# Christmas Events, Markets & Things to Do in Leonardtown

- **Subtitle**: Celebrate Christmas 2026 in Leonardtown with festive markets, holiday parties, Christmas dinners, family activities, Santa experiences, Christmas lights, live shows, brunches, concerts, and seasonal events. Discover the best things to do and book your tickets online.
- **Category**: Christmas
- **Display Name**: Christmas events
- **Type**: other

## Audience

- **Followers**: 433k+
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## About

As Christmas draws near in the Leonardtown in 2026, mark your calendars for a taste of festive enchantment! Beyond the traditional gatherings at home, exploring during this festive season can be enchanting. Whether planning a family trip or going solo, there's a sleigh-load of festive fairs, holiday craft shows, and Christmas services in the Leonardtown waiting to be explored. Check out the best events and parties in Leonardtown to make your Christmas unforgettable, and get ready for a season of joy and celebration!

## Christmas Events in Leonardtown

- **Event Name**: Christmas on the Square & Annual Tree Lighting
  - **Description**: 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
  - **Interested Audience**:
    - Count: 201
  - **Date**: Fri Nov 27 2026 at 04:30 pm – Fri Nov 27 2026 at 08:30 pm (-05:00)
  - **Event URL**: https://allevents.in/leonardtown/christmas-on-the-square-and-annual-tree-lighting/200030733435447
  - **Venue**: Town of Leonardtown
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czkvYmFubmVycy9jODZhZjFkMzI4NzQyY2IxZTYyYjU4NmYxZmNmYjNmZTBhMjM2YWZlZjc3NjBjNGVkNTcyNWIxZmNiM2I0OTE1LXJpbWctdzY0MC1oOTU5LWRjMDgwODA4LWdtaXI_dj0xNzkwMjcxMzQ3.avif
  - **Categories**: holiday, art, fine-arts, christmas, christmas-lights, kids
- **Event Name**: Home for The Holidays - A New St. Mary's County Holiday Tradition
  - **Description**: Home for the Holidays is a festive community event benefiting Christmas in April St. Mary's County, bringing families together to celebrate.About this EventHome for the Holidays is a festive community event benefiting Chr
  - **Date**: Sat Dec 05 2026 at 04:00 pm – Sat Dec 05 2026 at 09:00 pm (-05:00)
  - **Event URL**: https://allevents.in/leonardtown/home-for-the-holidays-a-new-st-marys-county-holiday-tradition/100001994254779730
  - **Venue**: Saint Mary's Fairgrounds
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czgvYmFubmVycy83ODVkMzFkOWRmMTM1YzE0YmYxNGY0MzNhMGZlMGQ0Y2M2MTJjYjI3ZDA4OGQ1NDlhYzI3NDFhNmMxOWEzZjJkLXJpbWctdzEwNTQtaDE0OTItZGNmMmRkYjYtZ21pci5qcGc_dj0xNzg0MjcwNzgw.avif
  - **Price**: USD 0 to 8
  - **Categories**: fitness, Kids, food-drinks
- **Event Name**: Pictures with Santa Clause
  - **Description**: Santa will be here checking his list twice. Stop by and see him before he starts his Christmas journey. He will be here from 11am to 3pm. Get your pictures with taken with him.  We will have vendors here to help you finish your last minute shopping.

We a
  - **Interested Audience**:
    - Count: 20
  - **Date**: Sat Dec 19 2026 at 10:00 am – Sat Dec 19 2026 at 04:00 pm (-05:00)
  - **Event URL**: https://allevents.in/leonardtown/pictures-with-santa-clause/200030724564039
  - **Venue**: Town Market LLC
  - **Banner**: https://dyn-image.allevents.in/generate-image?v=4&title=Pictures+with+Santa+Clause+&date=Sat+Dec+19+2026+at+10%3A00+am&bg=5
  - **Categories**: pictures-with-santa, shopping
- **Event Name**: Photos with Santa! (Pet **all species** and kid friendly)w
  - **Description**: 🎅✨ Photos with Santa at Balanced Paws Pet Care ✨🐾

It’s the most wonderful time of the year — and Santa’s stopping by Balanced Paws! 🎄
Join us for a fun, festive photo day that’s pet (all species!) and kid friendly. 📸🐶🐱🐰

