Holiday Happenings on the Eastern Shore

Craving to untether from your safe space and get a dose of holiday magic? Bored with virtual experiences? Don’t fret. Charming historic towns on Maryland’s Eastern Shore are offering creative ways to cheer even the most pandemic-weary.

Nothing like a stroll through Chestertown to reduce stress and ease anxiety. This year, the downtown historic district — a National Historic Landmark — is turning on the charm on Dec. 4 and 5 with “Chestertown Cheer.” Free carriage rides will take passengers past many of the stunning 18th– and 19th-century homes on Friday from 5 to 8 p.m. and on Saturday from 1 to 5 p.m. Santa will “mask up” and arrive via fire truck on Saturday at 11 a.m. to visit with children (safely distanced) until 2 p.m. Also on Saturday, a farmer’s market will line High Street from 8 a.m. to noon and the Chestertown Arts and Entertainment District will host a seasonal art walk from noon to 5 p.m., with exhibits and sales in galleries and other venues. History buffs can overnight at the meticulously restored White Swan Tavern Inn, which dates back to pre-Revolutionary War days. No wonder Chestertown gets so many kudos.

The Wallis-Wickes House in Chestertown. Courtesy Town of Chestertown.

James Michener knew what he was doing when he decided to live in Oxford while writing “Chesapeake.” Founded in 1683, this laid-back haven is filled with storybook 18th-, 19th– and early 20th-century homes artistically decorated for the holidays. Stroll along the Tred Avon River, a Chesapeake Bay tributary that wraps around the town, offering water views in every direction. No one should visit Oxford without dropping by the Robert Morris Inn, America’s oldest full-service Inn. Many a conversation about independence from Britain probably took place around the same 310-year-old red brick fireplaces and original oak timbers. And yes, George Washington slept here.

Downtown Easton kicks off the holiday season on Nov. 14 and 15 when 10 local nonprofits join restaurants and businesses for CommUNITY Day: Easton Arts & Culture Celebration. Drive or stroll down Hanson Street to enjoy “Art for the Outdoors,” an Avalon Foundation exhibition and sale of work by local artists. Watch an expert from Ice Lab carve a 300-pound pumpkin and view dozens more pumpkins displayed around town, along with creative results of the first ever Scarecrow Decorating Contest. For details, visit

Cambridge, one of America’s oldest colonial cities, is hosting Holiday Night Markets on Nov. 14 and Dec. 12 from 4 to 9 p.m., with over 30 vendors creating a festive open-air marketplace. Nature lovers, check out the Blackwater National Wildlife Refuge, 12 miles south of Cambridge, boasting more than 25,000 acres of wetlands, fields and forests ideal for biking, walking or driving along trails to view wildlife in a splendid setting. More information is available at

You can also take a historic drive on the Tubman Byway, a fascinating 125-mile scenic trip that has preserved the places where Harriet Tubman lived and fled slavery. Tubman, the “conductor” of the Underground Railroad, led many slaves to freedom before the Civil War. The self-guided driving tour, available HERE, includes 45 stops, many with markers and interpretive signs. Highlights include the Harriet Tubman Mural and Museum.

Stanley Institute in Cambridge. Courtesy Harriet Tubman Byway.

Known as the town that fooled the British during the War of 1812 — when it blacked out all its lights and raised lanterns out of town, causing the British to overshoot it — St Michaels will be shining bright this year when it hosts its annual Holiday Parade of Classic Cars on Nov. 21 from 10:30 to 11:30 a.m. Two Saturdays later, on Dec. 12 at 6 p.m., experience the harbor’s Lighted Boat Parade (weather permitting, of course). Afterwards, drive around town and view historic homes embellished with holiday lights. Fingers crossed, the British aren’t planning another invasion. Visit to find out more.

The Parade of Classic Cars in St. Michaels. Courtesy Talbot County Office of Tourism.



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