SOUTHERN MARYLAND — Get ready to celebrate the season! Santa Claus is coming to town! Dive into the holiday spirit with festive photo ops at your favorite local spots. From Santa sightings to Grinch gatherings, here’s your guide to all the best events happening around Southern Maryland!
If you have an upcoming event, we would love to share it! Please enter your event details on our Events Calendar.
CALVERT COUNTY
Rolling Acres Farm Christmas Weekend Spectacular taking place November 29 through December 1 (10 am to 2 pm), located at 3305 St. Leonard Road, Port Republic, MD – Santa will be onsite along with a professional photographer (McIntosh Images) to take 3 digital images with access to online photo album. The fun doesn’t stop there. There are plenty other memories to be made. Shop for the perfect Christmas tree this holiday season, while having fun making holiday crafts, and enjoying a hot cocoa bar. Farm activities will also be available for additional fun. There will be a food truck onsite to enjoy brunch, dinner, and breakfast with Santa. We can’t wait to spend the holidays with you on the farm! $5 presale price for online sales. $7 at the gate.
Light Up the Town on December 1 (4 pm to 6 pm), located at Chesapeake Beach Town Hall, 8200 Bayside Road, Chesapeake Beach, MD – It’s TIMMMEE to light up this Town and get into the Holiday Spirit! Visit with Santa, shop local vendors, indulge in sweet treats & holiday activities, and enjoy a very special performance from Beach Elementary String Orchestra!
Joyful Paws Holiday Open House on December 1 (11 am to 3 pm), located at Calvert Animal Welfare League, 1040 Prince Frederick Blvd, Prince Frederick, MD – Adoptable pets, Bake Sale, Ask the Trainers, Thrift Shop, Vendors, Taste of the Tides Food Truck, Professional Pet Photos with Santa and more!
Pictures with Santa on December 1 (11 am to 4 pm), located at Sophia’s Oasis For Equines, Inc. (SOFE), 9145 Mackall Road, Saint Leonard, MD – Santa is coming to town!! Your $20 picture package includes a picture with Santa as well as one of our horses in a beautiful Christmas barn setting. One time slot ticket is valid for ONE family! You can have as many people per family as you like. Your $20 is considered a donation to our rescue. Time slots are only 15 minutes long, so please be mindful of time and not overlap with the family behind you. Parking is also limited; carpool if/when possible.
Christmas Wonderland on December 5 (5 pm to 8 pm), December 6 (5 pm to 8 pm), and December 7 (4 pm to 7 pm), located at Emmanuel Church – Huntingtown, 3800 Old Town Rd, Huntingtown, MD – Make holiday memories at this FREE family event! You’ll experience: Pictures with Santa, Carriage rides (Friday only), Christmas movies, Story time with Mrs. Claus, Cookies and hot cocoa, Christmas crafts, and more!
Pancakes with Santa on December 7 (8 am to 1 pm), located at Calvert Career and Technology Academy, 330 Dorsey Rd, Prince Frederick, MD – Join us for a delicious pancake breakfast prepared by our Culinary students, crafts, fun, and of course photos with Santa! All you care to eat breakfast and entry to the event: In advance: $10 adults/$8 children. At the door: $15 adults/$10 children.
Christmas Town in Lusby on December 7 (10 am to 5 pm), located at East-John Youth Center, 11835 Mill Bridge Road, Lusby, MD – Holiday fun for the whole family! Santa, hayrides, vendors, music, food, silent auction, and more! Free admission. Call 443-985-2407 for more information.
Santa Clause is coming to Jakes Produce on December 7 (11 am to 4 pm), located at 2925 Yoes Corner Ln, Port Republic, MD – Santa Clause is coming to Jakes Produce and we couldn’t be more excited!! Join us for pictures and hot chocolate with Santa on December 7th AND December 14th! This event will be completely FREE!! Stop by Jakes produce and get your picture taken with Santa, grab some delicious hot chocolate from our hot chocolate bar, and then let us help you and your family pick out the PERFECT Christmas tree!
An Old-Fashioned Christmas: Light Up Linden on December 7 (11 am to 4 pm), located at Linden House, 70 Church Street, Prince Frederick, MD – Join us for a FREE family day of holiday fun on the historic grounds of Linden, home to Calvert County’s Historical Society. You’ll find live music, activities for all ages, food trucks, vendors, a visit and reading with Santa and closing the day with a tree lighting!
