A list of our favorite events around Annapolis, Eastern Shore and beyond for the month of August. Event dates may be subject to change. Also, be sure to check out our 2025 Philanthropic Event Calendar here.
Photo by Annapolis Rotary Club
80th Annual Rotary Club of Annapolis Crab Feast
Get crackin’! The Rotary Club of Annapolis celebrates 80 years of crab-picking, corn-shucking, and community pride at this beloved all-you-can-eat feast. Dig into crabs, BBQ, sides, and sweets—all while supporting local nonprofits. Join the fun Thursday, August 1st from 5 to 8 p.m. at Navy-Marine Corps Memorial Stadium in Annapolis. Come hungry and leave happy! More info: annapolisrotary.org | 410-921-1542
Photo by Arden Haley
Maryland Renaissance Festival
Step back in time at the Maryland Renaissance Festival, happening weekends August 24 through October 20 in Crownsville. This vibrant event features thrilling jousting matches, lively dances like the Tourdion, and captivating village stories of royal drama and local life. Explore over 140 artisan shops, enjoy delicious food from 40-plus vendors, and experience nonstop entertainment across ten stages and taverns. Special reduced admission runs the first three weekends (August 24–September 8), with peak pricing starting September 14. More info: marylandrenaissancefestival.com
Photo by George Sass
Watermen’s Appreciation Day
Get ready for a true taste of Chesapeake Bay culture at Watermen’s Appreciation Day, happening Sunday, August 10th from 10 a.m. to 4 p.m. at the Chesapeake Bay Maritime Museum in St. Michaels. This annual celebration, hosted in partnership with the Talbot Watermen Association, shines a spotlight on the men and women who work the waters and preserve Maryland’s maritime heritage. Enjoy a lively boat docking contest that’ll keep you on the edge of your seat, feast on freshly steamed crabs straight from the Bay, and soak up live music and good vibes all day long. Families will love the hands-on kids’ activities, food vendors, and beautiful waterfront setting. It’s a one-of-a-kind event that brings together history, tradition, and summer fun—all in one unforgettable day. More info: cbmm.org | 410-745-2916
50th Annual Annapolis 10 Mile Run
50th Annual Annapolis 10 Mile Run
Celebrate the 50th anniversary of the Annapolis Ten Mile Run on Sunday, August 24, starting at 7 a.m. at Navy–Marine Corps Memorial Stadium in Annapolis. This nationally ranked race features a scenic 10-mile course through historic Annapolis and over the Severn River. Don’t miss the Race Expo the day before on August 23 from 10 a.m. to 3 p.m., plus post-race entertainment and awards. Registration is limited—sign up early to join this milestone event! More info and registration: AnnapolisStriders.org | a10@annapolisstriders.org
“What would Jimmy Buffett do?” Tour 2025
Celebrate the spirit of Jimmy Buffett at the 2nd Annual Chris Sacks Band “What Would Jimmy Buffett Do?” concert on Friday, August 23, at Cult Classic Brewing in Stevensville. The Chris Sacks Band will be joined by Coral Reefer Band members performing all your favorite Buffett hits. Opening act Emily Guemple kicks off the evening. VIP and general admission tickets available—VIP includes meet and greet, exclusive seating, and more. Gates open at 4 p.m. for VIP and 6 p.m. for general admission. This is a ticketed, rain-or-shine event with offsite parking and shuttle service. More info and tickets: chrissacksband.com
Glen Burnie Pearls of Service 4th Annual Pier Perfection Day Party
Seersucker, Sundresses & Sneakers Day Party. Slip into your summer chic and head to the waterfront for a day party with purpose! The Glen Burnie Pearls of Service Foundation and AKA’s Omicron Gamma Omega Chapter host their 4th annual celebration at Kurtz Beach on Sunday, August 3rd from 3 to 7 p.m. Enjoy great food, a cash bar, music, outdoor games, local vendors, and a silent auction—all while supporting scholarships and community programs. More info: theglenburniepearlsofservice.org | 410-672-6227
Maryland State Fair
Join the fun this August at the Maryland State Fair, held at the Maryland State Fairgrounds in Timonium! The fair runs across three weekends: August 21–24, August 28–September 1, and September 4–7. Gates open daily at 10 a.m., with rides, food, live entertainment, and exhibits to enjoy all day long. Experience thrilling carnival rides, delicious fair food, livestock shows, live horse racing, concerts, rodeo events, and family-friendly activities. Whether you’re a local or visiting, the Maryland State Fair is the perfect way to celebrate the end of summer with fun for all ages! More info: marylandstatefair.com | 410-252-0200
