On land, events abound, including the largest Pride and Juneteenth parades in Maryland. The U.S. Naval Academy will welcome the class of 2027 on Induction Day (I-Day), and athletes and sports enthusiasts from around the world will converge at the Race Across America finish line at Annapolis City Dock. 


Signature Events 


June 2 - June 4 -- Let’s Go Music Festival (Crownsville) The brainchild of avid music fans and concertgoers, this three-day festival brings in top performers and national acts to the Anne Arundel County Fairgrounds every June. This year’s lineup of artists includes 311, Live, Chris Young, and many more. Get your tickets on the festival website; tickets are available for all three days or per concert.  


June 3 -- Annapolis Pride Parade and Festival (Downtown Annapolis) A visual dreamscape of the human spirit at its best. People, children, and pets of every walk of life dress in their rainbow finest and line the sidewalks of West Street to witness a dazzling parade of floats, dancing spirit dragons, musicians, motorcycles, and more. 


June 10 -- Annapolis Arts Day (Annapolis) Celebrate the arts on Saturday, June 10, and experience a full day of festivities inside and outside at Maryland Hall and along Inner West Street. After enjoying the artists, stay on West Street and experience Dinner Under the Stars! This is a free event and suitable for all ages. 


Plein Air Painter David Diaz
Plein Air Art Festival


June 4 – June 11 – Paint Annapolis, Plein Air Art Festival (Annapolis) Paint Annapolis is a week-long, juried, plein-air painting competition held each year that brings artists to Annapolis from around the world. The event, now in its 22nd year, is designed to explore in paint the unique colonial architecture, marine atmosphere, and overall energy of Maryland's capital. The week-long event hosts painting workshops, art shows, and an outdoor painting festival along Maryland Avenue with art, music, and dining! For a full listing of the week’s events, visit the website.  


June 17 -- Annapolis Juneteenth Parade & Festival (Downtown Annapolis) The mission of the Annapolis Juneteenth Celebration is to commemorate the emancipation of the last enslaved Africans in the United States. This year's theme is "Land of the Free, Home of the Brave". The focus is Generation Z and the need to protect the right to vote, the call for social and restorative justice, and the need for a next generation of free voices in America. Admission to the festival is FREE. 


Annapolis Juneteenth Logo


June 18 - June 28 -- Race Across America (Annapolis & Anne Arundel County) RAAM (Race Across America) returns to the shores of the Chesapeake Bay again this year! The 3,000-mile trans-continental event begins in Oceanside, CA and ends at Annapolis City Dock. Participants set out on June 14th and 18th and have 12 days to complete the race. Cyclists come in from around the world to participate in the event, come cheer on the athletes as they cross the finish line! 


June 29 -- USNA Induction Day (Annapolis) Roughly 1,200 young men and women from around the world (and their families) report to the U.S. Naval Academy to take their first steps toward becoming “plebes” (freshmen students).  


June 30 -- Zip Trip, Fox 5 DC (Annapolis City Dock) Fox 5 DC brings their popular Zip Trip morning show to the historic city front of downtown Annapolis! Watch the show live in Annapolis from 6 AM – 11 AM and enjoy features such as Tucker Tries It, Hometown Hero, Food Challenges, and so much more! Join the crew in the parking lot adjacent to The Choptank Annapolis and enjoy the show live! 


Hydrangeas in the gardens of the Chase Home Garden.
Secret Garden Tour


Local Festivals & Events 


June 1 -- An Evening of Elegance, Songs of the Season (Annapolis) Join Historic Annapolis for an evening of elegance at the William Paca Garden with mezzo-soprano Natalie Lewis, accompanied by acclaimed pianist Francesco Barfoed. Enjoy a glass of bubbly in a serene setting and be captured by the velvety voice of Ms. Lewis as she presents a program of arias and art songs reflective of the season, featuring works by Saint Saens, Gershwin, and Samuel Coleridge-Taylor. $25 General Admission; $20 for Students, Historic Annapolis Members & Military. Advance registration is recommended; space is limited. Doors open at 6 pm; rosé bubbly cash bar will be available. 


June 10 – Jun 11 -- Secret Garden Tour (Downtown Annapolis) The 2023 tour features private gardens in the Annapolis Historic District—Prince George Street, King George Street, Maryland Avenue, Hanover Street, and surrounding locations. This area holds a beautiful collection of homes built in various periods and architectural styles, including some of the great colonial mansions.  The gardens featured reflect the goals of the home gardeners: to have a beautiful space filled with flowers, trees, shrubs, grasses, and other garden elements, a space that is a pleasure to live in and an inspiration to work in. Tickets are $30 each, and the tour only runs June 10 – 11, from 12 – 5 pm. 


