Santa on stage, an art walk, carriage rides and live music to provide holiday cheer

From left, Matt Wiltbank, Paul Wilson and Larry Wiltbank of the Chestertown roads crew prepare to hang garland Tuesday afternoon, Nov. 10 on the front of the Kent County News office on High Street, as downtown decorations move from Halloween to the holidays.

CHESTERTOWN — Holiday traditions may look a little different this year in order for the Chestertown community to safely celebrate the upcoming festive season.

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 of 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 6 feet or more, and then pose for quick photos taken by local Boy Scout Troop 130.

Shop Small Saturday falls on Nov. 28 and businesses throughout downtown Chestertown will be participating. Small Business Saturday, a new release states, is 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 stays in the local community. That’s compared to $43 for chain stores and larger businesses.

Studies also show that small businesses donate 250% more than larger businesses to nonprofits and community causes, the release states. Shop Small Saturday is one opportunity for residents to acknowledge and return some of that support, especially in light of the negative impact the COVID-19 pandemic is having on small businesses.

While some beloved holiday traditions such as the Kent County Holiday Parade and Lighting of the Town have been canceled 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, Dec. 4 and all day Saturday, Dec. 5.

That Friday night, shops will be open until 7 p.m. or later, and stilt-walkers in lighted costumes will entertain and pose for photos. From 5 to 8 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 to 5 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 Historic Chestertown.

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