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  • Canvases of the Cosmos with Roland Comtois

    104 Railroad Avenue St Michaels, Maryland

    Visionary artist Roland Comtois invites the public to experiencean extraordinary weekend where art, light, and imagination converge during Canvases of the Cosmos, a captivating exhibition at Simpatico Trattoria, located at 104 Railroad Ave., St. Michaels, MD. Following acclaimed gallery exhibitions in Connecticut and Rhode Island, Roland Comtois presents the next

  • Baywater Classic Golf Tournament

    July 30: Baywater Classic Golf Tournament, Queenstown Harbor. Exciting contests and amazing prizes. Register your team at baywaterwomens.com or call 410-822-1869.

  • Trappe Vol. Fire Co. Annual Fair

    July 30-Aug. 1: Trappe Vol. Fire Co. Annual Fair. The fair is open from 6pm-10pm each night! We will have delicious food, fire truck rides, hayrides, games, cake wheel, silent auction & lots more. Music & entertainment by Shelley Abbott! Don’t miss our parade Saturday at 6pm.

  • Free Summer Adventure Movie Series – Raiders of The Lost Ark

    Talbot County Library, Easton, Maryland 100 West Dover Street, Easton, Maryland

    July 31: Free Summer Adventure Movie Series – Raiders of The Lost Ark - 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.

  • Classic Sicilian Bites Cooking Class 2 PM

    104 Railroad Avenue St Michaels, Maryland

    Join us for a class where we explore classic Sicilian flavors with 3 courses and 3 wines! Taught by Chef Dawn and Bobbi Parlett with an accompanied wine pairing. For more information, the menu, and to purchase tickets, click here: https://www.simpaticostmichaels.com/events-1/classic-sicilian-bites-cooking-class-2-pm

    $78

  • Classic Sicilian Bites Cooking Class 12 Noon

    104 Railroad Avenue St Michaels, Maryland

    Join us for a class where we explore classic Sicilian flavors with 3 courses and 3 wines! Taught by Chef Dawn and Bobbi Parlett with an accompanied wine pairing. For more information, the menu, and to purchase tickets, click here: https://www.simpaticostmichaels.com/events-1/classic-sicilian-bites-cooking-class-12-noon

    $78

  • Summer Sing Choir Festival

    Waterfowl Festival Building 40 S. Harrison Street, Easton, Maryland

    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,

  • Caroline-Dorchester County Fair

    Caroline County 4-H 8230 Detour Road, Denton, MD, United States

    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.

  • Oxford Regatta, including Log Canoes

    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.

  • The Rocke-who? The Rocketeer

    Easton Airport Easton, Maryland

    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.

  • Discover Treasures Hidden in Easton

    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

  • 24th Annual Peach Festival

    Preston Fire Hall 3680 Choptank Road, Preston, Maryland

    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.

  • St Michaels Community Center is holding an old-fashioned block party

    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

  • 2026 Free Summer Adventure Movie Series

    Easton Library MD, United States

    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.

  • Community Breakfast at the Oxford Firehouse

    Oxford Fire Co. 200 Oxford Rd., Oxford, MD

    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

  • Watermen’s Appreciation Day

    Chesapeake Bay Maritime Museum St. Michaels, MD, United States

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

  • For All Seasons’ School Supplies Giveaway & Resource Fair

    Elks Lodge 1622 502 Dutchman's Lane, EASTON, MD, United States

    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

  • Tred Avon Players presents Dirty Rotten Scoundrels

    Oxford Community Center 200 Oxford Rd., Oxford, MD

    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,

  • Monteray Farm’s 1st Annual Sunflower Fest

    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

  • Caroline County Humane Society Pints for Paws

    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.

  • Community Talk: Chesapeake Forum Program Preview Party

    Oxford Community Center 200 Oxford Rd., Oxford, MD

    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