June 10-11 -- National Outlet Shopping Day (Arundel Mills) Take advantage of this national shopping holiday and explore the largest outlet and value retail shopping destination in Maryland, featuring more than 200 stores showcasing the best names in fashion. And as a special promotion ahead of National Outlet Shopping Day, you could win an Arundel Mills Shopping package and Live! Casino & Hotel Prize package, with a total value of $1,000! Learn more on the website. 


Hancock's Resolution, a stone building with a large lavendar field in front
Hancock's Resolution Lavender Festival


June 10 -- The 33rd Annual Strawberry Festival (BWI Airport Region) The Ann Arrundell County Historical Society event at Benson-Hammond House features all your strawberry favorites – wines, jams, shortcakes, chocolate-covered strawberries – as well as crafts, music, and food trucks. The festival will run from 10 am – 3 pm. (Rain date is Sunday, June 11, 2023). 


June 11 -- Lavender Appreciation Day at Hancock’s Resolution (Pasadena) Tour the lavender field and farm, sample lavender shortbread cookies and tea, take the lavender trivia challenge, enjoy homemade lavender crafts, and take advantage of the beautiful lavender fields for a family photo op! 1 pm – 4 pm 


June 24 -- Eastport a Rockin’ (Annapolis) Created to expose local music to a larger audience, Eastport a Rockin’ has drawn attendees from throughout the neighborhood and across the region since 1997 and is known as the local music festival of the summer. 30+ bands will perform, keeping local, original music a key component of Eastport a Rockin’. 11 am – 8 pm, $100 Advance Purchase VIP Tickets Available. $150 VIP Tickets at the gate (if available) $30 Advanced General Admission Tickets, $40 General Admission tickets on the day of the event. 


Women standing by a National Outlet Shopping Day sign
Click here to enter the National Outlet Shopping Day Prize Giveaway


Father's Day Weekend is June 17 – 18! 


Visit Annapolis & Anne Arundel County has curated a list of weekend activities that make it easy for Dad to celebrate Father’s Day solo, with the family, or with the guys. Find out more at  www.visitannapolis.org


Golf in Anne Arundel County (Countywide) Chill out with Dad over a round of golf this Father’s Day weekend! Choose from a variety of courses or opt for a round of putt-putt or hit the driving range. For the best selection, book early.  


Parasailing, Chesapeake Bay (Chesapeake Bay) Check in and check out with Z Flight Parasail and Watersports. Take in views of historic Annapolis, the U.S. Naval Academy, and the Chesapeake Bay from high in the sky. Reservations are strongly encouraged.  


BWI Trail (BWI Airport Region) If dear old dad is the sporty type, take him and the rest of the crew for an outing on the paved 12-mile bike trail that circles BWI Airport. A parking lot and children’s playground are at the Thomas A. Dixon Observation Area, 1911 Dorsey Road, Glen Burnie. The best part? It’s FREE! 


Forward Brewing in the Eastport neighborhood of Annapolis
Explore the BWII Craft Brewery Trail in Anne Arundel County!


BWI Craft Brewery Trail (Countywide) If you are looking for a reason to roam – with a designated driver, of course – check out four great breweries within a 30-minute drive along the BWI Craft Brewery trail. Book private transportation. 


Jug Bay Wetlands Sanctuary (Southern Anne Arundel County) If celebrating outdoors with a picnic and hike are more your speed, consider Jug Bay. Featuring wetlands and a wildlife sanctuary, the park lies on the outer edge of Anne Arundel County at its border with neighboring Prince George’s County. 


Waterfront Dining and Beach Bars (Countywide) Beach Bars are a staple in Anne Arundel County, and Father’s Day weekend is the perfect time to check them out. Travel by car or boat and nibble your way through North County waterfront eateries enjoying Chesapeake Cuisine, or an Orange Crush, all the while enjoying perfect waterfront views. For a complete list of waterfront dining options, head to our website


Annapolis Blues Soccer Club (Annapolis) Enjoy a National Premier Soccer Club Match at Navy-Marine Corps Memorial Stadium with dear old Dad! Or if he is a true football fan, gift him with season tickets- the 2023 season kicks off on June 3rd! 


