Chestertown will celebrate the holidays safely this year with activities that include visits with a masked Santa, a Holiday Art Walk to downtown galleries, free horse-carriage rides, and live music.

Santa will be the first celebrity to use the new mobile stage being gifted to the Town by Main Street Chestertown. The stage, which was funded largely through grants from the Maryland Heritage Area Authority and the Robert F. Schumann Foundation,  will be set up in the parking lot next to the Nearly New Shop at the intersection of High Street and Spring Avenue.  For four Saturdays beginning Nov. 28, Santa, assisted by two of his elves, will arrive by firetruck and be on his stage from 11 a.m. to 2 p.m. He will chat with the children from a safe distance of six feet or more, and then pose for quick photos taken by local Boy Scout Troop 130.

Nov. 28 is also Shop Small Saturday throughout downtown Chestertown, part of a national initiative that encourages residents to support their local merchants as they make decisions about holiday shopping. According to American Express, which provides branded “Shop Small” giveaways to participating communities, for every $100 spent at a small business in the U.S., approximately $67 dollars stays in the local community. That’s compared to $43 for chain stores and larger businesses. Studies also show that small businesses donate 250 percent more than larger businesses to non-profits and community causes.  Shop Small Saturday is one opportunity for residents to acknowledge and return some of that support, especially this year as the COVID-19 pandemic creates extra challenges for small businesses.

While some beloved holiday traditions such as the Kent County Holiday Parade and Lighting of the Town have been cancelled this year to avoid large gatherings, downtown will turn on the charm for holiday shoppers and downtown visitors during a “Chestertown Cheer” weekend during First Friday December 4 and all day Saturday December 5.

That Friday night, shops will be open until 7:00 p.m. or later, and stilt-walkers in lighted costumes will entertain and pose for photos. From 5:00 to 8:00 p.m., free carriage rides will take passengers through the Historic District and past many of Chestertown’s beautiful 18th and 19th century houses. To maintain safe conditions, the carriages will take only two or four people at a time, and passengers must ride only with family or household members. Both the driver and his or her passengers must remain masked during the rides, and touchpoints will be sanitized between trips.

On Saturday, Dec. 5 the weekly Chestertown Farmers Market will line both sides of High Street with vendors selling produce, baked goods, greenery and crafts. A fire truck will deliver Santa for his second session of visits on his Holiday Stage at 11 a.m.

From noon to 5 p.m., the Chestertown Arts and Entertainment District will host a Seasonal Art Walk, with special exhibits and sales in galleries, studios and other art venues throughout the A&E District. Art lovers and shoppers can wander from venue to venue experiencing the magic and power of the arts, with masks and social distancing required at all stops along the way. Participating galleries include the Blueberry Pie and Art Society, Create, Diane Rappisi Fine Art, Hegland Glass, Les Poissons Gallery, Tish Fine Art, Robert Ortiz Studios with guest artists Vanna Ramirez and Fredy Granillo, River Arts, The Artists Gallery, and Linda Roy Walls Photographs and Memories. Art Walk maps will be available in downtown shops and restaurants before and during the event.

The free carriage rides will run from 1:00 to 5:00 p.m. Saturday.  Weather permitting, live music will be offered throughout downtown, and restaurants will provide indoor and outdoor seating for lunch items and treats.

Santa’s Stage and the Chestertown Cheer activities are co-sponsored by the Chestertown A&E District, the Downtown Chestertown Association, and Main Street Chestertown.

Contact Kay MacIntosh,
Or Andy Goddard,