A list of our favorite events around Annapolis, Eastern Shore and beyond for the month of September. Event dates may be subject to change.
Bay Bridge Paddle
The Bay Bridge Paddle offers a thrilling morning of SUP and kayak paddling that caters to all levels of experience on September 15th, beginning at Sandy Point State Park. Not only will you have a chance to take on the challenge of the paddle, but registration also includes admission to the Maryland Seafood Festival. This is your chance to make the most of your day and enjoy everything that the festival has to offer. The event offers three paddling courses to ensure that there is an option for every paddler. Don’t miss out on this bucket list item! Register and find more information at abceventsinc.com.
Maryland Seafood Festival
The Maryland Seafood Festival returns to Sandy Point State Park in Annapolis on September 14th and 15th. This weekend is a staple of Maryland heritage and Bay cuisine with loads of seafood vendors, local shopping and vendor options, a fantastic beverage selection with craft beer, live music, kids’ activities, and so much more. Most importantly, get ready for another year of The Crab Soup Cook-Off. Who will take home the trophy this year? Get tickets and find more information at abceventsinc.com.
Pops in the Park
The Annapolis Symphony Orchestra, conducted by Maestro José-Luis Novo, is performing the perfect end-of-summer soundtrack for the whole family. Enjoy Pops in the Park on September 1st at 5:30 p.m. at Quiet Waters Park (rain date: 9/2). The music program is sponsored by Anne Arundel County Arts Council and Anne Arundel County Department of Recreation and Parks. It’s the perfect way to close out your summer. Find more information at annapolissymphony.org.
Arts Alive
Arts Alive is in its 26th year as being the largest annual fundraiser for Maryland Hall. On September 6th, from 6 to 10 p.m., guests will enjoy cocktails, cuisine, live performances, and more. The event serves the mission of Maryland Hall to provide art for all, to inspire creativity, to uplift and celebrate diverse voices, and to tell important stories through a wide range of high-quality and engaging arts programming in the community. Find more information and get tickets to the event at marylandhall.org.
Photo by Jay Strausser
Annapolis Baygrass Festival
Oteil & Friends, The Infamous Stringdusters, Leftover Salmon, Sam Bush, and so many more entertainers will take the stages at Sandy Point State Park for the second Annapolis Baygrass Festival on September 21st and 22nd. Baygrass blends the finest progressive bluegrass, jamgrass, and Americana music with a gorgeous beachfront venue and a mission to protect the Chesapeake Bay and raise mental health awareness. Find more information and get tickets at baygrassfestival.com.
Boatyard Beach Bash
The 19th Annual Boatyard Beach Bash to benefit the Annapolis Maritime Museum will be back at the waterfront museum in Eastport on September 21st. This Jimmy Buffett/Parrot Head themed fundraiser soaks in the sounds of Key West with musicians that shape that lifestyle: world class musicians and members of the iconic Coral Reefer Band. Enjoy a night of music, dancing, and delicious food and drink. This year, the night will be in honor of Jimmy Buffett. Find more information at amaritime.org or boatyardbarandgrill.com.
Oktoberfest in Annapolis
Gather in West Annapolis for the annual Oktoberfest on Sunday, September 22nd! This family-friendly event offers something for everyone, with beer, live music, delicious food, and a variety of vendors. Thanks to a partnership with West Annapolis Elementary School, kids will enjoy a range of fun activities tailored just for them, making it a perfect outing for the whole family. Don’t miss out on the vibrant atmosphere and community spirit that make this event a local favorite. For more information, visit west-annapolis.com.
Annapolis Run for the Light House
The Annapolis Run for The Light House race committee is hosting its 15th annual Half Marathon, 5K, and Walk on Sunday, September 15th at Quiet Waters Park and the Hillsmere Community. All proceeds from this event support The Light House. Beyond providing food, clothing, and shelter, they also address the underlying causes of homelessness such as lack of marketable job skills, addiction, and the debilitating effects of both mental and physical health issues. For more information, please visit annapolisrunforthelighthouse.org.
14th Wendi Winters Blood Drive
On September 7th, American Red Cross is hosting the 14th Wendi Winters Blood Drive at the Crowne Plaza Hotel in Annapolis. This event is in honor of Wendi Winters, a proud Navy mom who lost her life in the tragic Capital Gazette shooting in 2018. Wendi’s heroic actions saved the lives of several colleagues at the Capital Gazette and since her passing, over 3,000 units of blood have been donated in her honor, which has the potential of saving 3,000 lives. Sign up for an appointment at redcrossblood.org.
