Sitting along the shores of Maryland’s Chesapeake Bay, Annapolis & Anne Arundel County is your perfect destination for filling the last few weeks of summer with waterfront concerts, crab feasts, 16th-century festivals, and… Did we mention crab feasts? Visit Annapolis & Anne Arundel County (VAAAC) invites visitors to access its more than 500 miles of scenic shoreline to craft their unique Chesapeake Bay Adventure. Plus, get back-to-school shopping done while you are here with Maryland’s tax-free week!
Let the Visit Annapolis & Anne Arundel County team uncover your next story! We are dedicated to connecting journalists and travel writers from around the world to the best stories about the Chesapeake Bay region. We can provide itineraries, trip-planning tips, and even more, provided your publication is perfect for our waterfront destination. View and filter more Things to Do at www.VisitAnnapolis.org/Events
NOTE: The event below, Arts Alive 25, was held on September 8, 2023.
August 1 – 6 – National Oyster Week 2023 (Anne Arundel County) Oysters clean Chesapeake Bay waters and provide habitat for other (delicious!) species like blue crabs, rockfish, and white perch. Did you know that eating oysters and recycling their shells leads to more oysters being returned to the Bay? Enjoy local oysters and give back to the Chesapeake Bay! Click the link to find out which area restaurants are participating in this delicious tradition!
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 more.
August 19 & 20 – Maryland Seafood Festival (Downtown Annapolis) The Maryland Seafood Festival has showcased great seafood, live music, arts and crafts, chef demos, and the crab soup cook-off to thousands of festival attendees for 55 years! This year, it’s all happening at Susan Campbell Park at City Dock in the heart of historic Annapolis. This is one festival you do not want to miss.
August 19 – CRAB 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 day’s champion. If you are not a sailor but enjoy a day of fun competition, join the fun by watching from shore! The shore party starts at 4 pm at Eastport Yacht Club.
August 26 – October 22 (Saturdays & Sundays) The 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 and popular events.
Local Festivals & Events
August 3 & 10 – Anchors Aweigh Music Tour (Naval Academy) The Anchors Aweigh Music Tour allows you to learn about the U.S. Naval Academy’s rich musical history from Retired Master Chief Dave Hanner. The tour unveils the history behind USNA’s beloved “Anchors Aweigh” song and the fascinating and often unknown history of Charles Zimmerman.
August 11 – Spirits & Spirits: Cruise & Walking Tour (Downtown Annapolis) During this walking tour and cruise combination experience, you’ll brave the Historic District on foot and hear spooky stories from your Ghost Guide. Continue along the haunted waterways of Annapolis and be entertained with nautical myths and pirate tales. Add extra “spirit” to your night with beverages available for purchase during the cruise portion of the tour.
August 13 – Carriages on West Street – Annapolis Corvette Show (Downtown Annapolis) Celebrate the history of West Street in Annapolis, along with modern-day high-performance “carriages” of today; this Corvette show is like none other. This Annapolis tradition has been wowing car enthusiasts since 1991.
August 13 – Wine in the Wind: Coastal Varieties (Annapolis) Head out onto the Chesapeake Bay aboard the stunning Schooner Woodwind and discover new lesser-known grape varietals from the coast and islands in the Mediterranean. Representatives will be on board to discuss the food and wine pairings while you enjoy the wind in your hair and an afternoon on the water!
August 16 – 14th Annual Juried Exhibit: Wild About Wildlife (Annapolis) The Annapolis Arts Alliance presents its 14th Annual Juried Exhibit, “Wild About Wildlife,” featuring artwork from over 40 local artists representing a variety of mediums. Explore all the wildlife art exhibits at Quiet Waters Park until October 1.
August 17-20 – 2023 U.S. Women’s Match Race Championship (Annapolis) Believe it or not, this women’s regatta is for anyone and everyone. Whether you’re ranked first in the world or are getting on a boat for the first time, this is your chance to get out on the water and compete. It’s all happening at Annapolis Yacht Club and includes a clinic and two race days out on the Bay.
August 20 – STEAM Sunday: Birds of Flight (Brooklyn Park) Learn about birds of flight from live animal ambassadors. This workshop will teach everyone about flying wildlife, from tiny hummingbirds to massive albatrosses. The workshop is free for all ages with registration, and kids can take home a fun animal craft.
