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Here is your guide to fun Christmas events during the 2022 holiday season. Think downtown block parties, holiday home tours, Victorian soirees, and, of course, the time-honored mechanical snowboarding.

If I missed a fun affair in your town, please put a link to event details in the comments here or send that link to me by email: SecretsoftheEasternShore@gmail.com. I will be updating and adding to this list as this season progresses.

Season-Long Events

Yuletide at Winterthur: Bask in the high life of days gone by while touring Henry Francis du Pont’s former mansion in Wilmington, Del. It will be decked out in full holiday splendor between Nov. 19 and Jan. 8. Details here. To time your visit with the occasional live jazz performances, caroling, and craft workshops, see this events calendar.

Holidays at the Nemours Estate: Alfred I. du Pont’s spectacular old estate in Wilmington, Del. will be all gussied up for the holidays from Nov. 15 to Dec. 30. Some of the decorative items are unique and quite historic. Much of it is inspired by the du Pont family’s French roots. Details.

Schellville Christmas Village: The magical Christmas village of Schellville will be back in Rehoboth Beach, Del. from Nov. 19 to Dec. 31. It started out years ago as a display of decorated miniature homes, but now encompasses train rides, an ice rink, a beer garden, the “maze of lights,” elf houses, and a “snow zone”, where you should be able to get in a snowball fight no matter the weather forecast. That snow zone is going to be bigger and better this year. Among other additions: a retro-arcade room, a 30-foot tall tubing/sledding hill, and an outdoor bar sponsored by The Starboard. Open Thursdays through Sundays. Details.

Holidays at Hagley: You can tour the mansion and grounds in Wilmington, Del. that’s the earliest of the du Pont family estates–this is the place where they started their entrepreneurial journey. Hagley Mansion will be decorated for the season, with gingerbread houses and more. Plus, an “Inventing the Holidays” exhibit focused on Yuletide entrepreneurship. Nov. 25 to Jan. 1. Details.

Festive Fridays Cape Charles: Head to Cape Charles, Va. on Friday evenings between Nov. 25 and Dec. 16. The Festive Friday affairs there have carriage rides, street performers, Santa visits, music, holiday movies at the Palace Theatre, and more. Details.

A Farmer’s Christmas: Experience “A Farmer’s Christmas Through the Years” at the Delaware Agricultural Museum in Dover, Del. from Sat., Nov. 26 to Sat., Dec. 17. Strolling carolers, holiday decor, holiday crafts, and more. Details.

Santa’s House on the Boardwalk: Santa will hold court on the boardwalk in Rehoboth Beach, Del. starting on Fri., Nov. 25 and then running on Saturdays and Sundays through Dec. 18. Details.

Christmas Garden of Trains in Cambridge, MarylandHoliday Lights and Santa Claus Express Train Rides: The historic Wilmington (Del.) and Western Railroad is like a museum on iron wheels. Their tourism-friendly schedule goes into holiday mode with a pair of special steam-powered Christmas rides–the Santa Claus Express runs Nov. 25-Dec. 23, and the Holiday Lights Express runs Dec. 9-Dec. 30. Details.

Donuts with Santa: The big man will arrive atop a farm tractor during these events at the Fifer Orchards Farm Store in Camden-Wyoming, Del.–Saturdays Nov. 26, Dec. 3, Dec. 10, and Dec. 17. Details.

Christmas Train Garden: I believe we are at 88 years now? That’s how long the volunteer Rescue Fire Company has been putting on a holiday model train show in this much-loved local tradition in Cambridge, Md. Open most days in December. Details.

The Whoville Village Holiday Park: The Whoville Village Holiday Park in Greensboro, Md. will be up and running Fridays and Saturdays in December, starting Fri., Dec. 2. Photo sessions not just with Santa, but the Grinch and Cindy Lou, too. Lots more fun stuff at this award-winning affair. Details.

Events by Date

Weekend Nov. 18-20

• Trimpers Rides is throwing a Christmas Carnival on Nov. 19 and 20 in the carousel building with rides, food, prizes, music, free ice skating, a petting zoo, and more. Details.

