A list of our favorite events around Annapolis, Eastern Shore and beyond for the month of September. Event dates may be subject to change.
Annapolis Baygrass Music Festival
Every jam saves the bay at Annapolis Baygrass Music Festival. The festival will take place on September 30th and October 1st at Sandy Point State Park. The Annapolis Baygrass Music Festival is a conservation-focused musical event where just by having fun you are helping the Chesapeake Bay. Enjoy music from Yonder Mountain String Band, Railroad Earth, Keller & The Keels, Melvin Sales & JGB, and so many more bands. Baygrass blends the finest progressive bluegrass music with a gorgeous beachfront venue and a core mission to protect and restore the bay. Buy tickets today at baygrassfestival.com.
Boatyard Beach Bash
The 18th Annual Boatyard Beach Bash to benefit the Annapolis Maritime Museum is back in Annapolis on September 9th from 4:30 to 10 p.m. Soak in the sounds of Key West with Coral Reefer band members Peter Mayer, Doyle Grisham, Eric Darken, Scott Kirby, John Frinzi, and more musicians. Radio Margaritaville host JD Spradlin will be the emcee of this year’s night of music. Order your tickets at amaritime.org.
25th Anniversary Arts Alive!
Maryland Hall is having their 25th Anniversary Arts Alive! party on September 8th from 6 to 10 p.m. Get ready to celebrate with nearly 500 community leaders, business executives, and arts patrons, raffles, a silent auction, food and beverages from local restaurants, live entertainment from The Nightlife Bands, and more! Get tickets and more information at marylandhall.org.
Annapolis Song Writers Festival
The Annapolis Song Writers Festival, molded after the Key West Songwriters Festival, the largest festival of its kind in the world, will be September 15th through 17th throughout Downtown Annapolis. Among the dozens of festival performances, Blondie will headline the 15th and LeAnn Rimes on the 17th, both at the City Dock stage at Susan Campbell Park. Other venues will include Rams Head On Stage, MC3 Annapolis, and Maryland Hall. Find a full lineup and get tickets to the festival at annapolissongwritersfestival.com.
Annapolis Run for the Light House
Annapolis Run for the Light House Half Marathon, 5K, and Walk will be held on September 17th at Quiet Waters Park in Annapolis. The 14th annual run provides a scenic half marathon and 5K walk/run along the trails of Quiet Waters Park and through the beautiful Chesapeake Bay-front community of Hillsmere Shores. All proceeds from the run will benefit The Light House in Annapolis, a well-known public charity working to end the cycle of homelessness and poverty. Find more information and sign up details at friendslhs.org.
Photo by Max Goldberg
Brett Young Birdland Summer Music Series
The final Birdland Summer Music Series performance will take place on September 15th at Camden Yards. After the Orioles game against Tampa Bay, Brett Young will perform. The summer music series helps empower youth and strengthens our community. $5 from every on-field pass purchased will benefit the Orioles Charitable Foundation’s Music & Arts Education Scholarship, which was created in 2019 to support deserving students and programs throughout Birdland. Find more information at mlb.com/orioles.
16th Annual St. Michaels Concours d’Elegance
The 16th Annual St. Michaels Concours d’Elegance on the Chesapeake Bay is headed to Kent Island Yacht Club’s lawn and docks on September 22nd through 24th. The weekend will be full of Chesapeake Bay yachting and motoring while guests enjoy locally-sourced cuisine, craft libations, vendor tents, live music, and more. Find a full calendar of events at smcde.org.
Chesapeake Film Festival
The 2023 Chesapeake Film Festival will be live this year on September 30th and October 1st at the Avalon Theatre and Ebenezer Theatre in Easton. The festival will feature screenings and discussions that transport attendees to the glory days of theatre. The festival will also go virtual October 2nd through 8th where you will have another week to enjoy outstanding films at your own convenience. Find more information at chesapeakefilmfestival.com.
Ride For Clean Rivers
September 17th will be the 19th Ride for Clean Rivers at Chesapeake College. Ride the beautiful back roads of Talbot and Queen Anne’s counties to support ShoreRivers work for clean waterways. Bring summer to a close with a great cause. The 62-mile ride will start at 8 a.m. and the 35- and 20-mile rides will start at 9 a.m. Register today and find more information at shorerivers.org.
Photo credit George Sass
Charity Boat Auction
The Chesapeake Bay Maritime Museum in St. Michaels hosts its annual Charity Boat Auction on Saturday, September 2nd. During this rain-or-shine event, donated boats and watercraft, ranging in size and performance from cabin cruisers to sailing dinghies and everything in between, will be auctioned off to the highest bidders, beginning at 11 a.m. This is an absolute auction with no reserves or minimums—everything must go! There’s also a flea market-style tag sale, starting at 8 a.m., featuring a variety of used boating gear. Visit cbmm.org/CharityBoatAuction for more information.
Maryland Folk Festival
Spend your weekend at the Maryland Folk Festival in Downtown Salisbury for a diverse celebration of arts, culture, and heritage. This big event will celebrate roots, richness, and variety of American culture with an assembly of fine musicians, dancers, craftspeople, and more! The festival will have a market and food courts, so be sure to experience it all! Find more information at mdfolkfest.com.
Shaw Bay Raft-Up Concert
ShoreRiver’s Shaw Bay Raft-Up Concert is the perfect time to relax with music and scenery on September 9th from 3 to 6 p.m. Grab your raft, dinghy, paddle board, kayak, or sailboat to Shaw Bay along the Wye River for a free concert. The Eastport Oyster Boys will be performing for the 20th time with ShoreRivers and the Wye River Band will be performing for the fourth time. This concert is held each year to raise funds and awareness for clean water efforts on Maryland’s Eastern Shore. Find more information at shorerivers.org.