A Magical Christmas Parade on December 7 (12 pm), located at Bay Avenue from 1st Street to 7th Street, North Beach, MD – Step into the magic of the holiday season as North Beach presents A Magical Christmas Parade! This annual event will bring the streets to life with holiday spirit, festive floats, and of course, a special appearance from Santa Claus!
Second Annual Community Tree Lighting on December 7 (4 pm to 9 pm), located at Town Square Lusby Shopping Center, 258 Town Square Dr, Lusby, MD – The official kick off to the holiday season! Join us for our second annual tree lighting ceremony and holiday block party! Bounce houses, DJ Dallas, mechanical bull riding, hot chocolate, bonfires, s’mores, Santa is stopping by, Black Sheep Jeeps In Lights, Madbyrd Confections, and so much more.
Annual Holiday Market: Sip & Shop on December 8 (11 am to 4 pm), located at No Thyme to Cook, 14624 Solomons Island Road South, Solomons, MD – This festive afternoon has something for everyone – from a visit with jolly Santa to a mini craft fair featuring local artisans, and a gourmet hot cocoa bar. Admission is free but the memories are priceless!
Kids Karaoke Christmas Brunch on December 14 (10 am to 2 pm), located at Atomic Seafood and Bar, 258 Town Square Dr, Lusby, MD – All things Christmas brunch with a special appearance by that rascal the Grinch!! Kids Karaoke and Christmas caroling!
Santa Clause is coming to Jakes Produce on December 14 (11 am to 4 pm), located at 2925 Yoes Corner Ln, Port Republic, MD – Santa Clause is coming to Jakes Produce and we couldn’t be more excited!! Join us for pictures and hot chocolate with Santa! This event will be completely FREE!! Stop by Jakes produce and get your picture taken with Santa, grab some delicious hot chocolate from our hot chocolate bar, and then let us help you and your family pick out the PERFECT Christmas tree!
Solomons Christmas Walk at Calvert Marine Museum on December 14 (6 pm to 9 pm), located at Calvert Marine Museum, 14200 Solomons Island Road, Solomons, MD – The museum is open and FREE to the public. Enjoy live musical entertainment in the Harms Gallery all evening. Visit with Santa and the Otter mascot, make holiday crafts, and shop in the Museum Store during the event. Santa’s Coffee House will be open with complimentary hot cocoa, coffee, and holiday cookies. Museum Members save 20% in the Museum Store Saturday and Sunday, Dec. 14 and 15.
CHARLES COUNTY
St. Charles Towne Center Santa Photo Experience every day at select times until December 24, located at 11110 Mall Cir, Waldorf, MD – Don’t miss Santa pictures at St. Charles Towne Center! Walk ups welcome every day until closing time. Please Note: Multiple families are scheduled during the selected 15-minute time.
Holiday Tree Lighting Event on November 29 (6 pm to 8 pm), located at Shops at Waldorf Center, 2952 Festival Way, Waldorf, MD – After a day of holiday shopping, join us as we officially kick off the holiday season with our 2nd annual tree lighting celebration! Santa, holiday music, Christmas crafts, and more to spread holiday cheer! Bring a new, unwrapped toy for Toys for Tots donation drive if you can!
Lunch with Santa on December 7 (11 am to 1 pm), located at Hughesville Volunteer Fire Department, 15245 Prince Frederick Road, Hughesville, MD – Come have Lunch with Santa! Crafts, door prizes, pictures, lunch! $10 for kids, $5 for adults if eating.
Olde Tyme Holiday Gathering on December 8 (3 pm to 6 pm), located at Town of La Plata, 305 Queen Anne Street, La Plata, MD – Celebrate the season with music, children’s activities, refreshments, horse-drawn carriage rides by Suttler Post Farm and a visit from Santa. The Christmas tree will be displayed in the circle at Town Hall and will be officially lit during the event. Food will be available for purchase from local favorites – Big Boy Taco, Judy’s Food Express, Mad Byrd Confections, Pizza Hotline and Shugies Cookies.
Newburg Volunteer Rescue Squad & Fire Department Co 14 Breakfast with Santa on December 14 (9 am to 1 pm), located at 12245 Rock Point Rd, Newburg, MD – Pancake breakfast 9 am to 11 am – $7 per person, kids under 2 free. Santa’s workshop, craft & games, pictures with Santa. Sparkle and Sass Dance Company will be performing at 11:30 am.