National Night Out Community Event
Celebrate community and connection at the Annapolis Regional Library’s National Night Out! On August 5th from 5:30 to 7:30 p.m., enjoy games, giveaways, and free food—all while mingling with neighbors and local first responders. It’s a family-friendly evening full of fun, friendship, and maybe even a visit from Sneaks the Cat! More info: aacpl.net | 410-222-1750
A Taste of Arundel Grown
Arundel Ag’s signature event will be held August 6 at Homestead Gardens in Davidsonville and celebrates local agriculture by showcasing food, beer, and wine primarily grown, raised, or produced in Anne Arundel County. The event supports local farmers and watermen by raising the visibility of what they produce, and by raising funds for the Agricultural Business Improvement Grant (ABIG) Fund and, in 2025, the Center for Applied Technology (CAT) North Future Farmers of America (FFA). More information | aaedc.org/agriculture/farmers-markets/a-taste-of-arundel-grown
Photo by Bernadette Bohman
Pirates & Wenches Weekend
Hoist the sails and break out your best boots—Pirates & Wenches Weekend returns to Rock Hall from August 8–10! This town-wide celebration transforms the waterfront into a swashbuckling paradise with live music, costume contests, kids’ activities, dockside parties, and plenty of pirate flair. Come by land or anchor offshore—just don’t forget your eye patch. Family-friendly and full of fun, it’s an adventure for all ages! More info: rockhallpirates.com | 410-639-7719
TVFC Old Tyme Fair
The TVFC Old Tyme Fair is back for 2025—now with new dates! Join the Trappe Volunteer Fire Company for three days of hometown fun, happening Thursday, July 31 through Saturday, August 2 at the Fire House grounds. Enjoy delicious food with nightly specials, hayrides, raffles, fire truck rides, games, a silent auction, and fun for the whole family. Don’t miss the beloved Saturday night parade, a local favorite! Mark your calendars—this small-town tradition is one you won’t want to miss! More info: facebook.com/TVFC30
Groove City Culture Festival
Celebrate culture, community, and Caribbean vibes at one of Cambridge’s biggest annual traditions! The Groove City Culture Fest returns on Saturday, August 16, bringing music, food, art, and family-friendly fun to the heart of downtown Cambridge. This vibrant and inclusive event welcomes all to enjoy a day of unity and celebration. This year’s highlight. A dazzling Caribbean Carnival! Come dressed in your feathered best and join the parade, or cheer from the sidelines as the streets come alive with color, music, and joy. Interested in joining the parade? Call 443-225-0819 More info: facebook.com/groovecityculturefest
Photo by Chesapeake Bay Maritime Museum
Charity Boat Auction
Set sail for a great cause at the Chesapeake Bay Maritime Museum’s annual Charity Boat Auction on Saturday, August 30, from 8 a.m. to 1 p.m. Join us at the beautiful waterfront campus to bid on a variety of donated boats—big and small—all to support CBMM’s mission of preserving Chesapeake Bay’s history, environment, and culture. This beloved Labor Day weekend tradition has raised vital funds for over 20 years, making a real difference in the community. Please note, for safety reasons, non-service dogs are not permitted. More info: cbmm.org | 410-745-2916
Picture by Hooked OC
White Marlin Open
Get hooked on the action at the White Marlin Open, the world’s largest billfish tournament, returning to Ocean City, Maryland, on August 4–8! This legendary event draws anglers and spectators from around the globe for a week of high-stakes sport fishing, million-dollar prizes, and serious summertime excitement. Whether you’re casting off or just watching the weigh-ins at Harbour Island from 4–9:15 p.m. daily, there’s something for everyone. Enjoy the spectacle, shop tournament merch, and be part of one of OC’s biggest summer traditions! More info: whitemarlinopen.com | 410-289-9229
Queen Anneʼs County Joust
The Queen Anne’s County Joust returns on Saturday, August 23, at 1 p.m. at the Tuckahoe Equestrian Center in Queen Anne. Come enjoy an exciting afternoon celebrating Maryland’s official state sport with thrilling rides, friendly competition, and a nod to tradition. Riders of all ages and skill levels will take to the track for this unique and family-friendly event. Open to all riders with a signed waiver (helmets required for participants under 18). More info: tuckahoeequestriancenter.com | 410) 822-8047
