Kent County MD - Holiday Events

For more information about these events go to

Small Jewels / Large Gems Art Show

Chestertown RiverArts, Chestertown, MD
Friday, December 6th
5:00 - 8:00pm

Art jewelry, beautiful scarves, wraps and hats; richly colored pottery, wooden vessels, paintings, pastels, cards, and more: the Holiday Show and Sale provides an abundance of creative and unique gifts perfect for the giving season. With most items priced under $100, there is something for every budget and every style.

Chester River Chorale's "A Chester River Holiday"

Presbyterian Church of Chestertown, MD
Friday, December 6th & Sunday, December 8th
Friday: 8:00pm & Sunday: 3:00pm

Voices span the generations as the Chorale is joined by Bay Area youth choruses to sing in Christmas and Chanukah accompanied by a small chamber orchestra. Works by Bach, Vivaldi, and Handel honoring the Nativity are featured, along with music commonly heard in Synagogue, led by Chestertown Cantor Gary Schiff. The chorale reprises its show-stopping rendition of 'Chanukah, Oh Chanukah', along with familiar carols and holiday tunes such as 'White Christmas' on which the audience can croon along.

2nd Annual Reindeer Stampede 5K Run/Walk & Reindeer Dash

Main Street, Rock Hall, MD
Saturday, December 7th
9:45am - 12:00pm

Come Run/Walk with us though the Winter Wonderland of Rock Hall on December 7th! This is a 5K Walk/Run that will lead in to the festivities planned for the town that day. There will be a RHES Reindeer Dash that will be Free for all children 10 yrs and under. All finishers will receive a medal.
9:45am - 10:00am — Registration
10:25am — Reindeer Dash
10:30am — 5k Run
11:30am — Awards Ceremony

Rock Hall Winterfest

Rock Hall, MD
Saturday, December 7th
12:00pm - 7:00pm

12:00pm — Durdings Open House
12:30pm — Sensitive Santa Parade Line Up at Bayside Foods
1:00pm — Sensitive Santa Parade Departs for Town Hall
6:00pm — Santa Arrives at Bulkhead with the KC Marching Band then Rides Fire Engine to Main St.
7:00pm — Santa lights Christmas Tree then moves to the Gazebo

Colonial Chestertown's Holiday House Tour

Emmanuel Church, 101 N. Cross Street, Chestertown, MD
Saturday, December 7th
12:00 - 3:00pm

Step back in time for the day and come to beautiful and historic Chestertown to experience the holiday season in true colonial style. On this self-paced tour, docents will guide you through several of Chestertown's most historic and significant buildings decorated in their holiday best. Tickets are available online or order by mail. Send a check and ticket request information to : 2013 Holiday House Tour, P.O. Box 771, Chestertown, MD. 21620.

Santa's Workshop

Kent County Community Center
Saturday, December 7th
1:00 - 4:00pm

Children and families will love to participate in this seasonal gathering featuring Santa! Come enjoy crafts, refreshment and don't forget your list! All crafts, refreshments, and pictures with Santa are included in the cost. $7 ($9 if registered late) Registration November 1st - 26th, 2013. For more information call 410-778-1948 or email Snow Date December 8.

Holiday Happening On The Flower Farm

Galena Blooms Farm, 589 Mill Lane Galena, MD
Sunday, December 8th
11:00am - 5:00pm

Come shop and relax at the farm! We will have many local and out of town quality vendors, holiday music, great food, hot drinks, local wine, a bon-fire, Santa will be here, and much much more! A great event that gets better every year!

Worton Elementary School's First Annual Winter Festival

11085 Worton Rd, Worton, MD
Sunday, December 8th
12:00pm - 4:00pm

Winter Festival Fun Community Vendors, Cookie Walk, Secret Santa Shopping, Silent Auction, Picture with Santa, Face Painting, Music, food, games and more! Please come join us for this wonderful event. Check out the WES website and WES Facebook page. All Proceeds to benefit the Worton Elementary School PTA.

Seasonal Sensation Holiday Dinner

Kent County High School
Tuesday, December 10th

KCHS students from the music and culinary arts departments combine their talents for an evening of holiday music and food. A silent auction will accompany the event. Please contact for ticket information. Limited tickets available.

Eastern Shore Wind Ensemble - Band Concert

Emmanuel Church, 101 N. Cross Street, Chestertown, MD
Sunday, December 15th

This free-admission program of holiday-season music will appeal to listeners of all ages. The audience is also invited to a post-concert reception for refreshments and socializing. The ESWE is an all-ages community concert band based in Chestertown and is directed by Dr. Keith Wharton. New members are welcome to join at any time, without audition or fee.

Harp & Soul: Songs for the Season

The Mainstay, 5753 Main Street, Rock Hall
Sunday, December 15th

Meredith Hadaway and friends celebrate the warmth of the season with the lovely and lively traditional songs, dance tunes and carols from the British Isles, Celtic lands and beyond. This will be a delightful afternoon of seasonal tunes with Hadaway on Celtic harp and concertina, Ben Bennington on guitar and vocals, Rebekah Hardy on oboe, Bob Ortiz on percussion, and Nevin Dawson on viola. Call for reservations. Admission is $15.

Polar Express PJ Storytime

Kent County Public Library, 408 High Street, Chestertown, MD
Thursday, December 19th
6:30 - 8:00pm

Come to a special after hour Pajama Storytime all about The Polar Express by Chris Van Allsburg. "Climb Aboard" and drink some hot chocolate while listening to the classic story about the magic of Christmas! Also, a special visitor from the North Pole and a craft activity. Call to reserve train ticket.

Messiah Sing-In

The Garfield Center for the Arts at The Prince Theatre, Chestertown, MD
Thursday, December 19th

The Messiah Sing-In is a cherished annual community singing event, featuring professional soloists, the glorious voices of the audience, and a string quartet. This year's Sing-In is sponsored by the Chester River Chorale, the Garfield Center, and the Kent County Food Pantry. In keeping with the premier of Handel's beloved oratorio, this year's Sing-in is a fundraiser with contributions going to the Food Pantry. Recommended donation for audience members--singing or not--is $20.

Holiday Film - "A Christmas Carol" (1951)

Kent County Public Library, 408 High Street, Chestertown, MD
Friday, December 20th

Drama/Fantasy 86 mins. An old bitter miser is given a chance for redemption when he is haunted by ghosts on Christmas Eve. Stars: Alastair Sim, Jack Warner, Kathleen Harrison Free and Popcorn, too!

6th Annual Gather Round

The Garfield Center for the Arts
Saturday, December 21st
3:00pm - 5:30pm

Priceless! (Donations welcome!) Bring a comfy pillow and blanket and snuggle together as you listen to holiday stories both familiar and new! Join us for an evening of storytelling featuring tales from Christmas, Hanukkah and Kwanza. We’ll provide cookies and cocoa. We ask that you consider contributing a canned food item.

Rock Hall Crawl

Rt. 20 and Main Street, Rock Hall, MD
Tuesday, December 31st

Bring in the new year...Eastern Shore (Mardi Gras) style. Parade of crazy hats: 6pm. Cash prize hat contest. Street Music throughout the night at several venues. Count down the new year, with the famous “Rockfish Drop” at midnight, Rock Hall Harbor Bulkhead. Rock Hall will host Annual Hat Competition.
7:30pm. Prizes awarded on Main St.
11:45pm Don long johns, bundle up and gather at the Bulkhead!
12 midnight STRAIGHT UP!