Ice Skate with The Grinch on December 22 (2 pm to 5 pm), located at Capital Clubhouse, 3033 Waldorf Market Place, Waldorf, MD – This event begins with The Grinch available to meet and have a photo op while you are enjoying the Whoville Hot Cocoa & Cookie Bar! The Grinch will then proceed to the ice rink to skate with all participants and then proceed back to the lobby to mingle with everyone wrapping up their fun time! Ice skating will be open and available to participants for the duration of the entire event, 2pm-5pm. SHEDULE: 2-3pm: Photo Op with The Grinch & Whoville Hot Cocoa & Cookie Bar. 3:15-4:15pm: Ice Skate with The Mean One. 4:30-5pm: Mingle with The Grinch! $25 in advance, $35 the day of or at the door (if capacity limit not already met). This event did sell out last year, so please get your tickets early to avoid missing out on the fun.
ST. MARY’S COUNTY
Holiday Market with The Grinch & Cindy Lou Who on November 29 (9 am to 7 pm), located at Town Market, 22675 Washington St Leonardtown, MD – The Holiday Market will be open with all types of vendors to help get you started on your Holiday Shopping. Watch out for the Cindy Lou Who as she will be around making sure the Grinch doesn’t make any trouble. Get your pictures taken with The Grinch and Cindy Lou Who to take home. We will have the Race Cars and Classic Cars on display for everyone to see as well as a Light Display.
Christmas on the Square & Annual Tree Lighting on November 29 (4:30 pm to 8:30 pm), located at Town of Leonardtown, 22698 MD-326, Leonardtown, MD – The holiday season begins in Leonardtown when Santa arrives for the annual Christmas Tree Lighting in the Town Square. The festivities begin at 4:30 PM with holiday music, entertainment, horse and carriage rides, sleigh rides, train rides, hayrides, live nativity, petting zoo, face painting, children’s crafts, hot drinks, fresh kettle korn and other fun activities! Many downtown restaurants and shops around the Town Square will be open and decorated for your holiday pleasure. The Leonardtown Volunteer Fire Department, Leonardtown Business Association, and the Commissioners of Leonardtown sponsor this traditional holiday event.
Bubby’s Christmas Farewell taking place November 29 through December 23 (5 pm to 9 pm), located at Flat Iron Farm, 45840 Hwy to Heaven Ln, Great Mills, MD – Join us for a heartfelt farewell at Flat Iron Farm as we celebrate Bubby Knott’s legacy during this beloved holiday tradition. This year’s theme is “Giving Back,” with a goald to raise $100,000 for local charities in honor of Bubby’s spirit of community support. Tntry as always is free, with exciting activities for everyone! We’ll also have charity drives and accept cash donations, ensuring that all proceeds go to Bubby’s favorite causes. Dazzling Christmas lights, photos with Santa Claus, local food trucks, entertainment and music, craft vendors and exhibitors, petting zoo and pony rides, family-friendly activities, hot chocolate & smores pit, christmas market, and weekly special events.
A Casual Christmas Starts on November 29 and takes place Fridays (6 pm to 9 pm), Saturdays (5 pm to 9 pm), and Sundays (1 pm to 4 pm) throughout December 28th, located at Mount Chance Farm, 23713 Mount Chance Farm Lane, Clements, MD – A Casual Christmas is a magical and unique Christmas experience sure to bring out the child in you. Our event takes place on a working farm in Clements, MD. Walk through our beautifully decorated equestrian barn where you can vote on your favorite stall, visit with friendly horses, shop from local vendors and artist and stop to see Santa. Just outside you will find face painting, hot chocolate, hay rides, pony rides, petting zoo, axe throwing, inflatables and more!
SMS Breakfast with Santa on December 1 (8 am to 11 am), located at Ridge Vol. Fire Department, 13820 Point Lookout Rd, Ridge, MD 20680 – Save the date for St. Michael’s School Annual Breakfast with Santa. This will be at the Ridge Vol. Firehouse. Come enjoy delicious foods, a good time with family and friends, get some last minute shopping in with local vendors and crafter, and don’t forget your picture with Santa.
