Find upcoming events on Maryland’s Eastern Shore, including festivals, live music, arts and culture, food and drink events, and seasonal celebrations. This local events calendar highlights what’s happening in Easton, St. Michaels, Oxford, Chestertown, and nearby Eastern Shore towns, making it easy for visitors and residents to plan their time in the area.
Looking for events near your rental? Browse vacation rentals by town.
|
Sunday
|
Monday
|
Tuesday
|
Wednesday
|
Thursday
|
Friday
|
Saturday
|
|---|---|---|---|---|---|---|
8 events,
Wine tastings Hours Monday - Saturday (12pm-5pm) Sunday (12pm-4pm) With 18 wines in our cellar, we have something for every pallet. Tasting Fee: $1.00 per wine sampled Glasses: Glasses of wine are available each and every day. We also will have sangria or mulled wine occasionally, depending on the weather and our whims. Bottles: After […]
$1
The St. Michaels Farmers Market features farmers and vendors selling locally grown and caught vegetables, meats, and fish, plus handmade crafts and live music.The St. Michaels Farmers Market features farmers and vendors selling locally grown and caught vegetables, meats, and fish, plus handmade crafts and live music.
Free
Available per person or Private Charter Join us for an unforgettable experience on our ice-cold Beer Tasting Cruises Be prepared for an unforgettable adventure on our beloved historic yacht Sail Selina II. Indulge in the aroma, taste, and quench your thirst with our cold, refreshing beers. A 2-hour tour on our beautifully kept sailing boat […]
$115
Enjoy a truly unforgettable wine tasting experience on the Chesapeake Bay with Sail Selina II. Our 2-hour St Michaels, MD wine tasting cruises are the perfect way to indulge in the basics of wine tasting while taking in breathtaking views of one of the most picturesque waterfronts in America. With limited availability for just six […]
$115
From local produce growers to watermen, from bakers to crafters and local artisans, the Easton Farmers Market provides an entire meal, home décor and unique gift items in a friendly and festive environment. The market is open every Saturday from April 15 to December 16, 2023 at 8 a.m. to 1 p.m. Live music starts […]
Free
The walk begins in front of the Chesapeake Bay Maritime Museum and makes its way through around the St. Michaels harbor and around St. Michaels historic downtown. Visit an old cemetery and hear stories about St. Mary’s Square where ghosts of unremembered dead once haunted a school that was on the Square. Visit the Victoriana […]
$25
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. […] 
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 […] |
8 events, |
8 events, |
8 events, |
8 events, |
10 events,
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
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 […] |
11 events,
-
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, […] |
9 events, |
8 events, |
8 events, |
8 events, |
8 events, |
8 events, |
8 events,
-
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 […] |
9 events,
-
🌾 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. […]
-
Come see the classics after the parade at the Talbot county Fall Fest Cruise in from 12pm to 2pm |
9 events,
-
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 […]
-
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
|
|||||
8 events,
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, […] |
10 events,
-
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
-
About this event 🍻🍷 Get ready to raise your glasses at Schellville's Beer and Wine Fest- Wicked Brew Bash! 🍻🍷 Join us for a delightful celebration of craft beers […]
$40
|
|||||
