Music takes over Maryland’s capital September 10–13 as the Annapolis Songwriters Festival returns for four days of performances throughout downtown Annapolis.
There’s a little bit of everything happening around the Chesapeake this week! Spend the weekend feasting at the Maryland Seafood Festival, discover the stories behind your favorite songs at the Annapolis Songwriters Festival, shop vintage and local finds, or get outside for live music, colorful runs, and waterfront adventures. From celebrating Chesapeake traditions and local history to supporting great causes throughout the community, there are plenty of ways to fill your September calendar. Grab your friends and family and make the most of another busy week around the Bay!
River Concert Series: Eastport Oyster Boys
September 9th; Historic London Town & Gardens; Edgewater 6:00pm
Celebrate the sounds and stories of the Chesapeake with the Eastport Oyster Boys! Known for their lively, interactive performances, the local favorites blend Americana, Celtic tunes, island rhythms, sea chanteys, rock-and-roll, and plenty of humor into a uniquely Chesapeake experience. Settle in along the waterfront for an evening of live music, local flavor, and Bay-inspired fun, with food and drinks available for purchase throughout the concert.
Annapolis Witches & Legends walking tour
September 9th; Annapolis Ghost Tours, Annapolis 7:00pm
Tis the Season! Discover the darker side of Annapolis history on a walking tour exploring Maryland’s witch trials, superstitions, and centuries-old legends. Hear the stories of those accused of witchcraft and learn how fear, rumor, and folklore shaped the city during the 1600s and 1700s. This 90-minute tour offers a fascinating—and slightly eerie—look into a lesser-known chapter of Annapolis’ past.
Annapolis Songwriters Festival
September 10th-13th; Downtown Annapolis, Annapolis 12:00pm
Music takes over downtown Annapolis during the Annapolis Songwriters Festival! Inspired by the legendary Key West Songwriters Festival, this four-day celebration brings songwriters and music lovers together at venues throughout the city, from favorite local watering holes to intimate theater settings. Catch live performances while discovering the voices, stories, and creative minds behind the songs you love—all with the Chesapeake Bay as the backdrop
Dining in Colonial Maryland - A 250th Program
September 10th; Oxford Community Center, Oxford 5:30pm
Take a flavorful trip back in time with Dining in Colonial Maryland, a special America 250 program exploring the foods and traditions of the past. Cookbook author and historian Joyce M. White will share the stories behind historic foodways and material culture, followed by a buffet inspired by dishes of the era and prepared by Momma Maria’s. Guests can also sip historic cordials from the cash bar while discovering what dining was really like in colonial Maryland.
Skipjack Heritage Days at Sandy Point State Park
September 12th; Sandy Point Stat Park; Annapolis 1:00pm
Celebrate the Chesapeake Bay’s maritime heritage during Skipjack Heritage Days, held in conjunction with the Maryland Seafood Festival at Sandy Point State Park! Your Seafood Festival admission includes one free ride aboard a historic skipjack, giving visitors the chance to cruise from Sandy Point Marina toward the iconic lighthouse and experience these traditional working vessels firsthand. Come back Sunday to watch the skipjack fleet parade across the Bay before racing toward Baltimore Lighthouse, all while enjoying the food and festivities of the Maryland Seafood Festival.
Annapolis Color Run By Color Craze
September 12th; Downtown Annapolis, Annapolis 12:00pm
Get ready to run, walk, dance, and get completely covered in color at the Annapolis Color Run by Color Craze! This high-energy experience turns a traditional run into a vibrant festival filled with music, celebration, and plenty of colorful surprises along the way. Whether you’re racing to the finish or simply there for the fun, it’s all about making memories and celebrating life in full color.
Maryland Seafood Festival
September 12th-13th; Sandy Point State Park, Annapolis 11:00am
Crack into a Chesapeake tradition as the Maryland Seafood Festival celebrates 60 years of seafood, music, and waterfront fun! Feast your way through a variety of seafood vendors while enjoying live entertainment, local shopping, refreshing drinks, contests, and activities for the kids. This milestone year also brings even more ways to celebrate Maryland’s coastal culture, making it the perfect weekend to gather your crew, come hungry, and enjoy one of the region’s favorite festivals by the Bay.
