Below are 25 fun holiday events and parties coming up on Delmarva. Small-town block parties, holiday home tours, Victorian soirees, much more. The first section is reserved for events that run across multiple upcoming weeks. Below that come events that are organized in week-by-week fashion from now through Christmas.
Before we get started, links to more Christmas fun:
15 Christmas concerts, 2025
10 big holiday light shows, 2025
30 civic tree-lighting parties, 2025
45 Christmas parades, 2025
OK, here we go with the Christmas fun:
SEASON-LONG EVENTS
• The mansions of Wilmington (Del.). Those DuPonts had a ton of money, and they knew how to spend it. Revisit ritzy holidays gone by with visits to Yuletide at Winterthur (Nov. 22 through Jan. 4, 2026); the Holidays at Hagley (Nov. 28 through Jan. 1, 2026); and/or the Noel at Nemours (Nov. 18 through Dec. 30).
• The Christmas village of Schellville is back in Rehoboth Beach, Del., Nov. 15 to Dec. 30 in Rehoboth Beach, Del. This “enchanted winter celebration” has train rides, an ice rink, a beer garden, a “maze of lights,” elf houses, a “snow zone”, retro-arcade room, a “Magical Maze,” a 30-foot tall tubing/sledding hill, and an outdoor bar. No reservations needed–they changed that policy. Open mostly Thursdays through Sundays, but check to be sure by clicking on “Events.” Details.
• Cape Charles, Va. will be throwing Festive Friday parties in its gorgeous old downtown–Nov. 28 and Dec. 5, 12, and 19. Late shopping, Santa, holiday movies, petting zoo, train rides, lots more. Details.
• Hard to believe, but the Rescue Fire Company Train Garden is now in its 91st year as a holiday tradition in Cambridge, Md. Dec. 1 through Dec. 31. Details.
EVENTS BY DATE
• The “Ice Ice Berlin” party on Fri., Nov. 28 includes dozen of ice sculptures to see, a live pipe-and-drum band, late shopping, a tree lighting, and more. Details.
• The Delaware Agricultural Museum in Dover, Del. is throwing its “A Farmer’s Christmas” kickoff party on Sat., Nov. 29. There will be vendors, artisans, performers, strolling carolers, and more. Details.
• This year’s rendition of “A Dickens of a Christmas” in Chestertown, Md is Fri/Sat Dec. 5/6. The town goes all 1840s London with bonfires, oysters, live music, carriage rides, home tours, book talks, and more. You don’t have to dress Victorian, but it would add to the fun if you did. Details. (Bonus option: The Historical Society will be doing fun ghost tours on Fri., Dec. 5.)
• Head to Milford, Del. on Sat., Dec. 6 for a pair of popular, time-honored Christmas events–the Holiday Stroll through downtown shops and the Christmas Market featuring local artisans. Details.
• Christmas in Odessa (Del.) on Sat., Dec. 6 has house tours, concerts, gingerbread houses, Santa, and more. Details.
• The Historic Lewes (Del.) Holiday House Tour is Sat., Dec. 6. Details.
• The Chincoteague Home for the Holidays house tour is also Sat., Dec. 6. Details.
• The “Christmas Daze” party in Preston, Md. is Sat., Dec. 6. Details.
• The Federalsburg (Md.) Historical Society is doing Christmas Candlelight Tours of the Historic Exeter house on Sat., Dec. 6. Details.
• The Yuletide Festival at Mount Harmon Plantation near Earleville in Cecil County, Md. is Sat/Sun Dec. 6/7. Old-school decorations & greens for sale, manor house tours, artisan marketplace, hearth-cooking demos, wassail, colonial re-enators, a food court, an open-air tavern, and more. Details.
• The various Christmas on the Creek festivities in Oxford, Md. run through most of December, but the big weekend is Sat/Sun Dec. 6/7 with gingerbread decorating, cookie walk, wreath-making, tree lighting, ferry-boat lighting, Breakfast with Santa, etc. Details.
• Historic Rackliffe House near Assateague Island (Md.) to experience a “Colonial Christmas” on Sat/Sun Dec. 6/7. Festive music, light refreshments, and a guided tour of the 1740s merchant-planter’s home. Details.
• The Sudlersville (Md.) Train Station Museum has a holiday open house and model train display on two Saturdays, Dec. 6 and 13. Scroll down here for details.
