51st Annual Annapolis Ten Mile Run
Summer may be winding down, but the local fun is still going strong! This week is packed with live music, waterfront adventures, festivals, local sports, and plenty of ways to soak up the final days of August. Cheer on Navy Women’s Soccer, cruise into the sunset, crack into a classic Maryland crab feast, discover new reads, or bring the whole family out for food and fun. From bluegrass and Bay views to pickleball, pirates, and the iconic Annapolis Ten Mile Run, there’s something for everyone to enjoy as we head into September!
Bay Grass Blues
August 27th; Ashling Kitchen & Bar, Crofton 6:00pm
Get into the Baygrass spirit with a free night of live local bluegrass, good drinks, and plenty of festival fun at Bay Grass Blues! Presented in partnership with the Annapolis Baygrass Music Festival, the evening will feature live music, drink specials, guest bartenders, ticket giveaways, and a few surprises along the way. Grab your friends, settle in for some great tunes, and get a taste of the Baygrass excitement before the festival arrives!
Thursday Night LIVE!
August 27th; Annapolis Town Center, Annapolis 6:30pm
Close out the Thursday Night LIVE! summer series with an evening of ska and reggae from The Players Band! Grab dinner from one of the nearby eateries, find a spot on the patio, or bring a blanket and settle in for live music outdoors. With upbeat tunes, great food, and a lively atmosphere, it’s the perfect way to soak up one more Thursday night of summer fun with friends and family.
Naval Academy Women's Soccer vs Maryland
August 27th; Navy Marine Corps Memorial Stadium, Annapolis 7:00pm
Bring your Navy spirit and cheer on the Midshipmen as Navy Women’s Soccer takes on in-state rival Maryland! Get ready for an exciting night of college soccer as the Mids defend their home turf and battle for local bragging rights. Rally your friends and family, wear your blue and gold, and come out to support the home team. Can’t make it in person? Catch the action live on ESPN+. Go Navy!
B.I.G. Book sale (Books for International Goodwill)
August 28th; B.I.G. Warehouse, Annapolis 3:00pm
Calling all book lovers! Browse more than 70,000 gently used books at the B.I.G. Book Sale and stock your shelves without breaking the bank. With books priced from just $1–$4, there’s plenty to discover for every kind of reader. Even better, your purchases support Books for International Goodwill’s mission to provide books to underserved communities in the U.S. and around the world. Come hunt for hidden gems, fill a bag with new-to-you reads, and support a great cause while you shop.
Drink & Dink Corporate Challenge and Networking Mixer
August 28th; The HALL at Live Casino & Hotel, Hanover 1:00pm
Mix business with a little friendly competition at the Drink & Dink Corporate Challenge and Networking Mixer! Whether you’re a pickleball pro or picking up a paddle for the first time, enjoy open play, networking, a DJ, prizes, food, and a cash bar in a lively, laid-back atmosphere. No partner or paddle is required, making it easy to jump into the action, meet fellow local professionals, and have some fun along the way. Come ready to mingle, play, and see which local business takes home the coveted Golden Pickle Trophy!
RICKSHAW LIZARD live onboard Watermark Sunset Cruise!
August 28th; Watermark Sunset Cruises, Annapolis 7:00pm
Set sail into the sunset with live music from Rickshaw Lizard aboard a Watermark cruise on the Chesapeake Bay! Sit back with a cool drink, take in beautiful waterfront views, and enjoy a 90-minute cruise filled with live music as the sun goes down over Annapolis. With beverages and snacks available from the onboard bar, it’s a fun and relaxing way to kick off your weekend and experience a summer night on the water.
Kids on the Creek
August 29th; Truxton Park Boat Ramp, Annapolis 11:00am
Get the kids outside and exploring at Kids on the Creek, a free family day filled with hands-on fun along Spa Creek! Hop aboard a boat ride, give paddleboarding a try, go fish seining, search for local critters, and explore the shoreline while learning more about the creek and the environment around it. With community booths, plenty of activities, and even a free lunch, it’s a fun way for the whole family to spend the day discovering Annapolis from the water.
