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Merry Christmas! Here is your handy-dandy guide to more than 50 holiday happenings on the Eastern Shore and in Delaware, from small-town holiday parties to music, dance, sing-a-longs, and much more.

(If you are looking for the region’s lineup of Christmas parades, this is the place to go for that handy-dandy guide.)


Tubman Travels: 32 Underground Railroad Journeys on Delmarva• The Downtown Milford Holiday Stroll is Fri., Dec. 1. Caroling, miniature horses, the Santa House, and more.

• The Easton Moonlight Madness shopping event on Fri., Dec. 1 will have caroling and other live music, along with raffle prizes and more.

• All the December Fridays  before Christmas–the 1st, the 8th, the 15th, and the 22nd–are Festive Fridays in downtown Cape Charles.

• Downtown Pocomoke City is throwing an Old-Fashioned Christmas bash on Fri., Dec. 1.

• The Salisbury Bike Party on Fri., Dec. 1 involves pedaling past some of the best holiday decorations around town. Don’t forget to decorate your bike!

• The weekend of Dec. 1-3 in Oxford will be full of Christmas on the Creek festivities.

• The Midnight Madness shopping extravaganza in St. Michaels is coming up on Sat., Dec. 2.

• The annual Christmas Open House at the Preston Historical Society will be held on Sat., Dec. 2.

• In Dover on Sat., Dec. 2, you can celebrate A Farmer’s Christmas at the Delaware Agricultural Museum.

• Celebrate a 19th Century Christmas on Sat., Dec. 2 at the Furnacetown living history museum near Snow Hill.

• Bethany Beach has a three-Saturday-in-a-row run of Weekend Wonderland festivities planned for Dec. 2, 9, and 16.

Eastern Shore Christmas Cards• The Tidewater Inn in Easton will be hosting their annual Carriage Rides through town on four Saturdays in December (the 2nd, the 9th, the 16th, and the 30th), as well as on New Year’s Eve.

• Accomac will have its Old-Fashioned Christmas party on Sun., Dec. 3.

• The Purnell Museum in Snow Hill will be hosting a Victorian Christmas on Sun., Dec. 3.

• The kid-oriented Twisted Chimney Christmas affair is coming up at Barrier Islands Center in Machipongo on Sun., Dec. 3. There will be storytelling and crafts involved.

• The Delaware Center for Inland Bays is looking for 100-plus volunteers to pitch in on a big Holiday Tree Planting at the Angola Neck Preserve near Millsboro. Shifts available Thu.-Sat., Dec. 7-9.

• Elkton has its big Cookie Throwdown with tastings in various shops around town on Fri., Dec. 8.

• There are lots of festive events and displays planned for Christmas in St. Michaels Weekend, Dec. 8-10.

• On the weekends of Dec. 8-10 and 15-17, Lynnhaven Baptist Church near Pocomike City will be putting on its Walk Through Bethlehem, a sprawling outdoor re-creation of the Christmas story.

• On Sat. Dec. 9, the Ocean View Historical Society will be celebrating an “1860 Coastal Christmas” that includes lots of living-history characters in addition to seasonal decor.

• Downtown Cambridge is planning a special Holiday Edition of its monthly Second Saturday event on Sat., Dec. 9.

• The Santa House on the boardwalk in Rehoboth will be up and running on Dec. 9, 16, and 23–all Saturdays.

• The Brownsville Nature Preserve in Nassawadox will have a Holiday Open House on Thu., Dec. 14. Campfires, wagon rides, apple cider, and more.

• There will be Holiday Carriage Rides in downtown Salisbury on Third Friday, Dec. 15.

• They will be celebrating Christmas in Elkton on Fri., Dec. 15.

• Little Vienna will be aglow come Luminaria Night on Sat., Dec. 16.

The Snow Queen will be traveling all the way from Bearland to the Lemon Tree Gallery in Cape Charles on Fri., Dec. 22. Rumor has it she may be bearing gifts.


