The Anne Arundel County Fair is back with five days of classic fair fun for the whole family!
September is serving up a little bit of everything around the Chesapeake! From waterfront music festivals and Jimmy Buffett-inspired island vibes to fall markets, live jazz, scenic races, and community celebrations, there are plenty of ways to get out and enjoy the week. Shop local makers, catch a show, paddle the Eastern Shore, or spend the weekend supporting great causes throughout the region. Whatever you’re in the mood for, your September calendar is about to get busy!
Anne Arundel County Fair
September 16th- 20th; Anne Arundel County Fairgrounds, Crownsville 5:00pm
The Anne Arundel County Fair is back with five days of classic fair fun for the whole family! Enjoy midway rides, livestock shows, live music, tractor pulls, entertainment, vendors, kids’ activities, and plenty of your favorite fair food. From the thrill of the rides to the charm of the agricultural exhibits, there’s something for everyone to enjoy at this longtime local tradition.Top of FormBottom of Form
New Village Academy Open House
September 17th; New Village Academy, Annapolis 5:00pm
See what high school can look like differently at New Village Academy’s Open House! Tour the school, meet the team, and learn how this free public charter high school combines small classes, project-based learning, internships, and personalized college and career support. Families can explore the school’s approach and learn more about enrollment for the upcoming school year.
Comics for Critters
September 17th; Harry Browne’s Restaurant, Annapolis 7:00pm
Laugh for a cause at Comics for Critters, an evening of stand-up comedy benefiting the animals of the SPCA of Anne Arundel County! Settle in for a night packed with laughs while supporting the organization’s work caring for local animals in need. Grab some friends, enjoy the show, and turn your night out into an opportunity to give back. It’s comedy with a cause, and plenty of laughs along the way!
AAWDC Workforce Impact Awards Reception
September 17th; Live! Hotel & Casino Maryland, Hanover 6:00pm
Celebrate 25 years of strengthening the local workforce at AAWDC’s inaugural Workforce Impact Awards Reception and Anniversary Celebration! Business leaders, community partners, and workforce champions will come together for an evening of networking, recognition, and celebration of the people making an impact across the region. The event will also raise funds for AAWDC’s Endowment Fund, helping support workforce solutions that benefit local businesses and the regional economy for years to come.
Peace Love Pickleball Tournament
September 18th; The Putaway, Millersville 6:00pm
Serve up some fun for a great cause at the Peace Love Pickleball Tournament! Cheer on players as they hit the courts in support of seven local nonprofits, including Hospice of the Chesapeake, while enjoying food, beer, wine, and plenty of friendly competition. Guests can also sharpen their game during a skills clinic, with racquets available for those who need one. Whether you play, cheer, or simply come for the fun, every swing helps make a difference in the community.
You're a Good Man, Charlie Brown
September 18th – 19th; Annapolis Mall, Annapolis 7:30pm
Spend the weekend with Charlie Brown, Snoopy, Lucy, Linus, and the rest of the Peanuts gang in You’re a Good Man, Charlie Brown! This award-winning musical brings the beloved comic strip to life through baseball games, homework struggles, crushes, catchy songs, and plenty of heartwarming moments celebrating friendship. Catch performances Friday, September 18th at 7:30 p.m.; Saturday, September 19th at 2 and 7:30 p.m.; or Sunday, September 20th at 2 p.m. It’s a nostalgic and fun-filled show for longtime Peanuts fans and a whole new generation to enjoy.
Girls on the Run Music Bingo FUNdraiser
September 18th; Homestead Gardens, Davidsonville 5:30pm
Test your music knowledge and have some fun for a great cause at the Girls on the Run Music Bingo FUNdraiser! Play along as songs replace traditional bingo numbers, with plenty of chances to sing, guess, and compete throughout the evening. Your ticket includes a bingo packet, with food and drinks available for purchase. Proceeds benefit the Girls on the Run of the Greater Chesapeake scholarship fund, helping make its programs more accessible to girls throughout the community.
For the Love of the Library
September 18th; Michael E. Busch Library, Annapolis 6:00pm
Celebrate everything the library makes possible at For the Love of the Library! Enjoy an evening of delicious food from Palate Pleasers, great conversation, and a special appearance by local author Nikki Payne, who will mingle with fellow readers and book lovers. Gather with the community for a fun night out while helping raise support for the programs, resources, and opportunities the library provides.
Black Water Refuge & RAR - Cambridge Adventure Paddle
September 19th; Black Water Refuge, Cambridge 10:30am
Paddle into adventure and explore the natural beauty of Blackwater National Wildlife Refuge! Glide through peaceful waters surrounded by marshlands, scenic landscapes, and the refuge’s diverse wildlife during this guided outdoor experience. After your time on the water, head into Cambridge to RAR Brewing to relax and toast to the adventure, with your first drink included. It’s the perfect combination of outdoor exploration and local flavor on the Eastern Shore.
