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.
 

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 […]

IRONMAN MARYLAND

At IRONMAN Maryland, part of the VinFast IRONMAN North America Series, race day does not make us individuals that are competing against ourselves. When we toe the line, we become a team of athletes that join forces to overcome whatever challenges race day brings. We are allies that stick by each other and offer words of encouragement. And […]

Artisans on the Choptank

Artisan Market featuring local artisans! We will have a DIY craft, flower bar, craft beer, food and music! No cost to attend! Rain or shine- we will set up outside weather permitting. This is two events in 2023!   September 16: 11am-3pm   December 2nd: 4pm-10pm

The Maryland Wine Festival of Carroll County

Carroll County’s 39th Maryland Wine Celebration! An Outdoor Event Featuring Wine, Live Music, and Local Vendors. Explorer Pass | $65* Enjoy an upgraded Maryland Wine Festival experience. The Explorer Pass includes admission to the Main Field, the Maryland Wine Explorer Village and includes: • Exclusive, curated Maryland-grown wine samples • Admission to an exclusive seating […]

$65

Wine Down at Laytons Chance Winery

It's that time of year!!!  Zeta Phi Beta Sorority, Incorporated, Iota Chi Zeta Chapter will host it's annual "Wine Down". This fun for all event will be held on Saturday, September 16, 2023 at Layton's Chance Vineyard from 4:30-8:00 pm. Tickets are $45 (until July 1st) which includes wine tasting, food, and entertainment. After July […]

Murder Mystery Dinner Cruise (September 16th)

Take a relaxing 3-hour cruise and live show on one of the most exciting attractions offered on Maryland’s Eastern Shore! The boat offers a fully enclosed lower deck with heating and air conditioning, as well as a covered upper deck with a great view of the river. Catered by Suicide Bridge Restaurant and features local […]

$85

Crab Feast in Annapolis

Crab Feast 2023 is finally here! Join us on Sun Sep 17, 2023 at 2 Pythian Drive Edgewater, MD 21037 for a day of fun, food, and festivities. This in-person event is perfect for all crab lovers out there. Get ready to indulge in the freshest and most delicious crabs you've ever tasted! Our event will start at 2:00 PM Eastern […]

$90

Maryland Folk Festival

Make your plans now to join us in Salisbury, Maryland, for the Maryland Folk Festival— a diverse celebration of arts, culture, and heritage. This large-scale multi-day outdoor event, celebrates the roots, richness and variety of American culture. It features hundreds of the nation’s finest musicians, dancers, craftspeople and other keepers of culture in performances, workshops, […]

Free

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, […]