Visit the County of Kent, Maryland for the Holidays!

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


Emmanuel Church Annual Christmas Bazaar

Saturday, November 17-18, 2018 | 8:30am - 2pm; Lunch 11:00 to 2:00
Location: Emmanuel Episcopal Church, 101 N. Cross Street, Chestertown
Admission: Free
Silent auction, Collectibles, Hand knitted items, Pre-owned jewelry, Plants, Christmas and Thanksgiving decorations, Gourmet goodies. The Preview Party will be Friday, November 16th, 2018; 5:30 - 7:30 p.m. Tickets for the Preview Party are TBD and include delicious hors d'oeuvres and beverages.

55th Annual Chestertown Antiques Show & Sale 2018

Friday November 23rd, Saturday 24th, Sunday 25th
Location: Johnson Lifetime Fitness Center

The Antiques Show includes many long-time favorite dealers consistently offering quality antiques, furnishings, accessories, art, jewelry, period pieces and silver. Admission $8. Free parking.

Santa Holiday Page

Santa’ Arrival & the Lighting of Chestertown

Friday, November 23, 2018   | 6:30-8pm
Location: Fountain Park, Chestertown

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

paradeChristmas Parade

Saturday, November 24, 2018 | 10:30 am
Location: High Street, Downtown Chestertown

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

The Garfield Center for the Arts features Tiny Tim

201 High Street, Chestertown
November 30 - December 9, 2018; Fridays 8pm | Saturdays 8pm | Sundays at 3pm

Take a break from the holiday bustle and enjoy a holiday 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

Festival of Trees

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. In the holiday spirit of giving thanks to the community for helping with the betterment of women and girls. For more information on how to donate a decorated tree, please continue to follow our site,

6th Annual Toy Train & Model Railroad Exhibit

December 1, 2018 | 10 am - 1 pm
Location: Main Meeting Room, 408 High Street Chestertown
Kent County Public Library

Kent County Public Library hosts its 6th Annual Toy Train & Model Railroad Exhibit, featuring tinplate trains from the 1920s & 1930s and magnificent operating layouts in O and Standard Gauge. 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.

Santa Arrives and Crab Basket Christmas Tree Lighting

  |  6:00 pm - Santa Arrives by Boat
Location: Town of Rock Hall - The bulkhead for Santa's arrival, then Main St. for tree lighting

Christmas festivities kick off for Rock Hall with the arrival of Santa and Mrs. Claus by boat 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 - to regale those present. Santa will travel by tram to Main Street to officiate the lighting of Rock Hall's distinctive Crab Basket Tree - a true original!

Following the tree lighting, Santa and Mrs. Claus will proceed to "Santa's House" in the Visitor Center to hear children's wishes for Christmas

Winterfest Wassail

December 7, 2018 | 4pm
Location: Rock Hall

Rock Hall welcomes you to enjoy extended hours at stores and shops throughout the town. Many businesses will be offering holiday discounts and specials to help kickstart this busy time of year. Rock Hall restaurants will offer discounts and specials to help fill you up and fuel your shopping adventure.

Santa Comes to Town!
Saturday, December 7, 2018 | 6pm
Location: Public landing on Bayside Avenue in Rock Hall

Santa arrives by boat at the public landing at about 6:00 PM, accompanied by the Kent County Community Band. Upon arrival, Santa is transported to Main Street where he "takes up shop" in "Santa's House" on Main Street to meet children and hear their Christmas requests while The Kent County Community Band continues to play Christmas tunes on Main Street during Santa's visit.

Santa Returns!
Friday, December 7, 2018; 6pm | Friday, December 14, 2018; 6pm
Location: Santa’s House Main Street Rock Hall

Annual Artisan Sale at The Artists Gallery

December 7th-31st 2018
Location: 239 High Street, Chestertown

A wide variety of handcrafted, creative work from the Gallery’s collection of artists on display and available for purchase.

For more information visit

Dickens Christmas FinallogoA Dickens of a Christmas Weekend 2018

Friday, December 7th through Sunday, December 9th
Main Street Chestertown presents “A Dickens of a Christmas” celebration throughout the historic downtown.

Chestertown’s First Friday
December 7th, 5pm-8pm

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 311-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

Gather ‘Round

Saturday, December 15, 2018
Garfield Center, 210 High Street, Chestertown

Christmas storytelling event at the historic Garfield Center for the Performing Arts at the Prince Theater! Hot chocolate, carols, and Christmas Joy.

For more information visit

Crab Basket Christmas Tree Lighting

December 2018
Location: Main Street
Contact: Town of Rock Hall

For more information: 410-639-7719; Email:

Join community members for Christmas music and the lighting of Rock Hall's Crab Basket Christmas Tree, featuring several hundred decorated baskets in memory/honor of loved ones.

Galena's Tree Lighting

Saturday, December 8, 2018 | 6pm
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.

Harp and Soul- Meredith Hadaway and Friends

Sunday ,   |  4:00 PM
LocationThe Mainstay - 5753 Main Street - The Mainstay - 5753 Main Street
$15 online and $18 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 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.

Hedgelawn Classical Series Presents Amanda Dame, Flute

Sunday ,   |  4:00 PM
LocationThe Mainstay - 5753 Main Street

Peabody at The Mainstay presents some of the most exciting young musicians at the Peabody Conservatory in a friendly interactive setting. The month we host flautist Amanda Dame in a program of holiday inspired classical music. 

A Winter's Eve: Free Band Concert by the Eastern Shore Wind Ensemble

Sunday ,   |  4:00 p.m.
LocationEmmanuel Episcopal Church - 101 N. Cross St. (at High St.)

The ESWE, the all-ages community concert band directed by Charles Thai and based in Chestertown, will present an hour-long program of holiday music, followed by refreshments in the parish hall.Founded in 2001, the band welcomes new members at any time, without audition, fee, or limits on section size. The band rehearses from 7:00 to 8:30 on Monday evenings in Room 116 of the Gibson Center for the Arts at Washington College, with rehearsals resuming in January. The next concert will be on Sunday, March 17, 2019. The band is supported by the Kent County Arts Council and community donations.


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

Monday ,   |  5:00 PM
LocationThe Mainstay - 5753 Main Street


Ring out 2018 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, music from 6 to 8pm.


Hat Parade

Monday, December 31, 2018 | 6:45pm

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 7:00 pm.

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