A crowd seated down west street enjoying dinner under the stars.
Dinner Under the Stars on West Street!


Recurring Seasonal Events


Dinner Under the Stars (Downtown Annapolis) On Wednesday evenings and Saturdays from May 20 through September 23, the first block of West Street shuts down to automobile traffic and welcomes visitors to dine and shop al fresco under a canopy of white lights reminiscent of the old cities of Europe (weather permitting).  


First Sunday Arts Festival (Downtown Annapolis) Every First Sunday of the month from May through November, the first blocks of West and Calvert Streets are filled with street vendors, performers, musicians, and more! This signature event encourages area residents and visitors to shop locally, discover new restaurants, and support the arts (weather permitting).  


Food Trucks (Countywide) Discover new cuisine and make everyone happy with a visit to Food Truck Tuesdays, Wednesdays, and Fridays throughout Anne Arundel County.  


Farmers Markets (Countywide) Summertime is the perfect time to set your sights on cleaner eating with a trip to our local Farmers Markets. Source organic vegetables and fruit, dairy, meat and poultry, local pies and jams, honey, and so much more! 


Farmers Markets


Thomas Point Shoal Lighthouse Tour (Annapolis): Tours depart the Annapolis Maritime Museum located at 723 Second St Annapolis, MD 21403. The vessel “Sharps Island” will be moored at the closest pier to the Horn Point Marina. All the money collected helps support the preservation of the lighthouse. Each day has two cruise times to choose from, either 9:00 am or 12:00 pm, and registration is on a first-come, first served basis, so get your name in early! (Tours are seasonal and run June-October, weather permitting). 


Tides & Tunes Concert Series (Annapolis) June 15- August 17, The Tides & Tunes Summer Concert Series offers 10 weeks of popular music–from rock to folk to blues–with the incomparable backdrop of the Chesapeake Bay. Concerts are FREE; however, donations are gratefully accepted. Food and spirits are available for purchase. Beverage sales support the Museum’s education program. No outside alcohol is permitted. Bring a chair or blanket. 


The Complete Works of William Shakespeare Abridged (Annapolis) Classic Theatre of Maryland presents all 37 William Shakespeare plays in 97 minutes! Three madcap men in tights weave their wicked way through all of Shakespeare’s comedies, histories, and tragedies in one wild ride that will leave you breathless and helpless with laughter! Tickets range from $55- and doors open at 6:30 pm. Ticket holders should arrive no later than 7:00 pm for the performance. Presented in the courtyard of Reynolds Tavern on Tuesdays, June – August. 


4th of July Boating Event
Fourth of July at Annapolis City Dock


Looking Ahead


July 4 -- City of Annapolis 4th of July Celebration (Downtown Annapolis) Join the city of Annapolis for a patriotic salute to our nation with marching bands, fire engines old and new, cars and vans, service clubs, scouts, and more! ROUTE: The parade kicks off at Amos Garrett and heads down West Street, the wrong way around Church Circle, and down Main Street. Stay for the fireworks over the harbor for a perfect end to your 4th of July weekend! Parade: 6:30 – 8 pm, Fireworks: 9:45 –10:15 pm. 


August 4-- Rotary Club of Annapolis 78th Annual Crab Feast (Annapolis) This crab feast is dubbed the World’s Largest Crab Feast, and for good reason! It’s an all-you-can-eat (and drink) event that invites folks from near and far to get their fill of Maryland’s famous blue crabs – plus Maryland vegetable crab soup, sweet Maryland corn on the cob, beef barbeque sandwiches, all-American hot dogs, watermelon, draft beer, and assorted sodas and water. Held rain or shine, 5 pm – 8 pm. Tickets are on sale now. 


August - October -- Maryland Renaissance Festival (Crownsville) Hear ye! Hear ye! Leave your modern woes behind and step into 16th-century Revel Grove— the 27-acre village overseen by King Henry VIII. Beginning August 26 and lasting through October 22, Lords and Ladies from faraway lands gather to experience one of Maryland's most extravagant events: The Maryland Renaissance Festival! Book early, as this event will sell out. Tickets go on sale on August 1, 2023.


A group of people wearing crab hats sitting around a table picking crabs
Annapolis Rotary Crab Feast


For a more comprehensive listing of events throughout Annapolis & Anne Arundel County, scroll through the Visit Annapolis & Anne Arundel County events page. Events are subject to change. Please get in touch with event organizers to confirm dates and times.