December 2nd; Downtown Annapolis
Shop local during Midnight Madness on December 2nd and 9th, 4 pm until Midnight, and on the Eleventh Hour on December 16th until 11 pm at 90 stores and 80 restaurants in downtown Annapolis. The downtown Annapolis area, including West Street, Maryland Ave, Main Street, and the City Dock area will be filled with traditional holiday decorations including beautiful storefront windows, garland, wreaths, holiday lights, a snowflake alley, light canopies, a large Christmas tree, and a menorah. This will create a fun, safe, outdoor environment for late-night shopping and dinner with your family. The event shopping hours will again this year start 2 hours earlier at 4 pm. This provides an opportunity for people to spread out arrival times and reduce crowding or to attend a happy hour.
Gallery Reception: The Art of Criticism
December 2nd, 5:30 p.m.; Maryland Hall, Annapolis
Join us in the Galleries for an evening of art and shopping. The Art of Criticism opens in The Openshaw Balcony Gallery and the Chaney Gallery features an Artisan Pop Up Shop for all of your holiday shopping. Light refreshments will be served in The Openshaw.
Book Launch: Stardust by the Bushel: Hollywood on the Chesapeake Bay's Eastern Shore by Brent Lewis
December 2nd, 6 p.m.; Cult Classic Brewing Company, Stevensville
From a thrilling train crash staged in Queenstown for 1917's 'The Whip', to modern hits like 'Runaway Bride' and 'Wedding Crashers', for over a century our unique and beloved Eastern Shore has lured filmmakers looking for a special place to whip up some movie magic. Join me at Kent Island's awesome Cult Classic Brewery on Thursday, December 2nd to celebrate the publication of my new book, STARDUST BY THE BUSHEL: HOLLYWOOD ON THE CHESAPEAKE BAY'S EASTERN SHORE. There will be smiling familiar faces to say hi to, copies of STARDUST available for sale and signing, plus great food and special theme drinks available for purchase too!
Home for the Holidays and Luminary Walk
December 3rd through 5th; Talbot Interfaith Shelter, Easton
Talbot Interfaith Shelter is proud to partner once again with the Hummingbird Inn and Easton Economic Development Corporation to light up downtown Easton this holiday season with its 2nd Annual Home for the Holidays Event! Attendees this year will enjoy an expansive holiday light display, Santa visits, crafts for the kids, dessert and beverages, live local music each evening from 6:00 – 7:00 p.m., and carriage rides on Sunday December 12th and 19th ($5 per person, children under 5 ride free).
Muddy Creek Artists Guild's Gifts from the Arts
December 3rd through 5th; South River Colony Main Street Shopping Center, Edgewater
Muddy Creek Artists Guild presents a professional art gallery experience, featuring works in an array of different media including painting, pottery, photography, jewelry, glass, mixed media and textiles. This is a great opportunity to engage with local artists, shop for unique, local artworks and gift items. Visitors are invited to get an exclusive Sneak Peek Thursday , December 2 at 5:30-8:00 p.m. and then Meet the Artist reception on Friday, December 4 at 5:00 p.m.–7 p.m. Both events will feature music, wine, and light refreshments. In addition, during Saturdays and Sundays enjoy "Studio Intrepid" hands-on workshops for all ages and FREE. Masks required.
December 3rd through 5th; Downtown Chestertown
Join us December 3-5, 2021 for the 4th Annual A Dickens of a Christmas in downtown Chestertown. Chestertown’s beautiful architecture is the backdrop for a lively London-themed weekend filled with Victorian entertainment, food, shopping, children’s activities, and more. Make sure to follow us on Facebook for the most up-to-date information.
Santa Paws - Pictures of Your Pet with Santa
December 3rd; Homestead Gardens, Davidsonville and Severna Park
Bring your furry friend to Homestead Gardens for pictures with Santa! This is a special event will support the SPCA. Make Holiday memories with your fur friend while supporting an important organization! This event will be held in Homestead Gardens Davidsonville and Severna Park stores. Check out www.homesteadgardens.com for updated event information.
