2109 Holidays Happenings Between the Bays

Festivals

Photo: Christmas
The Holidays are alive on the Delmarva Peninsula. Annual Parades, Festival, Tree Lighting and many other activities.

Here is just a few of the many 2019 Holiday Events and Activities happening on the Delmarva Peninsula.

Through the Season

The 27th Anniversary for Ocean City’s Winterfest of Lights begin on Thursday, November 21, with a magical tree lighting ceremony. Winterfest of Lights runs from now until December 31st. November 21-December 31. See how Ocean City, MD, sparkles this winter and visit the Winterfest of Lights! You’ll find more than one million holiday lights and hundreds of animated light displays throughout Northside Park. Relax and sip hot chocolate in the heated Winterfest Village pavilion, take a photo with Santa, and board the Winterfest Express to tour fairy tale themed exhibits. The one-mile journey takes you through 58 acres of lights and features a 50-foot Christmas tree.

Winter WonderFest November 17-December 31, 2019 – The open space of Hudson Fields in Milton, DE will be transformed into a holiday wonderland featuring the award winning Light Spectacular drive-through experience, Christmas Carnival, VisitDelaware.com Ice Rink, Schellville, and more! wonderfestde.org

Holidays at Nemours Estate November 16 – December 29, 2019
Step into the beautiful splendor of Nemours Estate. Enjoy Christmas trees, wreaths, and hundreds of feet of garland on grand display in the Visitor Center, Chauffeur’s Garage, Mansion and grounds. New this year, the Estate will feature a Gift Shop located in the Chauffer’s Garage operated by the Volunteer Auxiliary with all proceeds benefiting Nemours/ Alfred I. duPont Hospital for Children and its patients

Holidays at Hagley, Wilmington November 23, 2019 – January 1, 2020
Experience the du Pont ancestral home decorated for the holidays and the “Christmas Trees Past and Present” exhibition, celebrating the history of Christmas trees in America. Starting in the 1840s with a Victorian tabletop tree with handmade ornaments and candles; then to the 1930s with a tree decorated with colorful electric lights, shiny glass ornaments, and tinsel; and ending in the present with several modern reinterpretations of decorated trees.

Yuletide at Winterthur, Wilmington – November 23, 2019 – January 5, 2020
Enjoy the beauty and traditions of the season, from historic holiday decorations and celebrations to du Pont family Christmas customs. This year’s tour features nearly a dozen decorated Christmas trees. Reservations suggested. Closed on Thanksgiving Day and New Years Day

Santa Claus Express – the Wilmington & Western Railroad November 29 – December 23, 2019
Saturdays and Sundays
Meet Santa on the Wilmington & Western Railroad. The Jolly Old Elf rides the train and greets everyone on board and gives each child a chocolate treat. Be sure to bring your camera and ask Santa to pose for pictures with your child during this 1 1/2-hour round trip to Ashland. This event has assigned seating and reservations are recommended.
http://www.wwrr.com/ride/events/

Chesapeake City’s Winterfest of Lights
December 1, 2019 – January 4, 2020 – Month-long holiday event with Victorian Candlelight House Tour, horse-drawn carriage ride, Dickens carolers, ice-skating, holiday lighting. Don’t miss the Town Christmas Tree made entirely of crab pots.

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Saturday, November 23rd and November 30th, 2019

Christmas Train Garden – 10am – 2pm
The Preston Historical Society invites you to experience the magic of trains at their Christmas Train Garden. The exhibit will feature Lionel trains and will be set up by Patrick Lanahan. Admission is free.PrestonHistoricalSociety.com

Friday, November 22, 2019

Elkton Tree Lighting
At 6:00pm Santa arrives by Fire truck to Union Hospital to light the tree. Then walk with Santa to the Elkton Chamber & Alliance to light the Town tree and have pictures with Santa and light refreshments. Bobbie Ann’s Dance Studio will be performing Holiday favorites to the delight of everyone attending both tree lightings.

Saturday, November 23, 2019

Third Annual Greensboro Holiday Bazaar – Do your holiday shopping or bid on a silent auction item at this great fundraiser for His Hope Ministries! 10am – 2pm Greensboro Fire Hall.

November 29, 2019

Rehoboth Beach Tree Lighting & Holiday Sing Along at 6:30 p.m.

Santa arrival and Tree Lighting in Chestertown. Members of the Kent County Community Marching Band will play classic holiday songs beginning at 6:30pm, and will be joined by Olaf, Rudolph and the Grinch. Mayor Chris Cerino will light the town, and Santa will arrive on fire truck at 7pm. Santa will visit children in his house in Fountain Park until 8pm.

Saturday, November 30, 2019

39th Annual Goldsboro VFC Craft Show! Explore three rooms of crafts with unique handmade items. Food will be available for purchase. 9am – 3pm

Milton’s park and tree lighting celebration starts with music by The Al Frantic Band, followed by the Mt. Zion Choir! Stay warm with free hot chocolate from the Milton Lions Club and chocolate chip cookies from the Milton Community Foundation.