ESLC Annual LandJam
September 12th; Councell Farms, Cordova 1:00pm
Celebrate the Eastern Shore’s great outdoors at ESLC’s annual LandJam! Bring the whole family for an afternoon of live music from Black Dog Alley and Kentavius Jones, local food, craft brews, ice cream, and plenty of farm fun. Kids can explore Councell Farms’ Field of Fun with a corn maze, jumping pillows, a combine slide, and more, making this a lively fall outing for all ages.
Warriors in the Park 2026
September 12th; Severna Park Taphouse, Severna Park 1:00pm
Rock out for a great cause at Warriors in the Park! Three stages will feature a packed lineup of local talent, including John Haywood, Skribe, Daphne Eckman, Honey Sol, Honestly Soul Trio, Carleigh Jane, Justin LaFave, and many more. Between performances, enjoy food and drinks, raffles, and auctions, with all proceeds benefiting the Warrior Music Foundation and its mission.
Boating Party Fundraising Gala
September 12th; Chesapeake Bay Maritime Museum, St. Michaels 6:00pm
Dress up for an evening on the waterfront at the Chesapeake Bay Maritime Museum’s annual Boating Party fundraising gala! This year’s “Ode to the Oyster” celebration features cocktails, dinner, drinks, dancing, and special programming highlighting CBMM’s work across the Chesapeake. Proceeds will support the refresh of the museum’s Oystering on the Chesapeake exhibition and the relaunch of the historic 1920 buyboat Winnie Estelle, helping preserve and share the Bay’s maritime heritage for generations to come.
9/11 Heroes Run
September 13th; Navy Marine Corps Memorial Stadium, 11:00am
Honor the heroes of September 11 and those who answered the call to serve at the 9/11 Heroes Run 5K. Runners, ruckers, and walkers of all ages and fitness levels are invited to come together as the nation commemorates the 25th anniversary of 9/11. More than a race, this meaningful community event helps keep the promise to never forget while honoring first responders, service members, and all those who stepped up in the years that followed.
Naptown Flea x Lucky Girl Market
September 13th; Maryland Ave, Annapolis 10:00am
Shop local, score one-of-a-kind finds, and soak up the good vibes as Naptown Flea and Lucky Girl Market team up! Browse more than 60 vendors featuring vintage treasures, handmade goods, and local finds while enjoying food, drinks, and live music along the way. It’s the perfect excuse to spend the day strolling Maryland Avenue and supporting Annapolis’ creative community.
33rd Annual Bob Ferry Golf Classic
September 14th; Golf Club at South River, Edgewater 9:00am
Hit the links for a great cause at the 33rd Annual Bob Ferry Golf Classic benefiting the Boys & Girls Clubs of Annapolis & Anne Arundel County. Named in honor of former NBA player and Washington Bullets General Manager Bob Ferry, the tournament celebrates his lasting commitment to friendship, community, and supporting local youth. Gather your foursome for a day on the course while helping BGCAA continue creating opportunities for young people throughout the community.
Tunesday By Chronic Sailing
September 15th; Back Creek Eastport, Annapolis 6:00pm
Tunesday keeps the music flowing on Back Creek with Danah Denice taking the floating stage! Cruise over by boat, kayak, or paddleboard and enjoy a laid-back live performance aboard Chronic Sailing’s anchored catamaran as the sun begins to set. This free, family-friendly concert is the perfect way to unwind after work with great music, beautiful waterfront views, and plenty of summer vibes.
Sporting Clay Shoot
September 15th; Pintail Point Farm, Queenstown 11:00am
Take your best shot for a great cause at MTBMA’s Annual Sporting Clay Shoot! Whether you’re an experienced shooter or new to sporting clays, enjoy a day of friendly competition, networking, and outdoor fun, complete with a catered lunch, oyster station, raffles, prizes, and awards. Proceeds support the MTBMA Scholarship Foundation and its efforts to provide educational opportunities for students pursuing careers in Maryland’s transportation construction industry.
