Pack a picnic and enjoy an afternoon of live music with the Annapolis Symphony Orchestra at Pops in the Park!
Summer may be winding down, but there’s no slowing down the fun around the Chesapeake Bay! This week brings an exciting mix of live music, Navy traditions, outdoor adventures, local art, waterfront fun, and plenty of ways to celebrate Labor Day weekend. Catch a legendary performer, cheer on the Mids, paddle with your pup, browse local art, enjoy a picnic with the symphony, or soak up live music from the water. However you want to spend the first week of September, there’s plenty happening around the region to keep the summer spirit going!
Patti Smith Quartet
September 2nd; Maryland Hall for The Creative Arts, Annapolis 8:00pm
Experience an unforgettable night of music with the legendary Patti Smith Quartet. Known as the “Punk Poet Laureate,” Smith brings more than five decades of groundbreaking music, poetry, and fearless artistry to the stage with the same raw energy that made her one of rock and roll’s most influential voices. Joined by her powerhouse quartet, she’ll bring her iconic catalog to life through a performance that’s intimate, expressive, and unmistakably Patti Smith. Don’t miss the chance to see a Rock and Roll Hall of Famer live in Annapolis.
Dog Days Are Over: End-of-Summer Guided Hike
September 3rd; Bacon Ridge Natural Area, Annapolis 5:30pm
Celebrate the end of summer with your four-legged hiking buddy on a guided adventure through the scenic trails of Bacon Ridge Natural Area. Scenic Rivers Land Trust and trainers from Paws and Possibilities will lead the way, sharing insight into the surrounding forests, streams, and wildlife along with helpful tips for enjoying the outdoors with your dog. This relaxed, dog-friendly hike is a great chance to get outside, learn something new, and soak up one of the season’s final evenings on the trails. Space is limited and registration is required.
Marching Band Formal Parade
September 4th; Worden Field, Annapolis 4:30pm
Experience one of the Naval Academy’s most iconic traditions as the Brigade of Midshipmen takes to historic Worden Field for the first Formal Parade of the academic year. Led by the Naval Academy Band, the precision and pageantry of the Brigade make this a uniquely Annapolis experience. Come out to see this impressive display of military tradition and Midshipmen pride in action.
Hockey Night at the Baysox!
September 5th; Prince Georges Stadium, Bowie 5:30pm
Baseball meets hockey for a special night at the ballpark as the Chesapeake Baysox take on the Portland Sea Dogs! Celebrate the return of hockey season with an appearance by Washington Capitals alum Karl Alzner, interactive fun with the Capitals Street Team, and an exclusive Baysox hockey jersey giveaway for the first 750 fans ages 13 and up. Stick around after the game for fireworks and a Kids Run the Bases experience to cap off an action-packed night.
Graduate Annapolis x Red Bull Tailgate
September 5th; Graduate by Hilton, Annapolis 12:00pm
Get ready for Navy football with a high-energy pregame party at Trophy Room! Graduate Annapolis and Red Bull are teaming up for an afternoon featuring a live DJ, specialty cocktails, giveaways, and plenty of Navy spirit before the Mids take on Towson. Grab your crew, enjoy the pregame festivities, and get fired up for kickoff!
St Lukes Art League Art Show
September 5th – 7th; St Luke Church, St. Michaels 11:00am
Spend Labor Day weekend surrounded by local art at the St. Luke’s Art League’s annual outdoor Art Show Under the Tent. Browse more than 300 original paintings created by Art League members, with a wide variety of works on display right along Talbot Street. Art lovers and casual browsers alike can enjoy discovering one-of-a-kind pieces while exploring the heart of St. Michaels.
Pops in the Park at Down Park
September 5th; Downs Park, Pasadena 11:30AM
Pack a picnic and enjoy an afternoon of live music with the Annapolis Symphony Orchestra at Pops in the Park! Inspired by America250, this free outdoor concert celebrates the diverse sounds and stories that have shaped American music, featuring works by Copland, Gershwin, Bernstein, John Williams, and more. Maryland Poet Laureate Lady Brion will also join the orchestra for a special performance of Lincoln Portrait and selections of her original poetry. Bring your lawn chairs, blankets, family, and friends for a memorable day of music in the park.
Charity Boat Auction
September 5th; Chesapeake Bay Maritime Museum, St. Michaels 8:00am
Set your sights on the water at the Chesapeake Bay Maritime Museum’s annual Charity Boat Auction! This longtime Labor Day weekend tradition brings dozens of donated boats and watercraft to the auction block, giving bidders the chance to find everything from smaller vessels to top-quality boats. Guests can browse the selection before bidding begins and hunt for boating gear at a flea market-style tag sale. Best of all, every sale supports CBMM’s work to preserve and share the history, environment, and culture of the Chesapeake Bay.
Annapolis First Sunday Arts Festival
September 6TH; West Street Block, Annapolis 11:00am
Stroll through downtown Annapolis and spend the day celebrating local art, food, and music at the First Sunday Arts Festival! West and Calvert streets transform into a lively pedestrian festival featuring more than 150 artists and vendors, food trucks, live performances, and outdoor dining at local restaurants. Browse handmade finds, grab a bite, and enjoy one of Annapolis’ favorite monthly traditions with family and friends.
Historic Annapolis Dining Etiquette Experience
September 6th; federal House Bar & Grille, Annapolis 1:00pm
Polish your professional presence over an elegant three-course meal during the Historic Annapolis Dining Etiquette Experience. Learn the essentials of business dining etiquette while building the confidence and poise needed to navigate professional settings with ease. It’s a hands-on opportunity to sharpen your skills while enjoying a sophisticated dining experience in downtown Annapolis.
Pops in the Park - Quiet Waters Park
September 6th; Quiet Waters Park, Annapolis 5:00pm
The Annapolis Symphony Orchestra brings Pops in the Park back for a second performance, this time at Quiet Waters Park! Pack a picnic, spread out a blanket, and enjoy an evening celebrating the many musical traditions and voices that have shaped America, with a special opening performance by the Annapolis Symphony Academy Aries Youth Chamber Orchestra. Maryland Poet Laureate Lady Brion will also join the orchestra for Aaron Copland’s Lincoln Portrait and selections of her own poetry. Bring family and friends and enjoy this free evening of music surrounded by the beauty of the park.
Yappy Hour
September 7th; Capital SUP Nautilus Point, Annapolis 6:30pm
Make a splash with your four-legged best friend at Capital SUP’s Yappy Hour! This dog-friendly group paddle invites pups and their people to explore the Chesapeake Bay together by stand-up paddleboard or kayak. Led by Chan Mee and her pups Kaden and Adalynn, it’s a laid-back evening filled with fresh air, time on the water, and plenty of wagging tails.
Tunesday By Chronic Sailing
September 8th; Back Creek Eastport, Annapolis 6:00pm
Tunesday keeps the summer vibes going on Back Creek with another evening of live music on the water! This week, Ryan Keith takes the floating stage aboard Chronic Sailing’s catamaran for a laid-back performance surrounded by the beauty of the creek. Bring your boat, paddleboard, or kayak and settle in for good music, great company, and a sunset over the water. The concert is free, family-friendly, and open to the community.
