Event Picks for August 2026

Culture

A curated list of notable August events around Annapolis, the Eastern Shore, and nearby areas, featuring community festivals, concerts, sports, theater, fundraisers, family-friendly activities, and more. Event dates may be subject to change.

Navy Football Fan Fest

Get ready for football season at Navy Football Fan Fest on Saturday, August 8, from 2 to 4 p.m. at Navy-Marine Corps Memorial Stadium in Annapolis. Fans of all ages can meet the Midshipmen, collect player autographs, step onto the stadium field for games and activities, and take home giveaways from Navy Athletics partners. This free event offers a fun opportunity to celebrate Navy Football and build excitement for the upcoming season. More info: navysports.com/football

Maryland State Fair

Join the fun this August and September at the Maryland State Fair, held at the Maryland State Fairgrounds in Timonium! The fair returns across three exciting weekends: August 27–30, September 3–7, and September 10–13. Gates open daily with thrilling carnival rides, classic fair food, live entertainment, agricultural exhibits, livestock competitions, horse racing, concerts, and family-friendly attractions. Whether you’re continuing a longtime tradition or visiting for the first time, the Maryland State Fair is the perfect way to celebrate the season with fun for all ages. More info: marylandstatefair.com

‘Paws, Poses and Peace’ yoga and therapy dogs

Find a moment of calm during Paws, Poses and Peace on Thursday, August 20, from 6:30 to 8 p.m. at the Center for Hope & Healing in Pasadena. This unique community workshop combines gentle, trauma-informed yoga, guided meditation, and breathing exercises with the comforting presence of certified therapy dogs, creating a restorative experience for participants of all ages and abilities. Whether you’re seeking stress relief, emotional healing, or simply an evening of relaxation with four-legged companions, this welcoming program offers a peaceful way to recharge. More info: hospicechesapeake.org

Blue Crab Classic 2026

Compete in one of the region’s premier pickleball events at the 4th Annual Blue Crab Classic, taking place August 21–23 at PickleRage in Glen Burnie. Players of all skill levels can take to the courts throughout the weekend, with men’s and women’s singles on Friday, men’s and women’s doubles on Saturday, and mixed doubles wrapping up the tournament on Sunday. Whether you’re playing for the title or cheering from the sidelines, this three-day event promises exciting competition, great sportsmanship, and plenty of pickleball action. More info: annearundelchamber.org

National Night Out - AA Co

Build stronger community connections during National Night Out on Tuesday, August 4, from 6 to 8 p.m. at Kinder Farm Park in Millersville. This free, family-friendly event brings together residents and members of the Anne Arundel County Eastern District Police Department for an evening of fun, conversation, and community engagement. Enjoy games, prizes, Touch-a-Truck experiences, light refreshments, and interactive activities designed to strengthen relationships between neighbors and local law enforcement in a welcoming atmosphere for all ages. More info: nationalnightouteasterndistrict.org

Puppy Plunge 2026

Treat your four-legged best friend to a day at the beach during Puppy Plunge 2026 on Sunday, August 23, beginning at noon at Camp Letts in Edgewater. Hosted by the SPCA of Anne Arundel County, this beloved summer tradition features beach access for dogs, live music, food and drinks, local vendors, contests, and plenty of opportunities for furry friends to splash, play, and socialize. Best of all, proceeds from the event help provide care, shelter, and second chances for homeless animals throughout the community, making it a fun-filled day that supports a great cause. More info: aacspca.org

A Taste of Arundel Grown

Celebrate the flavors of Anne Arundel County at A Taste of Arundel Grown on Wednesday, August 5, from 5:30 to 8 p.m. at Homestead Gardens in Davidsonville. This farm-to-table event showcases the region’s agricultural community with locally inspired cuisine prepared by Wharf 38 Executive Chef Brandon Moser, complemented by local wine, craft beer, and live music. Guests can also browse a bouquet bar featuring fresh flowers from Zangs Farm, bid on unique items in the inaugural Arundel Grown Silent Auction, and enjoy an evening dedicated to supporting the county’s farmers, watermen, and producers. More info: annearundelchamber.org

Maryland Renaissance Festival

Step back in time at the Maryland Renaissance Festival, held weekends from August 29 through October 25 in Crownsville. Running Saturdays and Sundays, plus Labor Day on September 7, from 10 a.m. to 7 p.m., this beloved annual tradition transports visitors to a lively 16th-century English village filled with jousting tournaments, royal entertainment, artisan demonstrations, and costumed performers. Browse more than 140 unique shops, savor hearty fare from dozens of food vendors, and enjoy nonstop entertainment across multiple stages, making it one of Maryland’s most treasured fall events for all ages. More info: rennfest.com

BRASS vs SASS COMEDY SHOW

Get ready for a night of laughs at the Brass vs. Sass Comedy Show on Sunday, August 30, at 6 p.m. at Ashling Kitchen & Bar in Crofton. This battle-of-the-sexes comedy showdown features comedians Dewayne White and Renée Percy delivering sharp stand-up, hilarious audience games, and plenty of playful banter as they take on relationships and everyday life from their own perspectives. Whether you’re coming with friends, your partner, or flying solo, it’s the perfect way to cap off the weekend with great food, drinks, and nonstop comedy. More info: ashlingkitchen.com

81st Annual Rotary Crab Feast

Roll up your sleeves for one of Annapolis’s most beloved summer traditions at the 81st Annual Rotary Crab Feast on Friday, August 7, from 5 to 8 p.m. at Navy-Marine Corps Memorial Stadium. Hosted by the Rotary Club of Annapolis, this iconic fundraiser features an all-you-can-eat feast of Maryland crabs, along with a variety of other food options, beverages, and homemade treats from the popular bake sale. Proceeds from the event support numerous local nonprofit organizations, making this a delicious way to give back to the community while enjoying a true Chesapeake experience. More info: annapolisrotary.org

