The Best Events Happening in Southern Maryland During the Holiday Season

Make This Holiday Season Memorable- See What's Happening in SoMD!

Unwrap the Magic: Must-Visit Holiday Events in Southern Maryland

As the weather gets colder and the holiday spirit fills the air, Southern Maryland comes alive with festivities and events that will make your season truly special. From charming Christmas markets to dazzling light displays, there's something for everyone in this vibrant region. So grab your loved ones and get ready to celebrate the most wonderful time of the year in Southern Maryland!

Christmas Resort in National Harbor

ICE! featuring Rudolph the Red-Nosed Reindeer™

Experience the magic of the holiday season at Christmas Resort in National Harbor with Christmas at Gaylord National from November 19 to December 31, 2023. Dive into an enchanting holiday getaway with ICE! featuring Rudolph the Red-Nosed Reindeer, along with fan-favorite activities and live shows suitable for all ages.

Make your holiday extra special by staying as an overnight resort guest, enjoying exclusive privileges and making unforgettable memories. If you prefer a delightful day visit, immerse yourself in dazzling displays, savor delicious treats, and partake in festive activities. 

Annmarie Garden in Lights

Experience Dazzling Displays And Make Magical Memories At Annmarie Garden In Lights!

Step into the enchanting world of Annmarie Garden In Lights! From November 24, 2023, to January 1, 2024, witness a dazzling outdoor light show transforming the garden into a twinkling wonderland. Stroll along the forest path, captivated by lanterns and twinkling lights, sparking joy for all ages. Explore the Glowing Garden of the Poinsettias for Instagram-worthy moments.

Discover treasures at the Arts & Craft Fair, featuring handcrafted ornaments and jewelry by local artisans. Sip on cocoa, enjoy festive music, and immerse yourself in the spirit of the season. Create unforgettable memories with your loved ones at Southern Maryland's cherished light display, only here until January 1, 2024! Don't miss this extraordinary holiday tradition at Annmarie Garden In Lights – the true enchantment of the season!

Southern Maryland Holly Jolly Light Trail 2023 Southern Maryland's Holly Jolly Light Trail

The festive season is upon us, and what better way to ignite the holiday spirit than with Southern Maryland's Holly Jolly Light Trail! This community contest showcases the best and brightest holiday and Christmas decoration displays that Southern Maryland has to offer. It's more than just a light show; it's a celebration of creativity and imagination as each participating household or business brings their unique style to the grand display.

Immerse yourself in the enchantment of a mesmerizing journey through a trail adorned with twinkling lights. Step into a world of magic and wonder where the air is filled with joyful holiday music. Explore every corner and be delighted by scenes that come alive with vibrant colors and festive spirits. Southern Maryland transforms into a captivating carnival of lights, ready to ignite your senses and create cherished holiday memories for the whole family.

Join this magical event, hosted by The Southside Group of Home Towne Real Estate. Mark your calendars for the following important dates:

  • Registration: November 29 - December 4
  • Trail Map Published: December 7
  • Photos and Videos Due: December 9
  • Community Vote: December 21-26
  • Tour Guides: December 7-26
  • Winners Announced: December 28

Don't miss out on this extraordinary experience that will leave you with lasting memories of the holiday season. Get ready to be captivated by the beauty and wonder of the twinkling lights!

The Polar Express Movie Night @ Town MarketThe Polar Express Movie Night @ Town Market

Immerse yourself in the enchantment of the holiday season at Town Market in Southern Maryland on December 2nd, from 5:00 PM to 7:00 PM. Join us for a heartwarming screening of The Polar Express, a classic tale of self-discovery, Christmas magic, and belief. This must-see event promises a magical evening for all ages. Mark your calendars, invite friends, and experience the joy of the season at Town Market. Don't miss this essential stop on your list of Maryland festivities. It's a movie night like no other – an event you won't want to miss!

