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. 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.

Sept. 4: Outdoor Movie Night Transformers One – Movies start when it’s dark. Idlewild Park, Washington & Idlewild, Easton. Bring a chair and blanket. Sponsored by Preston Automotive Group. Discovereaston.com.

Sept. 5 & 6: Join members of the St. Michaels Art League (SMAL) for their biggest event, the annual “Under the Tent” Labor Day Weekend Show and Sale at St. Luke’s United Methodist Church, located at 304 South Talbot Street in St. Michaels. The exhibit is free and open to the

Sept. 5: Charity Boat Auction. The live auction begins at 11am along Chesapeake Bay Maritime Museum’s waterfront campus, where boats will be auctioned off to the highest bidders.

Transport yourself to the heart of Piedmont for an afternoon of authentic regional flavors, handcrafted dishes, and the wines that bring them to life. This is more than a cooking class — it's an immersive Italian experience. Join us as we explore the rustic traditions of Piedmont, Marco's Home area,

Sept. 10-12: Outdoor Pig Roast at the Amish Country Farmers Market, 101 Marlboro Avenue, Easton.

Sept. 10: Dining in Colonial Maryland – a 250th Program, 5:00pm at the Oxford Community Center. Cookbook author and historian Joyce M. White will be speaking about historic foodways and material culture. The talk includes a buffet of food from the time prepared by Momma Maria’s. In partnership with the

Sept. 10: The Oxford Community Center and the Oxford Museum Present “A Taste of History”, 5:30pm at the Oxford Community Center. Cookbook author and historian Joyce M. White. Speaker presentation with a food tasting included. Tickets $10. oxfordmuseummd.org

Sept. 12: Tides of Grace invites families from across Maryland’s Eastern Shore to come together for Family Fun Day, 2-5pm at the Caroline County 4-H Park in Denton, MD. Inflatables, carnival and giant yard games, craft and activity stations, face painting, temporary tattoos, a balloon artist, petting zoo, foam party,

Sept. 14: Grocery Bingo (2nd Monday due to Labor Day holiday) at the Cordova Firehouse. Doors open at 5:45 and games begin at 6:30. Refreshments are available. For more information, call Cathy at 410-924-6535.

Sept. 14: The next speaker meeting of the Tidewater Camera Club will be on September 14, at Unitarian Universalist Fellowship. The meeting will start at 7pm, Doors open at 6:15pm, All are Welcome. The speaker and topic will be available on the TCC calendar when details are known. The website