Thanksgiving Weekend Nov. 25-27

Ice Sculpture Santa Claus• Berlin, Md. kicks off the holiday season with ICE ICE Berlin on Fri., Nov. 25. 30-plus ice sculptures, civic tree lighting, Santa, and more. Details. Candlelight tours at the Taylor House Museum, too–details on that here.

• Embark on a Candy Land Adventure in downtown Easton, Md. on Sat. Nov. 26 as the local Women’s Club brings that old board game to life. Think life-sized lollypop woods, peppermint forest, etc. Queen Frostine will be on hand. Details.

• On Sat., Nov. 26, head to Harrison Street in Easton for Carols by Candlelight with choral music and local musicians, a Holiday Marketplace, and food trucks. Details.

Thursday, Dec. 1

• Enjoy Hospitality Night at the Zwaanendael Museum in Lewes, Del. on Thu., Dec. 1. Holiday decor, historical interpreters, music, refreshments, and more. Details.

Weekend Dec. 2-4

• Head to the Talbot County Courthouse in downtown Easton, Md. on Fri., Dec. 2 to visit a “Holiday Village with Frosty the Snowman”–photo ops, cocoa, cider, and “Frosty’s Winter Wonderland” on the big screen. Details.

• On three Fridays in December–the 2nd, the 9th, and the 16th–you can join Mrs. Claus at Mandala Pies in little Vienna, Md. for crafts, hot cocoa, and candy canes, and, of course, pie. Details.

• Chestertown, Md. puts on its Dickens of a Christmas party on Dec 2 and 3. Beer and bonfires and late shopping on Friday, plus carriage rides. Saturday morning “Bedlam” bed race followed by kids activities, house tours, food trucks, and “London Row” artisan vendors. Lots more, too. Details.

• Princess Anne, Md. traditionally celebrates the holidays on the first weekend of December. That should be the 2nd and 3rd this year, most likely with a Friday evening tree lighting with music, then a Saturday parade followed by pop-up bakers, strolling musicians, oyster sandwiches, holiday house tours, and then a candlelight reception at Teackle Mansion. Details should appear here at some point.

• The Holiday Open House at Rockwood Park and Mansion in Wilmington, Del. is Dec. 2 and 3. Holiday light displays of lights in the park, museum tours, Santa, and performances by local choirs and dance companies. Details.

• The annual Christmas on the Creek festivities in Oxford, Md. are the weekend of Dec. 2-4! Christmas bazaar, holiday house tour, the lighting of the dock trees, Santa’s arrival at Town Park aboard a fire truck, caroling, and more. The details are here.

Christmas Caroling• Pocomoke City, Md. is planning an Old-Fashioned Christmas celebration on Fri., Dec. 2. Holiday treats, kids crafts, local school choirs, tree lighting, and more. Details.

• The Festival of Trains in Chester, Md. is put on by the Queen Anne’s County Railroad Society at the Kent Narrows Outlet Center on the weekends of Dec. 3-4 and 10-11. Details.

• This will be the 21st time around for the famous Midnight Madness shopping extravaganza in St. Michaels, Md.–Sat., December 3, 2022 Details.

• This year’s edition of Christmas in Odessa (Del.) is Sat., Dec. 3. Self-guided walking tour of historic private homes and public buildings. Live music, a Christmas craft fair, and holiday greens for sale. Details.

• The holiday festivities in Rock Hall, Md. on Sat., Dec. 3 include Santa arriving by boat and the lighting of the downtown crab basket Christmas tree followed by s’mores at the campfire and Santa visits, Details.

• The Whitehaven Heritage Association will have an open house at the schoolhouse, church, and museum in that little Wicomico County, Md. town on Sat. Dec. 3 . Guides will talk about the history of the town and its famous ferry, which has been running for 335 years and counting. Details.

• Enjoy “Seafood with Santa” on Sat., Dec. 3 at the Hoopers Island Oyster Co. in Cambridge, Md. Oyster stew, grilled oysters, and other specialties available for sample or purchase. Souvenir gifts, too, including heritage oyster tins. Details.

• Dig out your jolliest suit and head to Kent Island, Md. for the annual SantaCon festivities on Sat., Dec. 3. Details.

