Special Events


October 24 and 25th ANNUAL GHOST WALK Hooded Ghouls guide visitors who become a part of a murder mystery, performed by a professional acting troupe, unfolding on the porches and other hallowed locations in the historic district of this 19th-century canal town. Tours begin at 5pm, last tour departs Town Hall at 9 pm.

Chesapeake City’s 3rd Annual WINTERFEST is a month-long celebration starting on November 30th

November 22: ANNUAL PET PARADE. Bring your pet for a walk around town in Chesapeake City’s annual Parade of Pets. Pets are limited only by the fact they must be able to walk tethered to their owner, be well-behaved and be people-friendly. Prizes are awarded for various categories such as: Best Dressed Pet; Pet and Owner Look-Alike, and more. Participants may register under the bridge by Chesapeake City Elementary School from 10:30 a.m. Parade begins at Noon and moves down to Bohemia Avenue, ending at Pell Gardens. FREE admission. More info: Contact: 410-885-2330; www.chesapeakecity.com.

November 30th through Christmas: 3rd Annual Chesapeake City WINTERFEST: Chesapeake City’s month-long Victorian Christmas celebration takes place on both sides of the C&D Canal with a blizzard of holiday lights and spectacular lighted displays along the waterfronts. The town basin becomes a Holiday harbor where Santa arrives on (November 30) aboard a water-borne sleigh, ready to hear the wishes of good little boys and girls. Come see the lights. Listen to the carolers. See the beautifully decorated homes and the holiday decorating competition. Listen to the sounds of the season in Pell Gardens. Visit the charming shops and celebrate the holiday spirit in world-renowned restaurants.


November 30: Bundle up and celebrate the start of the holiday in Pell Gardens. The lights are officially turned on at dusk, on both sides of the Canal, heralding the start of Winterfest Celebrations. The Chesapeake City Lion’s Club also presents the official Tree MORE:

Lighting accompanied by a traditional holiday music concert. Welcome Santa when his sleigh sails up to the town dock. Hot Cider and Hot Chocolate are available.
See the NEW Waterman’s Crab Pot Tree created with countless crab pots donated to Chesaepeake City’s Winterfest by the Bayshore Family. This feat of careful engineering can be seen at the point by the town docks.

From 6-9. FREE admission. No rain date. Pell Gardens. Contact: 410-920-7018.

Imagine packing up your family and heading out to the neighborhood pond for a holiday skating party. Now, you can do that in Chesapeake City!

A 40-ft by 32-ft synthetic ice rink is installed at Beck’s Landing on the banks of the C&D Canal and is open for public skating. Skate rentals are included in the admission (although skaters may also choose to bring their own skates). Rink is closed during inclement weather. Admission to the rink is $5 per person for 30 minutes skate time; children five and under free. Skating Rink is open Fridays, Saturdays and Sundays until Christmas Week when it is open daily until January 4th. It will then be open only on weekends until January 11th.

This special ice rink is loaned to Chesapeake City by Priscilla Hill Wampler, John Wampler, and Rob Bricotto. Priscilla Hill is a former Olympic figure skater and former coach to medal winning figure skaters including Johnny Weir.

Starting November 22: SEE SANTA EVERY SATURDAY until Christmas. 3pm to 6 pm. Santa Claus is in his workshop located in Historic Franklin Hall ready to listen to visiting children and believers of all ages. Games and crafts for children happen in Santa’s Workshop too! Shops will be open late.

December 6 and 20: Sing along with Victorian-era carolers from 3 pm ‘til 5 pm. Carriage Rides with the Clydesdales from Winbak Farm.

November 22, 29 and December 6: VICTORIAN HIGH TEA at The Blue Max Bed & Breakfast. Space is limited for these very special holiday events. $22.50 per person. Catered by the chefs at Chesapeake Inn. Tickets: 410-885-2781

December 13: CHRISTMAS CANDLELIGHT HOUSE TOUR. Experience old-fashioned yuletide hospitality and take the holiday decor tour of Chesapeake City’s historic district through 20 19th-century homes, B&Bs and churches. Horse and carriage rides and strolling Victorian carolers will put even Scrooge in the Christmas Spirit.

$12 Tickets in advance. $15 tickets on the day. Contact: 443-553-0071, www.chesapeakecity.com.


January 1: 5K RUN. An annual New Year’s Day Event. More info: 410-885-2161
Information Sheet
Registration Information