Annual & Holiday Events in Kent County Maryland



Chestertown Taste of the Town

Paint the Town
April 20 - 23, 2023

Fountain Park Chestertown, Maryland

Various locations throughout Chestertown.

"Paint the Town" is a 4-day event where artists have the opportunity to lose themselves while exploring the beautiful countryside and capturing it in their paintings. After three (3) days of painting, artists gather back together on Saturday afternoon to frame and hang their finished work in the RiverArts Gallery in preparation for sale at the "Wet Paint Show and Sale". Once the show is complete, the participating artists vote for "Best in Show" and "Best Body of Work". 

Galena Dogwood Festival

Dogwood Festival of Galena
May 13, 2023

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.

The festival kicks off with the Dogwood Dart 5k. There will be a parade beginning at 10 am starting at RT213 and Mill Lane that will proceed to the middle of the town and make its way to the firehouse where the festival will be held. Admission to the festival and parking will be free. Family fun for all that will include Inflatable Amusements, Beautiful Baby Contest, merchant and craft vendors, food vendors, games, and a Corn Hole Tournament that starts at 3 pm plus much more. For more information please call the Galena Volunteer Fire County.

Chestertown Tea Party

Chestertown Tea Party Festival
May 26 - 28, 2023

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 4 - 17, 2023

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.

The National Music Festival, in Historic Chestertown on Maryland's Eastern Shore, brings together world-class mentors and gifted apprentice musicians on the cusp of their professional careers. The two groups rehearse and perform together throughout Kent County in orchestral and chamber repertoire. All rehearsals are free and open to the public. Some concerts are free; others require a ticket. From a solo violinist to full symphony orchestra concerts, from Beethoven to hints of jazz — the festival will feature music to suit virtually every taste.

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”), Emily Daggett Smith (Mendelssohn, "Concerto for Violin in e"), and Natalie Helm (Saint-Saens, "Concerto for Violoncello No.1"). 

Please click here for the Festival Concert Schedule

Natn music fest 2012 4 The National Music Orchestra Richard Rosenberg conducts the Orchestra (1)
Rock Fishing Tournament

Guardian of the Pearl Rock Fish Tournament
June 9 - 11, 2023

Rock Hall, Maryland

The Rock Hall Volunteer Fire Company (RHVFC) is proud and excited to host The Pearl of the Chesapeake Rockfish Tournament, a three-day event that features a two-day tournament (June 10-11) and a Captain’s Meeting (June 9). Situated on the eastern shore of the Chesapeake Bay, Rock Hall is a charming village known as The Pearl of the Chesapeake. The tournament promotes heritage, tourism, and fishing for the town while raising funds for the RHVFC which serves it and surrounding communities.
For more sponsorship information and to register please visit
Fourth of July in Kent County

Fourth of July in Kent County
July 2023


Celebrate Independence Day in Kent County.  Join us for parades and celebratory fireworks in Rock Hall. Fireworks display to be held on Monday, July 3 at Rock Hall Harbor.  Raindate Wednesday, July 5.

The annual Waterman's Day celebration on July 2 (12noon - 2 pm), held at the Rock Hall Bulkhead, is a day full of family-friendly fun, food, vendors, and the "beloved" boat docking contest. 

The parade will be held in Rock Hall on Tuesday, July 4 at 10 am to feature local bands. Join the celebration afterward for midway games, talent show, and other family-friendly activities.

Other 4th of July activities are scheduled throughout the holiday. 

Kent County 4H Fair

Kent County 4H Fair
July 19 - 22, 2023

Chestertown, Maryland

Wednesday 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.

The Kent County Fair features great food, 4-H and community exhibits, animals, tractors, games, and entertainment. The focus of the fair is agricultural education and providing educational opportunities for county youth. The greased pig contest, bull-riding, and the 4-H livestock and cake auctions are popular events at this annual celebration supporting the young 4-H members. Each evening features different foods including a fish fry and pit beef, pork bbq, and chicken bbq. Plan a great escape right in your own backyard, or come for a visit for a small-town America experience. 

For more information about this event, and to check out the event schedule, click here.