• The Holiday Extravaganza on Sat., Dec. 3 at Evergreen Farms near Dover, Del. includes a petting zoo, pony rides, vendors, and the man in red. Details.

• The historic Hale-Byrnes House in Newark, Del. is having a holiday open house on Sat., Dec. 3. Details.

• On Fri./Sat. Dec. 2/3 the Lewes (Del.) Historical Society will be offering A Holiday Tour of Lewes with visits to decorated private homes and an outdoor Holiday Village and Market. Details.

• The Yuletide Festival and Holiday Marketplace will be held Sat./Sun. Dec. 3/4 at Mount Harmon Plantation in Earleville, Md. House tours, food court, an open-air tavern, hearth-cooking demos, and an Artisan Marketplace focused on decorations and greens. Details.

Audrey Christmas Tree• Enjoy 12 Days of Christmas on the Farm on Sat., Dec 3 and Sun., Dec. 4 at Mariner’s County Down near Berlin, Md. A decorated village, mulled cider, vendors, etc. Details.

• Adkins Arboretum near Ridgely, Md. will be holding a holiday open house in their gift shop on Sat./Sun. Dec. 3/4. Details.

• Tour historic homes and decorated churches in the Newtown Historic District of Salisbury, Md. during the holiday house tour on Sun., Dec. 4. The neighborhood is known for its Victorian-era gems. Details.

• Poplar Hill Mansion in Salisbury, Md. will have a Yuletide Open House on Sun., Dec. 4. Click on events here for details.

• On Sun., Dec. 4, the town of Accomac, Va. will celebrate an Old-Fashioned Christmas with choirs, hot chocolate, cookies, Santa, and community fellowship. Details.

• On Sun. Dec. 4 and Sat., Dec. 10 Mobray’s Garden Center in Cambridge, Md. will welcome kids who want to create “A Grinch Tree.” The grinch himself will be supervising. Tickets required. Details.

Mon., Dec. 5

• This year’s edition of Caroling on the Circle in Georgetown, Del. is Mon., Dec. 5. Gather in a sweet patch of traffic-circle greenery surrounded by historic buildings in the seat of Sussex County to sing carols. Hot chocolate and cookies afterward at the local firehouse. Bring along non-perishable food items—a food drive is part of the deal. Details.

Weekend Dec. 9-11

• The festivities at Christmas in St. Michaels, Md. on the weekend of Dec 9-11 include holiday music, the Tour of Homes, breakfast with Santa, a boat parade, the Talbot Street parade, the firing of the cannons, and more. Details.

• If you have your heart set this Christmas on walking into into bars full of drinkers in Santa suits, here you go: The second Delmarva SantaCon weekend of the season will unfold in Ocean City, Md., Dec. 9-11. Details.

• The New Castle (Del.) Historical Society is throwing a formal 1800s-style “Fezziwigs Ball” Friday, Dec. 9. Scroll to the date here for details.

• On three Fridays in December–the 2nd, the 9th, and the 16th–you can join Mrs. Claus at Mandala Pies in little Vienna, Md. for crafts, hot cocoa, and candy canes, and, of course, pie. Details.

• Christmas in Ridgely, Md. returns on Sat., Dec. 10 Set alongside the town’s railroad tracks you will find two Ice skating rinks, a giant snow globe, mechanical snowboarding, a frozen bounce house, carriage rides, Santa, Christmas characters meet and greet, life-sized gingerbread house, vendors, beer/wine igloo, and more. Details.

• This year’s Christmas in Onancock festivities are Sat., Dec. 10. Artisan markets, caroling, Santa, holiday lights driving tour, and more. Details.

• If things go as they have in past years, Snow Hill, Md. will throw its Victorian-flavored Dickens Weekend on Sat./Sun. Dec. 10/11 with caroling, street musicians. horse-drawn carriages, and house tours. This year’s details will probably appear here soon.

Christmas Events on the Delmarva Peninsula 2018• Join in the Reindeer Games at Middletown, Del. on Sat., Dec. 10. Scavenger hunt, carriage rides, Santa and his sleigh, more. Details.

