Festive holiday events continue this week including: Midnight Madness in Downtown Annapolis
December 4th; Boatyard Bar and Grill, Annapolis
Join us for an inspiring evening of camp memories as we discuss how to keep them vibrant, safe, and ready for generations of Girl Scouts! Each year, hundreds of girls create lifelong memories filled with adventure, learning, and friendship at our camps. Your support will help us maintain these treasured spaces and expand opportunities for every camper. Be part of the legacy—celebrate and make a difference with us!
December 4th and 5th; Talbot County Community Center, Easton
Santa will be taking a break from his busy schedule at the North Pole to visit the Talbot County Community Center to share holiday memories with the whole family! Kids will have an opportunity to sit on Santa’s lap to reveal their seasonal wishes and receive a special gift! Please bring your own camera to take a memorable photograph with Santa. Complimentary hot chocolate and cookies will be provided. Pre-registration is required as Santa’s helpers need to maintain quantity and quality skates and gifts.
Central Maryland Chamber Holiday Mixer & Silent Auction
December 4th, 5 p.m.; The Great Room at Savage Mill, Savage
Enjoy an evening of cheer while reconnecting with business acquaintances and making new contacts in the spirit of the holidays. This annual holiday social provides an opportunity to mix and mingle, engage and celebrate, reminisce and reinvigorate new business partnerships while gearing up for a new year of growth and prosperity in the region.
11th Annual Lights of Kindness
December 5th through 8th; Homestead Gardens, Davidsonville
The Rotary Club of South Anne Arundel County will celebrate the 11th anniversary of its highly successful Annual Lights of Kindness charity event, a Christmas tree decorating contest that will be held December 5–8 at Homestead Gardens in Davidsonville, Md. The goal is to raise awareness for both local charities and businesses to make our community a better place to live and work. Businesses partner with charities to decorate trees and members of the community vote for their favorite tree(s) in person and online to help raise funds for the charity and the Rotary club’s foundation. Half of the proceeds will be donated to the designated charity and half will be donated to the South Anne Arundel County Rotary Foundation. A cash donation prize will be split among the charities' top three decorated trees receiving the most votes.
Mid Atlantic Symphony Orchestra - Holiday Joy
December 5th, 7:30 p.m.; Todd Performing Arts Center, Wye Mills
It time for some Holiday Joy! Join us for Holiday Classics with the MSO, featuring soloist Jonathan Pierce Rhodes, tenor!
Bugatti: Reaching for Perfection Special Gala Preview
December 5th; Academy Art Museum, Easton
The Academy Art Museum announces its most ambitious exhibition to date, Bugatti: Reaching for Perfection, opening with a special gala preview on December 5, 2024. The exhibition will open to the public on December 6, 2024, and run through April 13, 2025. It will feature rare automobiles, sculpture, and furniture by the Bugatti family, along with other objects and ephemera related to the renowned marque. In addition to furniture borrowed from the Museum of Fine Arts, Houston, and the Virginia Museum of Fine Art, Bugatti: Reaching for Perfection will showcase works from two important private collections never-before seen together: eight bronze sculptures from the Arsidi-Scuderi Collection of Lugano, Switzerland, and five vintage Bugatti cars and other automotive elements from the North Collection of the Eastern Shore, Maryland. Highlights include two grand prix ace cars, two Type 57 touring cars, and a miniature “Baby.
December 5th; Downtown Annapolis
Downtown Annapolis Partnership proudly presents Midnight Madness—a Historic Downtown Annapolis holiday tradition that encompasses the charm and character of our most beloved memories of Norman Rockwell and Charles Dickens. We will adorn the streets and participating storefronts with holiday decorations, trees, garlands, snowflakes, bows, and lights to create a Downtown Winter Wonderland and free on-the-street entertainment.
Coastal Conservation Association Greater Baltimore Chapter Banquet
December 5th, 6 p.m.; Union Craft Brewing, Baltimore
The Greater Baltimore Chapter of Coastal Conservation Association (CCA) Maryland welcomes you to join us for a celebration of conservation, and all things Chesapeake Bay. As a recreational fishing based organization, we know that the public’s connection to the Chesapeake Bay through fishing and boating is what drives the passion to ensure that future generations will also enjoy what is so near and dear to us.
A Dickens of a Christmas Weekend
December 6th and 7th; Downtown Chestertown
Kent County's favorite holiday event. Step back into 1840's London and experience the holiday season as Charles Dickens imagined it. This two day event includes carriage rides, entertainment, home tour, food, book talks, merchandise, and more. And don't forget to come dressed like the dickens!
