50th Annual Annapolis 10 Mile Run
Annapolis (and beyond) is cranking the fun meter all the way up this week — we’re talking dog-friendly pumpkin spice lattes, pickleball showdowns, toe-tapping concerts, and summer festivals bursting with flavor. Add in paddle cruises, comic book adventures, epic fair food, and a puppy plunge that’ll have tails wagging, and you’ve got a lineup too good to miss. Grab your crew, clear your calendar, and dive in — your week just went from zero to unforgettable.
The Honest Kitchen’s Dog-Friendly Pumpkin Spice Latte Sampling
August 20th, 21st, Poindexter coffee, Annapolis 6:00am – 1:00pm
To celebrate the launch of its new seasonal variety – a Pumpkin Spice Latte made just for dogs – The Honest Kitchen, pioneer in human grade pet food, is partnering with Graduate by Hilton Poindexter Coffee locations for a weeklong sampling initiative. From August 19-26, pet parents are invited to stop by the Poindexter Coffee in Annapolis for an exclusive opportunity to try the new Pumpkin Spice Latte for dogs.
Chamber Music for Trumpet and Percussion
August 20th; The Mainstay, Rock Hall 7:00pm – 8:00pm
Percussionist Dane Krich and Trumpeter Luis Engelke bring an exciting and innovative program to The Mainstay titled “Brass and Percussion: The Classical Side.” The program includes works by J. S. Bach, Baroque-era composer Jean Joseph Mouret, and contemporary composers Mitchel Peters and Jason Dovel. Dimas Sedícias’s Engelkeana Agrestina, composed for Engelke, will have its world premiere at this concert.
Maryland State Fair
August 21st, 22nd,23rd, 24th; Maryland State Fairgrounds, Timonium
Three weekends of classic fair fun! Enjoy thrilling rides, live music, horse racing, and agricultural exhibits that showcase Maryland’s farming roots. Snack your way through endless fair food favorites, cheer at the rodeo, and wander through barns filled with prize-winning animals. From kids’ activities to concerts under the stars, it’s a summer tradition for all ages.
Blue Crab Classic Pickleball Tournament
August 22nd, 23rd, 24th; Pickle Rage, Glen Burnie
The 3rd Annual Blue Crab Classic Pickleball Tournament is back in 2025, hosted by the Anne Arundel Chamber of Commerce and Peake Social, at Pickle Rage indoor courts in Glen Burnie. This popular tournament kicks off Friday, August 22 with Men’s & Women’s singles. Men’s/Women’s doubles will play on Saturday, August 23 and mixed doubles will play on Sunday, August 24. Open to all ages rated 3.0+. Medals will be awarded following each bracket. Don't miss this fun event!
A Tribute to Death Cab for Cutie
August 22nd; Cult Classic Brewing Company, Stevensville 7:00pm – 10:30pm
It's been 20 years since PLANS was released. Join us for a reimagining of the album from local artists including Heartside, Seth Mitchell Band, Burnsie, and Darlington. Reserved Seats are $20 per person. General admission (Standing) is $10 per person in advance $15 at the door. Get here early, Cult Classic has 15+ beers on tap brewed in house, a full kitchen with from-scratch pizza, hand-pattied burgers and fresh-never-frozen jumbo wings, and a FULL BAR to get you through this most epic of evenings.
Trivia Night Fundraiser at Baldwin Hall
August 22nd; Historic Balwin Hall, Annapolis 7:00pm – 8:00pm
Get ready for a fun night of trivia, fellowship, and friendly competition at Historic Baldwin Hall. Come with a team of any size or attend solo and join a team when you arrive. It’s a great chance to meet new people and enjoy a lively evening together. Hope to see you at Baldwin Hall!
Annapolis Chamber Music Festival: Steampunk: Clearfield, Bruce and Bach
August 22nd; St. Martins Evangelical Lutheran Church, Annapolis 7:30pm – 9:30pm
Themes of renewal and reimagining abound in the concert that marries music from four centuries apart. J.S. Bach’s second orchestral suite teems with the composer’s signature ability to craft endlessly satisfying cycles of tension and release, all while featuring the virtuosity of the flute. British composer David Bruce’s “Steampunk,” inspired by the retro-futuristic aesthetic of the same name, adds the complex and arcane construction of wind instruments to the traditional sound and look of the strings. His piece is underpinned by mechanically-tinged basslines and motives that harken to ticking clocks and turning gears. Andrea Clearfield’s “Spirit Island” for flute, bass, and piano was inspired by more natural phenomena: a canoe trip through Maligne Lake in Jasper National Park in the Canadian Rockies. Shifting timbres and colors echo the changes in nature, from slow, glacial erosion to fast-changing light and weather.
Talbot County Library's 100th Birthday
August 23rd; Talbot County Free Library, Easton
Join us in celebrating the library’s 100th Birthday with a party that's fun for the whole family! Experience the magic of Little John's Gigantic Bubble Show and explore different size and types of bubbles with Little John in this fun, interactive program. See volcano bubbles, smoke bubbles, and get surrounded by a giant bubble! Enjoy cake and special treats, crafts and activities, readings of story-time favorites, and more. This is a free event, with no registration required.