Santa’s 20th Annual Tour of Hollywood Starts on December 1, located at Hollywood Volunteer Fire Department, 24801 MD-235, Hollywood, MD – Old St. Nick will be arriving at the Hollywood Volunteer Fire Department on Sunday, December 1st for your Annual Christmas Tree Lighting. Starting on the Friday after his arrival, Santa will be touring our community spreading his Christmas cheer! Santa’s Elves have sent Santa’s itinerary to the firefighters so that we can help Santa spread some holiday cheer to the fine folks of Hollywood! As a friendly reminder, Santa’s tours will begin at approximately 5:00pm each evening and will last until approximately 8:00 pm. Be sure to listen for our sirens to know that Santa is on his way! In case of rain or snow, we will reschedule that tour before Christmas. Please check our website site or visit our Facebook page for updated information regarding any change in schedules.
MBMS Holiday Bazaar on December 7 (9 am to 2 pm), located at Margaret Brent Middle School, 29675 Point Lookout Rd, Mechanicsville, MD – Santa and Mrs. Claus will be there for photos and we will have a kids activity table as well!!!! We have over 35 vendors that offer a variety of items so you are sure to find a gift for everyone and yourself!! There will also be indoor concessions and food trucks on site. Admission is FREE! We will be accepting monetary donations as all our proceeds directly benefit MBMS 6th grade students for school events such as quarterly incentives, school dances, and our end of the year celebration. We hope to see you there! Please reach out to Emma Ward at mbmsholidaybazaar@gmail.com if you have any questions.
Christmas Open House on December 7 (9 am to 5 pm), located at Cecil’s County Store, 20853 Indian Bridge Rd, California, MD – Join us for our annual Christmas Open House! Santa will be here from 9AM-11AM, and we’ll have plenty of fun activities and treats throughout the day. Don’t miss out on the holiday cheer!
Santa Visits Cedar Point on December 7 (10 am to 12 pm), located at Cedar Point Federal Credit Union, 22745 Maple Road, Lexington Park, MD – Come see Santa and Mrs. Claus and tell them what’s on your wish list! Bring your cameras and strike a pose with Jolly Old Saint Nick.
Festival of Trees on December 7 (10 am to 3 pm), located at University System of Maryland at Southern Maryland, 44219 Airport Rd, California, MD – This free community event showcases festive trees and wreaths sponsored and decorated by generous supporters. All proceeds benefit our local St. Mary’s County Hospice community! Tree & wreath display & auction, DIY photos with Santa from 10-12:30 & 1-3, Food trucks, Live music, Raffles, Kids’ activities, Free entry!
5th Annual Winter Market on December 7 (10 am to 4 pm), located at Southern Trail Distillery, 27227 Morganza Turner Rd, Mechanicsville, MD – Come out and do some shopping with local vendors and artisans in preparation of the Holidays. Grab your favorite Southern Trail spirits (for you or for a gift), a delicious Southern Trail cocktail and listen to the one, the only Bradley Turner (12:00-3:00). This year the Chopticon Band will also be here playing Christmas Carols at 11:00 & 3:30. And the Grinch may make an appearance. Mark your calendars for a great time!!
Christmas Open House at Summerseat Farm on December 7 (11 am to 2 pm), located at 26655 Three Notch Rd, Mechanicsville, MD – The Manor House will be beautifully decorated for Christmas with freshly cut greenery and vintage decorations. Please enjoy some warm cider, cookies and Christmas music while touring the house. Santa will be there to greet all the good little children (both young and old). Activities will include crafts for the kids and hayrides. The barn area will also be open so you can visit our pasture animals. Summerseat Farm is a 501(c)(3) nonprofit organization and these events help us maintain the property and care for our animals. All funds received directly benefit the farm as we are a 100% volunteer based organization. A $10 donation per family is requested.
Holidays In The Hanger on December 7 (11 am to 2 pm), located at The Patuxent River Naval Air Museum, 22156 MD-235, Lexington Park, MD – Join us for a magical day of holiday cheer at Holidays in the Hangar! We’ve got something for everyone—bring the whole family for a day filled with fun activities and festive treats! Pictures with Santa – Capture a special moment with Santa from 11:30-1:30. Face painting, arts & crafts, sweet treats & hot cocoa.
Lexington Park Holly Days Extravaganza on December 8 (1 pm to 4 pm), located at St Mary’s County Library – Lexington Park Branch, 21677 FDR Blvd, Lexington Park, MD – Holly Days Extravaganza will be open to the public both in and around the library! This event will feature pictures with Santa, arts and crafts for all ages, a vendor shopping experience, carolers from St. Maries Choral Arts, and festive decorations!
