Kent County, Maryland is The Place to Be This Holiday Season

Less than a two-hour drive from Philadelphia, Northern Virginia, and DC, Kent County Maryland is a scenic peninsula, where the Chester and Sassafras Rivers meander into the Chesapeake Bay. It is home to the historic towns of Chestertown, Rock Hall, Galena, Betterton, and Millington. Year-round experiences include a winery and distillery, museums, natural history, performing arts, art galleries and studios, natural resources, winter sunsets, and more.


With fall transitioning to winter, it’s time to set the pace for your holiday season with early holiday shopping at the Emmanuel Church Annual Christmas Bazaar November 16th–18th. Then turn up the holiday cheer on November 23rd with the 55th Annual, three-day Chestertown Antiques Show and Sale at Washington College. Santa arrives to Chestertown by firetruck on November 23rd at 6:30, accompanied by classic characters, holiday music, a twinkling downtown, and more. Santa’s second appearance is on November 24th during the Chestertown Christmas Parade at 10:30 a.m. The Garfield Center for the Arts presents Tiny Tim’s Christmas Carol on Fridays, Saturdays, and Sundays – November 30 through December 16. Be sure to check play times and get your tickets early at


You’ll also find Santa on December 1st at 6 p.m. when he arrives by boat at Rock Hall Harbor. Santa will be transported by Fire Truck to Main Street where he will take up shop in Santa’s House. You will be delighted to find music, Crab Basket Christmas Tree Lighting, and extended shopping hours.


Chestertown closes its downtown streets, transforms into a Victorian-era London, and celebrates “A Dickens of a Christmas” December 7th–9th. Too long to list all of the 3-day fun here, a sampling includes: Wassail Party, Ghost Walks, Festival of Trees, Fire Dancers, Live Nativity, Strolling Carolers, Fire Pits, Carriage Rides, Clay Studio Ornament Making, Vendors, Holiday House Tour, The Wheelmen, Stilt Walkers, Music, High Tea, Dickens’ expert, Michael Dirda book talk, Flying Flea Circus & Wahoo Medicine Show, Beers and Bonfires, Peoples Sweet Shoppe, Street Theatre, discounts from local shops, restaurants with specially themed menus, “Run like the Dickens” 5K, and more. For a complete schedule, visit


Other events around the County: Galena Tree lighting on December 8th at 6 p.m., features the Kent County Community Marching Band and Santa. The Crazy Hat Parade on Main Street in Rock Hall on New Year’s Eve begins at 6:45 p.m. and includes a chance to win many “hategories.” Winter Birding Walks at Eastern Neck National Wildlife Refuge on 1st Saturdays, November through March takes you to areas not usually open to the public.

No matter what time of year you choose to visit this beautiful and historic destination, Kent County will provide you with experiences that exceed your expectations. For more information on lodging, dining, events, and attractions please visit