• Here is the scoop on the 2017 edition of Yuletide at Winterthur, the Wilmington-area home of legendary collector Henry Francis du Pont.

• At a second famous old du Pont estate in Wilmington, the Holidays at Hagley festivities are an every day affair. Special Twilight Tours are also available on Tuesdays and Wednesdays starting on the 12th.

• In Ocean City, the big Winterfest of Lights runs through the end of the month.

• The Winter Wonderfest light show at Cape Henlopen State Park near Lewes runs to the end of the month as well.

Christmas CarolingSING-A-LONGS

• There will be Caroling on the Circle in downtown Georgetown, Del. on Mon., Dec. 4.

• There will be Caroling on the Green in Dover on Wed., Dec. 6.

• Music faculty from Salisbury University will be leading a Holiday Favorites Sing-a-Long at The Brick Room in downtown Salisbury on Fri., Dec. 8.

• The annual Candelit Caroling event at Adkins Arboretum near Ridgely is coming up Sat., Dec. 9. It sells out every year, so be sure and reserve in advance.

Sing-a-Long Chestertown will be held at Fountain Park on Sun., Dec. 17.


Zoo Lights & Christmas Nights at the Three Palms Zoo & Education Center in Clayton features light displays, moonlight strolls, campfires, and more. Fridays and Saturdays through December.

• The Crow Vineyard in Kennedyville will be set up for Pet Photos with Winemaker Santa on Sun., Dec. 3.

• The kid-oriented Critter Christmas festivities at the Salisbury Zoo will be held on two upcoming Saturdays, Dec. 9 and 16. The zoo also has a Cookies with Santa event on Sun., Dec. 3. Scroll down a bit at the links for info.

• The Santa House on the Boardwalk in Rehoboth has Pets-Only Hours set aside on Sat., Dec. 23.


• Santa Claus will be visiting various towns on the Eastern Shore of Virginia during a Fire Truck Tour planned for Sat., Dec. 2.

• There will be a Pizza with Santa Party on Wed., Dec. 6 at Northside Park in Ocean City.

• The Skate with Santa event at the Talbot County Community Center is set for Sat., Dec. 9.

• You can take a chilly dip with the big man during the Santa Swim event at Hyatt Resort in Cambridge on Sat., Dec. 9.

• The bar-hopping extravaganza that is Santa Con Ocean City will be held on Sat., Dec. 9.

• There is a Santa Con Kent Island party on Sat., Dec. 9 as well.

• You can go Running With Santa at Martinak State Park in Denton on Sun., Dec. 10.


Christmas Garden of Trains in Cambridge, Maryland• The annual Christmas Train Garden at the old Rescue Fire Company station in downtown Cambridge is a tradition that dates back more than 80 years. Open Dec. 1-30.

• The Delmarva Model Railroad Club will be holding it Holiday Open House affairs on the weekends of Dec. 2-3, Jan. 6-7, and Jan. 13-14.

• The Sudlersville Train Station Museum will have a model-train display running on the weekends of Dec. 2-3 and 9-10.

• The Christmas Train Village at the St. Michaels Community Center is part of Christmas in St. Michaels weekend, Dec.9-10.

• The Holiday Exhibit of Model Trains at the Seaford Historical Society runs through Jan. 14 and has a special focus “America’s Early Model Trains.”

• The Pocomoke City Volunteer Fire Department will have a Christmas Train Extravaganza on display, Dec. 10-14. On Sun., Dec. 10, Santa Claus will be arriving by helicopter to see the show and visit with his fellow train aficionados.


• The Avaolon Theatre in Easton has A Very Slambovian Christmas show coming up on Fri., Dec. 1.

• The Chester River Chorale will be performing its Holiday Concert in Chestertown on Fri., Dec. 1 and Sat., Dec. 2.

