Guide to 2026 Holiday Events in Lexington, MA

From festive tree lightings and seasonal concerts to holiday shopping and community celebrations, Lexington, Massachusetts offers plenty of ways to celebrate the holiday season.

Start your holiday shopping in Lexington Center, where local retailers stock everything from handmade chocolates, this season’s must-have winter boots, jewelry, apparel, and more. Slow down with a cozy lunch or dinner in town, then take in some of Lexington’s most iconic sites decorated for the season.

Ready to plan your trip? Be sure to add these events to your calendar:

Light Up Lexington: Holiday Tree Lighting

Kick off the holiday season at Light Up Lexington on Friday, November 27, at the Lexington Depot. This beloved community celebration brings friends, families, and visitors together in Lexington Center for an evening of holiday cheer.

Enjoy live music, hot chocolate, seasonal treats, and a special appearance by Santa Claus as you join in the countdown to the holiday tree lighting.

Small Business Saturday: Shop Local in Lexington

Make your holiday shopping a little more meaningful this year by supporting Lexington’s local businesses on Small Business Saturday!

Set out on November 28 to explore the independent shops and boutiques of Lexington Center, where you’ll find everything from books and specialty gifts to clothing, jewelry, home décor, and more. Take a break from shopping to enjoy lunch, coffee, or a sweet treat at one of Lexington’s many restaurants and cafés.

LexArt Annual Holiday Marketplace

Find one-of-a-kind gifts at LexArt’s Annual Holiday Marketplace, running from November 29 through Christmas Eve. Featuring handcrafted work by talented artisan members of the Lexington Arts & Crafts Society, this annual event is a favorite destination for holiday shoppers.

Browse a variety of handmade finds, including jewelry, ceramics, wooden toys, knitwear, woven goods, ornaments, paintings, photography, and more.

Holiday Performances at Cary Hall

Cary Hall has a festive lineup of events this December to help ring in the holidays in Lexington.

On December 2, The Vienna Boys Choir Presents Christmas in Vienna, a special performance serving as a beautiful way to welcome the holiday season with music.

The Lexington Symphony Holiday Pops’ annual holiday concerts are set for December 5 and 6, bringing seasonal orchestra music, special guests, and seasonal surprises to Cary Hall.

Visiting with little ones? Save the date for the 4:00 show on December 5 as the Lexington Symphony Holiday Pops for Kids brings the magic of orchestral music to families through a festive, accessible performance, complete with an appearance by Santa Claus.

Celebrate the holidays with The Irish Tenors as they bring their signature harmonies to Cary Hall on December 11. Featuring a blend of Irish classics and beloved Christmas music, this performance is a memorable way to enjoy an evening in Lexington this winter.

Celebrate Hanukkah: Lexington’s Menorah Lighting

Join the Lexington community in celebrating Hanukkah with the annual public Menorah lighting in Lexington Center on December 10.

This meaningful tradition brings neighbors and visitors together to celebrate the Festival of Lights and share in the joy of the season. Join local families and community members to come together in a spirit of light, tradition, and togetherness.

Plan Your Holiday Trip to Lexington

From festive performances and holiday lights to locally made gifts and seasonal traditions, Lexington is full of ways to make the season memorable.

As you plan your visit, be sure to check our events calendar. Seasonal events and festivities will continue to be added throughout the season!