The holiday season is one of the most magical times of the year in Chesterfield, and there’s no shortage of ways to celebrate. From festive light displays and cheerful performances to Santa visits and seasonal experiences, the county is filled with events that bring families, friends, and neighbors together. Whether you’re looking for a cozy night out, a fun holiday tradition, or something new to try, here are some of the best ways to make the season bright in Chesterfield.
ALL SEASON LONG
NAPA Kitchen + Wine – Winter Wonderland Experience
Step into a sparkling Winter Wonderland while enjoying delicious food, wine and curated cocktails. Perfect for a holiday date night or a cozy evening out. Reservations required.
Mid-November through January
15825 WC Main St. Midlothian, VA
Christmas Tree Lot at Hidden Wit Brewing Company
Pick your perfect Christmas tree, enjoy dinner, sip a beer and soak in the holiday cheer.
November – December
21110 Hull Street Rd. Moseley, VA
Westchester Commons – Photos with Santa
Snap your holiday photos with Santa—just don’t forget to bring your own camera! A fun (and free) way to capture the magic.
December 5–23
15786 WC Main St. Midlothian, VA
Windy Hill Golf Course
Step into Windy Wonderland Mini Golf, where every hole sparkles with holiday magic! Explore glowing mini golf courses, wander past festive inflatables, and soak in thousands of twinkling lights.
Starting Dec. 6
16500 Midlothian Turnpike Midlothian, VA
RESTAURANTS
If you’re looking for a spot that delivers both great food and a joyful jolt of holiday cheer, check out these local gems that have transformed their spaces into sparkling seasonal escapes: www.experiencechesterfield.com/blog/chesterfield-restaurants-that-shine/
TREE LIGHTINGS
* All tree lightings are free to the public.
Westchester Commons Tree Lighting
Celebrate the official start of the holiday shopping season with live entertainment, hot chocolate bar, s’mores by the fire pit, and of course, Santa! Plus, always guaranteed….SNOW!
November 21 | 7 p.m.
15786 WC Main St. Midlothian, VA
River City Sportsplex Tree Lighting (Clover Hill District)
November 26 | 6-7 p.m.
13030 Genito Rd.
Chester Tree Lighting (Bermuda District)
December 2 | 6-7 p.m.
12140 Harrowgate Rd.
Ettrick Recreation Center Tree Lighting (Matoaca District)
December 3 | 6-7 p.m.
20621 Woodpecker Rd.
Beulah Recreation Center Tree Lighting (Dale Distrcit)
December 4 | 6-7 p.m.
6901 Hopkins Rd.
Mid-Lothian Mines Park Tree Lighting (Midlothian District)
December 8 | 6-7 p.m.
13301 N. Woolridge Rd.
FREE EVENTS
Christmas Village at Chester Village
Step into a magical holiday market filled with twinkling lights, festive vendors, food, and entertainment. With cookie kits, live performances, Santa visits, and endless holiday cheer, it’s the ultimate family-friendly evening.
December 6 | 2- 8 p.m.
11810 Centre St. Chester, VA
King’s Korner – Grinch Brunch
Who stole Christmas? Not you! Enjoy a festive brunch with a Grinchy twist. Expect laughs, mischief, and maybe a little chaos as the Grinch pops in for photos, fun, and festive shenanigans. Perfect for kids, grown-ups, and Whos of all ages! This event is first come-first served.
December 7
7511 Airfield Dr. Chesterfield, VA
Henricus Historical Park – Christmas Through the Centuries
Explore what Christmas looked like, smelled like and sounded like throughout the centuries!
December 13 | 10 a.m.
251 Henricus Park Rd. Chester, VA
Metro Richmond Zoo – Miracle of Christmas
Experience the story of Christmas brought to life at the zoo with lights, music, and a joyful holiday celebration. Free admission.
December 20-22
8300 Beaver Bridge Rd. Moseley, VA
TICKETED EVENTS
Holiday Ho-Ho Hoedown at Shoofly Farm
Step into a simpler time at Shoofly Farm, where holiday magic comes wrapped in rustic charm. Snap barn-side photos with Santa, hop on a nostalgic winter-wonderland wagon hayride, meet the sweetest holiday horses, play in a snowy corn pit, and enjoy cheerful horse rides!
Dec. 6 & 13 | 11 a.m. to 3 p.m.
5031 Treely Rd. Chester. VA
The Art Factory – Photos with Santa + The Santa Experience
Make memories that last a lifetime with a special visit with Mr. and Mrs. Claus in a creative, family-friendly setting. Reservations required.
December 12 & 14
4810 Market Square Ln. Midlothian, VA
The Perkinson Center for the Arts & Education – I Want a Hippopotamus for Christmas
Get into the holiday spirit with this playful performance that’s sure to bring smiles. Tickets required.
December 12 | 7:30 p.m.
Sports Backers – CarMax Tacky Light Run
Dash through Midlothian’s famously festive Tacky Light displays on this spirited holiday run. Tickets required.
December 13 | 6 p.m.
Keep checking back—new holiday events will be added as the season gets closer!