Santa Visits Nicollettis on December 11 (4 pm to 7 pm), located at Nicollettis Pizza, 22741 MD-235, California, MD – Santa will be visiting Nicolletti’s again this year!! This is a free event! Stop by get your pictures taken and grab some pizza.
Come Out and See the Grinch & Christmas Shopping Spree on December 14 (9 am), located at Town Market, 22675 Washington St, Leonardtown, MD – Come out and see the Grinch along with Max and Cindy Lou. Get your picture taken with the entire gang. Vendors are here to help you finish your Christmas shopping as well. Pictures with The Grinch are 10am to 4pm. Simply Q Barbecue will be here serving up some your favorites all day long.
Combat Veterans Motorcycle Association® Southern Maryland Chapter’s Annual Santa Run on December 14 (9 am to 2pm), at several locations – The event provides the public the opportunity to donate holiday “wish list” items to the Charlotte Hall Veterans Home. 9 am: Drum Point and Chesapeake Ranch Estates at Clubhouse Dr. and Rousby Hall Rd (motorcycle procession will also ride through the two neighborhoods), 9:30 – 10 am: Lusby Ace Hardware, 10:15 – 10:30 am: Solomons Island Gazebo parking lot, 11-11:30 am: California WalMart parking lot, 12-12:15 pm: Leonardtown Square, 12:45 – 1 pm: Charlotte Hall WaWa, 1:15 Charlotte Hall Veterans Home.
Holiday Storytime and Cookies with Santa & Mrs. Claus on December 15 (1 pm to 3 pm), located at U.S. Colored Troops Interpretive Center, 21675 S. Coral Dr, Lexington Park, MD – Join St. Mary’s County for a free and festive Open House for all ages at the U.S. Colored Troops Interpretive Center in the Lexington Manor Passive Park featuring Christmas storytimes, holiday cookies/refreshments and more – including Santa and Mrs. Claus! Storytimes will occur at 1:30 p.m. and 2:30 p.m. You will also be able to view the exhibits at the interpretive center during this time. Admission: Free.
Santa Visits Nicollettis on December 18 (4 pm to 7 pm), located at Nicollettis Pizza, 22741 MD-235, California, MD – Santa will be visiting Nicolletti’s again this year!! This is a free event! Stop by get your pictures taken and grab some pizza.
ALVFD Breakfast with Santa on December 21 (8 am to 11 am), located at Leonardtown Volunteer Fire Department, 22733 Lawrence Ave, Leonardtown, MD – Join us for a delicious full breakfast including pancakes, eggs, sausage, bacon, hashbrowns, applesauce, milk, juice, and coffee! Adults $13, 10 years and under $6, and under 3 years are free. Santa will join us so bring your lists and your camera! There will also be activities for the kids! What a great family event!!! You don’t want to miss this one!!!
Picture with Santa Claus on December 21 (9 am to 6 pm), located at Town Market, 22675 Washington St Leonardtown, MD – Santa will be here checking his list twice. Stop by and see him before he starts his Christmas journey. Get your pictures with Santa and he will also see your Fur Babies as well. Scratch Mobile Kitchen will be serving up some homemade favorites.
Last Chance Christmas Market on December 21 (11 am to 4 pm), located at Dixon Family Farm, 27075 S Sandgates Rd, Mechanicsville, MD – Bring the family and Christmas cheer to our 2nd annual Last Chance Christmas Market! Join us on the farm for last-minute shopping with our awesome local artisan vendors, craft beverage vendors, food trucks, fire pit, live music, and free photos with Santa! Weather permitting! Check our socials for last-minute updates.
Other Ways to Talk to Santa
Santa’s Hotline is an international voicemail line for children of all ages to leave messages for the North Pole at no charge. Callers across the globe may dial Santa’s Hotline at 1-605-313-4000.
USPS Operation Santa Have your kids write their letters to Santa, and address it to: Santa Claus 123 Elf Road, North Pole 88888. Put a stamp on it and a return address and send it off to Santa! Then see what happens next. Letters received with full Santa addresses will be posted on the USPS Operation Santa site, where anyone can choose to “adopt” a child by sending a gift from their letter to them.
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