Chesapeake City’s Sixth Annual Winterfest of Lights kicked-off on Sunday, November 25 in Pell Gardens with a concert of holiday songs followed by Santa’s arrival by horse-drawn wagon. Santa turned on the lights on the Town Christmas Tree, as well as, all the other light displays on both the north and south sides of the canal. Thank you to those who came to celebrate with us!

There will be different activities each weekend throughout the holiday season such as music/carolers, Carriage Rides and Santa Claus at Santa’s Workshop in Town Hall on Saturdays from 2 pm-5 pm throughout December, and a Candlelight Tour of Chesapeake City’s Historic Homes on December 8!

As always, residents and businesses are encouraged to decorate their yards, porches, windows, and doors for the holiday season. It would be wonderful to see more lights and awesome, unique winter wonderland displays all over town this year to add to the joyful Winterfest atmosphere. Imagine how much more beautiful our town would look for the holiday season if everyone took part. Please become a part of the Winterfest Celebration this year – we have the best little Town, let’s make it BIG this holiday season; let’s make it the best Winterfest yet!

The Holiday Decorating Contest has two categories:

  1. RESIDENTS: two winners (one from north side and one from south side)
  2. BUSINESSES: one winner (includes businesses on north and south sides of town)

PRIZES: $100 gift card for each winning residence and a “Winner” display yard sign posted at each winning residences, as well as, the winning business.
JUDGING: Will take place on SUNDAY, DECEMBER 16, 2018 beginning at 6:30pm. Winners will be determined by 3 judges. You must register by noon on Dec. 14 to compete so we know where to take the judges! Please make sure your holiday display is ready by Dec. 16!

Winners will be notified/announced that evening.

If you are interested in participating in the Holiday Decorating Contest please fill out the below information and email it to Tonya (contact info. below) or drop it off at Town Hall. This form can also be found on the Town’s website at and on Facebook. If you have any questions, please contact Tonya Lockwood at Town Hall by phone at 410-885-5298 or by email at