Top 5 Local Events of the Week

We’re excited to announce we’ll be having a FREE kids fun zone at the Centreville Elementary School Holiday Fair! Come write a Letter to Santa, play some games and let the kids take a play break from shopping. Find more info HERE!

Chessie’s Top 5 Picks of the Week

Here’s Chessie’s Top 5 Picks of the Week! These events and activities have been handpicked for maximum family fun on our side of the bridge

12/5 – Skate With Santa in Easton at the Talbot County Community Center

Santa will be taking a break from his busy schedule at the North Pole to visit the Talbot County Community Center to share holiday memories with the whole family! Kids will have an opportunity to sit on Santa’s lap to reveal their seasonal wishes and receive a special gift! Please bring your own camera to take a memorable photograph with Santa. Complimentary hot chocolate and cookies will be provided. Pre-registration is required as Santa’s helpers need to maintain quantity and quality skates and gifts.

Fee: $20 per child 13 & under
Session I: Wednesday, December 4th, 2024
Session II: Thursday, December 5th, 2024
Time: 6:00pm–8:00pm
Where: Talbot County Community Center

12/6 – Dicken’s Festival 2024 in Chestertown

Enjoy an evening filled with oysters, food vendors, beer, wine, and bonfires! We will have our opening ceremony and listen to KCHS Jazz Band, Garnet Elementary Chorus, River Voices, and end the night with a jam session from The American Rogues! 5-9pm

12/8 – Mommy & Me Holiday Paint Party in Centreville 

Join us for a festive Mommy & Me Holiday Paint Party! Create magical memories painting whimsical, coordinating 11×14 canvases together. As a bonus, each participant can craft a personalized wood ornament to take home. Adding to the holiday cheer, a special surprise visitor from Santa will drop by to delight the kiddos! Perfect for bonding, laughter, and holiday spirit, this event promises an unforgettable experience for all. Don’t miss this chance to make the season extra special! Registration includes 1 adult and 1 child. Additional children welcome for a small fee.

12/8 – 321 Holiday Santa Train in Wilmington, DE

Join us for a special holiday train ride on the Wilmington & Western Railroad’s Santa Train. One of our most popular events in its 9th year!
Sunday, December 8, 2024, 2:00PM (train leaves at 2:30PM) until 4:00PM

Wilmington & Western Railroad
2201 Newport Gap Pike
Wilmington, DE 19808
$10/person

12/7 – Christmas Daze in Preston

Thanks to the generous donations of Preston local sponsors, and the Caroline County Council of Arts, the Town of Preston will host our CHRISTMASDAZE event at the Town Commissioners Meeting Room

DECEMBER 7, 2024 from 3-5PM
ALL DAY EVENTS 3-5 PM
– Christmas Craft
– Coloring
– Cookies and Hot Cocoa
– VENDORS MARKET
– Food Trucks
– Christmas Lights