Holiday Guide · 2026 Edition
Lighted boat parades, crab basket trees and small towns dressed for December. Here is what is happening, town by town.
Updated October 2026
From Courtney
In Rock Hall, Santa arrives by boat. In Chestertown, the whole downtown steps back into Dickens' London. In Chesapeake City, lighted boats parade down the C&D Canal.
This guide covers Cecil, Kent, Queen Anne's and Talbot counties, with Cecil included for the first time. I update it as each town announces its dates, so bookmark it and check back.
★ New dates added as towns announce them
The Season at a Glance
Click any event for details, times, and links.
The 2026 Season
December
Chesapeake City · North East
At the top of the Bay, where the C&D Canal meets the Elk River. New to this guide in 2026.
The Lions Club's annual Christmas tree lighting in Pell Gardens on Bohemia Avenue. Santa lights the tree and the lights throughout town, with live music and time to say hello to Santa afterward. Free, and no tickets needed.
Sunday, November 29 at 5 pm
Chesapeake City events →The county's Christmas parade comes down Main Street in North East, hosted by the Town of North East.
Saturday, December 5, start time to be announced
Event details →The Bohemia River Boaters cruise the C&D Canal in decorated boats and make their way to the Chesapeake Inn Restaurant and Marina, with families lining the banks, the waterfront restaurants and Pell Gardens. Bring a nonperishable food donation for the Chesapeake City Ecumenical Association.
Saturday, December 5, 6 to 8 pm
Chesapeake City events →Chestertown · Rock Hall
Historic brick streets and a working waterfront. Kent County's celebrations are small, local and very much on the water.
Downtown Chestertown steps back into 1840s London. Friday night brings food tents, late shopping, carriage rides and music on the main stage. Saturday fills High Street with an artisans market, Santa's House in Fountain Park, Tiny Tim's Corner for children, a holiday home tour and the Great Scrooge Off.
Friday, December 4 from 5 pm, and Saturday, December 5
Event details →Santa arrives by boat at the Bulkhead, then lights the crab basket tree on Main Street, each basket decorated to honor a loved one.
Saturday, December 5 at 6 pm
Event details →Centreville
Queen Anne's County celebrates in its county seat, with a parade through historic downtown Centreville.
Floats, music and holiday lights through downtown Centreville. This year's theme is Stars and Stripes and Holiday Lights: 250 Years of America.
Friday, December 4 at 6:30 pm
Event details →Easton · St. Michaels
Easton's historic downtown and the St. Michaels harbor put on two of the Shore's best-known celebrations, a short drive apart.
Decorated trees fill the Gold Room at The Tidewater Inn in support of Talbot Hospice. The Preview Gala is Friday evening, November 27, then the festival is open daily through December 1.
November 28 to December 1
Event details →Santa visits Thompson Park at 5:30, the tree is lit at 6, and the parade steps off at 6:30 with floats, marching bands and decorated vehicles winding through downtown.
Saturday, December 5
Event details →Four days of gingerbread houses, a marketplace and sweet shoppe, breakfast with Santa, a tour of homes and the Talbot Street Parade on Saturday morning at 10:30. The Lighted Boat Parade fills the harbor Saturday evening at 6.
Thursday, December 10 to Sunday, December 13
Event details →Beyond the Big Nights
Handmade gifts, baked goods and local art at pop-ups in nearly every town.
Most towns light a community tree in early December. Bring a thermos.
When they run, a lovely way to see the decorated streets at an easy pace.
Some towns open their historic homes, dressed for the season.
Thinking About a Move?
December is when you see what these towns are really like: the neighbors who turn out for the parade, the shops that know your name, the quiet that settles in after the summer visitors go home.
If you are wondering which town would suit you year-round, start with my guide to choosing the right town, then tell me what matters most to you and we'll start there.
A Guide for Every Season