Bring your furry, feathered, or s
  - **Date**: Sun Dec 13 2026 at 11:00 am – Sun Dec 13 2026 at 01:00 pm (-05:00)
  - **Event URL**: https://allevents.in/leonardtown/photos-with-santa-pet-all-species-and-kid-friendlyw/200030775168026
  - **Venue**: Balanced Paws Pet Care
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czMvYmFubmVycy9jMmIxOWM1NDc5N2UzOTZlOGI5MGQwOGQwNDY5OTQxNWIyMTFjMGIxOWM1N2FhN2M0MDU1NGMxYTMyYjQzMDViLXJpbWctdzEwODAtaDEwODAtZGNmOGY4ZjgtZ21pcj92PTE3OTExMzkyODY.avif
  - **Categories**: Nonprofit
- **Event Name**: Small Business Saturday with The Grinch & Cindy Lou Who
  - **Description**: Shop Local with our vendors to help get you started on your Holiday Shopping. There will be crafters, wood working, candles, custom apparel, jewelry, jams, jellies, salsa's, Christmas Trees, wreaths, desserts and food vendor on site.

Watch out for the Ci
  - **Interested Audience**:
    - Count: 16
  - **Date**: Sat Nov 28 2026 at 09:00 am – Sat Nov 28 2026 at 04:00 pm (-05:00)
  - **Event URL**: https://allevents.in/leonardtown/small-business-saturday-with-the-grinch-and-cindy-lou-who/200030475180538
  - **Venue**: Town Market LLC
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czIvYmFubmVycy9mZjdiYTcwOThkNDFlYzYzZjBiOWQxNWI5NmQ0NGEyODk5MDBiNDVkZTBiMjExNWY0MWY2N2Q3YzZiYTU5N2QxLXJpbWctdzQ0OS1oNDQ5LWRjZjhmOGY4LWdtaXI_dj0xNzg4MjAwMjc4.avif
  - **Categories**: dance, entertainment, shopping, christmas-markets-and-fairs, dog, holiday
- **Event Name**: Fur Babies with the Grinch and Holiday Market
  - **Description**: Bring your Fur Babies out to see and get their Christmas picture with the Grinch!! Pictures are from 10am to 3pm. 

Local vendors will be here to help you begin your Holiday Shopping. We will have custom apparel, tumblers, jewelry, woodwork, wreaths, dess
  - **Interested Audience**:
    - Count: 19
  - **Date**: Sat Dec 05 2026 at 09:00 am (-05:00)
  - **Event URL**: https://allevents.in/leonardtown/fur-babies-with-the-grinch-and-holiday-market/200030347650700
  - **Venue**: 22675 Washington St, The Bell Bldg Unit 106, Leonardtown MD
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  - **Categories**: christmas-markets-and-fairs, holiday, christmas, shopping
- **Event Name**: Holiday Market with The Grinch & Cindy Lou Who
  - **Description**: 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 an
  - **Interested Audience**:
    - Count: 98
  - **Date**: Fri Nov 27 2026 at 10:00 am – Fri Nov 27 2026 at 07:00 pm (-05:00)
  - **Event URL**: https://allevents.in/leonardtown/holiday-market-with-the-grinch-and-cindy-lou-who/200029368792903
  - **Venue**: Town Market LLC
  - **Banner**: https://dyn-image.allevents.in/generate-image?v=4&title=Holiday+Market+with+The+Grinch+%26+Cindy+Lou+Who&date=Fri+Nov+27+2026+at+10%3A00+am&bg=4
  - **Categories**: christmas-markets-and-fairs, holiday, christmas, sports, kids, shopping
- **Event Name**: Letters to Santa
  - **Description**: Stop by Town Market and drop off your letter to Santa.  There is a red mailbox marked for Letters to Santa. The North Pole Express will be making stops to pick up all your letters.

Please enclose a self-addressed and stamped envelope and you will receive
  - **Date**: Fri Nov 27 2026 at 11:00 am (-05:00)
  - **Event URL**: https://allevents.in/leonardtown/letters-to-santa/200030631006740
  - **Venue**: 22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD, United States, Maryland 20650
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czgvYmFubmVycy84MWEzMmFiM2QxNWM0MGVlZjgzZDI4YTkwMWVhZjg2NGJlZGRkNTViMjNkMDEyZDUxNDBiZDc0ZWE3MjJkNThkLXJpbWctdzEyMDAtaDY3NS1kY2Y4ZjhmOC1nbWlyP3Y9MTc4ODA0MTc0MA.avif
- **Event Name**: Come Out and See the Grinch & Christmas Shopping Spree
  - **Description**: Come out and see the Grinch and get your picture taken with him.   Vendors are here to help you finish your Christmas shopping as well. Pictures with The Grinch are 10am to 4pm

