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


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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.

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

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

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.  

Harp & Soul - Meredith Hadaway and Friends Harp and Soul Meredith Hadaway
December 11, 2022

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

Celebrate the Songs for the Season with the lovely and lively traditional songs, dance tunes & carols from the British Isles, Celtic lands & beyond. The core group of Meredith Hadaway (Celtic harp & concertina), Ben Bennington (guitar & vocals) and Rebekah Hardy (oboe) will be joined by their special guests Sue Matthews (vocals), Bob Ortiz (percussion), Nevin Dawson (viola) and singer and songwriter Pam Ortiz who will add some of her originals to the mix as well as adding her voice to the group. This will be an afternoon of delightful and unusual songs for the season and lots of holiday cheer.

New Year's Eve Potluck at The Mainstay with Joe Holt at the Piano
December 31, 2022 

Location: The Mainstay - 5753 Main Street, Rock Hall

Ring out 2022 at a Mainstay Potluck with the dynamic Joe Holt at the piano. Bring a dish to share with the group and fill up on good cheer and good food. The bar in the Byrd Room will be open and serving holiday favorites. Doors open at 5 pm, and Joe will serenade attendees as they dine.