Annapolis

Midnight Madness
Shop until midnight on Thursdays in December. Downtown stores offer holiday displays, treats, and discounts.

Spectacular Holiday Light Display
Enjoy an electric wonderland at Sandy Point State Park from November 19 to January 1. Over 60 displays, including a 16-foot teddy bear, light up the bay, benefiting the SPCA.

Christmas Tree Lightings
Join Annapolis Town Center on November 19 for entertainment, Santa's workshop, and hot chocolate. The Grand Illumination on November 26 features dancers, Santa, and a massive tree at Annapolis' City Dock.

Chocolate Binge Festival
On December 4, shop for sweets, enjoy hot cocoa and see a Gingerbread House display. Stay for the Grand Illumination of West Street.

Annapolis Holiday Market
Shop from 50 artists along City Dock from December 7 to 10. Enjoy cafe dining and live entertainment.

Eastport Yacht Club Lights Parade
On December 9, witness boats illuminated with thousands of lights in Annapolis Harbor, a magical holiday spectacle.

West Annapolis

West Annapolis Holiday Market
December 2nd sponsored by West Annapolis Civic Association. Shop with 30+ artisans and vendors, enjoy food and drinks, and get pics with Santa. 11 AM–6 PM in the Giddings and Annapolis Streets parking lot.

Easton

Festival of Trees
Saturday, November 26th until Wednesday, November 30th
A magnificent display of decorated Christmas trees with the theme "A Winter Wonderland" will be displayed in historic downtown Easton's Tidewater Inn (101 East Dover St.). These are available for sale over Thanksgiving Weekend from November 26th-30th and benefit Talbot Hospice.

Chestertown

A Dickens of a Christmas
Step back into 1840s London and experience the holiday season as Charles Dickens imagined. This two-day event includes carriage rides, entertainment, a home tour, food, book talks, merchandise, and more.

And don’t forget to come dressed like the dickens!

St. Michael's

Events occurring December 8th - 9th

Breakfast with Santa
   Date: Saturday
   Time: 8-10 AM
   Price: $10.00

Holiday Meals
   Date: Saturday

Holiday Music
   Date: Saturday - Sunday

Lighted Boat Parade
   Date: Saturday
   Time: 6 PM

'Light Up the Night'
   Daily after dark

Marketplace & Sweet Shoppe
   Date: Friday - Sunday

Talbot Street Parade
   Date: Saturday
   Time: 10:30 AM

Tour of Homes
   Date: Saturday - Sunday
   Price: $30.00

*Please note that specific times and additional information may be available when you click on each event.