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Phone: 410-778-0416
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400 High Street, 3rd Floor
Chestertown, MD 21620

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Annual & Holiday Events in Kent County Maryland

 

 

Chestertown Taste of the Town

Paint the Town
April 25 - 28, 2024

Fountain Park Chestertown, Maryland
www.chestertownriverarts.org

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". 

 

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Galena Dogwood Festival

Dogwood Festival of Galena
May 11, 2024

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 9:30 am. Activities will open from 10 a.m. - 3 p.m. in the community park.  Admission to the festival and parking will be free.There will be live music, vendors, children’s activities, dog contest, food and beer trucks, and more! 

 

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Chestertown Tea Party

Chestertown Tea Party Festival
May 26 - 28, 2023

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, 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.

 

Tea Party bb Tea Party 16.6CREDIT CHRIS CERINO Tea Party 16.3CREDIT CHRIS CERINO

 

 

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National Music Festival

National Music Festival ~ 10th Anniversary Year
June 4 - 17, 2023


Various locations throughout Kent County
www.nationalmusic.us

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)

 

 

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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
https://www.rockhallvfc.org/rockfishtournament

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Fourth of July in Kent County

Fourth of July in Kent County
July 2024

 

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 7 (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. 

 

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Kent County 4H Fair

Kent County 4H Fair
July 19 - 22, 2023

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.

 

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Betterton Appreciation Day

Betterton Appreciation 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 bvfc5.org.

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Pirates and Wenches Fantasy Weekend

Pirates and Wenches Weekend
August 11 - 13, 2023 

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.

Pirates Landing Page image bar

 

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Legacy Day 
August 18 - 19, 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: https://www.facebook.com/CharlesSumnerPost/

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Chestertown Jazz Festival 
September 7 - 9, 2023

Location: The Mainstay, 5753 N. Main St. Rock Hall, MD & Wilmer Park, 413 S. Cross St., Chestertown, MD

Contact: Chestertown Jazz Festival

URL:  https://www.garfieldcenter.org/gcaevents/category/annual/chestertown-jazz-festival/

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Rock Hall's Fall Fest

Rock Hall FallFest
October 14, 2023

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!

fallFest2

 

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Sultana Downrigging

Sultana Downrigging
October 27- 29, 2023

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.

Read more …...

Annual Chestertown RiverArts Studio Tour

 

 Chestertown RiverArts Studio Tour

October 21-22, 2023 and October 28-29, 2023

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 21-22 and 28-29. 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. www.chestertownriverarts.com/studio-tour.

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A Dickens of a Christmas Weekend 
December 1 - 2, 2023

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 carriage rides, 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/.

Read more …...

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.

Read more …...

  • Calendar of Events
    • Annual Events
    • Holiday Events
    • Georgetown 4th of July Events

Sign up for our Tourism

E-Newsletter

 

visitor guide cover

View our Digital Visitors Guide

Download PDF Version

 

 

Contact
Phone: 410-778-0416
tourism@kentgov.org 

400 High Street, 3rd Floor
Chestertown, MD 21620

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Government Center

400 High St. Chestertown, MD 21620
410-778-4600
kentcounty@kentgov.org





 

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