Leesburg Christmas EventsReady to unleash your holiday spirit? We’ve gathered all of the Christmas, Santa and holiday related events happening in Leesburg! Let us know if we’ve missed something!

Dec 1Delirium Ugly Sweater Party
Kick off the holiday season with your friends at Delirium Cafe Leesburg! Join us on the night that Leesburg gets “lit” (we’re referring, of course, to the annual Christmas Tree and Menorah Lighting Ceremony on the Town Green.) Don your tackiest holiday attire and enjoy food and drink specials, including savings on all the holiday brews (Delirium Noel, anyone?) Prizes, games, and giveaways! We have lots of fun up our (fair isle knit) sleeves.

Dec 1Leesburg First Friday – Dickens Carolers
Our Dickens Carolers will be out and about spreading holiday cheer through Downtown Leesburg!

Dec 2Breakfast with Santa
If your kids have been feverishly making their Christmas wish lists ( and checking them twice!), they would appreciate some face-to-face time with big man himself. So treat them to Breakfast with Santa at West Belmont Place in Leesburg on December 2! The whole family will enjoy a hot breakfast buffet (including a special kiddie buffet!), portrait with Santa and more holiday fun – including gingerbread decorating, reindeer food making, favorite sing-along songs of the season and a holiday movie. There are two seatings available for your convenience: 8:30AM and 10:00AM.

Dec 2Santa Paws Photos
Don’t miss our favorite photo event of the year…photos with the Grinch and Santa Paws!!!

Dec 2Family Snowflake Ornament Making
Are you looking for a fun a family night to make some great memories and heirlooms for Christmases to come? Sign up for our ceramic Christmas Ornaments class and add to your family tree and your favorite memories of Christmas past. Cooley Gallery Instructor, Lara Blackin will teach various texture techniques and wash away glazing to help you create lovely one of a kind, well 8 really, ornaments.

Dec 2Snowflake Celebration
Each winter season, The Arc of Loudoun at Paxton Campus has a holiday celebration… the Snowflake Celebration! Join us for a visit from Santa, food and drinks, holiday music, and more! This is our annual celebration of kids of all ages, all who are unique – just like a snowflake!

Dec 2Holiday Fine Arts and Crafts Show at Ida Lee
This show features over 90 local and regional artisans selling hand-made items including candles, stained glass, carved wood, jewelry, leather products, table linens, and much more.

Dec 2Bark the Herald Angels Sing
Join us on Saturday, December 2nd for our 3rd Annual Holiday Party! We’ll party the day away with children’s activities, a pet costume contest, and even a visit from Santa. Raffle baskets will be drawn throughout the day. Live music, food, and beverages will finish off our evening along with the conclusion of our all-day silent auction! We’ve got some great prizes this year including tickets to Disney, Southwest Airlines tickets, an Autographed Hall of Fame Running Backs helmet, and much more! So grab your whole family (including your fur babies) and join us for a fun-filled night. Proceeds will go to benefit the animal-assisted therapy programs at Heeling House, and it’ll be a great chance to buy some awesome holiday gifts!

Dec 3Free Holiday Cork Crafting
We supply all materials and you supply the imagination! Join us for a crowd favorite for cork crafting with Wendy. She has everything you need to create this adorable reindeer ornament. This event is free and is family friendly.

Dec 3Holiday Shopping Bazaar
Get your holiday shopping done at the Loudoun fairgrounds!

Dec 3Santa Paws at LVH
Santa Paws is coming back to Leesburg Veterinary Hospital and he is bringing award-winning pet photographer, Ellen Zangla.

Dec 5Holiday Kickoff Nova Housewives In The City
Join Andrea Khoury and Nova Housewivesinthecity for our annual happy hour to kickoff holiday season at Fords Fish Shack in Lansdowne! Swag bags for the first 50 attendees!

Dec 6Wreath Making Workshop at Oatlands
Join Oatlands Head Gardener Mark Schroeter as he leads a Wreath Making Workshop at Oatlands! Make a wreath to take home with you! Space is limited to 15. Cost is $40 per person.

Dec 7Tarara Winery Holiday Open House
Break out your Ugly Christmas Sweater, it’s time for the Holiday Open House! Let the sounds of good cheer guide you over to our Tasting Room on Thursday, December 7th 6pm-9pm. Everyone is welcome, we’ll have the wine pouring, the music flowing, and the good times rolling! Come hungry! We are offering an optional buffet created by the local foodie star Ford’s Fish Shack!

