Summer’s heating up and so is the lineup of events across the Chesapeake region! From the down-home charm of the Kent County 4-H Fair to the smooth sounds of the Lake Arbor Jazz Festival, there’s something for every mood and moment. Stroll the streets of Easton during Plein Air week, catch a cruise on the Wilma Lee, or settle in for live theater and local markets. Whether you're chasing sunsets, good eats, or great music—this week is packed with reasons to get out and enjoy it all.
Kent County 4H Fair
July 16th - July 19th; Kent Agricultural Center, Chestertown
The annual Kent County 4-H Fair will be held at the Kent AG Center in Chestertown on July 16th through 19th. The fair is a perfect family weekend with great food, 4-H and community exhibits, animals, tractors, games, and plenty of entertainment for all ages. Find a full list of vendors and things to do at kentcountyfair.org
Lake Arbor Jazz Festival
July 16th - July 20th; National Harbor
Lake Arbor Jazz Festival at National Harbor. The Lake Arbor Jazz Festival is embarking on a new journey and new format for its 15th anniversary! We’re taking the music, the energy, and our amazing music community to National Harbor, MD – a location that will offer our festival even more room to grow, thrive, and elevate your experience!
Wilma Lee Wednesday Night Races Watch Party
July 16th; Annapolis Maritime Museum, Annapolis 5:30pm – 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).
The Talent Machine Co. Presents: The Addams Family ~ A Musical Comedy
July 17th , 18th , 19th, 20th; 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."
Severna Park Blood Drive
July 18th; Gary’s Grill & Catering, Annapolis 8:00am – 2:00pm
Help save lives and support your community by donating blood at our upcoming drive, sponsored by the Greater Severna Park and Arnold Chamber of Commerce and the Good Neighbors Group. All donations benefit Luminis Health and can make a life-changing impact for patients in need. Donors must be in good health, 18–74 years old (or 16–17 with parental consent), and meet basic weight requirements. A photo ID is required. Be sure to eat a full meal and stay hydrated before donating. Walk-ins are welcome based on availability. For questions, call 443-481-4215. Give the gift of life—it only takes a moment to make a difference.
St. Michaels Farmers Market
July 19th; Downtown St. Michaels, Talbot County 8:30am – 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 19th 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 19th; 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.
English Country Dance
July 19th; Annapolis Friends Meeting Hall, Annapolis 6:30pm – 9:30pm
English Country Dance to delightful live music - Intro lesson at 6:30; dance at 7:00. Capped attendance, so pre-registration required via email to aefallon@verizon.net. Venue has filter fans for air circulation and ventilation. All dances taught, walked through and called. No experience or partner required. No food/drinks provided; please bring own drinking water. $10. Info: Jan Scopel, 443-540-0867, janscope@hotmail.com or Ann Fallon, 410-507-0934
Plein Air Easton
July 16th – 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
Annapolis Opera Presents: Stories Through Music
July 21st; 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!
Concert Series:
Waugh Wednesdays: Summer Concert Series - July 16th; Waugh Chapel Town Center: The 1974
Tides & Tunes – July 17th; Annapolis Martime Museum: Reverend Smackmaster & The Congregation of funk
Live On the Lawn – July 19th; Maryland Hall: Dirty Grass Players
Bayside Summer Concert Series – July 20th; Downs Park
Allen Pond Summer Concert Series – July 20th; Allen Pond Park: The Hubcaps
Tunesday: Summer Concert Series – July 22nd; ; Back Creek and Second Street Eastport: Callum