Book Fair!
Anne Arundel County Literacy Council is hosting its annual book fair and fundraising event on September 28th at Westfield Annapolis Mall, within the Community Room and Crate & Barrel Court space. Proceeds help low-income adults pursue their goals in literacy, math, diploma studies, ESL learning, and more. Learn more at icanread.org/bookfair.
Photo by Ken Tom
Blazers. Bourbon. Cigars.
The premier networking event for men in Annapolis is back at William Paca House and Gardens on September 26th, from 6 to 9 p.m. This fundraiser supports Historic Annapolis and their mission to Preserve. Protect. Connect. It’s the perfect opportunity to meet influential leaders, the region’s top entrepreneurs, business professionals, and visionaries representing our diverse community. In addition, enjoy bourbon, whiskey, and other fine liquor tastings, premium cigars and delicious food from the area’s top chefs. Find more information and get tickets at bbc.annapolis.org.
Annapolis Songwriters Festival
The Annapolis Songwriters Festival brings our love for music to the bay! The festival, which is modeled after the hugely successful Key West Songwriters Festival, has its own world-renowned watering holes and intimate theater settings, making our historic capital on the bay the perfect location for live music enthusiasts to get acquainted with the faces, voices, and stories behind the song. Lee Brice, Citizen Cope (pictured), JJ Grey and Mofro, Marc Cohn, and so many other songwriters will be at Rams Head and various other venues in Annapolis, September 12th through 15th. Find a full schedule and get tickets at annapolissongwritersfestival.com.
Photo by Edie Bernier
Maryland State Fair
We just have a few days left to celebrate our state at the Maryland State Fair at the fairgrounds in Timonium. Enjoy the fair in the last weekend of the 2024 season on September 5th through 8th. On September 7th, run to the infield to sing and dance to live music by Big Time Rush with Crash Adams. Get your final fix of fair food, livestock competitions, drinks, and rides for the whole family to enjoy. Find more information and get your tickets at marylandstatefair.com.
Girls on the Run Music Bingo FUNdraiser
Test your knowledge with music bingo at Homestead Gardens in Davidsonville to raise money for Girls on the Run of the Greater Chesapeake’s scholarship fund by increasing program access and bringing confidence to more girls. Bring your family and friends to play music bingo with songs from different music genres on September 20th starting at 6 p.m. The night will also allow you to check out Homestead Garden’s new Beer Garden and grab a pizza from a family-run pizza truck. Find more information at gotrchesapeake.org.
Festival On the Green
The Fall Festival On the Green, hosted by Greater Crofton Chamber of Commerce at Crofton Country Club, will be back on September 21st. The festival is a great opportunity for the whole family to enjoy the community. Meet people and business’ in the community with a day of vendors, demos, music, activities for children, food trucks, and more. This is a great way support local! Find more information at croftonchamber.com.
FrightReads Book Festival
The 4th Annual FrightReads Book Festival September 28th and 29th at Benfield Sportscenter in Millersville. This weekend offers Maryland’s number one horror book festival with two full days of activities. There will be over 100 of the most creative authors, celebrities, and crafters packed in one building. Both days will have costume contests, an improv show, and more. Find more information at frightreads.com.
Bowie Baysox
There is plenty of local baseball to enjoy this month while we finish out the 2024 Bowie Baysox season. The Baysox have a 6-home game series against Harrisburg September 3rd through 8th. Each night will have a different theme, with the series finish being a 1:05 p.m. game followed by a true Birdland Celebration. Tuesday, Wednesday, Thursday, and Saturday’s games will start at 6:35 p.m. and Friday’s game will start at 7:05. Enjoy Military Appreciation Night, High School College Fair, HBCU-Divine Nine Night, Cangejos Fantasmas de Chesapeake, and on Saturday there will be fireworks after the game. See some minor league games with the major league feel this September! Get tickets at milb.com.