Halal Food Fest
August 29th; Anne Arundel County Fairgrounds, Crownsville 3:00pm
Come hungry and celebrate flavor, culture, and community at Halal Food Fest! One of the region’s largest halal food events returns with plenty of delicious eats to discover alongside a lively, welcoming atmosphere for all. Gather your friends and family, sample your way through a variety of halal favorites, and enjoy an afternoon and evening centered around great food and community fun.
Tall Tales of Annapolis & the Chesapeake Bay
August 29th; Annapolis Sailing School, Annapolis 7:00pm
Dive into the colorful stories of the Chesapeake at Tall Tales of Annapolis & the Chesapeake Bay! Storyteller Jefferson Holland brings the Bay to life through original tales and songs featuring everything from despicable pirates and 3,000-year-old oyster shells to cannibal crabs and modern-day sailors. Blending local history with humor and a little imagination, this entertaining evening offers a fun and unexpected way to discover the people, places, and legends that make the Chesapeake so unique.
Maryland Hall Presents BloomHaven
August 29th; Maryland Hall for the Creative Arts, Annapolis 3:00pm
oak up an afternoon of bluegrass, community, and summer fun at BloomHaven’s “Road to Baygrass”: The Annapolis Fiddler’s Pick-nic & Bday Bash! Hosted by Sarah Larsen of the Black-Eyed Suzies in celebration of her birthday, this laid-back lawn party brings together live music, dancing, jam circles, surprise collaborations, and plenty of good company. Grab a lawn chair and settle in for a backyard-style bluegrass gathering that’s all about great tunes and easygoing summer vibes. Kids 12 and under attend free!
PDG Crab Feast
August 29th; Kurtz’s beach, Pasadena 12:00pm
Crack into a Chesapeake favorite while giving back at the PDG Crab Feast! Enjoy all-you-can-eat crabs, BBQ, sides, desserts, and beer while keeping the fun going with a DJ, dancing, raffles, games, cornhole, a moon bounce, and more. Bring your appetite and gather your crew for an afternoon of classic Maryland fun, all while supporting PDG Rehabilitation Services and its work with adults living with mental illness across the state.
51st Annual Annapolis Ten Mile Run
August 30th; Navy Marine Corps Memorial Stadium, Annapolis 7:00am
Lace up and hit the streets for one of Annapolis’ most iconic running traditions! The Annapolis Ten Mile Run returns for its 51st year, taking runners on a scenic course through the Historic District, across the Naval Academy Bridge, and through surrounding neighborhoods. Named one of the country’s top 10-mile races by Runner’s World, this year’s event also serves as the Road Runners Club of America’s 10-mile state championship. Stick around after crossing the finish line for live music, refreshments, and plenty of post-race celebration. With registration limited to 5,000 runners, don’t wait to claim your spot!
Mom's Day Out Lunch at Leo
September 1st; Leo, Annaplis 11:00am
School is back in session, and this one’s for the moms! Grab your friends and treat yourself to a well-deserved Mom’s Day Out at Leo, complete with delicious bites, refreshing spritz cocktails, and music from DJ Crawdads. Build your own bouquet at the Dandelion Stand flower bar, browse jewelry from Amethyst & Opal, and enjoy an afternoon made for catching up, unwinding, and celebrating the start of the school year.
Tunesday Concert Series
September 1st; Back Creek Eastport, Annapolis 6:00pm
Wind down your Tuesday with live music on Back Creek as Higher Hands takes the floating stage for the Tunesday Concert Series! Bring your friends and family, find a spot along the waterfront, and enjoy a laid-back evening surrounded by beautiful scenery and great music. With the tunes carrying across the water as the sun sets, it’s the perfect way to ease into September and enjoy another summer-style evening in Annapolis.
