Whether you want to celebrate Maryland’s history, culture, or crustaceans, you’ll find the appropriate event on our 2024 festival calendar. Music, art, food – oh, so much food – and family fun await, so gas up the car and hit the road!
February 16-17—Easton, MD
Live music, dozens of ice sculptures, an ice skating rink, and a kid-friendly “icehouse” are only some of the winter delights you’ll discover in Easton’s historic downtown.
A “Stews and Brews” party is planned for that weekend, too, where you can warm up with hearty stew and samples from 30 breweries, wineries, and distilleries.
May 4—Solomons, MD
After admiring the antique and classic boats on display from collectors around the region, you can learn how to make a traditional Maryland stuffed ham, watch Chesapeake Bay retrievers in action, learn how to shuck oysters, and marvel at demonstrations by traditional craftspeople. Be sure to make time to tour the Calvert Marine Museum, the festival’s host, and take a 30-minute cruise on the Wm. B. Tennison.
May 18—Baltimore, MD
In its 149th year, the Preakness Stakes is one of the biggest events to hit Baltimore each year. As the second jewel of the triple crown, the race is obviously the main attraction as everyone sets their sites on the Kentucky Derby winner.
But the Preakness has a lot more to recommend it, whether you are dressed to the nines in the stands or rocking out in the infield. Food, music, and betting on the ponies make for a raucous, memorable day.
May 23-26—Cumberland, MD
Created by the incomparable Del McCrory, DelFest is a Memorial Day music festival that pays homage to all things bluegrass. Legendary bands take the stage over four days, banjos twanging and fiddles sawing.
Although there are a variety of hotels in host city Cumberland, many people choose to spend the weekend camping out on the festival grounds, surrounded by the beautiful Appalachian Mountains and thousands of new bluegrass-loving friends.
May 24-26—Chestertown, MD
Join the Revolution at Chestertown’s Tea Part Festival this Memorial Day weekend. The center of this colonial extravaganza is the re-enactment of the tea party held by Chestertown residents in 1774, when they threw tea over the sides of the Geddes into the Chester River, just as Bostonians had done several months earlier. (This will be the 250th anniversary of that event!)
Visitors can also partake in a 10-Mile Run and 5K Run/Walk or a raft race, march along with the colonial parade, take a walking tour of the historic area, and so much more.
June dates to be announced—Baltimore, MD
Over 100,000 people come to Baltimore for Pride week each year to honor the contributions made to society by sexual and gender minorities.
Have your rainbow flag ready for events like the Pride Parade, the High Heel Race, and the 5K Run/Walk, as well as block parties, concerts, and a twerkout.
June 19—Oxon Hill, MD
National Harbor hosts a Juneteenth celebration that features a Black-owned marketplace, food vendors, and a variety of cultural performances. Last year’s performances included poetry readings, African drumming and percussion, and the DuPont Brass; this year’s schedule will be released in the coming months.
Weekends August 24-October 20—Crownsville, MD
Hasten thyselves to Revel Grove in Crownsville for the annual Maryland Renaissance Festival, where jousting knights and fair ladies provide endless entertainment.
Catch a play by the Bard, gobble a turkey leg, and lift a glass of grog at one of the most popular fall events in the state.
August 24-25—Ocean City, MD
Typically held on Father’s Day weekend, this year’s Ocean City Air Show has been moved to August so it can host Italian aerial daredevils Frecce Tricolori.
They will be joined by the F-22 Raptor Demo Team, who can “supercruise” at 1.5 times the speed of sound. Grab a sandy spot near the waves, look skyward, and enjoy the show.
August 31-September 2—Crisfield, MD
Now in its 77th year, Crisfield’s Labor Day Weekend celebration of the Chesapeake Bay Crab includes crab races, crab-picking and -cooking contests, pageants, a parade, and a spectacular fireworks show to cap the festivities. Nearby Deal Island also hosts its Skipjack Races the same weekend.
September date TBD, Annapolis, MD
A celebration of the perseverance, education, and cultural heritage of Africans, African Americans, and Caribbean people of African descent, the Kunta Kinte Heritage Festival brings arts vendors, African performers, and children’s activities to City Dock in Annapolis each fall.
September 20-22—Salisbury, MD
The Maryland Folk Festival is one of the longest-running celebrations of the roots, richness, and variety of American culture.
Over 350 traditional musicians, dancers, craftspeople and other artisans will share their skill via performances, workshops, and demonstrations. Eat your fill of regional and ethnic cuisine, dance in the streets, and buy (or make!) an art piece to adorn your walls.
October 3-6, October 10-14—Annapolis, MD
Sailors of all types will converge on Annapolis the first two weeks in October for The Powerboat Show (October 3-6) and Sailboat Show (October 10-14.)
Held at City Dock, you can get up close and personal with all types of boats, as well as nautical gear and accessories. Classes, food, and a tasting tent round out the event.
October 5—Frederick, MD
Celebrate Hispanic Heritage Month along Frederick’s Carroll Creek, as the town’s Hispanic residents share the richness and diversity of their cultures.
The fiesta features live music, dancing, traditional costumes, arts and crafts, kids’ activities, and great food.
October 19-20—Leonardtown, MD
Witness some of the fastest oyster shuckers in the world at the annual U.S. Oyster Festival, held in Leonardtown each October.
It is here champions are crowned for both the U.S. National Oyster Shucking Championship and the U.S. National Oyster Cook-Off. You can eat your fill of the bivalves, plus as much crab, shrimp, clams, and fish as you desire. One of the largest cultural heritage festivals on the Eastern seaboard, this festival celebrates the bounty of our local waters.
October 24-27—Ocean City, MD
One of the region’s largest outdoor festivals, Ocean City’s Sunfest brings tens of thousands of people to the beach for a four-day arts, crafts, music, and food fest.
This year’s line-up features 20 bands, including Spin Doctors, Ballyhoo!, Treehouse!, and a variety of tribute bands. Between the music and browsing over 200 craft vendors, you can relax around a beach bonfire, catch the pet parade, or get lost in a beach maze.
November 8-10—Easton, MD
The annual Waterfowl Festival in Easton attracts thousands of people and raises millions for wildlife and habitat conservation, education, and research.
This celebration of Eastern Shore culture offers a variety of demonstrations and hands-on activities, including diving dogs, duck and goose calling competitions, fly fishing casting lessons, retriever demonstrations, decoy painting, and a kids’ fishing derby. Plus, you can browse the arts pavilion and eat your fill of seafood and festival delicacies.
December dates to be announced, Chestertown, MD
Travel back in time to 1840s London for a quintessential Victorian Christmas in Chestertown. Musical groups will sing in the holidays, while you enjoy shopping, carriage rides ,and the Beers and Bonfires event.
You can also partake in English tea, participate in a Bedlam bed race, and meet Santa.
Lead Photo Credit: Kunta Kinte Heritage Festival
About the Author
Heidi Glatfelter Schlag is a marketer, history lover, and traveler who can often be found exploring museums, parks, small towns, and farms. She founded Culture-Link Communications, where she helps local nonprofits and small businesses build their brands. Heidi lives in Frederick, MD, with her husband and two dogs.