Kent County MD - Holiday Events

For more information about these events go to

Chestertown Winterfest Weekend

Chestertown, MD
December 5th - 7th

3 days of holiday fun for the entire family. Go to to see the calendar of events.

Chestertown's 1st Friday

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

Meander the red-brick, tree-lined sidewalks of Historic Chestertown, while enjoying extended shop hours and arts and entertainment throughout Downtown. Luminary bags are being decorated by local school children. Kristen Owen will need assistance in placing and collecting bags around town on Friday.
Santa will stroll around town and visit stores. Kent School students will be caroling. For a list of activities, please check this calendar for specific listings.

Pet Portraits with Santa Paws to Benefit The Humane Society

Coco's Pet Center Boutique, 335 High Street B, Chestertown, MD
Friday, December 5th
5:30pm - 7:30pm

As a part of Chestertown’s First Friday event, bring your pets out and about to enjoy the festivities in town while making a lasting memory of your pets and family with Santa. Photo portraits will be sent digitally. A suggested donation of $10 per pet portrait will benefit the homeless animals of The Humane Society of Kent County.

Winterfest Middle School Band Concert at the People Bank

Peoples Bank, Main Branch, High Street and Spring Avenue
Friday, December 5th
6:00pm - 7:00pm

The Kent County Middle School Band led by Mr. Leon Frison will perform from 6:00 to 7:00. Refreshments will be served.

Holiday Show and Sale

RiverArts, 315 High St. Suite 106, Chestertown, MD
December 5th - January 3rd
Mon - Sat: 10:00am - 5:00pm
Sunday: 12:00pm - 4:00pm

Want to shop local this year and support the artists and craftsmen in our community at the same time? Be sure to visit RiverArts Annual Holiday Show and Sale. Opening in the Studio Gallery on (Black) Friday, Nov. 28 and opening Gallery-wide on Dec. 5, this year's sale promises to be better than ever.

A Night in Bethlehem

First United Methodist Church
Friday, December 5th
6:00pm - 8:00pm

Join us for A Night in Bethlehem, a hands-on Holy Land Experience, where you will experience Bethlehem as it was when Jesus was born. Experience the market place with crafts and food and meet Mary and Joseph at the live nativity. For all ages.

Chester River Chorale's "A Chester River Holiday"

Presbyterian Church of Chestertown, MD
Friday, December 5th & Saturday, December 6th
Friday: 8:00pm & Saturday: 3:00pm

No French hens, but there is a French horn in the brass sextet that will back the Chester River Chorale as it sings in the winter holidays on Friday evening December 5 and Saturday afternoon December 6 at the Presbyterian Church of Chestertown. An organ and percussion ensemble and guest artists Cantor Gary Schiff and the Chester River Youth Choir will join the program. Suggested donation is $15 with children free. Visit for more information, or call 410 928 5566.

3rd Annual Reindeer Stampede 5K

Main Street, Rock Hall, MD
Saturday, December 6th

Come Run/Walk with us though the Winter Wonderland of Rock Hall on December 6th ! For our 3rd Annual 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. All registered Runners/Walkers will receive a long sleeve RHES Reindeer Stampede 5K Run/Walk T-Shirt.

31st Festival of Trees

The Weinberg Building at The Kent Center
Saturday, December 6th
10:00am - 8:00pm

The members of Soroptimist International of Kent County, MD, are pleased to bring back to the community the Festival of Trees. Visitors will have the opportunity to vote for their favorite tree. Santa will be there--so bring your camera. Free admission and handicapped accessible free parking. Contact Annie Stewart at 410-474-9680 or if your organization would like to display a tree. Sunday Hours 10am–3pm

Colonial Chestertown's Holiday House Tour

Emmanuel Church, 101 N. Cross Street, Chestertown, MD
Saturday, December 6th
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 6th
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 - each year.

Durding's Store Holiday Open House

Main Street, Rock Hall, MD
Saturday, December 6th
12:00pm - 1:00pm

Join us for our annual open house to include a special appeared by Mrs. Claus. Entertainment by Tom McHugh "Banjo Man". Holiday treats, games and sing-a-longs.

