Special Events

March 14 – St. Patrick’s Day Parade and Pub Crawl

Parade starts at 12pm. Starts under the bridge and goes down Bohemia Ave., loops around Pell Gardens and back to under bridge. Registration is free and begins at 10:30am under the bridge on the south side of town. Prizes for best float, best dressed and more. Mummers Band, floats, antique cars, Clydesdales and more. The Pub Crawl with start immediately after the parade. Visit the Hole in the Wall Bar, The Tap Room, Southside’s, Chesapeake Inn, and Schaefer’s for food and drink specials. Come enjoy a day on the canal!

July 3: Independence Celebration

Enjoy an evening of food, music games and fireworks. Festivities begin at 5pm in the Pell Gardens with food, music and games. Parade starts at 7pm and goes down Bohemia Ave and back to under bridge. No registration fee. All are welcome to participate. Fireworks start at dusk.

August 29: Lions Club Car Show

Over 500 vintage cars line the streets of Chesapeake City. Registration for cars available at www.chesapeakecity.com (maybe add the hyperlink to the registration page – which we will be providing soon). Show starts at 9am. Prizes at 2pm.

October 10: Fall Fest

Come to Chesapeake City for a fun day filled with hay rides, children’s games, food and bluegrass. Festivities are 2pm – 6pm. Bring a carved jack-o-lantern to be lit in the Pell Gardens at Dusk .

October 23-24: Ghost Walk

Walk the streets of Chesapeake City to hear a haunting tale. Tickets available on www.chesapeakecity.com starting in September. For more information call 410.885.2415.


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.

November 30: Lions Club Tree Lighting and start of WINTERFEST OF LIGHTS

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. Lighting accompanied by a traditional holiday music concert. Welcome Santa when his sleigh comes into town. This feat of careful engineering can be seen at the point by the town docks. From 6-7:30pm . FREE admission. No rain date. Pell Gardens. Contact: 410-920-7018.

November 29th through January 9th: 4th 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 (November 29) to town, 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. Visit the charming shops and celebrate the holiday spirit in world-renowned restaurants.


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. Skating Rink is open Fridays, Saturdays and Sundays until Christmas Week when it is open daily until January 10th. 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 21: 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 (Dates to be determined): VICTORIAN HIGH TEA at The Blue Max Bed & Breakfast. Space is limited for these very special holiday events. Catered by the chefs at Chesapeake Inn. Tickets: 410-885-2781
December 12: CHRISTMAS CANDLELIGHT HOUSE TOUR. Experience old-fashioned yuletide hospitality and take the holiday decor tour of Chesapeake City’s historic district through 12 + 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 starting November 5 on www.chesapeakecity.com. $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


Monday Night Bingo – Games begin @ 6:30pm, VFW Post 7687, 304 Basil Avenue, Chesapeake City, MD. Open to the Public. Wheelchair accessible. Collecting Non-perishable food items for local food pantry

Tuesday Night Bar Bingo – Games begin at 5:30pm, VFW Post 7687, 304 Basil Avenue, Chesapeake City, MD. Collecting Non-perishable food items for local food pantry

Wednesday Night – Wing Night with Karoake 6-9pm, VFW Post 7687, 304 Basil Avenue, Chesapeake City, MD. Open to the Public. Wheelchair accessible.Collecting Non-perishable food items for local food pantry

Friday Night Dinner – 6-9pm, take out orders 6-8pm, VFW Post 7687, 304 Basil Avenue, Chesapeake City, MD. Open to the Public. Wheelchair accessible. Collecting Non-perishable food items for local food pantry

Friday Night Music – Karoake and DJ Jayme Freeman 7-11pm, VFW Post 7687, 304 Basil Avenue, Chesapeake City, MD. Open to the Public Collecting Non-perishable food items for local food pantry