**Vendors spots available. Message us for further information**

Vendors Atte
  - **Interested Audience**:
    - Count: 14
  - **Date**: Sat Dec 12 2026 at 09:00 am – Sat Dec 12 2026 at 04:00 pm (-05:00)
  - **Event URL**: https://allevents.in/leonardtown/come-out-and-see-the-grinch-and-christmas-shopping-spree/200030475179116
  - **Venue**: Town Market LLC
  - **Banner**: https://cdn-ip.allevents.in/s/rs:fill:500:250/g:sm/sh:100/aHR0cHM6Ly9jZG4tYXouYWxsZXZlbnRzLmluL2V2ZW50czYvYmFubmVycy81MDY4NDUyOTVkYzMxZmIxYTg1YWM2NDMyZGI1MjhhNmQ1ZjY2Nzk5ZWI3ODk0N2RkYmQ4MTRmMmE5NmI5OTY0LXJpbWctdzYyMC1oNDA1LWRjMDgxODE4LWdtaXI_dj0xNzg3MDUxNDc3.avif
  - **Categories**: christmas, shopping

## Trending Events in Leonardtown

- **Event Name**: U.S. Oyster Festival
  - **Description**: The iconic U.S. Oyster Festival returns to St. Mary’s County Fairgrounds on October 17 - 18, 2026, bringing together oyster lovers, top shuckers, and seafood enthusiasts from across the region. Tickets are on sale now at usoysterfestival.org.

This year,
  - **Venue**: St. Mary's County Fairgrounds
  - **Banner**: https://cdn-az.allevents.in/events10/banners/723dbd5791fb624d1b6b815983165661c313c5cf2444ae9efc6215cf5bebd968-rimg-w1200-h628-dc085878-gmir?v=1790055054
- **Event Name**: Veterans Day Parade and Memorial Wreath Laying Ceremony
  - **Description**: The Commissioners of Leonardtown invite the public to salute America’s Veterans at the Annual Veterans Day Parade in Leonardtown! The parade steps off from St. Mary’s Ryken High School, proceeds through Town Square and is immediately followed by a Memoria
  - **Venue**: Town of Leonardtown
  - **Banner**: https://cdn-az.allevents.in/events1/banners/4a7dcd2b74f031c3ba15acac08cf1030c5e53b2ab3c8ac5a2df8afc94232a86a-rimg-w1200-h675-dcf8f8f8-gmir?v=1790271985
- **Event Name**: Rabies Clinic with SMAWL @ St. Mary's Fair Grounds
  - **Description**: Low-Cost Vaccination Clinics
     St. Mary’s Animal Welfare League, in partnership with St. Mary’s County Health Department, offers monthly low-cost rabies and distemper vaccinations, as well as microchipping to the public for their cats and dogs.

    Th
  - **Venue**: St. Mary's County Fairgrounds
  - **Banner**: https://cdn-az.allevents.in/events2/banners/8855e8aea69ca35882bed536e7272a6cd3b71f701c9b5e2966c36ea85e48fce5-rimg-w1200-h628-dcf8f8f8-gmir?v=1787746344
- **Event Name**: Coastal Arts Market
  - **Description**: Nonprofit showcases artisans of southern Maryland (Calvert, Charles, St. Marys counties): candles, gems, jewelry, leather, needlework, painting, pottery, quilling, quilting, soap, stained glass, woodworking, and more. Held 1 Saturday per month April - Jun
  - **Venue**: Leonardtown Wharf Park
  - **Banner**: https://cdn-az.allevents.in/events9/banners/851cf16c9e4beec0e60fdde385810887a645f2d775f40e8d58ea98b72b2d0bec-rimg-w1200-h676-dc888898-gmir?v=1790050051
- **Event Name**: Monster Mash Bash
  - **Description**: Get ready for a fang-tastic night of Halloween fun at the Monster Mash Bash, where ghosts, goblins, and ghouls of all ages are invited to join the festivities! This Halloween extravaganza is packed with activities, treats, and entertainment that will make
  - **Venue**: Leonardtown Wharf
  - **Banner**: https://cdn-az.allevents.in/events6/banners/77b81da018d8c9a39be14504d288b5d0418ebc8d23e569370a8cf489502a5ca2-rimg-w1200-h675-dcf8f8f8-gmir?v=1787462192
- **Event Name**: Jackson Perkins Live at the Rex Theatre
  - **Description**: 🇺🇸🎶 From serving our country to chasing his country music dream...

