A list of our favorite events around Annapolis, Eastern Shore and beyond for the month of September. Event dates may be subject to change. Also, be sure to check out our 2025 Philanthropic Event Calendar here.
Maryland Seafood Festival
Feast your way through a Chesapeake Bay tradition at the Maryland Seafood Festival, happening September 13–14 at Sandy Point State Park. Enjoy steamed crabs, fresh-shucked oysters, chef demos, local vendors, beer tastings, and a kids’ zone—all with beautiful bay views. With something delicious around every corner, this is your end-of-summer excuse to indulge in all thing’s seafood. Bring the whole family for a weekend of fun and flavor. More info: marylandseafoodfestival.com.
Anchors & Artisans Market
Spend a relaxing Sunday at the Anchors & Artisans Market on September 28 at Annapolis Town Center. Browse handmade goods from 40-plus local makers, enjoy live music, grab a bite to eat, and let the kids explore creative craft stations. It’s the perfect blend of shopping local and soaking up the last warm days of September with family and friends. More info: whatsupmag.com/events/anchors-artisans-market
Bay Bridge Paddle
Grab your paddleboard or kayak and take on the Chesapeake Bay during the Bay Bridge Paddle on Sunday, September 14. This one-of-a-kind race offers three course options under the iconic Bay Bridge, drawing paddlers of all levels to Sandy Point State Park. After the race, stick around for live music, food vendors, and festivities as part of the Maryland Seafood Festival. It’s equal parts adventure, community, and shoreline fun. More info: baybridgepaddle.com
For the Love of the Library
Celebrate stories and community at the “For the Love of the Library” fundraiser on Friday, September 19 at the Michael E. Busch Annapolis Library. This annual event features an evening of food, drinks, music, and fun—all in support of vital library programs across Anne Arundel County. Whether you’re a lifelong reader or simply love a good cause, this night is one for the books. More info: aacpl.net/foundation/love-of-the-library | 410-222-7371
Music by the Marsh; Celebrating 40 years at Jug Bay Wetlands Sanctuary
Join the celebration at Jug Bay Wetlands Sanctuary’s 40th anniversary event, Music by the Marsh, on Saturday, September 27 from 2 to 7 p.m. Enjoy live music, food trucks, nature walks, hands-on exhibits, and family fun at the scenic Emory Waters Nature Preserve. It’s a joyful day honoring decades of environmental education and habitat conservation along the Patuxent River. More info: jugbay.org | 410-741-9330
Annapolis RUN for The Light House
Lace up your sneakers for the Annapolis RUN for The Light House, taking place Sunday, September 14 at Quiet Waters Park. Choose from a half marathon, 5K, or 1.25-mile walk through scenic trails and waterfront neighborhoods. Proceeds benefit The Light House, helping individuals experiencing homelessness in our community. Whether you’re racing to win or walking with friends, your steps support a great cause. More info: annapolisrunforthelighthouse.org
Annapolis Baygrass Music Festival
Experience bluegrass with a purpose at the Annapolis Baygrass Music Festival, September 20–21 at Sandy Point State Park. This feel-good weekend features top Americana and jamgrass acts, plus local food, artisan vendors, and a strong focus on mental health and Chesapeake Bay conservation. Whether you’re grooving by the main stage or lounging in the grass, it’s a celebration of music, mission, and waterfront beauty. More info: baygrassfest.com
Season Opening Celebration: Black and White Gala
Step into an evening of elegance as the Annapolis Opera Guild hosts its annual Black & White Gala on Thursday, September 11 at The Atreeum at Soaring Timbers. Enjoy a sophisticated cocktail hour, a gourmet dinner from Palate Pleasers, and breathtaking live opera performances that kick off the season in true style. It’s the perfect opportunity to dress your best and support the arts in Annapolis. Expect fine dining, stunning vocals, and an atmosphere that’s both timeless and chic. More info: annapolisopera.org | 410-267-8135
Annapolis Songwriters Festival
Get ready for four days of music and storytelling at the Annapolis Songwriters Festival, September 11–14. From headline shows at Rams Head and Maryland Hall to intimate acoustic sets in local taverns, this festival brings together top songwriters from around the country. Stroll through downtown and discover pop-up performances, waterfront views, and the stories behind your favorite songs. It’s like Nashville meets the Chesapeake—come for the music, stay for the vibe. More info: annapolissongwritersfestival.com
