Holiday Happenings – 2019

Did you know Lexington, VA has been named the #1 Most Enchanting Place in Virginia for the Holidays?

The holiday festivities in Lexington Virginia start Thanksgiving Day and continue throughout the month of December. Come enjoy a traditional small town Christmas in Historic Lexington, Virginia. You will be glad you did.

Calendar of Downtown Happenings including music, theater & nightlife at downtown venues.  Sample itineraries below.

We look forward to welcoming you to historic downtown Lexington, the cutest small town in the Shenandoah Valley! 


Start Thanksgiving day with the Gobble Wobble 5K walk/run & children’s fun run.

Friday Nov 29th –Enjoy a Lexington Tradition, the Annual candlelight processional and Christmas tree lighting, starting at Stonewall Jackson Cemetery at 5:30pm.

Saturday Nov 30th – Love Lexington Lotto kicks off. Pick up your sweepstakes card at any one of the 20+ participating shops and restaurants. in Downtown Lexington. Gather stickers from each business and enter to win a $1000 shopping spree.


December 3rd – Enjoy Christmas at the Jackson house from 5-7 p.m. and get Mrs. Jackson’s Christmas cookie recipe, deemed the “Best Cookie Recipe Ever!” Head off to the Holiday Pops Concert at Washington and Lee University at 7:00 or Enjoy W & L Dancers Perform at 7:30.

December 5th– Lexington Lotto continues all day. Or arrive in time to enjoy dinner in one of our fine downtown restaurants before you head to Washington and Lee’s Lee Chapel to enjoy a Candlelight Service: A festival of Nine Lessons and Carols at 8:00 p.m.

December 6th-You will not want to miss the Annual Lexington Christmas Parade at6:00 p.m. where you can enjoy plenty of free hot cocoa and cider as you watch Christmas Floats, Marching Bands and even Santa Claus go by. Santa will be in Hopkins Green to get Christmas Lists and take pictures with the children after the parade is over. We hope you can come-plenty of parking in city parking garage and in city parking lots.

Come early and enjoy First Friday receptions and tastings in downtown Lexington.

December 7th–Come early to shop in over 40 unique shops, have lunch at any of our more than 20 downtown restaurants and play Love Lex Lotto where you could win a $1,000 shopping spree. Lotto ends December 24th.

December 7th Jingle Bell Run 10:00 a.m. join us on the Nelson Street Bridge for costume contests for you and your pets, raffle prizes and so much more. After your run, warm up with some hot cocoa and head downtown for a bite to eat.   Stop at Lee Chapel with the kids to enjoy Poinsettias at the Chapel, 9:00am to 1:00pm

December 14th — Join us downtown for some Holiday Cookies! Most merchants will have cookies on hand for shoppers to enjoy throughout the day. It’s a sweet way to say Thank You to all our shoppers.

After lunch, there is plenty of shopping to do in over 40 unique shops. Be sure and pick up a lotto card and enter in a drawing to win a $1,000 shopping spree.

Perhaps take a ride to Historic Brownsburg and enjoy Christmas in the Country where you can tour beautiful homes decorated for the Holidays.

Or stay in town and visit some of the historic sites downtown Lexington.  Stop by the historic Stonewall Jackson House, Lee Chapel at Washington and Lee University, the Marshall Museum at Virginia Military Institute or the Stonewall Jackson Cemetery.

Downtown Lexington website.

Lexington/Rockbridge/Buena Vista website

Blog post on 10 reasons to visit Lexington this holiday.