Saturday Morning Creek Cruise
August 23rd; Annapolis Maritime Museum Park Campus, Annapolis 9:00am – 11:00am
Ease into the weekend with a beginner-friendly eco paddle through scenic Back Creek. Spot wildlife, learn about local ecology, and enjoy a relaxing start to your Saturday. Book now!
Third Eye Kids Comic Day!
August 23rd; Third Eye Comics, Annapolis 11:00am – 9:00pm
Get ready for some fun with the whole fam during our THIRD EYE KIDS COMIC DAY! We’re celebrating all day at all stores – so grab your capes and suit up! We’ll have FREE THIRD EYE x KIDS COMIC DAY STICKERS available for all the little ones to snag! Plus get a FREE Third Eye Kids Collecting Starter Pack with any purchase of $100 or more!
Queen Annes County Joust
August 23rd; Tuckahoe Equestrian Center, Queen Anne’s County 1:00pm
Experience Maryland’s official state sport at its finest during the Jousting Tournament, happening this summer! Riders of all levels—from novice to professional—will gallop down an 80-yard track, aiming their lances at increasingly smaller rings in a thrilling display of precision, horsemanship, and tradition. With classes for all skill levels and a crowning ceremony for the victors, this is a spectacle you won’t want to miss.
“What would Jimmy Buffett do?” Tour 2025
August 23rd; Cult Classic Brewing Company, Stevensville 6:00pm – 10:00pm
We are proud to present the 2nd annual Chris Sacks Band “What would Jimmy Buffett do?” concert 2025 tour on August 23, 2025 tribute to Jimmy Buffett at Cult Classic Brewing, Stevensville MD. The Chris Sacks Band will be performing with Coral Reefer Band members Doyle Grisham, Nadirah Shakoor, Roger Bartlett and Tina Gullickson playing all of your favorite Jimmy Buffett songs. Opening act Emily Guemple.
Annapolis Chamber Music Festival: ACMF Turns 10!
August 23rd; St. Martins Evangelical Lutheran Church, Annapolis 7:30pm – 9:30pm
Our tenth season concludes with the premier of a newly-commissioned work by ACMF 2025 Composer-in-Residence, Jorge Amado. Composed to capture the spirit of community between all of us at ACMF, Amado’s work features the entire ACMF ensemble in a celebration of ten years of incredible music-making in Annapolis. The program kicks off with Jeff Scott’s “Startin’ Somethin’,” a jazz-infused wind quintet that gives a nod to the start of ACMF in 2016. We close with Brahms’ masterful Piano Quartet in G minor, a chamber music staple with a grandiose finale that’s sure to put an exclamation mark at the end of this summer’s season. See you there!
50th Annual Annapolis 10 Mile Run
August 24th, Navy Marine Corps Memorial Stadium Banquet Facility
The Annapolis Ten Mile Run is a 10-mile foot race organized by the Annapolis Striders, Inc., a 1000 member, all volunteer, non-profit 501 (c)(3) organization. Established in 1978 in Annapolis, Maryland, the club promotes physical fitness and mental well-being through distance running. The race is conducted according to the road racing guidelines of the Road Runners Club of America.
Anchors & Artisans Market
August 24th; Annapolis Town Center, Annapolis 11:00pm – 4:00pm
Anchors & Artisans Join Makers of Maryland in supporting small business and enjoying family friendly activities from 11am-4pm at Annapolis Town Center on the fourth Sunday each month through October. 40+ local makers & artists, Live music from local bands, Face painting & family friendly activities, Food & drinks from local businesses & So much more! We have makers selling everything from pottery, fresh pancakes, and artwork to permanent jewelry, dog collars and kids accessories. Browse handmade products and original art from 40-50 local vendors.
Fig & Flower: Flower Workshop - Summer Center Piece
August 24th; Fig & Flower, Annapolis 11:00am – 12:30pm
Step into our garden for a fun, hands-on workshop where you'll learn the art of floral arranging featuring all of summer’s finest blooms. Perfect for flower levels at all levels, this class will walk you through all the elements of flower arranging—choosing stems, balancing color and shape, and building a bouquet with intention. Weather permitting our classes will take place outside in our garden.
Puppy Plunge
August 24th; Camp Letts, Annapolis 1:00am – 2:00pm
Puppy Plunge 2025 is Here! Get ready for the splashiest dog day of the summer! Join us on Sunday, August 24, 2025, from 11 AM–2 PM at Camp Letts in Edgewater, MD for a paws-itively unforgettable event. What to Expect: Tiki Bar refreshments from Moveable Mixtures, Delicious eats from Crabtown Curbs Cuisine, Harborque, Timber Pizza, Bragg Cafe, Kona Ice, and Puppylicious Gourmet treats for your furry friends. A day full of fun, food, and doggy splashes!
Summer Concert series:
Thursdays in the Park – August 21st; Queen Annes County Center for the arts: Momma’s Black Sheep
ATC Summer Concert Series – August 22nd; Annapolis Town Center: The Bachelor Boys
Free Avalon Outdoor Concert Series – August 23rd; Avalon Theatre: US Navy Band Sea Chanters
Allen Pond Summer Concert Series – August 24th; Allen Pond Park: Ty Braddock & the Loyal Inmates
Tunesday: Summer Concert Series – August 26th; Back Creek and Second Street Eastport: Brandon Hardesty
