The holiday season is the perfect time to plan a special night out with someone you love. From sparkling light displays to cozy dinners and live performances, Chesterfield offers plenty of ways to make date night magical this holiday.
Start with a Dazzling Dinner
Begin your evening at NAPA Kitchen + Wine, where the annual Winter Wonderland transforms the restaurant into a festive escape. With twinkling lights, holiday décor, and a menu full of seasonal flavors, it’s the ideal setting to toast to the season.



Take in the Holiday Lights
No holiday date night is complete without a Tacky Light Tour. Hop aboard a luxury coach with Winn Transportation and enjoy the best of Chesterfield’s famously over-the-top holiday displays without worrying about directions or traffic. Sit back, relax, and take in the glow together.


Add a Touch of the Arts
For couples who love live performances, The Perkinson Center for the Arts and Education offers a full lineup of holiday concerts and theater productions. From heartwarming music to festive shows, it’s a perfect way to add culture and cheer to your night.


Other Festive Stops
If you’re looking to extend your evening, consider:
- Holiday drinks at a local brewery or winery like Triple Crossing, Three Leg Run, Ashton Creek Vineyard, or Providence Farms Cidery many of which feature live music in a cozy setting.
- A stroll through a decorated shopping district to pick out a special holiday gift. Check out Chester Village, Westchester Commons and Sycamore Square.
- Warming up with dessert or hot cocoa from a local café before heading home.
No matter how you design your evening, Chesterfield has everything you need for a holiday date night that’s both festive and unforgettable.