Photo by Ted Mueller
Get ready for a week packed with local flavor, artistic flair, and community fun across the Chesapeake region! Cruise the Bay with a cold drink in hand, catch jazz and fireworks at the Potomac’s biggest summer festival, and explore everything from plein air painting in Easton to musicals, farmers markets, and soccer under the stadium lights. There’s something for every pace and personality. Don’t let summer slip by—this week is full of moments worth making.
Wilma Lee Wednesday Night Races Watch Party
July 9th; Annapolis Maritime Museum, Annapolis 5:30 - 7:30pm
Join our crew for a two-hour extraordinary cruise enjoying the Wednesday Night Races on the Chesapeake Bay. Includes complimentary beverages (wine, beer, canned cocktails and soda).
Annapolis Opera Presents: Stories Through Music
July 9th; Maryland City Russet Community Library, Laurel 6;00pm – 7:00pm
Join the Annapolis Opera House for Stories Through Music, a lively and interactive concert experience designed especially for kids and families. This engaging program introduces young audiences to the magic of storytelling through classical and popular music favorites. Through fun narration, live performance, and audience participation, children will learn how melodies, lyrics, and rhythms come together to tell powerful stories. It’s a perfect way to spark imagination, curiosity, and a love for music — all in an entertaining and educational setting!
Potomac Jazz and Seafood Festival
July 10th – 13th; St. Clement’s Island Museum, Coltons Point
Get ready to groove! The Potomac Jazz & Seafood Festival is turning the big 2-5, and we're throwing a party you won't want to miss! Join us for four days of jazz, fun and waterfront vibes in beautiful Southern Maryland's scenic St. Mary's County. This isn't just a festival; it's a silver jubilee celebration of music, community and the stunning beauty of the Potomac River. The main event is on July 12.
Talbot County Fair
July 10th – 12th; Talbot Agriculture and Education Center, Easton
The Talbot County Fair is an annual celebration of agriculture, community, and family fun in Talbot County, Maryland. Featuring livestock exhibits, 4-H showcases, local crafts, live entertainment, and delicious food, the fair highlights the region's rural heritage and provides educational and recreational opportunities for all ages. It’s a cherished event that brings together residents and visitors to enjoy the best of Talbot County's traditions and talents.
Tuckahoe Steam and Gas Show
July 10th – 13th; Tuckahoe Steam and Gas Association, Easton
The Tuckahoe Steam and Gas Association is hosting the 52nd Annual Steam and Gas Show on July 10th through 13th at their campus in Easton. The non-profit, all volunteer organization helps preserve the historic Eastern Shore’s rural heritage. The weekend will be filled with steam engines, live steam train models, antique gas engines and tractors, home arts demonstrations, live music, blacksmiths, a tractor pull and so much more. Find more information at tuckahoesteam.org
Plein Air Easton
July 11th – 20th Downtown Easton, Easton
Join us in welcoming the 58 artists who will be spending the week painting all over Talbot County and be sure to view the exhibits of their work at Plein Air Easton Headquarters (new inventory added daily) and the Academy Art Museum (July 19 and 20). Spend the evening strolling through downtown Easton, enjoying live music, special sales and gallery receptions as we throw open our doors to welcome artists and visitors alike. Bring your paints and join us for a Nocturne Paint-out after sunset.
The Talent Machine Co. Presents: The Addams Family ~ A Musical Comedy
July 11th , 12th, 13th; Anne Arundel Community College Kauffman Theater, Annapolis 7:00pm- 9:30pm
Don't miss The Talent Machine's production of this special, often poignant, musical comedy, featuring an incredibly talented cast of performers aged 14 to 18. The show's director, Micheal Stromberg, describes the show this way:
"At its core, this production explores what it means to be 'normal.' In a society that often tries to fit us into boxes of expectations, The Addams Family reminds us to take pride in who we are, where we come from, and the experiences that shape us – and to remember that embracing differences can bring people together."
Annapolis Blues Men's Soccer Home Game
July 12th, 5:00 p.m.; Navy Marine Corps Memorial Stadium, Annapolis
The Annapolis Blues Men take on Charlottesville Blues FC in what promises to be a thrilling game full of energy and team spirit!
St. Michaels Farmers Market
July 12th; Downtown St. Michaels; Talbot County 8:30 – 11:30am
The St. Michaels Farmers Market (SMFM) is a non-profit, producer-only farmers market in charming St. Michaels on Maryland’s Eastern Shore, located downtown at 206 South Talbot Street, and taking place on Saturdays from April through November between 8:30 a.m. to 11:30 a.m., rain or shine. After more than 25 years of supporting local farmers and a sustainable food system, the SMFM has become a beloved community ritual, with more than two dozen vendors selling everything from fresh fruit, vegetables, and flowers through farm-raised meat, Chesapeake Bay seafood, baked goods, and more, all certified as grown or made within 60 miles of market. Also expect live music, family-fun activities, and community non-profit pop-ups throughout the year.
A.Y.C.E. BRUNCH @ Cult
July 12th Cult Classic Brewing Company, Stevensville 9:00am – 1:00pm
Feast your wallet on the hottest deal in town. CULT CLASSIC introduces an All-You-Can-Eat Brunch from 9am - 1pm every Saturday & Sunday. Load your plate with with all the eggs, bacon, sausage and UNCH you can handle. We've also got some waffle-y delicious toppings for your made-to-order waffles. Omelet you finish, but not before you load that lil egg pouch with all the freshest ingredients in the bar. Wash it all down with our Château Cult Mimosas or whatever makes you feel human.
Wilma Lee Heritage Cruises
July 12th; Annapolis Maritime Museum, Annapolis 1:00pm – 3:00pm
Experience Annapolis and the Chesapeake Bay like never before on this guided two-hour heritage tour aboard the historic Skipjack Wilma Lee. Learn about the city’s history and the ecology of the Bay while viewing landmarks like the Chesapeake Bay Bridge and the Naval Academy. Tour guides will identify and share fun facts about native Chesapeake Bay wildlife along the cruise. Perfect for families and maritime enthusiasts.
Summer Concert Series:
Waugh Wednesdays: Summer Concert Series – July 9th; Waugh Chapel Town Center: Remains of the Radio
Thursdays in the Park- July 10th; Queen Annes Center for the arts: Trinity Blues Band
Tides & Tunes – July 10th; Annapolis Maritime Museum: One Night only, classic rock
Bayside Summer Concert Series – July 13th; Downs Park
Live On the Lawn – July 13th; Maryland Hall: Dominique Bianco Feat. Tommy Holladay
Allen Pond Summer Concert Series – July 13th; Allen Pond Park: “257th Army Band”
Tunesday: Summer Concert Series – July 15th; Back Creek and Second Street Eastport: Mike Mchenry
