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.


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


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November 16 - December 24, 2023

November 16- December 24, 2023

Location: 315 High Street, Chestertown

RiverArts Annual Holiday Show is a great place to find wonderful handmade gifts crafted by our talented artisans. With price points to fit every budget, come by the gallery to find the perfect gift and support both the arts and artists in our community.

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November 18, 2023

November 18, 2023  |  8:30 am - 1:30 pm
Location: Emmanuel Episcopal Church, 101 N. Cross Street, Chestertown
Admission: Free

A variety of holiday items for sale, including Elegant Elephants, Botanical Delights, Gourmet goodies, Holiday ornaments, Jewelry and more. All proceeds go to local charities.

For more information, contact Emmanuel Church at 410-778-3477 or by email at


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Santa’s Arrival & Parade
November 24, 2023

November 24, 2023 |  6:00 pm - 8:00 pm
Location: Fountain Park, Chestertown

Kick-off the holiday season with Chestertown's annual Parade! One of Kent County’s favorite holiday traditions! Line up on High Street to see all of your favorites ring in the holiday season. The annual parade will begin at Dixon Drive and commence at the intersection of High and Spring Street. Enjoy marching bands, classic automobiles, floats and your favorite holiday characters. Kids can meet with Santa at his "house" in Fountain Park to hear all of their Christmas wishes.

For more information visit



Santa in his House
November 24- December 16, 2023

November 24, 2023  |  After the Christmas Parade

December 2, 9 & 16, 2023 |  10:00 am to 12:00 pm
Location: High Street, Downtown Chestertown

Visit Santa in his house, enjoy yummy treats and snap a photo! Enjoy Small Business Saturday by shopping at downtown shops and merchants.

For more information visit


It's almost Christmas, Charlie Brown!

December 1, 2023

Friday, December 1, 2023  |  8:00 pm
Location: The Mainstay - 5753 Main Street, Rock Hall
$20 online and $25 at the door/by phone

For his December First Friday program, pianist and impresario Joe Holt has produced an evening of seasonal music that pays tribute to jazz pianist/ composer Vince Guaraldi. Guaraldi scored it big in the 1960s with a hit record on AM radio. But no one could have predicted the next opportunity that came knocking on his door.

In 1963, while searching for music to accompany a planned Peanuts television special entitled A Boy Named Charlie Brown, television producer Lee Mendelson heard Guaraldi’s Grammy award winning hit "Cast Your Fate to the Wind" on the radio and offered Guaraldi the job of composing the score for the program. In his later reflections, Mendelson said, "it just blew me away. It was so right, and so perfect for Charlie Brown and the other characters.” It wasn’t long before Mendelson retained Guaraldi for the upcoming Peanuts Christmas special, A Charlie Brown Christmas.

The soundtrack contained the song "Christmas Time Is Here", and melodies that highlighted each character such as Charlie Brown's theme, Linus and Lucy, Frieda (with the naturally curly hair), and Peppermint Patty. Guaraldi defined the Peanuts sound, and just about everybody knows the music.

Joining Joe for this seasonal tribute will be Greg Burrows on drums and Tom Baldwin on bass.

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

  |  5:00 - 9:00 pm  
  |  8:00 am - 6:00 pm
Location: Downtown Chestertown
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 full schedule and more information visit

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December 1 - 17, 2023

December 1 - 17, 2023; Fridays 8:00 pm | Saturdays 8:00 pm | Sundays 2:00 pm
Location: Garfield Center for the Arts, 210 High Street, Chestertown

Take a break from the holiday bustle and enjoy a classic at the historic Garfield Center for the Arts in downtown Chestertown.

*Online ticket sales end 3 hours before an event. Tickets may still be available at the door. Call the Box Office at 410-810-2060 to check on ticket reservations.

Santa Arrives by Boat and Crab Basket Christmas Tree Lighting
December 2, 2023

  |  6:00 pm  
Location: Town of Rock Hall - The bulkhead for Santa's arrival, Main Street Rock Hall for the tree lighting  

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Christmas festivities kick off in Rock Hall with the arrival of Santa and Mrs. Claus by boat followed by a parade of boats all at the bulkhead at 6:00 PM. The Community Band will be on-hand to entertain - both at the bulkhead awaiting Santa's arrival and on Main Street. Santa will travel by firetruck to Main Street to officiate the lighting of Rock Hall's Crab
Basket Christmas Tree featuring several hundred decorated baskets in memory/honor of loved ones.

Following the tree lighting, enjoy tasty smores roasted over a community firepit and follow Santa and Mrs. Claus to "Santa's House" in the Visitor Center for children to make their Christmas wishes.

For more information, contact the Town of Rock Hall at 410-639-7611.

Deck the Hall, Town Hall
December 9, 2023

Saturday, December 9, 2023  |  6:00 pm
Location: Main Street Galena, Galena Town Hall

For more information call Galena Volunteer Fire Co. at 410-6548-5050.

Come to the Town of Galena to share in the spirit of the Christmas season. Santa and Mrs. Claus will be visiting Town Hall. Come visit to tell Santa what's on your Christmas list and enjoy holiday cookies and hot chocolate.

Mayor Carroll will do a Facebook "drive through Galena" to share the lights of the season on the hunt for the following categories: Best overall display, most colorful display, best traditional Christmas display, best business display and best "Griswald" Christmas display. Feel free to load the family van and do an "in-person" drive-through to experience the holiday lights firsthand.  


Meet You at the Movies Harp and Soul Meredith Hadaway
December 9, 2023

Saturday, December 9, 2023  |  4:00 pm

Location: Presbyterian Church of Chestertown - 905 Gateway Drive, Chestertown

Description: The Chester River Chorale presents “Meet You at the Movies”, a holiday concert featuring the unforgettable melodies from your most cherished Christmas movies spanning the last century of film. Enhanced by the accompaniment of a live, professional chamber orchestra, our program promises to awaken the Christmas spirit within us all. We look forward to sharing this joyful occasion with you and encourage you to join us for a delightful popcorn reception following the concert.

Harp & Soul - Songs of Hope and Peace Harp and Soul Meredith Hadaway
December 10, 2023

Sunday, December 10, 2023  |  4:00 pm

Location: The Mainstay - 5753 Main Street, Rock Hall
$20 online and $25 at the door/by phone

The Mainstay is delighted to present another musical celebration with the musical ensemble Harp and Soul’s seasonal visit, These perennial local favorites will offer a program they have titled “Harp and Soul: Songs of Hope and Peace.” The group consists of Meredith Hadaway (harp and concertina), Ben Bennington (guitar and vocals), Rebekah Hock (oboe), and Bob Ortiz (percussion and vocals). They will be joined by special guests, including singer/songwriter Pam Ortiz, pianist Joe Holt, and vocalist Sue Matthews. This year’s concert will feature songs of remembrance, hope, and above all, optimism for the future. Come celebrate the holidays with lovely and lively traditional music from the Celtic tradition and more.


New Year's Eve Potluck Supper
December 31, 2023 

Sunday, December 31, 2023  |  6:00 pm
Location: The Mainstay - 5753 Main Street, Rock Hall


Say goodbye to the challenges of this past year and share your hopes for the new year at The Mainstay’s New Year’s Eve Pot Luck Celebration. Bring a covered dish and join us for this community gathering of friends, neighbors and the familiar faces of music lovers. Joe Holt will once again tickle the ivories for the party. Things get underway at 6 PM.