its Broadway premiere, we’re excited to present this groundbreaking musical about falling in love, finding your voice, and living for today.

Thursday Night with the Stars Thursday, June 30 6:30 p.m. to 8:00 p.m. Susan Campbell Park, City Dock, Annapolis

Thursday Night with the Stars kicks off its dockside outdoor music line with a finalist in the Baltimore Blues Festival, Kings of Crownsville. Come and enjoy the summer breeze off the water while listening to this six-piece New Orleans music team. Bring your comfy chairs! Sponsored by the Annapolis City Art in Public Places Commission.


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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Contact Susan Seifried at via or phone at 410-280-0445, ext. 303