Betterton Appreciation Day

Betterton Day
August 5, 2023

Betterton, Maryland

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

Follow the parade down Main St. to the fun found at the beach. LIVE music, games, food, crafts, and vendors fill the beach. Take a walk around and check things out with your friends and neighbors or hang out on the beach all day. This family-friendly event starts at 10:30 a.m. and runs through 5:00 p.m. For more information, please call 410-348-5678, or visit

Pirates and Wenches Fantasy Weekend

Pirates and Wenches Weekend
August 11 - 13, 2023 

Rock Hall, Maryland

Come by land, or come by sea, and enjoy a two-and-a-half-day town-wide theme party you will not soon forget! This is a wonderful opportunity to bring your boat and anchor out on the Chesapeake Bay or raft up with your mates. There is plenty of anchorages, dockage, and raft-up space available – as well as plenty of parking for those arriving by land. This exciting event, which offers activities for all ages, is less than a tank of gas from Philadelphia, Baltimore, Washington D.C, and Northern Virginia. Costumes "Arrrr" encouraged!

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


For more information and a complete weekend schedule, click here.

Pirates Landing Page image bar


Legacy Day 
August 19 - 20, 2023

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:

Rock Hall's Fall Fest

Rock Hall FallFest
October 8, 2022

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.

Come enjoy the fall beauty of Kent County when you attend Rock Hall's annual Fallfest celebration. Enjoy free family fun with MUSIC, CRAFT VENDORS, a totally FREE Kids Kourt, FOOD, and OYSTERS! Please join us for this annual celebration of community. Originally developed as a "thank you" to Rock Hall for being awesome, this festival has morphed into a full day of music, food, and fun for everyone. With the addition of oysters in the past few years, we've taken the event over the top. Raw oysters being shucked by local watermen and fried oysters piled high to make for a full belly and a smile on your face!



Sultana Downrigging

Sultana Downrigging
October 27 - 30, 2022

Chestertown, Maryland

Sultana’s Downrigging Weekend Tall Ship and Wooden Boat Festival has evolved into one of the largest annual Tall Ship gatherings in North America. Visitors who come to the festival can expect to see a waterfront packed with ships, schooners, and wooden boats; performances by world-class musicians; lectures by nationally recognized authors and filmmakers; plenty of opportunities to go sailing as part of a fleet of “Tall Ships”; and the chance to spend the weekend in Chestertown – one of America’s best-preserved historic seaports. Don’t miss it!

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 in North America, 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.

For more information about the festival and to view the event schedule, please click here.


Annual Chestertown RiverArts Studio Tour

Chestertown RiverArts Studio Tour
October 22-23 & Oct  29-30, 2022

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.

Ever wonder what an artist’s studio really looks like? Chestertown RiverArts Annual Studio Tour allows the visitor a chance to take a sneak peek inside Kent and Queen Anne’s Counties' creative spaces. This free, self-guided tour on the picturesque Eastern Shore of Maryland takes place over two Fall weekends rain or shine. More than 50 artists, many nationally known, invite visitors in to talk, check out how they work, and provide the opportunity to buy original artwork at studio prices. 

The art is as diverse as the artists who create it, with styles ranging from traditional to avant-garde, expressed in a variety of media that include painting, photography, sculpture, metalwork, pottery, fiber, woodcraft, jewelry, furniture, glass, and more. Studios are also varied with several studio galleries, independent studios in two small art complexes, and many at the artist’s homes – some detached from the main house and some inside the home itself. In a few instances, there are artists displaying their work at a venue other than their own studio. 

Situated on a scenic peninsula where the Chester and Sassafras Rivers meander into the Chesapeake Bay, Kent County has retained its serene beauty despite the passage of time. Located on the banks of the Chester River, Chestertown is the oldest mid-Atlantic port of entry. It has been designated by the state of Maryland as an Arts and Entertainment District; its mayor, Chris Cerino remarked, “The downtown arts scene has grown by leaps and bounds in the past decade…Chestertown is fast becoming a regional arts destination.” In addition to the charm of Chestertown, out-of-towners often remark on how much they enjoy the tranquility of the countryside, water views, and small, friendly towns. 

It is recommended that visitors start their tour at the RiverArts Gallery, 315 High Street, Suite 106 where there will be an exhibit of works by the artists on the tour to help decide on must-see venues. Brochures are available from local Chestertown establishments and at RiverArts. 

A Dickens of a Christmas Weekend 
December 2 - 4, 2022

Main Street Chestertown presents “A Dickens of a Christmas” celebration with live outdoor music performances throughout the historic downtown.

As an arts-rich community with strong literary, musical, and theatrical talents, Chestertown invites visitors to enjoy a memorable weekend filled with authentically themed holiday fun. The charm of our historic 313-year-old river town will be the backdrop to a lively display of Dickens-era holiday attractions: carriage rides, street theater, live music, food vendors, decorated house tour, and more!

For more information visit

Holiday events in Kent County, MD

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

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