The small towns of Maryland’s Eastern Shore are great getaway spots most anytime, but the holiday season brings out a special sense of neighborliness that anyone can enjoy.
Chestertown, in Kent County along the Chester River, lures visitors with its Colonial charm throughout the year, but Dec. 7–9, the town turns Victorian with its second annual “Dickens of a Christmas” celebration.
Townspeople and shopkeepers get into the spirit by dressing in Victorian garb, and the streets become a stage for street theater, with visitors transported back to Dickens’ time. Fountain Park hosts vendors and entertainment, and you can take a carriage ride or a house tour, visit some of the pop-up shops, or just take in the vibe.
Stalls on the street offer the meat pies, Scotch eggs, fish and chips, and oysters common in Dickens’ day. Restaurants offer specially themed menus and there are plenty of children’s activities. You can even enjoy sweet and savory treats at high tea in the Hynson-Ringgold House, with seatings at 1 p.m. and 3 p.m. on Saturday. George Washington really did sleep here, so raise a cup to the first president.
It’s hard to miss Jerry Brown and his monkey Django, dressed in their Victorian holiday best, but there are also fire dancers, stilt walkers, and even Phydeaux’s Flea Circus and Wahoo Medicine Show to enjoy. And, new this year is the American Magic-Lantern Theater, a pre-“moving pictures” experience.
When the sun goes down on Saturday, the music draws you to the fire pits at the foot of High Street, where you can sample cold microbrews or board the Chester River Packet for snacks and other refreshments.
The works of Charles Dickens, especially “A Christmas Carol,” capture the spirit of the season and Chestertown captures Dickens perfectly.
Christmas in St. Michaels
St. Michaels, in Talbot County, also celebrates the season, Dec. 7–9, with its annual Christmas in St. Michaels weekend.
The Marketplace and Sweet Shoppe offers artisan-crafted items and culinary delights baked by chefs at local inns and restaurants. Take in the gingerbread creations on display and vote for your favorite at the Woman’s Club on St. Mary’s Square.
There’s a Breakfast with Santa on Saturday morning at Lighthouse Oyster Bar and Grill. For the adults, there’s an old-fashioned Eastern Shore dinner Saturday, 11 a.m.–3 p.m., at Union United Methodist Church.
The Saturday morning Christmas parade on Talbot Street includes Santa and Mrs. Claus. Following the parade, there are lots of activities for the kids at Santa’s Wonderland at St. Michaels School.
The weekend’s tour of homes is one of the longest-running in Maryland and includes both historic homes in the village and countryside homes.
The weekend’s musical entertainment features music before the parade and choirs from 11 churches that entertain Saturday at 1:30 p.m. at Union UMC. A combination of choirs entertains Sunday, 6–7 p.m., at Christ Church.
Still further south
Somerset County, at the southern tip of Maryland’s portion of the Eastern Shore, opens its holiday season Dec. 1 in Princess Anne with a Christmas parade and festival.
The Olde Princess Anne Days Christmas Tour features period homes decorated for the holidays. The Teackle Mansion is the site of a candlelight reception and dinner.
Attention shifts to Crisfield on Dec. 7 for the Christmas parade and Santa’s House, followed on Dec. 8 by a tea with Mrs. Claus that includes snacks and a holiday reading at the J. Millard Tawes Homeplace.
“A highlight here is New Year’s Eve in Princess Anne,” said Julie Widdowson, who promotes the area. “It’s a real street festival, with pop-up vendors, live music, and downtown merchants all contributing to a great kitschy experience.”
The Marshall Muskrat Dive comes at midnight, as a taxidermied muskrat ziplines the length of Main Street to the delight of everyone.
“The muskrat is important to the heritage of this area and Marshall is dressed to the nines for the occasion,” Widdowson said. “The Washington Inn even serves an upscale muskrat pot pie!”
Central Maryland celebrates
All of Maryland embraces the holidays, but the scattering of towns and vibrant city of Frederick in Frederick County provide some interesting contrasts. You can ride with Santa on the Walkersville Southern Railroad; embrace the small town Christmas celebrations in Brunswick, Middletown, or Thurmont; or discover Frederick’s downtown, with its special shopping and entertainment on the first four Saturdays of December.
Check out the Museums by Candlelight event Dec. 8, when museums and historic attractions throughout the county offer period demonstrations, refreshments, crafts, holiday decorations, and free fun.
Frederick’s Weinberg Center for the Arts provides the culture with “The Nutcracker,” Handel’s “Messiah,” and “A Christmas Carol” to brighten the season. Then, on Dec. 26, the city known for its clustered church spires offers its Candlelight Tour of Historic Houses of Worship, which welcomes guests with special programs, choirs, and nativity scenes.
Just to the west, Washington County offers the same types of small town celebrations in Boonsboro, Williamsport, Funkstown, and Middletown, with a variety of open houses, tree lightings, and special activities.
The annual memorial illumination at Antietam National Battlefield on Dec. 1 lights up the park with more than 23,000 candles paying tribute to the casualties from America’s single bloodiest day.
The area pays tribute to its German heritage with Christkindl markets in a variety of locations and with “German Christmas at the Hager House” on the first two weekends of December. The 275-year-old home of the city’s founder is decorated for the holidays.
The website calendar is full of events that are family-friendly, leading up to Hagerstown’s own New Year’s Eve tradition, the Krumpe’s Donut Drop at 5 p.m. Dec. 31.
A bit closer to home, in Howard County, the Symphony of Lights in Columbia’s Symphony Woods, Nov. 22–Dec. 30, is a regional tradition. Santa takes up residence in Columbia Mall on Nov. 30, but takes time to visit Historic Savage Mill on Dec. 1.