• The Easton Choral Arts Society will be performing seasonal classics in shows on Fri., Dec. 1 and Sun., Dec. 3.

• The touring Home for the Holidays show by The Ten Tenors is in Ocean City on Sat., Dec. 2.

The Nutcracker Ballet• The Cartoon Christmas Trio, a first-rate jazz combo than really does specialize in music from classic Christmas cartoons, will be at the Milton Theatre on Sun., Dec. 3.

• The Glenn Miller Orchestra is at the Avalon Theatre in Easton on Wed., Dec. 6.

The Texas Tenors will venture “Deep in the Heart of Christmas” on Thu., Dec. 7 at the Dover Downs Casino.

The Mid-Atlantic Symphony will be spreading some “Holiday Joy” on Thu., Dec. 7 in Easton, Sat., Dec. 9 in Ocean View, and Sun., Dec. 10 in Ocean Pines.

• Enjoy Christmas tunes with New Orleans legend Aaron Neville at Dover Downs Casino on Fri., Dec. 8.

The Tidewater Singers will be performing “The Peaceable Kingdom” by Randall Thompson on Fri., Dec. 8 in Easton; Sat., Dec. 9 in Oxford; and Sun., Dec. 10 in Cambridge.

The Salisbury Symphony Orchestra has a Joyeux Noel show planned with guest harpist Jacqueline Pollauf on Sat., Dec. 9.

• The Capital Ringers will be performing handbell versions of holiday classics on Sat., Dec. 9 at the Milton Theatre.

• A new community ensemble, The Smyrna Singers, will be giving their first-ever show at the Smyrna Opera House on Sat., Dec. 9.

• The holiday-oriented Onancock Music Festival is coming up on Sun., Dec. 10 at Market Street United Methodist Church in Onancock.

• If you are looking for something a little out of the ordinary this Christmas season, there is the Bluegrass Nutcracker coming up in Cambridge on Fri., Dec. 15.

• A tribute to Streisand & Sinatra is on tap Sun., Dec. 17 at the Milton Theatre.


Eastern Shore Road Trips: 27 One-Day Adventures on DelmarvaMiracle on 34th Street is running at the Clear Space Theatre in Rehoboth through Dec. 10.

• The Garfield Theatre in Chestertown is also putting on Miracle on 34th Street, Dec. 1-17.

• The Possum Point Players of Georgetown, Del., are putting on the comedy FrUiT CaKeS on the weekends of Dec. 1-3 and 8-10.

• See the The Best Christmas Pageant Ever, a musical at the North Street Playhouse in Onancock on the weekend of Dec. 8-9.

• Beggar’s Christmas: A Play will be performed at the Palace Theatre in Cape Charles on the weekend of Dec. 9-10.

• The First State Ballet Theatre will perform The Nutcracker in Georgetown, Del. on Wed., Dec. 13.

• The Sussex Ballet is performing The Nutcracker in Lewes on Fri., Dec. 15, and then again in Ocean City on Sun., Dec. 17.

• See A Christmas Carol at the Avalon Theatre in Easton, Dec. 15-23.

• The First State Ballet Theatre will have three more performances of The Nutcracker on the weekend of Dec. 22-23, all in Wilmington.


• The Christmas Tour of Lewes is Sat., Dec. 2.

• The Chincoteague Homes for the Holidays Tour is Sat., Dec. 2.

• The Onancock Christmas Homes Tour is Sat., Dec. 9.

• The Milton Holiday House Tour is Sat., Dec. 9.

• The Christmas in St. Michaels Tour of Homes is the weekend of Dec. 9-10.

• The Historic Cape Charles Cookie Trail on Sun., Dec. 10 leads into various B&Bs and private homes in the historic district there.

• The Holiday House Tour in Cambridge is Sun., Dec. 10.

Here’s wishing you and yours a Christmas season full of fun times together and joyous memories.

–Posted by Jim Duffy on Nov. 27, 2017




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