December 4th, 4 p.m. - 10:30 p.m.; Children's Theatre of Annapolis
CTA is hosting their first Drive In Movie Double Feature in their theatre’s parking lot on December 4, 2021 and Santa will greet and pose for pictures with all attendees. On December 4, 2021, CTA’s parking lot will turn into a drive-in theatre with two movies playing on a large screen with sound playing from a special radio station piped into the cars. The first movie on the big screen is “Klaus,” A simple act of kindness always sparks another, even in a frozen, faraway place. When Smeerensburg's new postman, Jesper, befriends toymaker Klaus, their gifts melt an age-old feud and deliver a sleigh full of holiday traditions. (Run time is approximately 1 hour & 37 minutes). The second is “Jingle, Jangle,” Decades after being betrayed by his apprentice, a once joyful toy maker finds new hope when his bright young granddaughter arrives on his doorstep. (Run time is approximately 2 hours & 2 minutes). The schedule for the even is:
December 5th, 5 p.m.; Downtown Chestertown
Visit Chestertown December 3rd through 5th to see a large display of trees decorated by businesses, organizations and local families. The trees will be displayed at 1st UM Church during the Winter Festival and is open 5-7 p.m. on Friday, 10 - 7 p.m. Saturday, and noon to 3 p.m. on Sunday. Bring your camera and see Santa and Mrs. Claus from 12-2 p.m. on Saturday and Sunday. Find more information about this free community event at Townofchestertown.com
December 3rd, 5-7 p.m.; MFA Circle Gallery, Annapolis
Please join us for The Art of Wine, a fundraiser with the Maryland Federation of Art. The event will be held on Friday, December 3 at 5 pm at the Maryland Federation of Art’s Circle Gallery.
Rescue Fire Company Train Garden
December 3rd, 6 p.m.; Cambridge Rescue and Fire Company
The RFC Train Garden has been a Cambridge Christmas Tradition for nearly nine decades! Each December, we operate daily, providing new memories and rekindling old ones. Beginning in 1934, members of Rescue Fire Company began operating a holiday train display for the community, carrying on a tradition that began in the Baltimore area. Though the train garden tradition remains strong in the Baltimore area, many of our peers from the 1930s and 1940s are gone. The RFC Train Garden is the longest continually operating fire department train display in the United States.
December 3rd through 31st; Annapolis City Docks
Annapolis' favorite holiday activity makes its return for the 2021 holiday season. Miss Anne will be adorned with reindeer spirit for an intimate 45-minute "sleigh ride" including hot cocoa, holiday music, and good cheer. Captain Santa is at the helm during this festive evening cruise on Spa Creek. Bring your own cozy blanket to keep you warm. This is the perfect opportunity to start a family holiday tradition. In the spirit of the season, a portion of proceeds will be donated to Historic Annapolis.
December 3rd, 7 p.m.; Avalon Theatre, Easton
The Mid-Atlantic Symphony Orchestra continues its tradition of sharing seasonal cheer when it presents its popular Holiday Joy program, with acclaimed French soprano Norah Amsellem as guest soloist. Featuring a selection of seasonal favorites, the festive program will be presented on December 3 at 7 PM at the Avalon Theatre in Easton, MD; on December 4 at 7 PM at Cape Henlopen High School in Lewes, DE; and on December 5 at 3 PM at the Ocean City Performing Arts Center in Ocean City, MD.
December 3rd, 7 p.m.; Grace Pointe Community Church of the Nazarene, Severn
Relive the events of the very first Christmas portrayed in this dramatic, multi-scene drive-thru event with live cast and animals, lighting, and special effects. Experience the true meaning of the season in the story of redemption from the Creation and humanity’s fall into sin, to the birth of Christ and his death on the cross. Donations accepted.