• The Sights and Sounds of Christmas will be on display at Camp Mardela near Denton, Md. on Sat., Dec. 10 and Sat., Dec. 17. Kids crafts, hay rides, holiday lights, live music, and more. Details.

• The folks in New Castle, Del. are planning a Spirit of Christmas celebration on Sat., Dec. 10 with free concerts, holiday goodies, crafts vendors, and Christmas home tours. Details.

• Did you know that Southern Delaware used to be known as the “Land of Holly” for its hand-crafted wreaths? That bit of history will be honored on Sat., Dec. 10 at the Milton (Del.) Holly Festival with food, house tours, vendors, and more. Details.

• The Festival of Trains in Chester, Md. is put on by the Queen Anne’s County Railroad Society at the Kent Narrows Outlet Center on the weekends of Dec. 3-4 and 10-11. Details.

• Santa and the missus will be holding court at the town hall in Galena, Md. on Sat., Dec. 10. Scroll down here for details.

• Historian Joe Paden will be leading a Christmas Church Tour in Somerset County, Md. on Sat., Dec. 10. Details.

• Santa’s Train Wonderland is probably going to be up and running on the weekend of Dec. 10 and 11 at the Delmarva Discovery Center in Pocomoke City, Md. It’s the work of the local Pocomoke Train Club. Details should be up here soon?

• Head to A Little Farm and Nursery in Stevensville, Md. for Christmas on the Farm with Santa visits, trees, wreaths, and crafty workshops on Sat., Dec. 10. Details.

• On Sun. Dec. 4 and Sat., Dec. 10 Mobray’s Garden Center in Cambridge, Md. will welcome kids who want to create “A Grinch Tree.” The grinch himself will be supervising. Tickets required. Details.

Thurs., Dec. 15

• Head to the Nature Conservancy’s Brownsville Preserve near Machipongo, Va. on Thurs., Dec. 15 for a Holiday Open House with wagon rides, house tours a campfire, cider, and holiday treats. Details.

Weekend Dec. 16-18

Merry Christmas from us two to you and yours!

• On three Fridays in December–the 2nd, the 9th, and the 16th–you can join Mrs. Claus at Mandala Pies in little Vienna, Md. for crafts, hot cocoa, and candy canes, and, of course, pie. Details.

• The Sights and Sounds of Christmas will be on display at Camp Mardela near Denton, Md. on Sat., Dec. 10 and Sat., Dec. 17. Kids crafts, hay rides, holiday lights, live music, and more. Details.

• The streets of little Vienna, Md. will be sparkling with luminaria on the evening of Sat., Dec. 17. House tours and more as well. Details.

• Take the young ones in your life to “Tea with Santa and Mrs. Claus” on Sat., Dec. 17 at Poplar Hill Mansion in Salisbury, Md. Click on events here for details.

• The Christmas on Pine celebration on Fri./Sat., Dec. 16/17 in Cambridge, Md. will have a tree lighting, live music, vendors, campfires, s’mores, Santa, and more in a historical gem of an African-American neighborhood. Details.

• Enjoy “An Island Christmas” on Sat./Sun. Dec. 17/18 on Tilghman Island, Md. Lighted boat parade, caroling, and other festivities. Details.

• Several Delmarva cemeteries participate in this effort to make sure that wreaths adorn veteran graves for Christmas. You can volunteer to help lay the wreaths on Sun., Dec. 18. Or you can make a donation to support the charity that organizes things. And of course, you can visit one of the cemeteries during Christmas week to pay your respects. Details.

Fri., Dec. 23

• Head to Odessa, Del. on Fri., Dec. 23 for a special evening candlelight tour of the 1774 Corbit-Sharp House led by the curator of the exhibit Christmas of Christmas vignettes, “Oliver Twist; or, The Parish Boy’s Progress.” The tour closed with a drink at historic Cantwell’s Tavern. Details.

Sun., Dec. 25

• Merry Christmas to you and yours!

–posted by Jim Duffy for Secrets of the Eastern Shore/Whimbrel Creations LLC in October 2022. Thank you for spending a little time on our site.

 

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