Jay Fleming's 10th Annual Holiday Party
December 6th; Annapolis Maritime Museum
Jay Fleming’s tenth annual holiday party will be held at the Annapolis Maritime Museum from six to nine in the evening on December 6th! This party is always a fun time – Tangier Sound oysters on the half shell, beer from Forward Brewing, and wine at an incredible venue right on the water!
December 6th, 7:30 p.m.; Maryland Hall, Annapolis
“Yuletide carols being sung by a choir” – a very big choir – The Annapolis Chorale – are the hallmark of this longest running holiday event in the area! J. Ernest Green, The Annapolis Chorale, Annapolis Chamber Orchestra along with special guests Broadway star Derrick Davis and pianist Mark Berman take the stage for this annual holiday favorite that includes a joyous blend of everyone’s favorite songs, like “White Christmas” and “It’s the Most Wonderful Time of the Year.”
December 6th through 8th; Wicomico High School Auditorium, Salisbury
Eastern Shore Ballet Theatre presents the 34th Nutcracker. All performances are held in Wicomico High School Auditorium in Salisbury, Maryland
Easton Choral Arts is proud to present "Gloria!"
December 6th, 7:30 p.m.; Christ Church, Easton
Easton Choral Arts is proud to present ‘Gloria!’ a concert that radiates the joy and splendor of the Christmas season. At the heart of this program is Vivaldi’s iconic ‘Gloria,’ a timeless masterpiece that has warmed the hearts of countless audiences for centuries.
December 7th; William Paca House and Garden, Annapolis
You are cordially invited to celebrate a colonial holiday with Historic Annapolis! Bring the entire family to welcome yuletide at the William Paca House and Hogshead Trades Museum. It’s the year 1774! Experience the holiday traditions, music, and stories of Christmases past. Spend a fun afternoon with us at this joyous celebration! Your Colonial Yuletide admission includes both sites, and you may begin your experience at either location
December 7th and 8th; Kent Narrows Outlet Center
Come start the holidays off right by attending the 2024 Festival of Train! Kid’s of all ages will thrill at the displays, lights and sounds that herald the arrival of the holiday season. Although admission and parking are free – donations (thank you) made at the event inch us closer to saving the Centreville Station Freight Depot – a true piece of Eastern Shore history and heritage. When you visit we hope you take the time to learn more about the society, it’s mission and it’s wonderful members.
Queen Anne's Chorale Holiday Spirit
December 7th, 7 p.m.; Todd Performing Arts Center, Wye Mills
Drawing from upbeat seasonal repertoire, Queen Anne’s Chorale presents music that will get you in the “Holiday Spirit” with selections for our traditional audience. A sing-along and reception are part of the fun! Children 13 and under are free!
December 7th; West Street Annapolis
From hot chocolate, to holiday shopping to a visit with Santa Claus, you won't want to miss this year's Holiday Market! Located in the parking lot of 20 Ridgely, at the corner of Annapolis Street and Giddings Avenue.
December 7th, 10 a.m. to Noon; Firestation #8, Annapolis
Join the South Forest Drive Business Association (SOFO) for a joyful holiday morning where children can share their wish lists with Santa. The event will include festive music, light refreshments, and all the magic of the season, creating memories to treasure. Bring the whole family, and don’t forget your camera to capture the excitement of meeting Santa!
December 7th; Cult Classic Brewing, Stevensville
Dress in your favorite Christmas costume, throw a saddle on Rudolph and party from Cult Classic to El Jefe to Pour House and back. Each of your favorite bars will have different events so suit up and spread that holiday cheer at the jolliest FREE community event raising money for local charities.
December 7th, 5:30 p.m.; Annapolis Mall
Chabad of Anne Arundel County presents Chanukah Wonderland at the Mall! Fun and activities for all ages, latkes galore, doughnuts, menorah lighting and more for the whole family at the Crate and Barrel court in front of Stoney River
December 7th, 6:30 p.m.; Downtown Easton
Hope you’re ready for some holiday cheer! Easton’s holiday parade will take place December 7nd, 2024. With a myriad of vehicles, novelties, and floats this parade is sure to showcase the very best of Easton during the Christmas season. Join in the festivities! Before the parade, Santa arrives in Thompson Park at 5:30 followed by a tree lighting at 6:00 PM.
