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.
 

Cambridge Farmers’ Market

Operating May through November in 2023, Every Thursdays from 3pm – 6pm, the Long Wharf Farmer’s Market is a local favorite!  What’s better than a waterfront Farmer’s Market? The market […]

Free

Tall Ship Kalmar Nyckel Sails in Cambridge (June 2nd)

Come sail away with Kalmar Nyckel for a 2.5-hour sail and have an adventure of a lifetime! The Tall Ship of Delaware returns to Cambridge, MD on Friday, June 2 through Sunday, June 4. Discover the remarkable story behind Kalmar Nyckel, a full-scale replica of the merchant ship that brought Swedish settlers to North America […]

$65

St. Michaels Yacht Beer Tasting Cruise

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

St. Michaels Yacht Wine Tasting Cruise

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

Chesapeake Bay Champagne Sunset Sail

Looking to go sailing at sunset while sipping champagne? This is the sunset champagne charter for you! Come join us for a relaxing 2 hour cruise near Annapolis. Your St Michaels MD sail boat ride includes a personalized tour with our first class captains & crew on all our boating trips including our romantic sunset […]

$115

Easton Farmers Market

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

Tall Ship Kalmar Nyckel Sails in Cambridge (June 3rd)

Come sail away with Kalmar Nyckel for a 2.5-hour sail and have an adventure of a lifetime! The Tall Ship of Delaware returns to Cambridge, MD on Friday, June 2 through Sunday, June 4. Discover the remarkable story behind Kalmar Nyckel, a full-scale replica of the merchant ship that brought Swedish settlers to North America […]

$65

Sail on the Skipjack Nathan (June 3rd)

Nathan sails from May through October. Each sail is two hours long and generally includes an oyster dredging demonstration. Sails are unique depending on wind, weather, captain and crew. Advance reservations are recommended and accepted online use the link below, until midnight of the day before the sail. We carry up to 20 passengers per […]

$40

St. Michaels Brewfest 2023

On June 3rd, from 12:00 pm - 4:00 pm come out to the St. Michaels Brewfest 2023! They offer Three Pouring Venues, Over A Dozen Breweries, Art, Glassware, Food, and more! Tickets are limited and can be purchased on the website below, Offering General admission and a VIP cruise tickets are still available! St. Michael's […]

$55 – $110

Annapolis Pride Parade & Festival

With over 6,000 people in attendance, 2019 launched the Inaugural Annapolis Pride Parade & Festival– a visual dreamscape of the human spirit at its best. People, children, and pets of every walk of life dress in their rainbow finest and line the sidewalks of West Street to witness a dazzling parade of floats, dancing spirit dragons, […]

Free

Kent Island Farmers’ Market

With over 30 local vendors at KENT ISLAND FARMERS’ MARKET at Cult Classic Brewery Year-round every Thursday. Hours 3:30- 6pm through Spring, Summer and Fall. January through March 3:30- 5:30. […]

Free

Tall Ship Kalmar Nyckel Sails in Cambridge (June 4th)

Come sail away with Kalmar Nyckel for a 2.5-hour sail and have an adventure of a lifetime! The Tall Ship of Delaware returns to Cambridge, MD on Friday, June 2 through Sunday, June 4. Discover the remarkable story behind Kalmar Nyckel, a full-scale replica of the merchant ship that brought Swedish settlers to North America […]

$65