Boat Parade and Santa's Arrival at Rock Hall Harbor!

The Bulkhead
Saturday, December 6th

Come celebrate with this timeless Rock Hall tradition! It all starts with the boat parade of lights in Rock Hall harbor. Once Santa arrives at the Bulkhead, the Rock Hall Volunteer Fire Company will deliver him to Main Street! Stop by for free refreshments, and a photo with santa

Kent County Fire House Toy Ride

Start: Galena VFC, End: Rock Hall VFC
Sunday, December 7th

Give Santa a hand this year! Leave an unwrapped toy at your firehouse and the bikers and chase cars will pick them up for Santa to deliver right here in Kent County! The ride will begin at Galena VFC, stopping at all county firehouses, ending at Rock Hall VFC, with Santa at 4:00PM! Questions, contact Jay Jacobs at 410-708-0596. Organized by the Rock Hall Bike Fest Committee.

"A Home for the Holidays" Open House at The Humane Society

HSKC - 10720 Augustine Herman Hwy, Chestertown, MD
Sunday, December 7th
12:00pm - 3:00pm

Enjoy complimentary, festive snacks and drinks at the shelter and meet animals awaiting forever homes. Consider giving a pet the forever home it deserves. If you submit an adoption application the day of the event and it is later approved, HSKC will waive the adoption fee!

Galena Blooms 4th Annual Holiday Happening

589 Mill Lane, Galena, MD
Sunday, December 7th
10:00am - 4:00pm

This year our annual party will include 15-20 of our regions finest vendors! We'll have a bonfire, chili and corn bread, Bill Wright spinning Holiday tunes, Crow Farm wines, Santa's coming too! Come out and shop local, and have a really great time!

7th Annual Seasonal Sensations Dinner and Show and Silent Auction

Kent County High School
Tuesday, December 9th

Dinner prepared by culinary arts students and a holiday show performed by high school musicians and singers. Proceeds benefit the KCHS Music Boosters and KCHS culinary programs.

Harp and Soul: Songs for the Season

The Mainstay, 5753 Main Street, Rock Hall, MD
Sunday, December 14th

The Mainstay celebrates “Songs for the Season” as Harp and Soul present the lovely and lively traditional songs, dance tunes & carols from the British Isles, Celtic lands & beyond. Meredith Hadaway (Celtic harp & concertina), Ben Bennington (guitar & vocals), Rebekah Hardy (oboe), Bob Ortiz (percussion), and Nevin Dawson (viola) will be joined by soprano Meghan Cooney Ferster and singer/songwriter Pam Ortiz for an afternoon of holiday cheer. Admission is $15. Call for reservations.

Free Holiday Band Concert by the Eastern Shore Wind Ensemble

Emmanuel Church, 101 N. Cross Street, Chestertown, MD
Sunday, December 14th

The Eastern Shore Wind Ensemble will present a program of Christmas and Hanukkah music. The band invites the audience to join them for post-concert refreshments. Directed by Dr. Keith Wharton, the ESWE is the all-ages community concert band based in Chestertown. It gives four concerts during its Sept.-May season and welcomes new members at any time, without audition or fee. The next concert will be on March 15, 2015. The band is partially supported by the Kent Co. Arts Council.

Messiah Sing-In
Garfield Center for the Arts at the Prince Theatre
Thursday, December 18th

Hallelujah! Join members of the Chester River Chorale and professional musicians at the Garfield Center for the Arts at the Prince Theatre at 8 p.m. Thursday, December 18, to benefit the Kent County Food Pantry. Sing along or just listen at the annual event sponsored by Garfield and the Chorale. A $20 donation lets you join in this holiday treat.

Rock Hall Crawl New Year's Eve Festivities!
Rock Hall
Wednesday, December 31st

Come join us New Year's Eve for a town wide party! Hat Parade starting at 6:45pm at the corner of Main Street and Route 20, then gather at the Bulkhead at 11:45pm for fireworks and fish drop!