December 8th, 3 p.m. and 7 p.m.; Todd Performing Arts Center, Wye Mills
When the Lord of Snow and Ice visits the green valley of Elmerton and falls in love with the beautiful Fauna, her sister Flora runs away, taking the springtime with her. Only an evergreen can bring the sisters back together again. Join us for an old-fashioned folk tale about the first Christmas Tree.
December 8th, 8 a.m.; Heroes Pub, Annapolis
Join us on Sunday December 8th from 8-11am as we welcome over 35 of your favorite local small businesses, Santa and his crew and our 4th Annual Heroes Market raffle to benefit the River Arts District Asheville. Artists, bakers, creative gifts, clothing and more!
December 12th; Downtown Annapolis
Downtown Annapolis Partnership proudly presents Midnight Madness—a Historic Downtown Annapolis holiday tradition that encompasses the charm and character of our most beloved memories of Norman Rockwell and Charles Dickens. We will adorn the streets and participating storefronts with holiday decorations, trees, garlands, snowflakes, bows, and lights to create a Downtown Winter Wonderland and free on-the-street entertainment.
December 13th through 15th; Oxford Community Center, Oxford
We are delighted to announce the inaugural Oxford Holiday Market, a festive event taking place from Friday, December 13 to Sunday, December 15, 2024 in the historic town of Oxford, Maryland. This charming event promises to be a highlight of the holiday season, offering a weekend filled with unique artisan gifts, delicious food, and holiday music.
December 13th, 7:30 p.m.; Maryland Hall, Annapolis
December 14th, 3 p.m.; Severna Park High School
Get ready to experience one of the most beloved traditions in Annapolis—the Annual Holiday Pops concert! This festive season, join the Annapolis Symphony Orchestra and 70 world-class musicians as we bring the joy, beauty, and warmth of the holidays to life with a dazzling mix of classical music, carols, and heartwarming holiday tunes.
December 14th through 15th; St. Michaels
The houses in town are within walking distance of each other, which gives visitors a great opportunity to stroll through town and soak up the historic atmosphere. Most of the homes, built in the 18th and 19th centuries, had at one time been the residences of watermen and seafarers. Many of these homes have since been restored, expanded, and adapted to today’s life style.
December 14th, 10 a.m.; Downtown Chestertown
Come to the Chestertown Arts & Entertainment District’s ART WALK. Dozens of artists and artisans will be selling works at galleries, storefronts, at a Pop-Up Gallery. Live music will also be happening throughout town. For information email hester@kentculture.org or call the Kent Cultural Alliance at 410-778-3700
December 14th; Hyatt Regency Chesapeake Bay Resort, Cambridge
Take a dip in the Choptank River on Saturday, Dec. 14, to help the Care and Share Fund, Inc. raise funds for the needy and other worthy projects in Dorchester County. The Santa Swim happens at the Hyatt Regency Chesapeake Bay Resort in Cambridge, MD. Swimmers bring monies from their personal fundraising as the entrance fee for the swim.
December 14th, 10:30 a.m.; Talbot Street, St Michaels
Who doesn’t love a traditional Christmas parade complete with marching bands, antique cars and boats, fire engines, horses, kazoo bands and llamas?! Perhaps you may even see a penny farthing. Santa and Mrs. Claus will arrive to close out the parade. Come early on Saturday morning to get a great spot along the parade route for the largest holiday parade on the Eastern Shore. Bring a lawn chair and a funny hat. Join the fun!
December 14th; Charles Carroll House, Annapolis
Join CoreShark H2O and 250 guests at our winter fundraiser, Bay Bells & Shark Tails. This event at the historic Charles Carroll House on Spa Creek in downtown Annapolis offers a bird’s eye view of the Eastport Yacht Club Lights Parade from a heated tent. At the same time, guests enjoy a full open bar, abundant experiential food stations, shucked-to-order oysters from Madhouse Oyster Company, silent auction, raffle items and dancing to the amazing beat of Radio City!
December 14th, 6-8 p.m.; Eastport Yacht Club, Annapolis
It's a beloved Annapolis tradition! Every year on the second Saturday in December, magic happens on the water of the Annapolis Harbor—boats suddenly appear out of the cold winter night illuminated with thousands of colored lights and crewed by jolly revelers!
December 14th, 6 p.m.; St. Michaels Harbor
Once again we are excited to present the Lighted Boat Parade on Saturday night, December 14 at 6pm, around St. Michaels Harbor. Last year we had 18 entrants that wowed us with their creativity and decorating skills.