Letters to Santa Drive-Thru 

Hosted by The Southside Group, join us in Leonardtown, MD for an enchanting holiday experience at our Letters to Santa Drive-Thru event, held at the St. Mary's Sunshine Center. This event is designed to bring out the childlike wonder in all of us as we craft our personal wish lists and have the opportunity to meet the jolly Santa Claus himself. As you drive-thru our festive wonderland, be ready to be pleasantly surprised and have the opportunity to meet the real Santa Claus. Save the date—December 3, 2023 anytime between 3-5 pm - for this unique celebration that promises to add an extra sprinkle of joy to your holidays. Make sure to mark your calendar and join us for an unforgettable experience that will leave you with cherished memories and a heart full of holiday cheer!

Annual Kris Kringle Christmas Market

 Annual Kris Kringle Christmas Market

Get into the festive spirit at the Annual Kris Kringle Christmas Market at Charles County Fair. This enchanting event boasts light displays, local crafts, Santa's arrival, holiday fireworks, and more. Enjoy the Christmas tree lighting, music from local school groups, and a Christmas Village. Shop for fresh holiday decorations sourced locally. Don't miss the tree lighting on December 8th at 5:00 pm, with Santa on-site throughout. Admission is $5.00, benefiting local charities. Join us for a joyful holiday experience in Southern Maryland! 

Solomons Christmas Walk 2023

 Solomons Christmas Walk Solomons MD 20688 Lights

Celebrate the 42nd Christmas Walk in Southern Maryland with the Solomons Business Association! Enjoy the Lighted Boat Parade on December 9th, starting at 6 p.m. Explore the Solomons Vendor Village and participate in the festive house and business decorating contest with an Island/Nautical theme. Don't miss the holiday fun – join for a magical season in Solomons!

Suttler Post Farm Clydesdale's 

Suttler Post Farm Clydesdale's 

Get ready for a festive experience at Suttler Post Farm Clydesdales' Holiday Open House on December 9th and 10th from 11 am to 4 pm in Southern Maryland. See the Clydesdales adorned for Christmas and support a great cause—proceeds benefit Hospice of St. Mary's. Admission is $10, with free entry for kids 6 and under. Enjoy food, artisans, and vendors at this heartwarming holiday event!

Details at

Ice Skate with The Grinch

Ice Skate with the Grinch

Skate into the holiday spirit with the Grinch in Waldorf, Southern Maryland on December 10! Join us for a festive family day featuring a photo op, Whoville Hot Cocoa Bar, and ice skating with the mean green machine. Mingle with the Grinch and enjoy family fun from 11 am to 1:50 pm. Admission includes hot cocoa, a family photo op, ice skating, and rental skates. Register for $20 in advance or $25 at the door (subject to capacity limits). Don't miss this Grinch-tastic event on December 10!

Register at

A Casual Christmas 

A Casual Christmas Clements MD

Experience a Casual Christmas at Mount Chance Farm in Southern Maryland on December 23 from 2-6 pm! Enjoy festive holiday activities for the whole family, including photos with Santa, pony rides, petting zoos, kids' crafts, a Grinchmas Hayride, and much more. Get ready for some surprises and create joyful memories at this seasonal attraction!

Drive Thru Children's Christmas Party

Drive Thru Children's Christmas Party

Experience joy at the Drive Thru Children's Christmas Party on December 17 from 2-4pm at 28165 Hills Club Rd, Mechanicsville, MD 20659. Cruise through the beautifully decorated firehouse, wave at Santa, and receive a special stocking filled with surprises. Kids can drop off wish lists in Santa's mailbox, ensuring their dreams come true on Christmas day! Admission is free, and donations supporting the Mechanicsville Volunteer Fire Department are welcome at Join this magical Christmas event, create merry memories, and spread holiday cheer. Save the date for a joyous celebration in Southern Maryland!

As the holiday season approaches, Southern Maryland transforms into a magical winter wonderland, brimming with festivities and joy. Be it the enchanting light displays, jubilant parades, or heartwarming community get-togethers, there are events for everyone. So whether you're looking to create delightful memories with loved ones, find that perfect holiday gift at local markets, or simply indulge in the merry atmosphere, Southern Maryland is the destination to be. Let's embrace the season of giving, spread cheer, and make this holiday season truly unforgettable. Join us in celebrating the most wonderful time of the year in Southern Maryland!

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