Santa sightings in Charlottesville | Charlottesville Area Moms

Look no further! Charlottesville Moms has put together a list of events to see Santa this holiday season!  

Do you see an event missing?  Email [email protected] .  I will add updates to this list to keep you in the know! 

*Please be aware that some events require reservations! Reserve your spot quickly because some time slots are already sold out!  


Holiday Tree Lighting

Date: Saturday, November 23

Time: 12 PM-7 PM

Where: The Shops at Stonefield

Craft Cville Holiday Market on Bond St.  – Noon-7pm, Free photos with Santa – 11am-6pm, MoxBox Family Photo Booth  – 4pm-6pm, Trackless Train Rides  – 4pm-6pm, Face Painting  – 4pm-6pm, Tree Lighting  – 6:15pm. Bring a New Unwrapped Toy for Toy Drive for Mason’s ToyBox! One Day Only $20 Bonus on $100 Stonefield Gift Cards! Christmas Tree & Wreath Sale available. 


Santa Arrival at Fashion Square Mall

Date: Saturday, November 23

Time: 9:30-12 PM

Santa Arrives at 10:00 AM! Santa Village is in the North Court. Use Mall Entrance Near Red Robin.  

Check Santa Holiday Hours HERE!


Sundays with Santa 

Date: Sundays in December

Time: 12-2 PM

Where: Shenanigans 

601 W Main St, Charlottesville, Virginia 22903

Price: FREE

Santa Claus is coming to Shenanigans and Green Bean Baby Boutique this December! Come visit Santa every Sunday from 12-2.  Bring the kiddos to see Jolly Old Saint Nick and snap a photo while you’re here! Shenanigans is proud to host a mailbox for Santa letters all season long.  So bring your letter to Santa or write it when you get here with our supplies.


Charlottesville’s Grand Illumination 

Date:December 6, 2019

Time: 4:30 PM- 9:30 PM

Where: Sprint Pavilion

700 E Main St, Charlottesville, Virginia 22902

This popular community event is free for all ages and features live music, kids’ crafts, fun games and activities, and over 20,000 LED lights illuminating the holiday tree at City Hall Plaza! Check out the schedule of events for loads family fun including the arrival of Santa Claus! 


Annual Holiday Parade

Date: Saturday, December 7
Time: 9:30-11:30 AM
Where: Barracks Road Shopping Center
1117 Emmet St N, Charlottesville, Virginia 22903

You are cordially and merrily invited to join us as we kick off the holiday season with the Barracks Road Annual Holiday Parade, featuring Santa Claus, colorful floats, costumed characters, impressive marching bands, horse-drawn carriages, and community members. Parade Route: The parade will travel from Harris Teeter to Kroger, so grab your bit of sidewalk early.


Santa Pancake Breakfast 

Date: Sunday, December 8

Time: 4 seatings: 9:00 AM, 9:20 AM, 11:30 AM, 11:45 AM

Where: Virginia Discovery Museum

Reserve your seats for Santa Pancake Breakfast online, in person at the Museum, or over the phone at (434) 977-1025 x102. The early reservation deadline is Dec. 1, and reservations made Dec. 2-6 incur an additional $15 table charge per party. Space is limited, so register early!


Santa Visits Three Notch’d 

Date: Sunday, December 15 

Time: 12- 3 PM

Where:  Three Notch’d Brewing Company

520 2nd St. SE, Charlottesville, Virginia 22902

Price: FREE

Stop by and get your family photo taken while enjoying holiday themed drinks and food. We will have free crafts for kids, hot chocolate and cookies for everyone! It is FREE to visit with Santa -you can purchase photos from our friends at Park Life Photography who will be on-hand again this year to capture this special memory. Please email us at: [email protected] to book a table for lunch or dinner during your visit!


