Get outside and enjoy Anne Arundel County’s best summer events, including Wednesday night sailboat racing and live music at City Dock; and if you’re looking to dine outside (and maybe play some Pickleball), Dinner Under the Stars will be calling your name. Nobody celebrates the Fourth of July like Downtown Annapolis, and the Maryland Renaissance Festival returns in August! July also marks the 60th anniversary of the Civil Rights Act, and Anne Arundel County has a digital guide to plan your Civil Rights journey through the region.  


July – SeptemberCity Dock Concert Series (Downtown Annapolis) Enjoy the sights of the Chesapeake Bay and the sounds of local bands at Susan Campbell Park on the shores of the Annapolis Harbor in Downtown Annapolis. Pack up your chairs and blankets and enjoy an evening of FREE fun, plus, depending on the night, free salsa or tango lessons.  

July 2 – 60th Anniversary of the Civil Rights Act (Anne Arundel County) July 2, 2024, marks the 60th anniversary of the Civil Rights Act of 1964, a historic law that made discrimination based on race, color, religion, sex, and national origin illegal. To celebrate this historic milestone, Visit Annapolis & Anne Arundel County has put together a list of 60 sites pivotal to the movement in our region. Download our 24-page, full-color printed guide, including maps, historical information, photographs, and more, to discover the region's Civil Rights movement and inspirational stories of resilience and resistance. 

July 2 & August 13Tunesday Floating Concert Series (Annapolis) Paddle up with a kayak or paddleboard rental from Capital SUP and listen to a live concert perched on a catamaran courtesy of Chronic Sailing while floating and enjoying the tidal creeks of Annapolis! On July 2, it's Jordan Sokel from Pressing Strings, and on August 13, enjoy music from DJ Jay Crawdads! Before the concert, enjoy beer from Pherm Brewing & Chessie's Wharf and sandwiches by Capriotti's at their Eastport Nautilus Point location. 

July 10 - August 28 - Wednesday Night Races (Annapolis) Join us for match racing fun every Wednesday from April through August as the Woodwind and Woodwind II compete during the Annapolis Yacht Club (AYC) Races. Both boats will start on the AYC starting line at 6:45 pm and sail on a pre-set racecourse. If racing isn't your thing, Annapolis Sailing Cruises also offers beer-tasting cruises on Tuesdays, history sunset sails, and Sunday fun day sails, making it the perfect addition to your summer adventure bucket list! Book on their website.


Colorful sailboats on the bay
Wednesday Night Races and an Annapolitan tradition!


July 10 - September 8Wednesday Night Races – Watch Party (Downtown Annapolis) You don’t have to be a sailor to get in on the Wednesday Night Sailboat Races fun! Join the Annapolis Maritime Museum & Park’s skipjack crew for two hours for a front-row view of sailors battling it out on the water. Your cruise includes complimentary beverages and the best views of Annapolis. 

July 3 – September 28Dinner Under the Stars (Downtown Annapolis) On Wednesday and Saturday evenings through September 28, the first block of West Street shuts down to automobile traffic and welcomes visitors to dine, shop al fresco, and even play pickleball under a canopy of white lights reminiscent of the old cities of Europe (weather permitting).  Wine and dine with friends and bring your pups; friendly, leashed pups are welcome! 

July 4Annapolis 4th of July Parade and Fireworks (Downtown Annapolis) Come join Annapolis’ patriotic salute with a parade and booming fireworks. The parade kicks off at Amos Garrett and West Street, wraps its way (the wrong way) around Church Circle, and ends on Main Street. Anywhere on the parade route is the place to be! The festivities end with fireworks launching from a barge in Annapolis Harbor. More information about viewing spots and parking can be found by clicking HERE.  

July 4 Annapolis Fireworks Cruise (Annapolis) How about viewing the Fourth of July fireworks from the water? Step aboard a Watermark boat for the best seat in town as you cruise around the historic harbor. Enjoy a full bar, the best views, and America’s independence in one spot! 