Join us at the Rex Theatre on Saturday, October 17 as rising country artist Jackson Perkins takes the stage! An active-duty U.S. Marine, Jackson is quickly making a name for himself with
  - **Venue**: 22695 Washington St, Leonardtown, MD, United States, Maryland 20650
  - **Banner**: https://cdn-az.allevents.in/events7/banners/c663a093134c4a93a18aaa6161f822af19d68908de4b0fdbd10f44931d09b816-rimg-w1200-h500-dc080808-gmir?v=1787325198
- **Event Name**: Christmas on the Square & Annual Tree Lighting
  - **Description**: 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
  - **Venue**: Town of Leonardtown
  - **Banner**: https://cdn-az.allevents.in/events9/banners/c86af1d328742cb1e62b586f1fcfb3fe0a236afef7760c4ed5725b1fcb3b4915-rimg-w640-h959-dc080808-gmir?v=1790271347
- **Event Name**: Faire Witch: Ladies Night Out
  - **Description**: Grab your favorite witches and join us for an enchanting evening of sipping, shopping & all the spooky fall vibes. 

Think unique vendors, spooky-chic finds, seasonal cocktails, photo worthy moments, and a little bit of magic.

More details, vendors a
  - **Venue**: 22695 Washington St, Leonardtown, MD, United States, Maryland 20650
  - **Banner**: https://cdn-az.allevents.in/events7/banners/ea184d169e12ccb840141d5a56423fe5adf7b4714accb6c6f8d3ee4a11e52484-rimg-w1200-h500-dc080808-gmir?v=1787110447
- **Event Name**: St. Marys County Early Learning Center's Trunk or Treat
  - **Description**: Join the SMELC first Annual Trunk or Treat. This event is open to enrolled Families and the Community. RSVP Today!About this EventJoin us for a fun-filled evening of Trunk or Treating, costumes, candy, dec
  - **Venue**: St. Mary's County Early Center
  - **Banner**: https://cdn-az.allevents.in/events6/banners/6f8615ccf15eea03e5644c61a1ff96a7b1a5b7a431a01e340a15904b4f1d50b9-rimg-w1200-h800-dcf8f8f8-gmir.jpg?v=1791266481

## Browse Christmas Events by Date

- [Christmas Events Today in Leonardtown](https://allevents.in/leonardtown/christmas--today)
- [Christmas Events This Weekend in Leonardtown](https://allevents.in/leonardtown/christmas--this-weekend)
- [Christmas Events in October in Leonardtown](https://allevents.in/leonardtown/christmas--october)
- [Christmas Events in November in Leonardtown](https://allevents.in/leonardtown/christmas--november)

## FAQs

- **Q**: What are the top Christmas events in Leonardtown?
  - **A:** Christmas on the Square & Annual Tree Lighting (Fri Nov 27 2026 at 04:30 pm at Town of Leonardtown), Home for The Holidays - A New St. Mary's County Holiday Tradition (Sat Dec 05 2026 at 04:00 pm at Saint Mary's Fairgrounds), Pictures with Santa Clause (Sat Dec 19 2026 at 10:00 am at Town Market LLC), Photos with Santa! (Pet **all species** and kid friendly)w (Sun Dec 13 2026 at 11:00 am at Balanced Paws Pet Care), Small Business Saturday with The Grinch & Cindy Lou Who (Sat Nov 28 2026 at 09:00 am at Town Market LLC).
- **Q**: How can I find Christmas events in Leonardtown?
  - **A:** You can discover upcoming Christmas events in Leonardtown on AllEvents.in. Browse by date, venue, or price to find events that match your interests.
- **Q**: How do I buy tickets for Christmas events in Leonardtown?
  - **A:** You can buy tickets directly through AllEvents.in. Many events offer online booking with options for free, paid, and early-bird tickets.
- **Q**: What are the popular venues for Christmas events in Leonardtown?
  - **A:** Some popular venues hosting Christmas events in Leonardtown include Town of Leonardtown, Saint Mary's Fairgrounds, Town Market LLC.
- **Q**: What is the price range for Christmas events in Leonardtown?
  - **A:** Prices for Christmas events in Leonardtown range from up to USD 8. Many events also offer free entry.
- **Q**: Who are the top organizers for Christmas events in Leonardtown?
  - **A:** Popular organizers hosting Christmas events in Leonardtown include Town of Leonardtown, Christmas In April St. Mary's County, Town Market LLC.
- **Q**: Are there any online Christmas events available?
  - **A:** Yes, many Christmas events are available online. You can filter for virtual events on AllEvents.in to attend from anywhere.
- **Q**: How can I get notified about new Christmas events in Leonardtown?
  - **A:** Follow the Christmas category on AllEvents.in to get notified when new Christmas events are listed in Leonardtown.

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## Christmas events from nearby cities

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