Chestertown’s annual community Christmas parade, featuring marching bands, floats, fire trucks, and of course, the guest of honor, Santa! 10am

Sunday, December 1, 2019

1st Annual Cape St. Claire Tree Lighting at 5:30pm. Tree will be lit up at 6:00pm. Santa will be there as well as hot chocolate.

Chesapeake City Tree Lighting LIONS CLUB ANNUAL TREE LIGHTING
DECEMBER 1 @ 6:00 PM – 8:00 PM
Seasonal musical entertainment provided by students from Bohemia Manor Chorus. Santa arrives by Clydesdale carriage to throw the switch, lighting the tree and all the Winterfest Lights throughout the town.

Wednesday, December 4th, 2019

The Town’s Christmas Tree in Byrd park will be lit at 5:30. All the holiday decorations in the park will light up during the ceremony. There will be singing, readings, free hot chocolate for children and even a visit from Santa!

Thursday, December 5 2019
Friday, December 6, 2019 – Sunday, December 8, 2019
Chestertown’s Dickens of a Christmas Weekend
mainstreetchestertown.org/dickens-2019

Friday, December 6, 2019

Newark’s Winterfest promises to be a wonderful addition to the holiday season. Holiday entertainment, roasting chestnuts, caroling, tree lighting, ice carving demonstrations, and much more will fill this wonderful evening of fun for the whole family. Winterfest is a joint effort by the Newark Parks and Recreation Department and the University of Delaware. Special Olympics of Delaware holding their annual Reindeer Run. Rain Date: December 7, 2019

Milford Holiday Stroll, 5 – 8 p.m
Enjoy a festive evening on Walnut Street featuring holiday carolers, wagon rides, refreshments, entertainment and of course, Santa Claus! Stop into the local businesses for some holiday shopping.

Federalsburg Lions Club annual Christmas Tree Lighting at 6:00 pm at the town triangle on West Central Avenue. The sounds of the season from various groups as well as hot chocolate, cookies AND this year we will have SANTA himself! Since there were so many good little boys and girls this year and he is so busy, Santa will only be riding in the Parade so this is the time to visit with Santa and take a picture!

Saturday, December 7, 2019

Christmas in Odessa – Self-guided walking tour of private homes and public buildings, many dating from the 18th and 19th centuries, decorated for the holidays.
The purpose is to fund college scholarships for local high school seniors. In addition to the house tour, there are many special events, which are included in the ticket price.

Christmas Tour of Lewes, 10 a.m. – 4 p.m.
Experience historic Lewes, as homeowners open their doors to the community during this signature winter event. The Lewes Historical Society’s properties are decorated for the season and a greens sale will be held at Freddie’s Barn. Many community organizations welcome visitors as the First Town in the First State readies itself for the holidays.

Lewes Christmas Parade – 5 p.m.
This 87th annual parade through downtown Lewes is followed by a tree lighting ceremony and Christmas caroling in Zwaanendael Park.

Rock Hall’s Arrival of Santa via boat and Tree Lighting. Santa arrives at 6pm at the Bulkhead and moves to Main Street for the lighting of the Crab Basket Tree

Monday, December 9, 2019

Snow Hill Christmas Parade, Snow Hill, Maryland at 06:45 pm, Rain date December 11th. Call 410-632-9860, leave a message to register!

Wednesday, December 11, 2019

The Chesapeake Bay Maritime Museum in St. Michaels, Md., is inviting the public to celebrate the holidays with an open house that includes libations, light refreshments, caroling, store discounts, free gift wrapping, door prizes for CBMM members, and more. 4–7pm.

Saturday, December 14 and Sunday, December 15, 2019

Snow Hill’s Dickens Weekend celebrating Dickens and A Christmas Carol. Live performances, readings, music, art, and shopping!

December 14, 2019

The Spirit of Christmas, New Castle, DE – 9:30 a.m. – 5:30 p.m.
This town-wide celebration opens private homes and local churches, fully decorated for the season. Musical events, a holiday market and more will get you in the holiday spirit.

Home for the Holidays Parade, Dover, DE – 6:30 p.m.
Celebrate the holiday season with thousands of sparkling lights during this night-time Christmas parade through the heart of downtown Dover. Stores will be open for holiday shopping and Santa will be at his house on Loockerman Plaza to hear Christmas wishes

Join Betterton VFC at 6pm as they ride around town with Santa and serenade the town with Christmas carols. Beverages and cookies provided.

December 15, 2019

Breakfast with Santa at Betterton VFC. Menu includes pancakes, eggs, breakfast meats and juice. Picture included. $10, 4 and under are free.

Friday, December 20, 2019

Elkton’s Main Street Old Fashioned Christmas of Free Horse & Carriage Rides and Joyful Carolers at 5 PM – 8 PM

***This list is just the beginning and will be updated through the Holiday Season***

Editor’s Note:
If you know of an event or activity that is not on this list, please let us know so it can be added. Events@ShoreToBeFun.com or just leave a comment.

Updated:
November 24, 2019