• Visit Poplar Hill Mansion in Salisbury, Md. on Sun., Dec. 7 for a “Yuletide Open House.” Click on “Events” here for details. You’ll also find info there for a Tea with Santa and Mrs. Claus event on Sat., Dec. 13.
• Downtown Cambridge, Md. will be celebrating “Mistletoe on Main” on Sun., Dec. 7 with a cocktail crawl, a special Chrismtas shop, a kids corner, and more. Details.
• The Holiday House Tour of the Newtown neighborhood in Salisbury, Md. is Sun., Dec. 7. Details.
• “Woodburn, Illuminated” is one-night-only affair in Dover, Del. on Tue., Dec. 9 that aims to re-create the way holiday lights were done in centuries gone by. The historic governor’s mansion, Woodburn, will be adorned with old-school “transparencies,” illuminations created with candle light. Stroll the grounds. Admire the house decor. There will be s’mores and cocoa involved. Details.
• The Nature Conservancy’s beautiful Brownsville Preserve in Nassawaddox, Va. has a Holiday Open House on Wed., Dec. 10. Tour the historic house. Warm up around a fire with cider and homemade treats. Details.
• The Sonshine Equine teaching center in Millsboro Del. has a live nativity on Fri., Dec. 12. Details.
• The festivities during Christmas in St. Michaels, Md. weekend Dec 12-14 include holiday music, the Tour of Homes, breakfast with Santa, a boat parade, the Talbot Street parade, the firing of the cannons, a community supper, and a whole lot more. Details. Plus, the Chesapeake Bay Maritime Museum in that same town will get into the act on Sat., Dec. 13 with a Winter on the Chesapeake event with carriage rides, a one-man reading (with 18 different voices/characters) of “A Christmas Carol,” wreath-making, lighted boat parade, and more. Details on that.
• At 11am on Sat., Dec. 13 Santa will pull up by boat to the Wharf in Onancock, Va. and kick off the “Christmas in Onancock Festivities.” After that, a tour of homes, the music at Historic Cokesbury, an artisan market, more. Details.
• The big “Christmas in Ridgely” Winter Festival is Sat., Dec. 13. In addition to an array of holiday-lights displays, there will be ice skating, train rides, food trucks, libations, vendors, fireworks, and more. Scroll down for details at this link.
• Head to Cult Classic Brewing in Stevensville, Md. on Sat., Dec. 13 for the birth of a new tradition–the first-ever Holiday Book Festival. Meet lots of local authors (including Jim Duffy of Secrets of the Eastern Shore) while enjoying libations and festivities. Details. (Big thanks to the Eastern Shore Writers Association for putting this together. All of us Delmarva authors really appreciate it.)
• Celebrate “A Christmas on Pine” in the historically African-American Pine Street neighborhood of Cambridge, Md. on Sat., Dec. 13. Vendors, fire pits, caroling, etc. Details.
• The Delmarva Discovery Museum in Pocomoke City, Md. has a “Holidays at the Museum” event on Sat/Sun Dec. 13/14. Santa, train display, and more. Scroll down to date for details.
• Rock Around the Zoo parties happen at the Salisbury (Md.) Zoo on Sat., Dec. 13 and Fri/Sat Dec. 19/20. Stroll twinkling light trails, join in with caroling to the zoo animals, live music, Santa, cocoa, treats, etc. Details.
• Parksley, Va. is throwing an Old Fashioned Christmas on Sat., Dec. 13 with kids crafts, a white elephant table, seasonal goodies, a gingerbread house competition, and more. Santa will be holding court at the Eastern Shore Railway Museum. Details.
• The Frosty Family Festival at the Wicomico Civic Center is Sun., Dec. 14. Carousel, live music, silent disco, wandering storybook characters, vendor village, monster truck rides, etc. Wear-your-PJs screening of Polar Express that evening, too. Details.
–posted by Jim Duffy for Whimbrel Creations LLC/Secrets of the Eastern Shore in Nov. 2025. Merry Christmas to one and all!
NOTES:
• Alas, the Whoville village in Greensboro, Md. is not happening this year.
• Alas, the Spirit of Christmas in New Castle, Del. is not happening this year, though last I saw the town and its volunteers was hoping to put together some fun holiday event on Sat., Dec. 13.
• If the work that went into this helped you plan a merry Christmas season and you’re not in the market for any of our Christmas cards or Secrets of the Eastern Shore books, you could also say thanks here through a Secrets of the Eastern Shore Tip Jar.