4th of July Boating Event
Visitors gather after the July 4th  parade for fireworks in downtown  Annapolis.


July 6Annapolis Blues Home Game (Annapolis) It’s the summer of soccer in Naptown! The Annapolis Blues is one of the newest National Premier Soccer League Expansion Club Teams, and they are having a fantastic 2nd year! With their last regular season home game at Navy-Marine Corps Memorial Stadium on July 6, it’s the perfect family fun night. (Tickets start at $10) 

July 9Blues & Gold at the Annapolis City Dock (Downtown Annapolis) Overlooking Annapolis’ beautiful waterfront, join the Blues & Gold as they perform classic blues and blues-inspired music by artists including B.B. King and Eric Clapton. All Naval Academy Band concerts are free and open to everyone. 

July 13 & 14Revolutionary London Town (Edgewater) Experience the days of 1776 and explore what “independence” really means. Meet individuals from London Town’s past and listen to a reading of the Declaration of Independence, try your hand at colonial crafts, and play tavern games in the newly restored William Brown House. Food trucks will be available from Kona Ice of Annapolis (Saturday & Sunday) and Salt and Pepper BBQ (Saturday). 

July 20 & August 17African American Heritage Tour (Downtown Annapolis) Trace the journey of African Americans and explore their impact on Annapolis on this 2-hour walking tour. Your period-attired guide will highlight the importance of historic spots around Annapolis, including where slave ships entered 300 years ago, the Alex Haley statue, and uphill to the State House and statue of Thurgood Marshall.   

July 13- August 29Tides & Tunes Concert Series (Annapolis) The Tides & Tunes Summer Concert Series at Annapolis Maritime Museum & Park offers 10 weeks of popular music–from rock to folk to blues–with the incomparable backdrop of the Chesapeake Bay. Concerts are on Thursdays, and 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.  


Stateside Cup FC Futbol logo


July 31The Stateside Cup (Navy-Marines Corps Memorial Stadium) International soccer is coming to Annapolis this summer! The Stateside Cup, a three-team, three-city tour, will visit the Navy-Marine Corps Memorial Stadium on Wednesday, July 31 at 8:00 p.m. Premier League clubs Crystal Palace and Wolves will square off in an epic battle in the heart of Annapolis, don't miss it! This is a first for Anne Arundel County, and we know it will be an amazing crowd for all sports fans. Tickets are on sale now! 


August 2Rotary Club of Annapolis 79th 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 8-11 Plebe Parents Weekend (Naval Academy) Plebe parents have been waiting six long weeks for this one. After a month and a half of their students learning the foundation of the Academy’s four-year professional development curriculum, their parents will make their way back to Annapolis for four days with a packed itinerary on The Yard. Congratulations to the Class of 2028!

August 13Carriages on West Street – Annapolis Corvette Show (Downtown Annapolis) Celebrating the history of West Street in Annapolis, along with modern-day high-performance “carriages” of today, this Corvette show is like none other. Starting back in 1991, this show is an Annapolis tradition. 


A group of people wearing crab hats sitting around a table picking crabs
The World's Largest Crab Feast!


August 17C.R.A.B. (Chesapeake Regional Accessible Boating) Cup & Shore Party (Eastport) Kicking off at noon, more than 90 sailboats participate in a family-friendly, competitive pursuit race to determine who will be the champion of the day. If you are not a sailor but you enjoy a day of fun competition, you can still join in the fun watching from shore! Then the shore party starts at 4 PM at Eastport Yacht Club! Proceeds benefit C.R.A.B., a non-profit dedicated to accessible sailing, boating, and water-based activities on the Chesapeake Bay. Their adaptive sailing center sits on the water in the Annapolis-Eastport neck. 

