Events on Maryland’s Eastern Shore

 
Looking for something to do in Maryland’s Eastern Shore? You’re in luck! The area is full of exciting events that are sure to delight locals and visitors alike. Whether you’re interested in food and drink festivals, live music, art exhibits, or cultural celebrations, there’s always something happening in this vibrant community.
 

Chesapeake Film Festival

Save the dates! The 2023 Chesapeake Film Festival (CFF) will be LIVE Sept. 30 and Oct. 1 at two historic venues in Easton, MD. The Festival goes VIRTUAL October 2 through 8, bringing you more fabulous films to watch anytime, anywhere. The hybrid festival begins with a LIVE weekend (Sept. 30 and Oct. 1) featuring […]

Mid-Atlantic Small Craft Festival

Hundreds of amateur and professional boat builders, model boat builders and enthusiasts come from all over the region to display their skiffs, kayaks and canoes. Watch many of these one-of-a-kind vessels race along the Miles River along CBMM’s 18-acre waterfront campus.

Free

Easton’s Fall Kickoff 2023

Autumnal decorations and the feeling of seasonal warmth will be all around downtown Easton for a two day Fall celebration! Fall Kick Off /October First Friday Gallery Walk Giant pumpkins will decorate the downtown streets at this festive annual event. Events around town will celebrate the theme “Fall into Chesapeake!” Galleries will be open for First […]

Easton Fall Craft Fair 2023

OCT. 7, 2023 -- The second annual Easton Fall Craft Fair will take place from 10am to 3pm on Saturday, Oct. 7 at Trinity Cathedral, 315 Goldsborough St. in downtown Easton.   The indoor-outdoor fair is free and will feature 35 artisans selling one-of-a-kind crafts, from jewelry and pottery to seaglass art, crocheted toys, embroidery, […]

8th Annual Easton Beer Fest

Easton Volunteer Fire Department Ea315 Leonard Rieck Drive, Easton, MD, 21601, Easton, MD, United States

SUPPORT LOCAL - DRINK LOCAL The 8th Annual Craft Beer Fest will be held on Saturday, October 7, 2023 from Noon to 4pm (VIP’s Enter at 11am). Maryland’s largest under cover craft beer festival will feature 40+ Breweries, Wineries and Distilleries will be pouring 120+ Craft Beers, Ciders, Seltzers, Wines & Spirits from the Mid-Atlantic […]

$50

Oktoberfest in Berlin

Berlin Oktoberfest & Sidewalk Sale 2 Bands! Authentic Oktoberfest music featuring The Edelweiss Band! Plus local favorite The Dunehounds perform sponsored by The Sterling Tavern Cascading Carlos Juggling Shows – Scales n Tales Animal Show Plus the Fall Sidewalk Sale! MORE Beer stations this year and featuring a variety of OCTOBERFEST beer too! German food featuring […]

Talbot County Fall Harvest Fair

Talbot Agricultural Center 10659 Hiners Lane, Easton, MD, United States

🌾 2023 Fall Harvest Fair - Celebrate the Season with Us! 🌾 Join us for a day of wholesome fun and community spirit at the Fall Harvest Fair on Sunday, October 15th, located at 10659 Hiners Lane, Easton, MD 21601. This event promises a fantastic time for families, friends, and all who cherish the joys of autumn. […]

Cruise-In at the Harvest Festival

Talbot Agricultural Center 10659 Hiners Lane, Easton, MD, United States

Come see the classics after the parade at the Talbot county Fall Fest   Cruise in from 12pm to 2pm

Tilghman Island Day 2023

On Saturday, October 21st, 2023, from 10:00 a.m. until 7:00 p.m. the Tilghman Island Volunteer Fire Company will hold its annual Tilghman Island Day Celebration. A crowd favorite, the workboat-docking contest is scheduled for 1:00 p.m., with a work boat race to follow at 2:30 p.m. Other exhibits include local artisans. There will be live […]

Schellville’s Fall Fest in Rehoboth

Tanger Outlets Seaside 36470 Seaside Outlet Drive Rehoboth Beach, DE 19971, Rehoboth Beach, DE, United States

The folks that brought you Schellville's holiday extravaganza are getting ready for a fun fall fest. Indulge in a delightful culinary journey featuring the finest food trucks with scrumptious treats, quench your thirst with refreshing drinks, and explore the incredible creations of local artisans. Family activities include pumpkin painting, face painting, hair braiding, balloon making, […]

$10

Sea Witch Festival in Rehoboth

Rehoboth Avenue 509 Rehoboth Beach, DE,19971, Rehoboth Beach, DE, United States

About the Sea Witch® Festival The annual Sea Witch Festival is Rehoboth Beach’s free family-friendly Halloween celebration. Dress up and enjoy the parades, live entertainment, contests and more in downtown Rehoboth Beach. The Sea Witch Festival is Friday through Sunday, Oct. 27-29, 2023. Sea Witch Festival Activities All through downtown Rehoboth, and at local businesses, […]

OysterFest

Get ready to sip, slurp, and savor at the Chesapeake Bay’s favorite fall festival!  The event features live music on two stages, boat rides, retriever demonstrations, oysters, and more.

Free