Eastern Shore of Virginia and Maryland Events December 2023

Festivals, parades and celebrations on the Eastern Shore of Virginia and Maryland's Eastern Shore in December of 2023.


November 16 - December 24, 2023 - Winterfest of Lights - Ocean City, Maryland's holiday lights display at Northside Park. Wednesday – Sunday from 5:30 p.m. – 9:30 p.m. (Monday through Sunday – Christmas to New Year’s Eve) Admission is $6 for guests 12 years and older and FREE for children 11 years and younger. The Winterfest of Lights is subject to closure for inclement weather. Ocean City, MD.

December 1 & 2, 2023 – Dickens of a Christmas 2023 – This two day event invites visitors to step back in time to the 1840’s London of Charles Dicken’s Christmas Carol. There will be carriage rides, entertainment, home tour, food, book talks, merchandise, and more. Attendees are encouraged to “dress like the Dickens”. Chestertown, Maryland.

December 1 & 2, 2023 – Plein Air Crisfield – Artists from around the country visit Crisfield for this event, creating paintings of local scenes which will be on exhibit and available for sale at the Somerset County Arts Council’s West Main Street Gallery in Crisfield on December 1 & 2. Crisfield, MD.

December 2, 2023 – The Cambridge – Dorchester County Christmas Parade – Lineup is at 4:00pm and the Parade starts at 5:00 pm. Cambridge, MD.

December 2, 2023 - Ocean City Christmas Parade - The parade begins at 11:00am. The parade travels from Old Landing Road to 120th Street. Ocean City, MD.

December 2, 2023 - Chincoteague Christmas Parade - This year's theme is A Gingerbread Christmas. The parade begins at 5:00pm on Main Street. Chincoteague, VA.

December 2, 2023 – 4th Annual Crisfield Lighted Boat Parade – Begins at Somers Cove Marina at 6:00pm and will proceed by the Crisfield city dock, Wellington beach, Crisfield American legion, and end at Tawes nursing home, and then return to the marina. Crisfield, MD.

December 2, 2023 – Annual Crab Basket Tree Lighting and Vendor Fair – Held in the lot in front of Fisherman’s Inn/ Crab Deck in Kent Narrows. Tree lighting is 6:00pm. Vendor fair from 2-6 before the tree lighting. Kent Island Area, MD.

December 2, 2023 – Bohemia River Boaters Christmas Boat Parade – Decorated lighted boats parade down the canal and into the basin arriving at Chesapeake Inn. Chesapeake City, MD.

December 2, 3, 9 & 10 2023 – Festival of Trains – 10,000 square feet of indoor trains and displays. Admission and parking are free. Donations are accepted to support preservation of the Centreville Station Freight Depot. Kent Narrows Outlet Center. Kent Island Area, MD

December 8 – 10, 2023 – Christmas in St. Michaels – A weekend full of events, including lighted boat parade, Talbot Street parade, special holiday meals, holiday music concerts, tour of homes, and marketplace. St. Michaels, MD.

December 9, 2023 – Chesapeake City Candlelight House Tours – 6:00pm to 9:00pm. Check in begins at Franklin Hall. Chesapeake City, Maryland.

December 9, 2023 – Holiday Artisans Market – Many of the resident artist studios at Historic Onancock School will be open, joined by additional vendors selling their wares in the main Gallery. 10:00am to 3:00pm Historic Onancock School. Onancock, VA.

December 9, 2023 – Onancock Christmas Homes Tour – An Onancock holiday tradition. 1:00pm to 5:00pm. Onancock, VA.

December 9, 2023 – Poplar Hall Christmas Parade of Horses and Christmas Market – Christmas Parade of Horses, handmade artisan goods, live Christmas music, and great food from Chesapeake City’s finest restaurants. Chesapeake City, MD.

December 10, 2023 – Onancock Christmas Parade – Onancock’s annual Christmas parade begins at 5:00pm and runs along Market Street from College Avenue to the Town Gazebo Park. Onancock, VA