August 20 – Puppy Plunge (Edgewater) The SPCA of Anne Arundel County is wrapping up the dog days of summer with a puppy plunge fit for pups of all sizes! This family-friendly event will have food for humans and dogs, live music, open dog beaches, and a puppy pie-eating contest.
August 25 – Summer Drive in Movies Under the Stars (Bay Ridge Shopping Center) Close out the summer with a free outdoor showing of “Jaws” at the Bay Ridge Shopping Center in Annapolis! Live music will kick off the evening, so grab some local takeout and plan for a picnic evening!
August 27 – Annapolis Ten-Mile Run (Annapolis) This race through historic Annapolis and over the Severn River has been listed as one of the top ten 10-mile races in the country by Runner’s World Magazine. The Annapolis Striders, a non-profit group that promotes physical fitness and mental well-being through distance running, sponsors this exciting road race. Registration is open now while it lasts!
Before Back to School
August 10 – 13 – 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 as a Midshipman, parents will return to Annapolis for four days with a packed itinerary on The Yard. Congratulations to the Class of 2027!
August 12 – USNA Student Youth Leadership Program (Naval Academy) Developing leaders for tomorrow begins today! Open to students ages 13-15, ‘campers’ will spend a half-day in the Student Youth Leadership Program learning and developing applicable leadership skills from some of the brightest of today’s leaders at the USNA.
August 13 – 19 – Maryland Tax-Free Week (Statewide) Cash in on significant savings as you shop around the county for back-to-school basics. Eligible items include backpacks, clothing, shoes, and accessories priced at $100 or less at any store. From downtown Annapolis boutiques to the largest retail destination in Maryland at Arundel Mills, you will find steals and deals during this once-a-year shopping extravaganza.
Recurring Seasonal Events
Dinner Under the Stars (Downtown Annapolis) On Wednesday and Saturday evenings through September 23, 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).
First Sunday Arts Festival (Downtown Annapolis) Every First Sunday of the month through November, the first blocks of West and Calvert Streets are filled with street vendors, performers, musicians, and more! This festival encourages residents and visitors to shop locally, discover new restaurants, and support the arts (weather permitting).
Farmers Markets (Countywide) Summertime is the perfect time to set your sights on cleaner eating with a trip to a local Farmers Market. Source organic vegetables and fruit, dairy, meat and poultry, local pies and jams, honey, and more!
Thomas Point Shoal Lighthouse Tour (Annapolis) Tours depart the Annapolis Maritime Museum 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, 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 (Eastport) August 17, 24, & 31. 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 FREE; however, donations are welcome. 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.
Looking Ahead – SAVE THE DATE
September 2 & 3 – Pops 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 renditions of uplifting, danceable pop tunes, patriotic songs, and Broadway music to close out summer!
September 9 – Navy Football Kickoff (Annapolis) It’s a showdown between Navy and Wagner College at Navy-Marine Corps Memorial Stadium. The Midshipmen’s 2023 football season kicks off with a 3:30 pm game, giving you plenty of time to set up your tailgate and celebrate a new season!
September 14 – 17 – Annapolis Songwriters Festival (Annapolis) Get ready for Blondie, LeAnn Rimes, and many other incredible songwriters at one of the premier music festivals on the shores of the Chesapeake Bay in Maryland’s Music Capital – Annapolis. Modeled after the hugely successful Key West Songwriters Festival, the Annapolis Songwriters Festival brings the love for live music to the Bay. Like Key West, Annapolis has its own world-renowned watering holes and intimate theater settings, making Maryland’s state capital the perfect location for concert enthusiasts to get acquainted with the faces, voices, and stories behind the songs.
October 5-8 – Annapolis Powerboat Show (Downtown Annapolis) The City Docks of Annapolis will buzz with excitement as boat lovers from around the globe return to celebrate the 50th anniversary of the U.S. Powerboat Show. Spend days exploring powerboats of all varieties and shopping for boat supplies, navigation equipment, and other marine accessories.
October 12-15 – Annapolis Sailboat Show (Downtown Annapolis) The U.S. Sailboat Show is just three days after the U.S. Powerboat Show—this annual celebration of sailing features floating docks lined with sailboats from manufacturers around the world. Peruse multihulls, monohulls, cruisers, racers, sailing dinghies, and more. Show tents line the shore, stocked with the latest in nautical gear and accessories, electronics, communication equipment, sails, rigging, education, charter companies, clubs, and more!