Brunch with Santa @ Chiles Peach Orchard  

Date: Saturday, December 21 or Sunday, December 21


Saturday: Breakfast Buffet with Santa – served 11:00am – 2:00pm($14.99/adults, $9.99 under 12), Craft Station – all day, Visits with Santa – 10:00am – 4:00pm, S’mores, hot chocolate, and adult beverages by the fire pit (weather permitting)

Sunday: Breakfast Buffet with Santa – served 11:00am – 2:00pm ($14.99/adults, $9.99 under 12), Craft Station – all day, Visits with Santa – 10:00am – 4:00pm, S’mores, hot chocolate, and adult beverages by the fire pit (weather permitting)

Where: Chiles Peach Orchard

1351 Greenwood Rd, Crozet, Virginia 22932

Come celebrate the holidays with lots of sales in our store, breakfast, lunch, crafts, s’mores by the fire pit, and of course, a visit from the jolly man himself!


Trip to the North Pole! 

Crozet Trolley Co. and Knight’s Gambit Vineyard

Dates: December 7, 14, 21, 22, 23, 24

Times: 1-3pm and 3:30-5pm

Where: Leaving from Crozet’s Downtown Square (near Crozet Bicycle)

Price: $20/person

Calling all children!!  All aboard for a ride to the “North Pole,” where you’ll play reindeer games, enjoy hot chocolate and cookies, receive a small gift, and maybe even meet Santa! This is for  adults and children (most appropriate for ages 3-9.) Children age 2 and under are free if they sit in a lap. (Children 2 and under with their own seat pay full price.) Our beautiful “North Pole” is a White Hall gem: Knight’s Gambit Vineyards. And Christmastime magic is not just for the tiny tots. Adults can buy a glass or two of wine while the kids play. Don’t worry, we’re driving!  Questions? Email [email protected] or call 434-422-7660 .


Cookies with Santa 

Dates and Times: 

Friday, November 29: 4:00 PM, 5:00 PM, 6:00PM

Saturday, November 30: 10:00 AM, 11:00 AM, 1:00 PM, 2:00PM, 3:00 PM

Sunday, December 1: 1:00 PM, 2:00 PM, 3:00 PM

Thursday, December 5 : 4:00 PM, 5:00 PM, 6:00 PM

Friday, December 6: 4:00 PM, 5:00 PM, 6:00 PM

Saturday, December 7: 1:00 PM, 2:00 PM, 3:00 PM

Where: The Shops at Stonefield 

Price: $20/ child

Join the Junior League of Charlottesville for our annual event, Cookies with Santa! We’re in the Shops at Stonefield for this festive event, sign up for your slot by clicking the link for tickets. Each time slot gives you and your children time with Santa to take pictures and enjoy cookies. Please arrive a few minutes prior to your scheduled reservation time. Kids will have their pictures taken with Santa and then Santa will end the session with a story! Kids will be treated with yummy sugar cookies and a fun holiday coloring book! We look forward to seeing you and your family and creating photographs to last a lifetime!


Storytime with Mrs. Claus @ Boars Head Inn 

Dates: December 1, December 8, December 15, December 22

Time: 2:00 PM- 3:00 PM

Where: Ednam Hall at Boar’s Head

200 Ednam Drive, Charlottesville, VA 22903

Price: $15 per child

Straight from the North Pole, Mrs. Claus arrives to spend an afternoon with us to read some of your favorite Christmas stories. The North Pole Bakery has also sent along some treats to share. You may come in your jammies! Don’t forget your camera to capture this special event!


Breakfast with Santa @ Boars Head Inn 

Dates: November 30, December 7, December 14, December 21

Time: 9:00 to 11:30 AM

Where: The Pavilion at Boar’s Head Resort

Price: Adults $40.00, Children (Ages 6-12) $20.00, Children (Ages 0-5) Free of Charge

Let your holiday spirit soar as you glide on a horse-drawn carriage through the resort to admire holiday décor. There will be wonderful picture opportunities with the jolly one accommodated by a magnificent breakfast display from Chef Dale and his culinary team. Call for reservations: 1-855-220-6620 and choose option 6


Santa’s Toy Workshop @ Boars Head Inn 

Date: Saturday, December 14

Time: 3:00- 4:00 PM

Where: The Ballroom at Boar’s Head Resort

Price: $20/ Child

Ho! Ho! Ho! Come join us for a magical afternoon in Santa’s Workshop. We will spend the time building toys with Santa and enjoying some North Pole treats and hot cocoa.


Santa @ King Family Vineyards

Date: Sunday, December 15

Time: 10 AM- 1 PM

Bring your cameras to take pictures with Santa! 


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