Annual & Holiday Events in Kent County Maryland

Paint the Town
April 23 - 27, 2025

Fountain Park Chestertown, Maryland
https://www.ctownra.org/paint-the-town-2025

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". 

Dogwood Festival of Galena
May 10, 2025

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 a parade down Main Street, beginning at 10:00 a.m. Vendors will be set up from 10:00 a.m. to 3:00 p.m., and the festival will continue until 7:00 p.m. Stick around for Dogwood After Dark from 7:00 to 10:00 p.m., featuring live music from a band!

Admission to the festival and parking are free. Enjoy live music, vendors, children’s activities, a dog contest, food and beer trucks, and more!

Contact: Town of Galena, MD

Phone: (410) 648-5151

Email: infodogwooddays@gmail.com

URL:  https://townofgalena.com/dogwood-festival

Chestertown Tea Party Festival
May 23 - 25, 2025

Friday evening, all day Saturday and Sunday
Downtown Chestertown
http://www.chestertownteaparty.org/

In response to the British Parliament’s closing of the port of Boston, the citizens of Chestertown, Maryland met in May of 1774 and set forth “Resolves” forbidding importing, selling, or consuming tea in Chestertown. According to local legend, residents then gathered at the town center, marched down High Street to the brigantine Geddes, which was anchored in the Chester River, and tossed her cargo of tea overboard. The annual reenactment of that event is the centerpiece of the Chestertown Tea Party Festival. The re-enactment is scheduled for Saturday at 2:00 p.m. All Festival events take place along the Chester River and in the historic district of 18th-century Chestertown, Maryland. There is no admission charge to the Festival.

Start training now for this year’s Classic Distance 10 Mile Run and 5k Run/Walk. Or join the festival-goers that line High Street each year to cheer the passing of colonial militia, marching bands, costume-garbed children, and more in the Colonial Parade. A Walking Tour of the historic district is offered to visitors and local residents. The tour is conducted by trained docents who are residents of Kent County. Not only can you purchase many handcrafted Colonial goods at the Festival, but you can also see a live demonstration of how those items are made. On Sunday, we are celebrating the 250th Anniversary of the Chestertown Resolves and Tea Toss. Challenge yourself and your engineering skills by competing in this year’s Annual Raft Race. You’ll be amazed at the sights and sounds of the Chestertown Tea Party Festival!

Tea Toss Reenactment, Colonial Parade, Street Party, Raft Race, Street Performances, Colonial Crafts, Strolling Musicians, Local Fare, 5k & 10-mile run, and more including a Wine and Craft Beer Tasting held on Sunday at Wilmer Park from noon to 4 p.m. The event will feature local Maryland wineries and craft brewers.

National Music Festival ~
Season XIII
June 1 - 14, 2025

Various locations throughout Kent County
www.nationalmusic.us

The Festival, a division of OuterArts Maryland, Inc., combines world-class mentor musicians and gifted pre-professional apprentice musicians for an intense Festival experience the first two weeks of each June. All apprentices receive full scholarships and housing, mostly with host families in private homes. The two groups rehearse and perform side by side in orchestral, chamber, solo recital, choral, and chamber opera repertoire. In two weeks, these musicians present over 30 concerts and over dozens of free open rehearsals for music lovers from around the world.

Each year the Festival serves approximately 110 apprentices and employs approximately 30 mentors (including the Artistic and Executive Directors, who also teach). Musicians come to the Festival each year from more than 15 countries and 30 U.S. states. The average age of apprentices is 22, although some are older and have already completed their advanced degrees and begun their careers.

Concerts and free open rehearsals take place in a variety of venues including churches, theaters, art galleries, and local businesses. In addition to its performances, open rehearsals, and broadcasts on National Public Radio, the National Music Festival will record compact discs to be distributed globally. Current recording projects include the music of Phanos Dymiotis and music for orchestra with narration (Liane Hansen, narrator).

The Festival’s performances and pre-concert talks provide affordably priced entertainment and education to its patrons, including children. All rehearsals are free and open to the public. Attending rehearsals is a particularly good way to introduce young children to concert music!

Please click https://nationalmusic.us/calendar/. 

Guardian of the Pearl Rock Fish Tournament
June 6 - 8, 2025

Rock Hall, Maryland

Fourth of July in Kent County
July 2025

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

The annual Waterman's Day celebration on July 6th (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 Friday, July 4th 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
July 16 - 19, 2025

Chestertown, Maryland
www.kentcountyfair.org

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
August 1 & 2, 2025

Betterton, Maryland

Join us for Betterton Day!

Kick off the festivities on Friday evening with an exciting night of food trucks, cold beer, a live DJ, and a spectacular fireworks display!

Then on Saturday, don’t miss the parade down Main Street starting at 11:00 a.m., ending at the beach where the fun continues with live music, games, food, crafts, and local vendors.

Spend the day with friends and neighbors—explore, relax on the beach, and enjoy the family-friendly atmosphere! The event runs from 11:00 a.m. to 4:00 p.m.

Admission is free, with parking and rides available.

For more details, call 410-348-5678

Pirates and Wenches Weekend
August 8 - 10, 2025 

Rock Hall, Maryland
www.rockhallpirates.com

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.

Legacy Day 
August 15 - 17, 2025

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: https://sumnerhall.org

Chestertown Jazz Festival 
September 6, 2025

Location: Wilmer Park, Chestertown, MD

Contact: Chestertown Jazz Festival

URL:  https://www.garfieldcenter.org/gcaevent/2025-chestertown-jazz-fest/

The 29th Annual Chestertown Jazz Festival, "Jazz by the River," is scheduled for Saturday, September 6, 2025, at Wilmer Park in Chestertown, Maryland. The festival is held from 12 pm to 6 pm. 

Key details about the festival:

• Date: Saturday, September 6, 2025
• Time: 12 pm to 6 pm
• Location: Wilmer Park, Chestertown, MD
• Event Name: "Jazz by the River"

Rock Hall FallFest
October 11, 2025

Rock Hall, Maryland
www.rockhallfallfest.org

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!

 Chestertown RiverArts Studio Tour

October 18-19, October 25-26, and November 1-2, 2025

Chestertown, Maryland

For those of you who would love the chance to chat with artists about their inspirations and see how they actually create their amazing work choose from 60 artists on the Chestertown RiverArts self-guided studio tour October 18-19, October 25-26, and November 1-2. It’s fun and it’s free! There’s a broad range of media and styles. See lots of different studio set-ups, some in Chestertown and Rock Hall and others out in the beautiful countryside of Kent and Queen Ann counties. Start at the RiverArts Gallery, 315 High Street, in the breezeway, for the exhibit of their works and pick up a brochure to help you plan your day or weekend. https://www.ctownra.org/studio-tour. Studios will be open November 1&2 during Downrigging Weekend.

Sultana Downrigging
October 31- November 2, 2025

Chestertown, Maryland
https://downrigging.org/

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.

A Dickens of a Christmas Weekend 
December 6 - 7, 2024

Kent County's favorite holiday event. Step back into 1840's London and experience the holiday season as Charles Dickens imagined it. This two day event includes entertainment, home tour, food, book talks, merchandise, and more. And don't forget to come dressed like the dickens!

For more information visithttps://mainstreetchestertown.org/dickens/.

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.