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.

Easton Music Bingo at Doc’s Downtown Grille

MUSIC BINGO - Free to play, Prizes to win! No ticket required, first-come, first-served. Possession of a ticket does not guarantee a seat at the gameshow. Contact the venue to discuss best time to arrive to get a seat. Play That Funky Bingo is like regular bingo but instead of calling numbers, we play parts of songs. […]

Feasting Over Fire Series with Chesapeake Chefs

Chestertown’s Brampton Inn and Chesapeake Chef Service are teaming up to present a series of alfresco dinner party’s highlighting the Eastern Shore’s farmers, watermen, cheesemakers, and many more. Reserve Your Seat at the Table: Feasting Over Fire Dinner Series with Chesapeake Chef Service at Brampton Inn Experience a quintessential Eastern Shore tradition and join us […]

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 […]

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 […]

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 […]

38th Annual Festival of Trees

“Caroling, Caroling Through the Town” is the theme for the 2023 Festival of Trees which will be held in The Gold Room of The Tidewater Inn from Saturday, November 25 to Tuesday, November 28, 2023. In a magical holiday setting, fifty beautifully decorated trees sponsored by individuals and businesses will be on display. In addition, […]

37th Annual Christmas In St. Michaels

Christmas in St. Michaels ∴ A Weekend Celebrating Joy! ∴ Christmas in St. Michaels will be held December 8-10, 2023.  We look forward to welcoming you all to our festive events throughout the weekend.  Click the Events tab above to see all that we have planned.   Look forward to purchasing your favorite ornament – […]