Annapolis

Midnight Madness

Experience late-night shopping in downtown Annapolis on Thursdays, December 5 and 12, from 4:00 p.m. until midnight, and on December 19 from 4:00 p.m. to 11:00 p.m. Participating stores along Main Street, Maryland Avenue, and West Street will remain open late, offering holiday displays, treats, special discounts, and sales for shoppers.

Lights on the Bay

Enjoy a two-mile scenic drive featuring over 70 animated and stationary light displays at Sandy Point State Park from November 28 through January 1. The event runs nightly from 5:00 p.m. to 10:00 p.m., weather permitting. Proceeds benefit the SPCA of Anne Arundel County.

Christmas Tree Lightings

• Annapolis Town Center Tree Lighting: Join the annual event on November 21, featuring all-day entertainment, Santa's workshop, hot chocolate, and carriage rides.

• Grand Illumination of the Annapolis Tree: Held on December 1 from 4:00 p.m. to 7:00 p.m. at City Dock, this event includes performances and a visit from Santa.

Annapolis Chocolate Binge Festival

On December 1, from 11:00 a.m. to 5:00 p.m., West Street hosts the festival featuring chocolate vendors, hot cocoa, and a Gingerbread House display at the Visit Annapolis Visitor Center. The event concludes with the Grand Illumination of West Street at 5:00 p.m.

Annapolis Holiday Market

Shop from 50 artists in an open-air market along City Dock from December 12 to 15. Enjoy café dining and live entertainment during your visit.

Eastport Yacht Club Lights Parade

On December 14, from 6:00 p.m. to 8:00 p.m., watch boats adorned with thousands of lights parade along the Annapolis Harbor and Spa Creek. This annual event is a highlight of the holiday season.

Military Bowl

The 2024 Go Bowling Military Bowl will kick off on Saturday, December 28, at Navy-Marine Corps Memorial Stadium in Annapolis, Maryland. This year's game will feature teams from the ACC and the American Athletic Conference, kicking off at 5:45 p.m. ET and televised on ESPN.

West Annapolis

West Annapolis Holiday Market
Scheduled for Saturday, December 7, 2024, from 11:00 AM to 5:00 PM. This festive event will feature hot chocolate, holiday shopping, and a visit with Santa Claus. It will be held in the parking lot of 20 Ridgely, at the corner of Annapolis Street and Giddings Avenue.

Budweiser Clydesdales
Don't miss seeing these majestic animals. The horses will be parading on West Street on December 27th.

Easton

Festival of Trees
November 30 – December 3
Friends of Hospice presents the annual "Festival of Trees" with the theme "Holiday Traditions." This event features beautifully decorated Christmas trees at the Tidewater Inn, accompanied by performances from local choral and musical groups. Proceeds benefit Talbot Hospice.

Santa's Fun Run/Walk 5K
November 30, 9:00 AM – 11:00 AM
Starting and ending at Idlewild Park, participants can run or walk the 5K course along Rails to Trails. The event is family-friendly, with timed runs and awards for runners, and walkers are encouraged to join.

Santa's Workshop
November 30 and December 1, 11:00 AM – 4:00 PM
Meet Santa and enjoy holiday craft stations, games, music, and a selfie station. A festive experience for all ages.

Carols by Candlelight
November 30, 5:00 PM – 7:00 PM
Held on South Harrison Street, this free event features performances by choral groups, choirs, and bell ringers. Attendees receive complimentary candles and songbooks, with hot cocoa and holiday treats provided by local businesses. The evening begins with a Christmas tree lighting by Santa.

Starlight Shopping in Easton
December 5, 12, and 19, 5:00 PM – 7:00 PM
Downtown stores extend their hours until 7:00 PM, offering free carriage rides starting at the Visitor Center on 11 S Harrison St. Enjoy carolers, a pop-up bar at the Tidewater Inn, and the "Bugatti, Reaching for Perfection" exhibit at the Academy Art Museum. Spend $50 in any downtown business during Starlight Shopping to receive a signature ornament (one per person, while supplies last).

Frosty's Village
December 6, 5:30 PM – 8:00 PM
For All Seasons invites you to an evening with Frosty, featuring free activities including professional photos with Frosty and friends, holiday crafts, complimentary cocoa, cider, winter treats, and a continuous showing of "Frosty's Winter Wonderland" on the big screen.

Easton Choral Arts presents "Gloria"
December 6, 7:30 PM & December 8, 4:00 PM
Easton Choral Arts presents "Gloria," a concert celebrating the joy and splendor of the Christmas season, featuring Vivaldi’s iconic "Gloria" and other festive pieces.

Easton's Old Fashioned Holiday Parade
December 7, 6:30 PM
Easton’s largest parade of the year includes creative and decked-out floats, classic cars, marching bands, holiday characters, and appearances by Mr. & Mrs. Claus. The parade starts at 6:30 PM, with Santa arriving in Thompson Park at 5:30 PM, followed by a tree lighting at 6:00 PM.

Breakfast with Santa
December 8, Seatings at 9:00 AM & 9:30 AM
Held in the Gold Ballroom at the Tidewater Inn, enjoy a breakfast buffet tailored for both children and parents, featuring favorites like omelets, a waffle station, eggs benedict, and more. Bloody Marys and Mimosas are available for adults. Buddy the Elf will join as the Master of Ceremonies.

The Avalon Foundation Presents "The Sound of Music"
December 12 – 22
The Avalon Foundation presents the classic musical "The Sound of Music," featuring unforgettable songs and performances by over 130 community members. All ticket proceeds support the Foundation’s year-round mission to provide diversified arts and educational programs.

2nd Annual Gingerbread Challenge
December 12, 6:00 PM – 8:00 PM
Join the Tidewater Inn for an evening of spirited competition, delectable treats, and the chance to claim the coveted sweet champion title. Reservations are available based on tables for specified guest counts. This is an adult-only event.

First Night Talbot
December 31, 6:00 PM – 12:00 AM
A family-friendly, alcohol and drug-free New Year's Eve celebration of the arts in Easton. Events are spread out among venues in downtown Easton, culminating with the world-famous Crab Drop at midnight (and 9:00 PM for early birds).

Chestertown

Farmers' & Artisans' Market
November 30, December 7, 14, 21, and 28, 8:00 AM – 12:00 PM
Visit your favorite local food and artisan vendors on High Street to purchase delicious veggies, flowers, crafts, and more.

Hometown Holiday
November 29
Kick off the holiday season with one of Downtown Chestertown's most iconic events, the arrival of Santa and Mrs. Claus on a fire truck. Enjoy festive holiday music, candy, and some of the most iconic characters of the holiday season enjoying the downtown.

Dickens of a Christmas
December 6 – 7
Step back into 1840’s London and experience the holiday season as Charles Dickens imagined it. This two-day event includes entertainment, home tours, food, book talks, merchandise, and more. Don't forget to come dressed like the Dickens!

First Friday
December 6, 5:00 PM – 8:00 PM
On the first Friday of the month, downtown shops stay open until 8 PM, and galleries stage openings and special events.

Winter Art Walk
December 14
Come to the Chestertown Arts & Entertainment District’s Art Walk. Dozens of artists and artisans will be selling works at galleries, storefronts, restaurants, and around town. Live music will also be happening throughout town.

St. Michael's