5th Annual Pier Perfection

Dress in your favorite seersucker, sundress, or sneakers and head to Kurtz’s Beach in Pasadena on Sunday, August 2, from 3 to 7 p.m. for the 5th Annual Pier Perfection. Hosted by the Glen Burnie Pearls of Service Foundation in partnership with Alpha Kappa Alpha Sorority, Incorporated®, Omicron Gamma Omega Chapter, this waterfront fundraiser features music, catered food, a cash bar, local vendors, outdoor games, and a silent auction—all benefiting college scholarships and community service initiatives. It’s an afternoon of summer fun with a purpose, set against the scenic Chesapeake Bay. More info: theglenburniepearlsofservice.org 

ThriveFest2026

Start the school year with confidence at THRIVEfest 2026 on Monday, August 10, from 4 to 6 p.m. at Thrive Behavioral Health in Millersville. This free family event offers dinner, backpacks and school supplies for registered students, hands-on activities, crafts, cotton candy, and helpful community resources for local families. Designed to make back-to-school preparation a little easier and a lot more fun, the evening brings together support, connection, and family-friendly activities in one welcoming space. More info: thrivebh.com

51st Annual Annapolis Ten Mile Run

Challenge yourself on one of the nation’s premier road races at the 51st Annual Annapolis Ten Mile Run on Sunday, August 30, beginning at 7 a.m. from Navy-Marine Corps Memorial Stadium in Annapolis. Hosted by the Annapolis Striders, this nationally recognized race takes runners on a scenic course through the city’s historic streets, across the Naval Academy Bridge, and into picturesque waterfront neighborhoods. Whether you’re chasing a personal best or soaking in the race-day atmosphere, participants can look forward to a memorable finish complete with live music, refreshments, and a commemorative finisher’s quarter-zip. More info: annapolisstriders.org

Watermen's Appreciation Day

Celebrate the rich heritage of the Chesapeake Bay during Watermen’s Appreciation Day on Sunday, August 9, from 10 a.m. to 4 p.m. at the Chesapeake Bay Maritime Museum in St. Michaels. This annual festival honors the region’s hardworking watermen with exciting workboat docking competitions, freshly steamed local crabs, live music, artisan vendors, family-friendly activities, and demonstrations celebrating the traditions of life on the Bay. Visitors can also explore the museum’s exhibits and historic campus while enjoying one of the Eastern Shore’s signature summer events. More info: cbmm.org

3rd Annual “What would Jimmy Buffett Do?”

Break out the tropical shirts and island spirit for the 3rd Annual What Would Jimmy Buffett Do? tribute concert on Saturday, August 22, from 4 to 9 p.m. at Cult Classic Brewing Company in Stevensville. The Chris Sacks Band joins members of Jimmy Buffett’s legendary Coral Reefer Band for an evening celebrating the music and laid-back lifestyle of the beloved singer-songwriter. Along with live performances, guests can enjoy food and drinks, local vendors, raffles, and plenty of Parrothead fun in a festive, beach-inspired atmosphere. More info: cultclassicbrewing.com

Pirates and Wenches Weekend 2026

Set sail for a swashbuckling adventure during Pirates & Wenches Weekend, taking over Rock Hall from Friday, August 7, through Sunday, August 9. This town-wide, family-friendly festival transforms the waterfront into a lively pirate haven with sea shanties, rum tastings, live entertainment, a bustling Main Street marketplace, children’s activities, harbor festivities, beach events, and the popular Buccaneers Ball. Whether you arrive by land or by sea, this beloved annual celebration offers three days of pirate-themed fun for all ages. More info: rockhallpirates.com

Queen Anne County Joust 2026

Celebrate one of Maryland’s oldest traditions at the Queen Anne County Joust on Saturday, August 22, at 1 p.m. at the Tuckahoe Equestrian Center in Queen Anne. Watch riders of all ages and skill levels compete in Maryland’s official state sport as they race down the track in a test of precision, horsemanship, and tradition. This family-friendly event offers a unique opportunity to experience a cherished piece of the state’s equestrian heritage, with a rain date scheduled for August 24. More info: marylandjousting.com

White Marlin Open 2026

Experience one of Ocean City’s most iconic traditions during the 53rd Annual White Marlin Open, taking place August 3–8, 2026. Known as the world’s largest and richest billfish tournament, this internationally recognized event draws hundreds of boats and thousands of anglers to compete for millions of dollars in prize money. New for 2026, participants will fish three out of six days, providing greater flexibility while spectators can enjoy the excitement of daily weigh-ins, waterfront festivities, and the electric atmosphere that has made the tournament a summer favorite for more than five decades. More info: whitemarlinopen.com

Delmarva Shorebirds August Home Games

Catch America’s pastime on the Eastern Shore as the Delmarva Shorebirds welcome fans to Arthur W. Perdue Stadium in Salisbury for four exciting homestands throughout August. The month begins with a weekend series against the Hickory Crawdads on August 1–2, followed by a six-game matchup with the Salem Red Sox from August 11–16. The Shorebirds close out the month with a six-game series against the Fredericksburg Nationals from August 25–30. From postgame fireworks and giveaway nights to family-friendly promotions and classic ballpark traditions, there are plenty of opportunities to enjoy a summer evening at the stadium while cheering on Delmarva’s hometown team. More info: theshorebirds.com