Saturdays & Sundays from August 26 – October 22The Maryland Renaissance Festival (Crownsville) Hear ye! Hear ye! Step into the 16th-century Revel Grove and leave your modern woes behind. RennFest has something for everyone. From turkey legs to toasting with mead to jousting and cheering on your own Kingdom, it’s no wonder this immersive experience is one of Maryland’s most extravagant events. Tickets go on sale July 5 for multi-day tickets and single-day/weekend tickets on August 1. Mark your calendars; this event sells out every year.  

August 31Navy Football Kickoff (Annapolis) It’s a showdown between Navy and the Bucknell Bison at Navy-Marine Corps Memorial Stadium. The Midshipmen’s 2023 football season kicks off with a 12:00 PM game, giving you plenty of time to set up your tailgate and celebrate a new season! 


people on a grassy hill in front of an outdoor ampitheatre for a concert
Close out summer with a free orchestra performance from the Annapolis Symphony at Pop over to Pops in the Park.

August 31 & September 1Pops in the Park (Pasadena & Annapolis) Join the Annapolis Symphony Orchestra at Downs Park in Pasadena and Quiet Waters Park in Annapolis on Labor Day weekend for two FREE performances! Grab your picnic blanket and listen to performances of uplifting and danceable pop tunes and patriotic songs, plus a movie and Broadway music to close out summer! 

BONUS! August 11-17Maryland’s Tax-Free Week (Countywide) Cash in on some savings as you do some shopping around the County. While, yes, this does include back-to-school items like backpacks, it also includes clothing, shoes, and accessories priced at $100 or less at any store. Shop small at local boutiques in the heart of historic Annapolis, or head to Arundel Mills, Maryland’s largest discount retail attraction! Grab those souvenir shirts to show off where you visited this summer! 


September 12-15 -- Annapolis Songwriters Festival (Downtown Annapolis) The 3rd annual festival takes place throughout Downtown Annapolis, with artists performing at the City Dock stage located in Downtown Annapolis at Susan Campbell Park. Free events will occur in bars and restaurants throughout Downtown Annapolis along the 'Songwriters Trail' from Westgate Circle to City Dock. Other ticketed venues include Rams Head On Stage, MC3 Annapolis, and Maryland Hall. 

September 14-15 Maryland Seafood Festival (Downtown Annapolis) A 56-year tradition, the Maryland Seafood Festival has been showcasing great seafood, live music, arts and crafts, chef demos, and the crab soup cook-off to thousands of festival attendees. This year, it’s bigger and better than ever with a return to Sandy Point State Park! Dig in on crabs, oysters, and all the seafood you could want, plus great live music, contests, and cook-offs. 


A group of vendors sell seafood and people wait in line to place their order.
The Maryland Seafood Festival returns to Sandy Point State Park.


September 21-22 -- Annapolis Baygrass Festival (Sandy Point State Park) The Annapolis Baygrass Festival is a conservation and community-focused musical event that blends the finest progressive bluegrass, jamgrass, and Americana music with a gorgeous beachfront venue and a mission to protect the Chesapeake Bay and raise mental health awareness. You will enjoy 14 of the best local and nationally touring bands on two alternating stages and an interactive workshop pavilion. Perfect for the whole family! 

October 3-6 Annapolis Powerboat Show (Downtown Annapolis) The City Docks of Annapolis will be buzzing with excitement as boat lovers from around the globe return to celebrate the 50th anniversary of the US Powerboat Show. Spend days exploring powerboats of all varieties and shopping for boat supplies, navigation equipment, and other marine accessories. 

October 10-14 Annapolis Sailboat Show (Downtown Annapolis) Or if sailing is your style, the US Sailboat Show is just three days after the Powerboat Show. From seasoned sailors to first-time boat buyers, this five-day event highlights new and premier boats. Check out educational opportunities for all skill levels, like the highly sought-after Cruisers University. Make plans today to maximize your time at the Boat Shows.  

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 contact event organizers to confirm dates and times.