December 3rd through 26th; Annapolis Market House
Welcome the holidays with an evening walking tour of Annapolis. Glowing lanterns will light your way as you stroll around Maryland’s state capital, trimmed in greenery. Our period-attired guide will share holiday traditions of times past among colonial mansions, Victorian homes, quaint shops, and the interior of the historic Hammond-Harwood House. Every Friday, Saturday & Sunday except for 12/11 and 12/24 &25th
December 3rd, 7 p.m.; Garfield Center for the Arts, Chestertown
For three weekends in December, visit Garfield Center for the Arts in Chestertown to see your favorite Ogre. Shrek: The Musical is based on the Dreamworks animated film where a disagreeable ogre, Shrek must rescue a fairytale princess from a fiery dragon to save his swamp alongside his new companion, a talkative, obnoxious Donkey. The production will open December 3rd and run weekends through December 19th with performances at 7 p.m. on Fridays and Saturdays, as well as 2 p.m. on Sundays. Visit garfieldcenter.org to buy tickets!
December 4th, 7:30 a.m. to 2 p.m.; Downtown Annapolis
Join us as we decorate downtown Annapolis for the Holiday season! It is an annual tradition for the Jaycees of Annapolis to decorate storefronts of local downtown businesses with lighted garland and wreaths. We separate into teams and work together to hang greens that will light up Annapolis at night. Currently, our plan is to use Market House (25 Market Place, Annapolis MD) as the meeting location.
December 4th, 11 a.m. - 4 p.m.; Kent Narrows Outlet Center
Queen Anne's Railroad Society is hosting The Festival of Trains on Saturday and Sunday, December 4th and 5th as well as 11th and 12th at the Kent Narrows Outlet Center. Admission is free and the festival is open 11 a.m. to 4 p.m. each day.
December 4th, 2 p.m.; William Paca House and Garden, Annnapolis
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. It’s the year 1771, and you’ll learn about holiday traditions of 18th century Annapolis and hear stories of Christmases past from living historians who will bring these historic homes to life on this merry day. The Annapolis Living Historians return to the William Paca House and Garden to celebrate the festivities! As you stroll through the Georgian mansion's bedecked hallways, you'll encounter William and Mary Paca and their friends filling the home with laughter, games of chance, gossip and political news of the day. Enjoy the musicians of Beldam musical group as you stroll the grand rooms and learn about 18th-century dining and hospitality.
Santa Arrives by Boat and Crab Basket Christmas Tree Lighting
December 4th, 6 p.m.; Rock Hall Harbor
Christmas festivities kick off in Rock Hall with the arrival of Santa and Mrs. Claus by boat followed by a parade of boats all at the bulkhead at 6:00 PM. The Community Band will be on-hand to entertain - both at the bulkhead awaiting Santa's arrival and on Main Street. Santa will travel by firetruck to Main Street to officiate the lighting of Rock Hall's Crab Basket Christmas Tree featuring several hundred decorated baskets in memory/honor of loved ones.
December 4th, 6 p.m.; Town of Galena
The Town of Galena invites you to share the Christmas Spirit with Santa, Mrs. Claus, and the Galena Volunteer Fire Company on December 4th at 6 p.m. Enjoy holiday cookies and hot chocolate on Main Street and Mayor Carroll will do a Facebook "drive through Galena" to share the lights of the season to find the best displays in town. For more information, call Galena Volunteer Fire Company
December 4th, 6 p.m.; Downtown Easton
Kick off the holiday season early in December by watching Easton's Holiday Parade. The night will begin with a tree lighting at 6 p.m. followed by the parade at 6:30 p.m. This parade will include an abundance of vehicles, novelties, parade floats, reindeers, elves, and more. For more information, visit eastondc.com
Queen Anne's Chorale Holiday Concert
December 4th, 7 p.m.; Centreville United Methodist Church
As we head towards the 2021 Holiday Season, Queen Anne’s Chorale is pleased to announce two concerts: Saturday, December 4th (7:00pm) and Sunday, December 5th (3:00pm) at the Centreville United Methodist Church located at 608 Church Hill Road (Rt 213). The theme is “A Family Christmas” with selections that will delight the children in all of us. In addition to seasonal favorites that families will enjoy, there will be the traditional audience sing-along, and a light reception afterward.
December 5th; Annapolis and West Street
Chocolate Lovers come together to enjoy a day to celebrate the art of Chocolate. There is something for everyone including about 35 Chocolate vendors, shopping from dozens of local artists, drinks, food, and live music, and did we mention Chocolate.
