The Maryland Seafood Festival returns to Sandy Point State Park in Annapolis on Saturday and Sunday, September 13–14, from 11:00 AM to 7:00 PM.
From teeing off for a cause to paddling under the Bay Bridge, this week’s calendar is packed with one-of-a-kind experiences. Annapolis will be alive with music, markets, seafood feasts, and heritage festivals, while yoga, comedy, and vintage shopping round out the mix. Whether you’re craving a night of elegance, a day on the water, or a reason to lace up your running shoes, there’s plenty waiting to be discovered.
Bello Machre 41st Annual Golf Tournament
September 10th; Queenstown Harbor Golf Resort, Queenstown 10:00 am – 4:00pm
Tee off for a cause at Bello Machre’s annual golf tournament, where players enjoy a great day on the greens while supporting children and adults with developmental disabilities. This beloved fundraiser combines friendly competition with community spirit, offering participants a chance to make a lasting difference while enjoying a memorable day of golf.
Anne Arundel County Fair
September 10th – 14th; Anne Arundel County Fairgrounds, Annapolis
From tractor pulls to pig races, the fun never stops during Anne Arundel County Fair week. Held at the county fairgrounds in Crownsville, this family-friendly tradition offers thrilling rides, live entertainment, agricultural exhibits, and plenty of fair food favorites—including funnel cakes. Gather your friends and family for a week of classic fair fun celebrating community and county pride.
Yin and Peaceful Yoga in Downtown Annapolis
September 11th; 17 Francis St, Annapolis 12:00pm – 1:00pm
Pause and recharge with a refreshing, all-levels yoga flow every Thursday at 12:00 PM. This guided group session offers a calming break in the middle of the day, with the option to extend your wellness time for up to an hour through self-guided practices such as breathwork, journaling, and quiet stretching. Perfect for both beginners and experienced yogis, Mid-Day Yoga is a simple way to relax, reset, and return to your day feeling centered and energized.
Season Opening Celebration: Black and White Gala
September 11th; The Atreeum at Soaring Timbers, Pasadena 6:00pm – 9:00pm
Celebrate the start of the opera season with a night of sophistication and artistry hosted by the Annapolis Opera Guild. The evening begins with a lively cocktail hour, followed by a gourmet seated dinner prepared by Palate Pleasers, and concludes with captivating live performances. This annual event supports the Annapolis Opera and its mission to bring the transformative power of opera to the community.
Annapolis Songwriters Festival
September 12th; Calvert and West Street, Annapolis 7:00pm – 11:00pm
Inspired by the famed Key West Songwriters Festival, the Annapolis Songwriters Festival brings top talent and unforgettable music to the shores of the Chesapeake Bay. For four days, downtown Annapolis comes alive with performances in intimate theaters, historic venues, and the city’s best-known bars and restaurants. Music lovers can connect with the voices and stories behind the songs, discovering the artistry of both national names and local rising stars. With its blend of waterfront charm and vibrant nightlife, Annapolis offers the perfect setting for this unique celebration of live music.
Maryland Seafood Festival
September 13th; Sandy Point State Park, Annapolis 11:00am – 7:00pm
The Maryland Seafood Festival returns to Sandy Point State Park in Annapolis on Saturday and Sunday, September 13–14, from 11:00 AM to 7:00 PM. A true celebration of Maryland heritage, the festival features fresh seafood prepared in every style, local vendors, craft beer, kids’ activities, and live entertainment. Highlights include the Crab Soup Cook-off on Saturday, Jimmy’s Famous Seafood’s steamed crab pre-orders, and the popular Naptown Seafood Sampler offering tastings from area restaurants. With stunning Bay views as the backdrop, this rain-or-shine event is a must for seafood lovers of all ages.
Kunta Kinte Heritage Festival
September 13th; Navy marine Corps Stadium, Annapolis 10:00am
Annapolis City Dock hosts the annual Kunta Kinte Heritage Festival on Saturday, September 13, celebrating African and African American culture through art, food, music, and storytelling. Festival goers can explore the Arts & Crafts Village with handmade goods, enjoy authentic cuisine from the Global Flavors Food Court, and experience live dance and music performances throughout the day. Headliners include R&B icon Jon B, gospel legends The Canton Spirituals, and In Gratitude, an Earth, Wind & Fire tribute band, alongside local artists. With family-friendly activities, cultural exhibits, and a lively waterfront setting, the festival is a vibrant celebration of legacy and community.
Oyster Thyme Feast
September 13th; 12:00pm – 5:00pm
Celebrate the Bay with an evening of oysters, fine wine, and community at Oyster Thyme Feast. Guests will enjoy a luxurious spread of raw oysters alongside oyster-inspired dishes such as creamy oyster stew, crispy fried oysters, and cornbread oyster po’boys. Each bite is paired with exceptional wines thoughtfully selected by Chef Rik to highlight the flavors of the Chesapeake. More than a feast, this event blends culinary artistry with a commitment to giving back to the Bay, making it an unforgettable dining experience.
Annapolis RUN for The Light House
September 14th; Quiet Waters Park, Annapolis 8:00am – 11:00am
The 16th annual Annapolis RUN for The Light House takes place on Sunday, September 21, offering scenic half marathon, 5K, and walk routes through Quiet Waters Park and the waterfront community of Hillsmere Shores. This unique race experience combines natural beauty with community spirit, attracting runners and walkers of all levels. All proceeds support The Light House in Annapolis, a nonprofit dedicated to breaking the cycle of homelessness and poverty. Join fellow participants for a meaningful race that makes a lasting impact.
Bay Bridge Paddle
September 14th; Sandy Point State Park, Annapolis 7:15am – 1:00pm
The Bay Bridge Paddle returns to Sandy Point State Park’s East Beach on Sunday, September 14, 2025. This signature paddling event offers races and recreational opportunities for all levels, set against the iconic backdrop of the Chesapeake Bay Bridge. Participants and spectators alike can enjoy a day on the water celebrating community, fitness, and the Chesapeake Bay lifestyle. Proceeds benefit the Foundation for Community Betterment, supporting local initiatives that make a lasting impact.
Annapolis Vintage Market
September 14th; Vintage Vibe Finds, Annapolis 11:00am – 5:00pm
Discover one-of-a-kind treasures at the Annapolis Vintage Market on Sunday, September 14, from 11:00 AM to 5:00 PM at 40 Hudson Street, Unit 107. Hosted by Vintage Vibe Finds and Artfully Acquired, this outdoor market features more than 15 curated vintage vendors offering unique finds, along with live music and a food truck on site. Held rain or shine, the market is the perfect spot to shop, eat, and enjoy a fun day with the local community.
