Aug. 1: Summer Sing Choir Festival, 7pm at the Waterfowl Festival Building, 40 S. Harrison St., Easton, 7pm. Free Admission. Allegro Academy's most anticipated event, the Summer Sing Choir Festival invites singers from across the Mid-Shore to join the intergenerational community choral event. Come Alive!: Music from Stage and Screen,

Aug 1: Outdoor Summer Concert – USNA Band Electric Brigade – 7pm. Harrison Street in front of the Tidewater Inn, Easton. No Rain Venue.

Aug. 1: The Oxford Community Center Welcomes Steve Lowe and The Lowe Downs, 7:30pm. Tickets $20. oxfordcc.org.

Aug. 5-8: Caroline-Dorchester County Fair. For a full schedule of events and information on livestock shows, contests, demonstrations, and more family fun. Visit https://carolinedorchestercountyfair.com or find us on Facebook@ Caroline Dorchester County Fair.

Aug. 6-8: Cordova Country Fair.

Aug. 7, 8, 9: Eastern Shore Threshermen & Collectors Association 66th Annual Old-Time Wheat Threshing, Steam and Gas Engine Show at 5806 Federalsburg Hwy., Federalsburg. Free admission. Free parking. Daily parade. Large flea market. Free music: The Ramblers Country Music Fri. evening, Flatland Drive Bluegrass Sat. evening. Music Sunday 5pm.

Aug. 7-9: Oxford Regatta, including Log Canoes. Watch the races along the Tred Avon River from one of our numerous waterfront areas in Oxford, Maryland! Oxford Regatta – Log Canoes, Opti’s, Stars & Shields, Penguins & Adult ILCA, Jr. C420, JR.

Aug. 7: The Rocke-who? The Rocketeer! Bring a chair and a blanket for cinema under the stars! Our movie nights are free for all ages. Come and enjoy this thrilling, classic adventure at the Easton Airport, 8:30-10:30pm.

Aug 8: Discover Treasures Hidden in Easton! Easton is host to a bevy of fantastic vintage and antique markets, all brimming with unique finds for the discerning eye. From curated collections to thrifty catch-alls, there's a shop for everyone with an interest in finding that perfect previously-owned piece. Spread out

Aug. 8: 24th Annual Peach Festival, 9am-2pm, at the Preston Fire Hall, 3680 Choptank Rd., Preston. Local peaches, ice cream, baked goods, scrapple sandwiches, soft crab sandwiches, crafters and vendors. Benefits Bethesda Methodist Church. For information call 410-673-7538. office@bethesdapreston.faith.

Aug. 8: St Michaels Community Center is holding an old-fashioned block party, 12-3pm. Food, music, face-painting, games and service vendors will be on-site. Bring the family! 103 Railroad Ave, St Michaels. For more information, ValP@StMichaelsCC.org

Aug. 8: 2026 Free Summer Adventure Movie Series – Stand By Me – 2pm. Talbot County Free Library, 100 W. Dover Street, Easton. Free admission. Refreshments will be served. Presented by the Talbot County Free Library and the Chesapeake Film Festival.

Aug. 9: Community Breakfast at the Oxford Firehouse, 300 Oxford Road, Oxford, 8am-11am.. $12/adult, and kids under 12 eat free! Please check for event updates at https://www.facebook.com/OxfordFireCo

Aug. 9: Watermen’s Appreciation Day – 10am–4pm. Chesapeake Bay Maritime Museum, 213 N. Talbot Street, St. Michaels.

Aug. 12: For All Seasons' School Supplies Giveaway & Resource Fair. Join For All Seasons for a fun evening featuring FREE BACKPACKS, school supplies, community resources, games, food, raffles, and more to help students start the school year with confidence. Thank you to our generous sponsors for making this event

Aug. 13-23: Tred Avon Players presents Dirty Rotten Scoundrels. Musical Comedy. Music and Lyrics by David Yazbek, Book by Jeffrey Lane. Directed by JW Ruth. Two con men, a beautiful woman and the elite of the French Riviera collide in a “sexy and irreverent farce.” After meeting on a train,

Aug. 15:  Monteray Farm’s 1st Annual Sunflower Fest, 9am-2pm. Admission $10 includes 3 stems of you pick sunflowers, one ticket for multiple door prizes, half of all admission proceeds will help children battling cancer. Local vendors, food trucks, face painting for the kids, live music, photo opts galore, stroll through

Aug. 15: Caroline County Humane Society Pints for Paws, 12-5pm, Cow Barn, Ridgely, MD. Brewery Tastings, Food trucks, Live music, Vendors, Line Dancing, and Children’s Area. $25 pp includes 10 tastings. $40 gets you a t-shirt.

Aug. 19: Community Talk: Chesapeake Forum Program Preview Party, 5-7:00pm at Oxford Community Center. The Chesapeake Forum's Preview Party is a festive, community-oriented social event designed to introduce the upcoming semester's course catalog to lifelong learners. Attendees get a first look at the new roster of classes, trips, and hands-on

Aug, 21: Join us for our 2026 GOSPEL CONCERT SERIES at 6:30pm-9pm, We will have The Pine Ridge Boys (SC) and Mark Dubbeld Family (VA). A Love offering will be taken, and bottled water will be available (no food in church). For information, call Holiday Park 410-482-6797. All are welcome—Bring

Aug. 21: Movie Night at Prager Family Center for the Arts American Graffiti – 7:30pm. Ebenezer Theater, 17 South Washington Street, Easton. Concessions available for Movie Nights include popcorn, slices from Roma Alla Pala, fresh baked cookies, and selections from the bar, including feature cocktails. 420-560-6358.

Aug. 22: What better way to end summer break than a pool party at the Bay Hundred Community Pool, St. Michaels, 3-5pm.

Aug 29: 2026 Free Summer Adventure Movie Series – National Treasure - 2pm. Talbot County Free Library, 100 W. Dover Street, Easton. Free admission. Refreshments will be served. Presented by the Talbot County Free Library and the Chesapeake Film Festival.