Dec 7Stay-At-Home Mom’s Office Holiday Party
Grab a friend and come eat drink and be merry at the “Stay-At-Home Mom’s* Office Holiday Party” hosted by your friends at Posh Seven, and your new soon to be go-to restaurant-The French Hound. You work everyday. You deserve an office party of your own.

Dec 9Bad Moms Christmas Night
You work hard so now it’s time to drink. Leave the kids with a babysitter or your husband and come out to enjoy drink specials made just for you. Let our bartenders know why you’re a Bad Mom and enjoy the night! We’ll have our heated tent outside blasting 80s and 90s hits all night for you to dance and think what it was like before you had kids!

Dec 9Sankt Nikolaus Brunch
Fröhliche Weihnachten! Join us for a morning of German Christmas festivities at our first annual Sankt Nikolaus Brunch benefiting the Marine Corps Toys for Tots! St Nikolaus will be paying Black Hoof a visit to take pictures and kick off the holidays. Live music will be provided by Nathaniel Davis. A German Continental Brunch Buffet will be available.

Dec 9Jingle Jam
Leesburg’s holiday rock n’ roll concert features many local and regional artists playing traditional holiday tunes- with a little edge. The Jingle Jam Band: Todd Wright, Jon Carroll, Gary Smallwood, Michael Sheppard, Mark Williams, Cal Everett, Dan Garvin, Kim Pittinger, Prescott Engle, Stilson Greene

Dec 10Loudoun Chorale Holiday Concert
Come join the Loudoun Chorale as they present the “Holiday Time Machine” which will explore music from the year 1200 to newly commissioned work for the Loudoun Chorale

Dec 10Naughty or Nice Christmas Cabaret
New York City: a sometimes naughty, sometimes nice kind of town. Grab some eggnog and join some of the best vocalists in the Northern Virginia area as we bring you our own NYC-style holiday cabaret. Sentimental, harmonious, funny, heartfelt and unpredictable songs will get you in the mood for this crazy time of year. Let your hair down, put on your coziest sweater and fuzziest slippers, and kick off your season with love and laughter!

Dec 11Deck the Halls
Hope for the Holidays! We are “decking the halls” of Mobile Hope. The Lounge at MOBILE HOPE is a safe space for homeless or precariously housed teens to feel AT HOME. We need volunteers to clear out the space and help us make the new space AWESOME!

Dec 13High Heeled Holiday Party Loudoun
Sip. SHOP. Support. Socialize. Show off your shoes to benefit Dress for Success. Join us for the…Fifth Annual High-Heeled Holiday Party

Dec 17Brunch with Santa and Lansdowne Resort and Spa
Enjoy Brunch with Santa this holiday season. Santa will be available in the Lansdowne Waterfall Terrace for pictures – bring your own camera.

Dec 17Glass Ornament Laser Etching Workshop
Etch two glass ornaments for your tree using the laser cutter! Bring your custom graphics or we can help you design them when you come. The class includes two glass ornaments, laser time, and graphics help. Just in time for the holidays!

Dec 17Community Christmas Pageant
O come, all ye faithful! In the St. James’ Community Christmas Pageant, children and youth of all ages from St. James’ Church and the wider Leesburg community are invited to tell the story of the Birth of Christ in words and familiar carols.

Dec 20Christmas Caroling
Cap and I would like to invite you to our neighborhood for Christmas caroling again this year. Last year was just wonderful and perfectly old fashioned. Our neighbors have been requesting repeat visits to their homes too! We will start at 6 pm and finish up after 30-45 minutes with cookies, hot cocoa and wine around the fire pit. (Festive attire earns you an extra cookie!) I have song sheets so don’t worry about not knowing the words. I hope you are able to join!

Dec 23-24Cookie and Wine Pairings
Join us Saturday December 23rd and Sunday December 24th for Fabbioli Wines and Cookie Pairings for the Holidays! Just $5 with a regular tasting or $10 without.

Dec 25Christmas Day Brunch
Christmas will be here before you know it! Impress your family with a Christmas Day Brunch prepared by Executive Chef Marcus and his culinary team! You will enjoy delicious selection of breakfast entrees, an omelet station, smoked pork and salmon and a fantastic vegetarian winter stew.You will love the popular seafood bar, and make sure to leave room for the decadent desserts from our pastry chef.