Eastern Shore 10/10 Picks

19th Annual Chesapeake Film Festival October 8 – 10, 2026 | Easton, Maryland The Chesapeake Film Festival's 19th Season continues the organization's tradition of bringing exceptional independent cinema, filmmakers, and meaningful conversations to the Eastern Shore. Get ready for an unforgettable cinematic experience! The Chesapeake Film Festival will be showcasing as many as 47 of the finest independent films at the beautifully historic Ebenezer Theater, the Academy Art Museum, and the Talbot County Free Library. Don’t miss your chance to be part of this exciting celebration of film and creativity. Reserve your seats at this special price and be among the first to experience the magic! Early Bird Tickets, including an All Access Pass PLUS the VIP Reception, are just $150 until Aug 31 when tickets will again be $175. For movie descriptions,

The Chincoteague Island Farmers and Artisans Market & Kitchen Art Gallery at the Chincoteague Cultural Alliance, 6309 Church Street, will kick off the 2026 season on May 9th from 9am - 1pm with 45+ vendors offering fresh local seafood, produce, other good things to eat and a wide array of arts & crafts. Follow the Chincoteague Island Farmers and Artisans Market Facebook page for more information! Chincoteague Island Farmers & Artisans Market & Kitchen Art Gallery Schedule: Saturdays from May 19 to October 31 Wednesdays from June 17 to September 30 (except Tuesday July 28 during Pony Week) Holiday Market Nov 28 – Saturday of Thanksgiving Day Weekend Free parking, free admission MARKET - Featuring local seafood, produce & other locally made foods, a wide array of arts & crafts, plus live

Attention Kids & Parents: Join the Chincoteague Cultural Alliance on the porch each week during the Island Farmers and Artisans market for a FREE kids craft! Kids must be accompanied by an adult.

About the 53rd Annual Chincoteague Oyster Festival The Chincoteague Oyster Festival is held each year to celebrate Chincoteague "Salts", mark the arrival of oyster season, and promote the seafood industry that is integral to Chincoteague Island. Enjoy all you can eat seafood, live music from Island Boy (a festival favorite for over 30 years), Extravaganza Raffle, Best Space Awards, and so much more! Tickets are $65 per person (Children under 5 are FREE) Add On: Early Access Passes! For $200 two people can gain access to the festival grounds as early as 9:00am to setup their space. These passes are an add-on and must be purchased in addition to regular tickets. Those who purchase Early Access Pass may take the space they need for their group, but no larger than a 20x20 space. Please be considerate and leave enough space for everyone to enjoy the festival! VIP Spaces Available Again this Year! Reserve your own space for the Chincoteague Oyster Festival within a special VIP area!! This area is limited to 10 spaces and includes 10 wristbands, a 20'x20' reserved space and one picnic table. Spaces are $1,500 and will be reserved on a first come/first pick basis, so don't delay in purchasing yours now! You can also purchase a 15'x15' tent for an additional $500. TO PURCHASE TICKETS & EARLY ACCESS PASSES: Stop by - 6733 Maddox Blvd. (we are in the circle) Purchase Online (fees apply) VIP PASSES MUST BE PURCHASED THROUGH THE CHAMBER OFFICE, SO CALL OR STOP BY

A festival with activities, entertainment, food, arts and craft vendors and live demonstrations showcasing the heritage of Crisfield. Demonstrations include crab picking, oyster shucking, decoy carving, seafood cooking, fish cleaning, net making & repair baking a Smith Island cake and more. Exhibits from the Pocomoke Indian Nation, the Chesapeake Bay Foundation, Janes Island State Park, the Coast Guard and others will be there. Bring a Chair and enjoy local entertainment all day. Food will be available including the Crisfield Lion’s famous Crab Cakes, local BBQ and deserts. This is an event for the whole family and Admission is FREE. The festival is held behind the JM Tawes Historical Museum and the Somers Cove Marina in Crisfield, MD. Sign up for our Newsletter

May – October Sundays 9am – 1pm, Rain or Shine Petting Farm: 9am – 11am Live Music funded by a grant from the Worcester County Arts Council Located on Pitts Street, Commerce Street and Main Street

This year's Rackliffe Colonial Harvest Festival:"Celebrating 250 Years of Harvest & Heritage, will take place on the grounds of historic Rackliffe Hou...