Visit the County of Kent, Maryland for the Holidays!
(Check often for 2021 Updates)

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

Visit the County of Kent, Maryland for the Holidays!
(Check often for 2021 Updates)

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


The Garfield Center for the Arts features "Shrek: the Musical" 

December 3 - 19, 2021

December 3 - 19, 2021; Fridays 8pm | Saturdays 8pm | Sundays 3pm
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

Emmanuel Church Annual Christmas Bazaar

November 20, 2021

Saturday, November 20, 2021  |  8:30am - 2pm; Lunch 11:30 to 1:30
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.

Country Crafts Guild Show

2021 (TBD)

TBD - Friday, November & Saturday - November | TBD
Location: TBD

A wide variety of country crafts available for purchase. Be sure to visit both days.

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Santa’ Arrival & the Lighting of Chestertown

2021 (TBD)

TBD - Friday, November  |  6:30-8pm
Location: Fountain Park, Chestertown


The Kent County Community Marching Band will herald the arrival of Santa by firetruck with holiday music, while Chestertown's Historic District comes aglow with twinkling holiday decorations.

 Annual Toy Train & Model Railroad Exhibit

2021 (TBD)

TBD - Saturday, November   |  10 am - 1 pm
Location: Chestertown Branch - Main Meeting Room, 408 High Street Chestertown
Kent County Public Library

If you're nostalgic for toy trains or mesmerized by model railroads, be sure to mark your calendar for Kent County Public Library's Annual Toy Train & Model Railroad Expo! This exhibit is made possible thanks to the enthusiasm, knowledge, and generosity of father-son team of Bob and David Singer. Free admission & all ages welcome.

Christmas Parade

2021 (TBD)

TBD - Saturday, November   |  9:45 am - 12 pm
Location: High Street, Downtown Chestertown

Kick off the holiday season with Chestertown's annual Parade! One of Kent County’s favorite holiday traditions! Enjoy marching bands, classic automobiles, floats and your favorite holiday characters.

Rock Hall Hometown Christmas 

2021 (TBD)

TBD - Saturday, November   |  11 am
Location: Main Street Rock Hall

Carriage rides (3 carriages capable of carrying a total of 14 passengers) will be availabie throughout the day with the following guidelines:

  • Riders will be required to social distance while standing in line, wear masks, and ride in family groups.
  • Each family will be required to provide their name and address.
  • The carriages do not have seats facing each other and they will be sanitized after each ride.

Come and enjoy the Christmas festivies in Rock Hall. Main Street shops will be hosting mini-events and open houses. There will be plenty of family-friendly activities to do and see in Rock Hall for the start of the Holiday Season!


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A Dickens of a Christmas Weekend 
December 3 - 4, 2021

Saturday, December 4th
Main Street Chestertown presents “A Dickens of a Christmas” celebration with live outdoor music performances throughout the historic downtown. Please wear masks and practice social-distancing.


Previous Years' Event Schedule below:
Chestertown’s First Friday

December 4th, 5 pm - 9 pm

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 or

Winterfest Wassail

Friday, December 6, 2019  |  5 pm - 7 pm Wassail Party Historical Society.resized
Location: Chestertown

Chestertown and The Historical Society of Kent County welcomes you to enjoy extended hours at the museum and shop during the holiday kick-off evening. Enjoy a cup of warm cider and tasty delicacies while the classic movie "A Christmas Carol" plays softly in the background creating an atmosphere of holiday cheer. 

Festival of Trees

Saturday, December 7, 2019  |  10 am - 5 pm
Location: Chestertown

Welcome the beginning of the Christmas season with Soroptimist International of Kent & Queen Anne’s Counties partnered with First United Methodist Church to present the Festival of Trees.This is a community event that allows all ages to visit a display of trees decorated by businesses, organizations, as well as families. It's a way of saying "thank you" to the community for helping Soroptomist with the betterment of women and girls. For more information on how to donate a decorated tree, please continue to follow our site,

Galena's Tree Lighting

Saturday, December 7, 2019  |  6 pm
Location: Dogwood Drive, Main Street Galena, the Galena Town Hall, Galena Fire Company

For more information call Galena Volunteer Fire Co.

Come to the Town of Galena to share in the spirit of the Christmas season. Join in the Galena Volunteer Fire Company’s parade beginning at Dogwood Drive! They will be escorting Santa through town on a fire truck. The Kent County Marching Band will be parading to! Preceding down Main Street to the Town Hall, Santa will disembark from the parade to light the town’s Christmas Tree and greet the children. Light Refreshments will be provided at the Town Hall. The parade will end at the Fire House.

Santa Arrives by Boat and Crab Basket Christmas Tree Lighting
(Rescheduled for 2021)

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

Nutcracker in a Nutshell

Tuesday, December 10, 2019  |  7 pm
Location: Garfield Center for the Arts, 210 High Street, Chestertown

Tchaikovsky's holiday classic, slightly revised and only 30 minutes in length. Presented by students of Ballet with Becky. Admission is free.

For more information visit

Feast of the 7 Fishes - Rock Hall Style
(Rescheduled for 2021)   Feast of the 7 Fishes

Location: Rock Hall     

Seven popular Rock Hall restaurants will offer a special appetizer, entree' and dessert. The participating restaurants are: Anchor & Plow (shrimp), Harbor Shack (salmon), The Pearl on Main (crabs), Bay Wolf (scallops), Osprey Point (clams), Waterman's (oysters) and Wheelhouse (rockfish). Dine around Rock Hall, one or both nights! Reservations are recommended. 

Harp & Soul - Meredith Hadaway and Friends Harp and Soul Meredith Hadaway

Sunday ,   |  4 pm
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.

Santa Claus Conquers the Martians

Friday, December 20, 2019  |  7 pm
Location: Garfield Center for the Arts, 210 High Street, Chestertown

For more information: 410-810-2060

Join The Garfield Center for the Arts for a one-night movie presentation of "Santa Claus Conquers the Martians". All ages welcome.

New Years Eve Potluck at The Mainstay with Joe Holt at the Piano

Tuesday,  |   5 pm
Location: The Mainstay - 5753 Main Street, Rock Hall

Ring out 2019 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 5pm, and Joe will serenade attendees as they dine.

Rock Hall Hat Parade and Rockfish Drop
(Rescheduled for 2021)  new years hat parade 2015 2 400x300

Tuesday, December 31, 2019   |   6:45 pm

The Hat Parade on Main Street starts the New Year's celebration off right. Parade lineup and registration at 6:45 pm in the Gazebo. Parade starts at 7 pm.

Decorate your hat for a chance to win many "hategories"! See for more information.