Annual & Holiday Events in Kent County Maryland



Chestertown Taste of the Town

Paint the Town
(Rescheduled to 2021)

April 2021 (date to be determined)
Fountain Park Chestertown, Maryland

Various locations throughout Chestertown.

Artists paint the local scene for three days and make their paintings available for sale at the Wet Paint Reception and Sale on Saturday at the RiverArts Gallery. On Sunday, there is a two-hour Quick Draw; these paintings are then shown in Fountain Park from 11:00am-12:00pm. These works are judged, and also for sale. The public also has an opportunity to vote for the “People’s Choice Award.

Galena Dogwood Festival

Dogwood Festival of Galena
(Rescheduled to 2021)

May 2021 (date to be determined)

Main Street of Galena, Maryland

The annual Galena Dogwood Festival, is a fun, family-friendly event bringing together craft and food vendors from around the region to celebrate the start of the Upper Eastern Shore’s gorgeous spring weather and the beauty of charming Galena, Maryland and its dogwood lined streets.


Chestertown Tea Party

Chestertown Tea Party Festival
(Postponed until 2022)

May 20 - 22, 2022
Friday evening, all day Saturday and Sunday
Downtown Chestertown

The annual Chestertown Tea Party Festival, held over Memorial Day weekend, marks the anniversary of one of the area’s most notable historic events, when the citizens of Chestertown—in an act to show resistance to British rule—tossed a ship’s cargo of tea overboard into the Chester River in 1774. The festival’s Tea Toss Reenactment is the centerpiece of the event, which also includes a Friday night Block Party, Saturday 5K and 10-mile races, craft beer and local wine samples, craft vendors, street performances, a parade and more.


National Music Festival

National Music Festival
(August 1 - 14, 2021)

August 1 - 14, 2021

Various locations throughout Kent County

The National Music Festival transforms Kent County into a hub of music. The nationally recognized event pairs gifted apprentice musicians with world-class mentors. These performers set out together for open, free, rehearsal and incredible performances in venues across the Eastern Shore.


Music in the Park

Chestertown's "Music in the Park" Summer Concert Series
(Rescheduled to 2021)

Alternating Saturdays Beginning June to August 
7:00pm - 8:30pm
Fountain Park in Chestertown, Maryland

Chestertown’s Music in the Park Summer Concert Series provides visitors with an opportunity to experience a variety of music from their lawn chairs during free performances by local and regional artists. Taking place on alternate summer Saturdays, these concerts highlight all types of music including big band, jazz, bluegrass and rock.


Rock Fishing Tournament

Pro-Am Rock Fish Tournament
(Rescheduled to 2021)

June 2021 (date to be determined)
Rock Hall, Maryland

Take your fishing to the next level at the annual Maryland Watermen’s Association Pro-Am Rockfish Tournament. ‘Hook the Big One’ or catch the Jewel of the Chesapeake in this weekend long competition.


Fourth of July in Kent County

Fourth of July in Kent County
(Some events canceled for 2020)

Celebrating the Fourth of July in Kent County will be a bit different this year. Although, fireworks are canceled, there will be other activities to enjoy with your family!

Kent County 4H Fair

Kent County 4H Fair
(Rescheduled to 2021)

July 2021 (date to be determined)
Chestertown, Maryland

Thursday through Saturday, there is something for everyone as always from great food, arts and crafts, tractor pulls and midway rides. Do not forget the 4-H Livestock and Cake Auctions! It is a great and fun way to support our young 4-H members.


Betterton Appreciation Day

Betterton Day
(Rescheduled to 2021)

August 2021 (date to be determined)
Betterton, Maryland

Join us for a fun-filled day at Betterton Beach! Parade starts down Main St. at 10:30am followed by rides, crafts, food and vendors at the beach. Free Admission. Parking and Rides Available.


Pirates and Wenches Fantasy Weekend

Pirates and Wenches Fantasy Weekend
(August 13 - 15, 2021)

August 13 - 15, 2021
Rock Hall, Maryland

Rock Hall’s Pirates and Wenches Fantasy Weekend is a town-wide theme party now in its 11th year. The weekend long, town-wide, theme party features a Sea Shanty Sing A Long, Rum Tasting, Decorated Dinghy Contest, Caribbean Beach Party, Buccaneer’s Ball, 5K Run/Walk, Entertainment and Pirate Performers, Costume Contests, Treasure Hunt and much more!


Legacy Day (August 20 & 21, 2021)

August 20 & 21, 2021

Legacy Day celebrates the rich cultural heritage of African Americans in Kent County. It is an opportunity for all residents to have a great time recognizing their shared history. Legacy Day is offered free of charge to the community – thanks to the generous support of individuals, organizations and businesses. Catch up with the 2020 virtual celebration at:


Harry Potter Festival

Chestertown Jazz Festival presents Jazz Film Festival Drive In

Saturday ,   |  6pm
Location: Broken Spoke Winery - 942 Glebe Rd, Earleville, MD 21919
Contact: Chestertown Jazz Festival

Jazz fans will enjoy movies under the stars at the lovely eastern shore winery – Broken Spoke Winery in Earleville, Maryland.Double Feature – Two Great Jazz Films




Harry Potter Festival

Chestertown HP Festival
(Rescheduled to 2021)

October 2021 (date to be determined)

The Chestertown HP Fest is back and better than before in 2020 and Chestertown is ready to celebrate! Join us for a fun filled HP Wizarding Weekend!


Rock Hall's Fall Fest

Rock Hall FallFest
(Rescheduled to 2021)


October 10, 2020
Rock Hall, Maryland

Rock Hall FallFest pays homage to the almighty oyster by inviting guests to savor oyster stew and fried oysters while browsing dozens of artisan and craft booths. While the oyster is the star of the show, this festival features all the highlights of Kent County, including a variety of live music performances, children’s activities and the opportunity to explore beautiful Rock Hall, Maryland.

Sultana Downrigging

Sultana Downrigging
(October 29 - 31, 2021


October 29 - 31, 2021
Chestertown, Maryland

Sultana Downrigging Weekend fills Chestertown’s gorgeous waterfront with equally gorgeous schooners, ships and beautiful wooden boats. Now one of the largest Tall Ship and Wooden Boat Festivals on the East Coast, this event welcomes participating vessels from throughout the region and provides festival attendees with the opportunity not only to see and explore these ships but to venture out on the water during scheduled sails. In addition to the ships, the festival also includes world-class musical performances, dynamite food from local restaurants and the chance to try local spirits.


Annual Chestertown RiverArts Studio Tour

Chestertown RiverArts Studio Tour
(Rescheduled to 2021)


October 24 and 25, October 31 and November 1, 2020
Chestertown, Maryland

Taking place over the course of two October weekends, the Chestertown RiverArts Studio Tour includes more than 50 working studios throughout Kent and Queen Anne’s Counties. Guests will be invited to explore creative studio spaces, watch artists at work, talk with them about their craft and purchase works at studio prices. Participation in the tour is free, and because it is self-guided, visitors can enjoy this art immersion at their own pace.


Holiday events in Kent County, MD

Visit the County of Kent, Maryland for the Holidays!
(Check for 2020 Updates)

The spirit of the holidays can be found all over Kent County. Join us in celebrating this festive season.