Santa Claus is Coming to Naptown

When my brother and I were children, we would ask our father every year, “Do you believe in Santa?” He would stand up taller, gaze into the distance with a wistful look in his eye and say, “I believe in the spirit of Christmas!” We bought it—and he breathed a sigh of relief that he dodged the question for another year!

But Dad was onto something. For those who celebrate Christmas, whether they still believe, have outgrown their belief, or were never convinced in the first place, Santa embodies all the best qualities we try to have during the holiday season: joy, comfort, and kindness.

It’s a good thing that Santa is magical, because this season he’s in so many places at once! You can find him all over Annapolis, Anne Arundel, and beyond. On land, water, and in the air, Santa is here to grant all your Christmas wishes.

Homestead Gardens

There’s truly no place like Homestead for the Holidays! Walking into the garden center is like entering a winter wonderland, filled with sparkling decorations and a festive atmosphere. Breathe in the fresh pine scent while exploring their selection of Christmas trees. And Santa is ready to meet you, your little ones, and your pups! Get your pictures with Santa taken for free at any of Homestead’s locations in Davidsonville, Severna Park, and Smyrna.

Santa sees pets on Santa Paws days, December 4 and 5. Take them on those days so they can get all the love and attention from Santa that they deserve!

Address: Davidsonville–743 West Central Avenue, Davidsonville, MD 21035; Severna Park–522 Ritchie Highway, Severna Park, MD 21146; Smyrna–5580 Dupont Parkway, Smyrna, DE 19977
Price: Free!
Registration Required: Yes, for Davidsonville and Severna Park.

Annapolis Mall

Embark on a new holiday adventure at Santopolis. This season, you don’t have to wait in line with fidgety little ones. They can do some coloring, write a letter to Santa, or jump into all the different photo opportunities while waiting to meet the big man. Children on the nice list (which is all of them, of course!) will leave with a mini-candy cane.

They have evenings for pets on December 1 and December 8. They also have a sensory-friendly morning on December 7 before the rest of the mall opens. Keep our community warm and bring a coat to get $5 off of Package A+!

Address: Annapolis Mall, Near the Crate and Barrel, 2270 Annapolis Mall Road, Annapolis, MD 21401
Price: Packages range from $39.99 to $59.99
Registration Required: No, but recommended.

William Paca House and Garden

Step back in time to 1775 for a Colonial Yuletide holiday. Learn which celebrations have changed—and which have endured. Historical reenactors will entertain with stories of Annapolitans of old while you participate in crafts and enjoy some light refreshments. Revolution might be on the horizon in 1775, but there is still plenty of festive cheer with music and magic for the season. You can find some of that magic in the garden’s summer house, where Santa will be available to meet with families.

Date/Time: Saturday, December 6, 2025, from 2 PM to 5:30 PM.
Address: 186 Prince George Street, Annapolis, MD 21054
Price: $15 for adults. Discounts for members, military, children 3-17. Free for 2 and under. Includes access to both William Paca and Hogshead.
Registration Required: No, but recommended. Walk-ups are welcome only as space permits.

Jolly Express Cruise by Watermark

Set sail on Miss Anne for a nautical “sleigh ride!” This popular Annapolis tradition lets families enjoy a festive 45-minute cruise on Spa Creek. Snuggle up under a blanket while Santa or Mrs. Claus pilots the boat. An elf will serve hot cocoa to keep you warm.

There is room for 21 people on the boat, so you’re likely to make some new friends. If you want the “sleigh” to yourself, you can book a private tour. A portion of the proceeds are donated to Historic Annapolis.

Address: Slip 2, Annapolis City Dock, 1 Dock Street, Annapolis MD, 21401
Price: $28 for adults. $15 for children 11 and under.
Registration Required: No, but recommended.

Willow Oak Flower & Herb Farm

Travel north from Annapolis to reach the North Pole Lights Walk at Willow Oak Flower & Herb Farm. Enter a magical land and be sent on your way by a North Pole Fairy. Take your time on this self-guided walk enjoying the dazzling light displays. Santa is waiting for visitors in the Summer Cabin.

Address: 8109 Telegraph Rd, Severn, MD 21144
Price: $13.25 for adults. $9.25 for children 12 and under.
Registration Required: No, you can buy tickets in-person.

West Annapolis Holiday Market

The West Annapolis Business Associations hosts this holiday market, complete with Santa himself! You’ll find the perfect gift from West Annapolis’ antiques and boutiques. Get your Christmas shopping done for the year, then relax with a cup of hot cocoa.

Date/Time: Saturday, December 6, 2025 from 11 AM to 4 PM. Santa will be there from 11 AM to 1 PM.
Address: 20 Ridgely Ave., Annapolis, MD 21401
Price: Free.
Registration Required: No.

Annapolis Italian Christmas Market

Come say “ciao” to Babbo Natale at this event, hosted by the Order Sons & Daughters of Italy in America, Annapolis Lodge. You’ll find activities, music, and a selection of handmade gifts that everyone in your family will love. And the food is certain to be delicious! There will be soup, pizza, hot chocolate, espressos, cannolis, and more! Proceeds of sales support local charities and scholarships.

Date/Time: Sunday, December 7, 2025 from 10 AM to 3 PM
Address: 620 Ridgely Ave., Annapolis, MD 21401
Price: Free.
Registration Required: No.

Santa Speedo Run

There’s nothing like going for a run on a cold winter’s day…but this run will be extra chilly. This infamous race begins at O’Brien’s Oyster Bar and Seafood Tavern with check-in and liquid courage. Then, it’s on your marks, get set, SPEEDO down Main Street! Yes, the Santas featured here may be more for the adults than kids. Spectators can see all the imaginative costumes that might leave little to the imagination. The after party lasts until 3 PM with music by the Timmie Metz band. It’s all in good fun and for a good cause—organizers will collect donations of food and new, unwrapped toys.

Date/Time: Saturday, December 13, 2025. Registration begins at 11 AM and the run (or stroll) begins at 12:30 PM.
Address: O’Brien’s Oyster Bar and Seafood Tavern, 113 Main Street, Annapolis, MD 21401
Price: $30 (and a lot of nerve) to participate. Free to see it on race day.
Registration Required: Not for spectators. Runners should register prior to the event as spots are limited.

Annapolis Fire Santa Run

This time, you don’t have to travel far to see Santa. He will trade in his sleigh for a fire truck and visit neighborhoods all over Annapolis. When he stops by, you can donate a toy that he will deliver to children in need before Christmas Day. If you’re on the nice list, you may get a candy cane in return!

Date/Time: Sunday, December 14, 2025
Address: Check here for times that Santa will reach your neighborhood. (Note: This year’s post links to a 2024 document; watch their Facebook page for updated information.)
Price: Free.
Registration Required: No, just be ready for Santa to come to your community.

Breakfast with Santa

At The Rumor Meal in Pasadena, you and your family can join jolly ol’ St. Nick for a breakfast buffet and coffee bar. All-you-can-eat pancakes, French toast, and even breakfast pizza! Be sure to bring a non-perishable food donation to get a free kids meal that you can use in January or February.

Date/Time: Sunday, December 21, 2025 from 9 AM to noon.
Address: 4730 Mountain Rd., Suite 4, Pasadena, MD 21122
Price: Their Sunday brunch is $20 for adults and $15 for children 12 and under.
Registration Required: No, but reservations are recommended by calling (443) 673-7342.

You can find Santa at any of these places, as well:

Make sure you plan to visit Saint Nicholas, and tell him your wishes this season. Soon enough, he and his reindeer will fly off while he shouts, “Dash away, dash away, dash away, all!”