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.
 

Sail on the Skipjack Nathan (July 8th)

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

Wine & Unwind with Local Artists at Layton’s Chance

  Wine & Unwind with Marianna Styles Sunday, July 9, 2023 from 1:00 PM to 4:00 PM EDT Sip wine, enjoy live music by Marianna Styles No fee, no reservation. Layton's Chance Vineyard & Winery Summer Concert with Uprizing Saturday, July 22, 2023 from 6:00 PM to 9:00 PM EDT Uprizing will be playing music […]

Free

Plein Air Easton

Plein Air Easton is the largest outdoor art competition in the nation and is celebrating its 19th year in 2023. Competition artists who have been juried in will descend on Easton to have their canvas' officially stamped on July 13th. Public, ticketed and free events (for the kids too) take place all week long beginning […]

Summer Music at Blue Ruin Cocktail Bar & Restaurant

Offers small plates with intense flavors and specializes in over 150 different kinds of cocktails! Join Blue Ruin for live music on these dates! July 14th - Bryan Russo 8-10pm July 21st - Jayme Dingler 8-10pm July 22nd - Garrett Roe Karaoke 7-10pm July 28th - Alli Pinsky 8-10pm July 29th - Sam Pugh 7-10pm […]

Free

Sail on the Skipjack Nathan (July 15th)

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

Saucy by the Shore Festival 2023

FELLOW SAUCE LOVERS!  Join us for a Deliciously Epic Adventure.  Taste Bud Exploding Local & National Sauce Companies! Varieties of Award-Winning Savory, Sweet, Hot, Tangy & more! FIND YOUR FLAVOR: Free Samples from Most Attending Sauce Vendors. Several Hot Sauces have been featured on the Hit YouTube series: Hot Ones! ​AWESOME LIVE MUSIC ON STAGE, […]

$20

Murder Mystery Dinner Cruise (July 15th)

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 […]

$85

Sail on the Skipjack Nathan (July 22nd)

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 […]

$40

U.S. Navy Band Cruisers Summer Outdoor Concert Series

The Avalon Summer Outdoor Concert Series is located on Harrison Street between Dover and Goldsborough Streets, begin at 7pm. They are free and open to the public. Bring some chairs and prepare to enjoy a pleasant evening of musical fun with your friends and family or call Hunters Tavern to make a dinner reservation on […]

Free

The 78th Annual Annapolis Crab Feast

Held rain or shine since 1946, the Annual Rotary Crab Feast is one of the longest-running and most popular summertime traditions in Annapolis! Known as “the world’s largest crab feast,” the all-you-can-eat (and drink) event invites folks from near and far to get their fill of Maryland’s famous blue crabs – plus Maryland vegetable crab soup, sweet […]

$90

The 9th Annual Sudlersville Peach Festival 23′

Friday, August 4 6PM until Fireworks Saturday, August 5 10AM – 4PM Sudlersville Peach Festival is co-hosted by the Sudlersville Volunteer Fire Company. With the best local bands providing live music, community non-profit groups serving great homemade food from pit beef to peach cobbler, local vendors offering their best hand-made crafts, and lots of great […]

Free