The World is Your Oyster Festival
The Bay’s biggest bivalve bash is back on September 26th at the B&O Railroad Museum in Baltimore. Get ready to shuck, slurp, and sip your way through Maryland’s finest oysters, seafood, and libations with Oyster Recovery Partnership, which celebrates 30 years. This event is the perfect celebration of the Bay’s revival, the resurgence of its native oysters, and our incredible community that has made it all possible. Find more information and get your tickets at oysterrecovery.org.
Photo by Rebecca Placek
Historic Stevensville Classic Car Show
Streets will be closed on September 7th for the Historic Stevensville Classic Car Show. Classic cars and trucks will maneuver through town and park on Love Point Road and on the Train Station greens in Historic Stevensville for everyone to admire. The day will consist of trophies, dash plaques, food trucks, music, kids activities, and free tours of historical sites. Find more information and rsvp at stevensvilleartsandentertainment.org.
Ride for Clean Rivers
On September 15th, strap on your helmet, and clip in your shoes for the 20th Ride for Clean Rivers, raising money for ShoreRivers. The race will start at Chesapeake College and will be a great opportunity for you to ride the beautiful back roads of Talbot and Queen Anne’s Counties to support work for clean waterways. Find more information at shorerivers.org.
Chestertown Jazz Festival
Garfield Center for the Arts is hosting the 28th Annual Chestertown Jazz Festival at Wilmer Park in Chestertown on September 7th from noon to 6 p.m. Jazz by the River will feature food, wine and beer, and music by Sylvia Hackett Frazier and the Anointed Vessels (traditional gospel opening), Prince-Rodgers Grateful Jazz (jazz with a Grateful Dead flair), Brent Brickhead (award-winning saxophonist), and David Stryker Quartet featuring Warren Wolf. Be sure to get your tickets at garfieldcenter.org.
Chesapeake Film Festival
The 17th Chesapeake Film Festival begins at the Garfield Center for the Arts in Chestertown on September 12th with an engaging lineup of environmental short films. This mini-festival previews the grand, three-day celebration of independent filmmaking, which will be at Ebenezer Theater in Easton, September 27th through 29th. Be sure to see the full line up of independent films featured this year (including The Genius of Gianni Versace Live, pictured) at chesapeakefilmfestival.com.
Photo by Becca Newell
St. Michaels Concours d’ Elegance
On September 27th through 29th, see some of the most extravagant vehicles at Kent Island Yacht Club for the 16th Annual St. Michaels Concours d’ Elegance. This is a grand day of casual elegance, classic motoring, antique wooden speedboats, classic yachting, and great food. The day will also have a beautiful, waterfront view that you won’t want to miss. Find more information at smcde.org.
Wild Goose Chase
Since 2008, Blackwater National Wildlife Refuge has been using the Wild Goose Chase Women’s Bicycle Ride as one of their main fundraising events of the year. This is the perfect ride for ladies who love nature and enjoy Blackwater National Wildlife Refuge and the flat scenic Dorchester country roads. The ride will be on September 29th, starting at Blackwater Wildlife Refuge. Come out on September 28th for many other events as well! There will be bird walks with an experienced birder, nature rides with a guide who will give information about the Refuge, a Harriet Tubman ride led by Susan Meredith, and yoga classes for cyclists! Find more information at friendsofblackwater.org.
Fore a Cause Golf Fundraisers this Month
There are many golfing opportunities that also give back to our community and September is a great month full of charity tournaments. Many nonprofits are hosting their annual golf outings this month. Below is a list of several tournaments to raise money for important nonprofits.
September 11th
Bello Machre Golf Tournament at Queenstown Harbor (Queenstown); bellomachre.org
September 20th
Haven Ministries Annual Golf Tournament at Prospect Bay Country Club (Grasonville); haven-ministries.org
September 23rd
GiGi’s Playhouse Golf Tournament at Queenstown Harbor; gigisplayhouse.org
September 26th
Hospice of the Chesapeake Annual Golf Tournament at Queenstown Harbor; hospicechesapeake.org
September 27th
Dorchester Chamber Challenge Golf Tournament at the Hyatt Regency Chesapeake Bay Resort and Spa (Cambridge); dorchesterchamber.org
September 30th
Birdies for Benedictine at Talbot Country Club (Easton); benschool.org
31st Annual Boys & Girls Club of Annapolis and Anne Arundel County Bob Ferry Golf Classic at The Golf Club at South River (Edgewater); bgcaa.org
