The Best Events in the Chesapeake this December

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A Christmas tree and presents by a fireplace
(Brett Sayles via Pexels)

A Colonial Yuletide

Dec. 6, 2-5:30 p.m.

William Paca House and Garden | 186 Prince George St., Annapolis, MD 21401

Celebrate Christmas with historic holiday traditions dating back to the 18th century!

$15; $5 for ages 3-17; free for ages 2 and younger | annapolis.org/events/yuletide-2025

Holiday Paw-ty & Adoption Event

Dec. 7, noon-3 p.m.

Crownsville Canine | 2007 A Lineage Lane, Crownsville, MD 21032

Holiday party for dog owners and enthusiasts featuring an ugly sweater contest and adoptable dogs

$12.51 for dogs; free for humans | crownsvillecanine.com

An Annapolis Christmas

Dec. 15 & 16, 7 p.m.

Rams Head on Stage | 33 West St., Annapolis, MD 21401

Annapolis-based musicians will be performing classic holiday songs and originals.

$65.74 | ramsheadonstage.com

Holiday Pops at Maryland Hall

Dec. 19, 7:30 p.m.

Maryland Hall for the Creative Arts | 801 Chase St., Annapolis, MD 21401

A traditional holiday concert performed by the Annapolis Symphony Orchestra

$65-$135 | annapolissymphony.org

Candlelight: Christmas Carols on Strings

Dec. 21, 8:30-9:45 p.m.

Annapolis Waterfront Hotel | 80 Compromise St., Annapolis, MD 21401

A lowkey Christmas concert featuring a string quartet playing carols by candlelight

$67.50-$84 | feverup.com