Annual & Holiday Events in Kent County Maryland



Chestertown Taste of the Town

Paint the Town

2022 (TBD)
Fountain Park Chestertown, Maryland

Various locations throughout Chestertown. (More details to come).

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
2022 (TBD)

May 2022 (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
May 27 - 29, 2022

May 27 - 29, 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
10th Anniversary Year

June 5 - 18, 2022

Various locations throughout Kent County

The National Music Festival transforms Kent County into a hub of music. The nationally recognized event will feature music to suit virtually every taste -- from symphonies and chamber music to hints of jazz. More than 30 concerts and over 200 open rehearsals are scheduled throughout the festival in venues across the Eastern Shore.

It will be an exciting season, including riveting music by Beethoven, Gershwin, Mendelssohn, Strauss, and Tchaikovsky. Several mentors will be featured as concerto soloists, among them guitarist Camilo Carrara (Vivaldi, “Concerto for Lute in D”) and violinist Simon Smith (Korngold’s cinematic “Concerto for Violin”). More details will be announced soon. We plan to proceed with our Resonance concert series, and have six concerts scheduled from October 2021 through April 2022.


Music in the Park

Chestertown's "Music in the Park" Summer Concert Series
2022 (TBD)

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
2022 (TBD)

June 2022 (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
2022 (TBD)

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

July 15 - 17, 2021
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
2022 (TBD)

August 2022 (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 Weekend

August 13 - 15, 2021
Rock Hall, Maryland

Rock Hall’s Pirates and Wenches Weekend is a town-wide theme party. The weekend long event features live entertainment and Pirate performers, custume contests, treasure hunts, kids' activities, merchants and more fun for the whole family.  


Legacy Day 

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 virtual celebration at:


Harry Potter Festival

Chestertown HP Festival - Cancelled

The organizers of the Chestertown HP Festival Weekend regret to announce that the festival has been canceled for this year. Ordinarily, organizing volunteers and fundraising for the event would have started at the beginning of the year. With the ongoing pandemic and uncertainty of future health regulations it has been difficult to secure volunteers and do the planning needed to put on this magical event. Many of our organizers are parents and small business owners who have had to focus their many talents and time elsewhere during this challenging year. We appreciate their enthusiasm and continued support of this unique festival and hope that it will be able to continue in the future...


Rock Hall's Fall Fest

Rock Hall FallFest

October 9, 2021
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
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


October 2021 (TBD)
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 often for 2021 Updates)

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