Visit Kent County for the Holidays!

The spirit of the holidays can be found all over Kent County. Craft shows and fairs, holiday concerts, parades and house tours are just a few of the many events happening this holiday season in Kent County. Join us in celebrating this festive season.

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Emmanuel Church Annual Christmas Bazaar

Saturday, November 18, 2017 | 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 17, 5:30 - 7:30 p.m. Tickets for the Preview Party are $15 and include delicious hors-d'oeuvres and beverage.

kartKART Antiques Show

Friday, November 24, 2017 | 4pm-7pm
Saturday, November 25, 2017 | 10am-5pm
Sunday, November 26, 2017 | 11am-3pm
Location: 300 Washington Ave. Chestertown, Washington College, Johnson Lifetime Fitness Center
Admission $8. Free parking

Annual antique show and sale benefiting Kent Association of Riding Therapy, an organization supporting special needs children and adults through horseback riding therapy. The Antiques Show includes many long-time favorite dealers consistently offering quality antiques, furnishings, accessories, art, jewelry, period pieces, and silver.

Santa Holiday Page

Santa Arrives in Chestertown

Friday, November 24, 2017   | 6:30pm
Location: Fountain Park, Chestertown

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

paradeChristmas Parade

Saturday, November 25, 2017   |  10am
Location: High St, Downtown Chestertown, Maryland

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.

dickensIntroducing the “Dickens of a Christmas” weekend with a Fezziwig Party by Main Street Chestertown

Thursday November 30, 2017, 6pm-9pm
Location: Hynson Ringgold House | 106 South Water Street, Chestertown
Tickets: $75, can be purchased online or by check, made payable to Main Street Chestertown-118 N. Cross Street, Chestertown, MD 21620.

Washington College President and Mrs. Kurt Landgraf join the Main Street Chestertown organization in hosting this preview party to Chestertown's first Dickens of a Christmas Festival. Special themed drinks, full dinner buffet, and fiddle music by Nevin Dawson will be followed by a special interactive presentation by New York-based songwriters/singers The Levins titled "Raise a Glass to Charles Dickens." For more information, visit or contact

festivaloftreesFestival of Trees | First United Methodist Church

105 North Mill Street, Chestertown
December 1-3, 2017; Admission: Free
“Dickens of a Christmas” First Friday, December 1, 5pm-7pm
Saturday, December 2, 10am-5pm
Sunday, December 3, 11am-3pm

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. First United Methodist will be transformed into a magical place where the artistic talent and the spirit of giving in our community will come alive.

For more information on how to donate a decorated tree, please contact Vicki Quinn To present your special entertainment talent, please contact Connie Morris or to purchase a poinsettia, please contact Rita Kulley.

Winterfest Wassail

December 1-3, 2017 | 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 special as well, to help fill you up and fuel your shopping adventure.

Chestertown's 1st Fridays

Friday, December 1, 2017   |  5 - 8pm
Location: Downtown Chestertown, Maryland


Take a break from the hustle and bustle of the holiday season by visiting Kent County during December’s First Friday in Chestertown. Meander the red-brick, tree-lined sidewalks of this historic city and explore the beauty of its dynamic Arts and Entertainment District. Check off your holiday shopping list while enjoying extended shop hours throughout downtown.

Holiday Shop and Dine Local

December 1-3, 2017
Location: Rock Hall, Maryland  

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 special as well, to help fill you up and fuel your shopping adventure.

Cratchit and Tim drawing LGE media

A Dickens of a Christmas Weekend 2017

Friday, December 1st through Sunday, December 3rd
Main Street Chestertown presents “A Dickens of a Christmas” celebration beginning Friday evening through Sunday morning Dec. 1-3, 2017, throughout the historic downtown.

Friday, December 1st
Chestertown's First Friday, 5 - 8pm

Saturday, December 2nd
8am-Noon Farmers Market in Fountain Park
11am-1pm Visit Santa in Fountain Park
1pm-4pm Historic House Tour, Tickets: $20 in advance; $30 day of the event
3pm Tea & Crumpets at Hynson Ringgold, Seating is limited, please reserve your Tickets $35
7pm-9pm Beers and Bonfires on the Town Landing, $5/beer

Sunday, December 3rd
8am Run like the Dickens 5K, Dickens costumes are encouraged! Check back for updates.

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! Visit or

miracleMiracle on 34th Street

201 High Street, Chestertown
December 1-17, 2017
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. $20 General | $15 Senior | $10 Student.

Crab Basket Christmas Tree Lighting

Saturday, December 2, 2017   | 7pm
Location: Main Street
Contact: Town of Rock Hall
Phone: 410-639-7719

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.

paintnsipPaint 'n Sip

Saturday, December 2, 2017   | 2 - 4pm
Location: 12441 Vansants Corner Rd, Kennedyville, MD 21645
Contact: Crow Vineyard & Winery
Phone: 302-304-0551

We will be painting the “Believe” design on a 10×10 piece of wood. The design is a snowman with falling snow and the word “Believe” – perfect for winter or as a holiday gift. All instruction and painting materials included. One glass of wine is included for all painters. No experience necessary and you will leave with a finished painting in 2 hours. For reservations please visit Crow Believe Paint and Sip.

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Santa Comes to Town!

Saturday, December 2, 2017  |  6:00pm
Location: Public landing on Bayside Avenue in Rock Hall, Maryland

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!
Location: Santa’s House Main Street Rock Hall
Friday, December 8, 2017 | 6pm
Friday, December 15, 2017 | 6pm
If you miss Santa on December 2nd don’t panic! Santa will be back to town in “Santa’s House”, December 8th and December 15th at 6pm.

Pet Photos with Winemaker Santa

Sunday, December 3, 2017   | 12 - 4pm
Location: 12441 Vansants Corner Rd, Kennedyville, MD 21645
Contact: Crow Vineyard & Winery
Phone: 3023040551
Bring your pet to Crow Vineyard & Winery and take their photo with Winemaker Santa and his trusty intern Elf!

Galena's Tree Lighting

Saturday, December 9, 2017 | 6pm
Location: Dogwood Drive, Main Street Galena, the Galena Town Hall, Galena Fire Company

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.

holidaybasketHoliday Basket Extravaganza

Sunday, December 10, 2017   | 12 - 4pm
Location: 12441 Vansants Corner Rd, Kennedyville, MD 21645
Contact for reservations: Crow Vineyard & Winery Holiday Basket and click on the register button
Phone: 302-304-0551

Visitors will create a special gift box, basket or tote and fill it with featured local vendors’ products that complement the wines and beef from the Crow Farm and Vineyard. Appetizers will be provided, and wine will be available to purchase by the glass or the bottle. There is no charge for the event, Crow Vineyard just asks that you support the local vendors.

mailboxswagKingstown Farm, Home and Garden Horticulture Meeting: Mailbox Swag

Tuesday, December 12, 2017   | 6 - 7pm
Location: Kingstown Farm, Home & Garden
Phone: 410-778-1551

We will create mailbox swags using fresh greens. $7 per swag. All supplies will be provided.