FS8 Annapolis Grand Opening
September 19th; FS8 Studio, Annapolis 2:00pm
Celebrate the arrival of FS8 Annapolis at its Grand Opening Party! Tour the brand-new studio, meet the owners and trainers, and discover FS8’s high-energy, low-impact workout combining Pilates, strength and toning, and yoga-inspired movement. The celebration will feature food, drinks, giveaways, raffle prizes, and a station where guests can design their own T-shirt or sweatshirt. Whether you’re a fitness regular or looking to try something new, stop by and see what FS8 is all about!
Hospice Cup Regatta & Shore Party
September 19th; Horn Point Marina, Annapolis 5:30pm
Set sail for a great cause at the Hospice Cup Regatta, America’s largest charity yacht race! More than 100 boats and nearly 1,000 sailors come together for a day of racing in support of nonprofit hospice care in the community. You don’t have to be a sailor to join the fun—head to the Shore Party after the races for food, drinks, golf off the dock, live and silent auctions, and music from Gretna Green. It’s a beloved Annapolis tradition that combines life on the water with an important mission.
BAYGRASS 2026: Annapolis Baygrass Music Festival
September 19th & 20th; Sandy Point State Park, Annapolis 10:00am
Feel the rhythm by the Bay at the Annapolis Baygrass Music Festival! This two-day beachfront celebration brings bluegrass, jamgrass, Americana, and more to side-by-side stages, along with local food, fresh oysters, craft drinks, yoga, games, kids’ activities, vendors, and conservation workshops. Beyond the music, Baygrass supports Chesapeake Bay protection and restoration as well as mental health awareness and wellness resources. Come for the jams, stay for the waterfront festival vibes, and have fun while supporting two meaningful missions.
Ballet in the Garden
September 19th; Hammond Harwood House, Annapolis 5:00pm
Step into the garden for an enchanting evening of dance with Ballet in the Garden! Set against the beautiful grounds of the historic Hammond-Harwood House, this intimate open-air performance offers an exclusive preview of Ballet Theatre of Maryland’s upcoming season, featuring classical, neoclassical, and contemporary works. Dress for the garden party, sip a complimentary glass of wine, and enjoy a one-of-a-kind ballet experience in one of Annapolis’ most picturesque settings.
21st Annual Boatyard Beach Bash
September 19th; Annapolis Maritime Museum & Park, Annapolis 4:00pm
Escape to Key West without leaving Annapolis at the 21st Annual Boatyard Beach Bash! This waterfront celebration honors the music and legacy of Jimmy Buffett with six hours of live performances from members of the iconic Coral Reefer Band and an incredible lineup of island-inspired musicians. Enjoy Jimmy Buffett classics, coastal favorites, crafted cocktails, gourmet bites, and plenty of laid-back tropical vibes along the Bay. Grab your fellow Parrotheads and get ready for one unforgettable night in paradise!
Anchors + Artisans
September 20th; Annapolis Town Center, Annapolis 11:00am
Shop small and celebrate local creativity at Anchors + Artisans! Browse handmade goods from more than 50 Maryland makers, artists, and creatives while enjoying a lively day of shopping and community fun. This month’s market will feature live music from Hat and Hair Trio, adding the perfect soundtrack as you explore one-of-a-kind finds. Come discover something new and support the talented makers right in your backyard!
Community Harvest Supper
September 20th; Inn at Perry Cabin, St. Michaels 3:00pm
Gather around the table for the inaugural Community Harvest Supper, a celebration of the food, people, and community that make the Eastern Shore special. St. Michaels chefs and local farmers will come together to create a family-style feast, complemented by a welcoming reception, live music, dancing, and silent and live auctions. The evening supports the St. Michaels Community Garden, Community Center, and Farmers Market, making every seat at the table part of something bigger. Come hungry and celebrate the bounty of the season with the community!
Annapolis RUN for The Light House - HALF | 5k | walk
September 20th; Quiet Waters Park, Annapolis 8:00am
Run, walk, and make every mile matter at the 17th Annual Annapolis RUN for The Light House! Choose from a half marathon, 5K, or walk featuring scenic routes through Quiet Waters Park and the Chesapeake Bay-front community of Hillsmere Shores. This popular event has sold out for the past five years, bringing the community together while raising critical funds for The Light House. Every registration supports its mission to help break the cycle of homelessness and poverty in the Annapolis community.
Jazz Garden Ramble @ Historic London Town & Gardens
September 22; Historic London Town & Gardens, Edgewater 6:00pm
Stroll through the gardens after hours during a special evening of live jazz at Historic London Town & Gardens! Members of Baltimore’s The Funn Band, led by renowned educator and performer Charles Funn, will provide the soundtrack as guests wander among blooming asters, crocuses, and other seasonal beauty. Sip themed cocktails along the way and enjoy a relaxed evening where music, nature, and garden views come together. This event is for guests ages 21 and older.
Tunesday By Chronic Sailing
September 22nd; Back Creek Eastport, Annapolis 6:00pm
Float into the evening with Tunesday by Chronic Sailing, Annapolis’ on-the-water concert series! This week, Jimi Haha takes the floating stage aboard an anchored catamaran for a laid-back live performance on Back Creek. Cruise over by boat, kayak, or paddleboard and enjoy the music surrounded by waterfront views as the sun begins to set. This free, family-friendly gathering is a uniquely Annapolis way to enjoy live local music on the water.