Oyster Thyme Feast
Savor the flavors of the Bay at the Oyster Thyme Feast, happening Saturday, September 13 at Harvest Thyme Tavern in Davidsonville. This all-you-can-eat oyster celebration features raw, fried, and Rockefeller oysters paired with wines selected by Chef Rik. A portion of proceeds supports oyster recovery efforts in the Chesapeake, so you can indulge for a good cause. Seating is limited, so get your ticket before it’s shucked and gone! More info: harvestthymetavern.com | 443-203-6846
The Big Dill World’s Largest Pickle Party
Pickle lovers, rejoice! The Big Dill returns to Power Plant Live! in Baltimore on September 20–21 with all things briny and bizarre. From pickle-eating contests and giant inflatables to themed cocktails and live music, this event is as quirky as it is fun. Whether you’re team sweet or sour, there’s something for every pickle personality. Costumes encouraged—pickle pride required. More info: bigdill.com
32nd Annual Bob Ferry Golf Classic
Hit the green for a good cause at the 32nd Annual Bob Ferry Golf Classic on Monday, September 15 at The Golf Club at South River. This annual fundraiser benefits the Boys & Girls Clubs of Annapolis & Anne Arundel County, supporting programs that empower local youth. Expect a day of friendly competition, great networking, and meaningful impact—plus a chance to show off your swing. More info: bgcaa.org | 410-263-2542
A Night with Ray Weaver
Singer-songwriter Ray Weaver returns to his hometown for a soulful night of stories and songs on Monday, September 15 at Killarney House Irish Pub. Enjoy an intimate acoustic performance alongside a delicious three-course dinner, all for just $40. With heartfelt lyrics, warm humor, and a deep connection to the local community, Ray’s performance promises an unforgettable evening. Perfect for date night or a meaningful Monday out. More info: killarneyhousepub.com | 410-798-8700
Fall Festival on the Green
Celebrate the start of fall at the beloved Fall Festival on the Green, taking place Saturday, September 27 from 10 a.m.–3 p.m. in Crofton. Hosted by the Greater Crofton Chamber of Commerce, this free community event features food trucks, craft vendors, games, inflatables, and live entertainment for all ages. Bring the family, grab a pumpkin spice treat, and enjoy the crisp autumn air. More info: croftonchamber.com | 410-897-2069
Al Green at The HALL at Live! Casino & Hotel Maryland
Feel the soul and soak in the nostalgia as legendary singer Al Green performs live on Friday, September 19 at The HALL at Live! in Hanover. With timeless hits like “Let’s Stay Together” and “Tired of Being Alone,” this is a once-in-a-lifetime chance to see a true icon in an intimate setting. Doors open at 6:30 p.m.—don’t miss your chance to catch this unforgettable concert. More info: maryland.livecasinohotel.com | 443-445-2930
St. Michaels Concours d’ Elegance
Step into a world of vintage luxury at the St. Michaels Concours d’Elegance, taking place September 26–28 at the Kent Island Yacht Club. Admire rare classic automobiles and sleek wooden yachts while enjoying live music, upscale vendors, and fine waterfront views. Sunday’s public show is perfect for car enthusiasts and families alike, offering a stylish day on the Bay. More info: smcde.org | 410-643-4101
Ride for Clean Rivers
Hop on your bike for a good cause at the Ride for Clean Rivers, taking place Sunday, September 21. Hosted by ShoreRivers, this scenic cycling event features 20-, 35-, and 62-mile routes through the beautiful backroads of Talbot and Queen Anne’s counties. Enjoy rest stops, waterfront views, and a picnic celebration—all while supporting clean water efforts on the Eastern Shore. More info: shorerivers.org | 443-385-0511
3rd Annual Lil’ Amp’s Bent Rods Fishing Tournament
Cast your line for a cause at Lil’ Amp’s Bent Rods 3rd Annual Fishing Tournament on Saturday, September 13 (rain date: September 14). Launching from Red Eye’s Dock Bar in Grasonville, anglers compete for big prizes—$15,000 for the heaviest striped bass and $2,500 for the largest catfish. The day includes weigh-ins, live music, and a celebration, all while raising funds for Project Restart. It’s a feel-good way to spend a day on the water. More info: notmychildinc.org | 410-216-9309
