Holiday Season in Lexington: Concerts, Handmade Gifts, and Lights Around Town This December

On Monday, Nov. 30, the Hancock-Clarke House closes for the rest of the year. The night before, Cary Memorial Hall starts a run of holiday shows that lasts into the middle of December. For anyone in town, that weekend marks a handoff. The historic house goes quiet for the winter, and December's action moves indoors and onto one stage, with a few quieter evenings around it.

If you're planning December in Lexington, start with that shift. Most of the season fits into about two weeks, and one weekend in that stretch is busier than the rest.

Thanksgiving weekend starts the season

The first event of the holiday stretch is a race. The Lexington Legacy 5K starts at 9 a.m. on Saturday, Nov. 28. Its listing on Visit Lexington says all proceeds support the Lexington Cross Country and Track and Field Teams, and registration runs through RunSignup. It's a good way to work off Thursday's dinner and help local runners at the same time.

Sunday, Nov. 29 brings two openings. The LexArt Holiday Marketplace opens for the season that day and stays open through Christmas Eve. That evening at 7 p.m., Cary Memorial Hall hosts Shaun Cassidy's "UNWRAPPED: Songs & Stories For The Holidays," the first holiday show on the hall's events calendar.

The next day, the historic season ends. The Lexington Historical Society's Hancock-Clarke House schedule shows the house closed from Nov. 30 through Dec. 31. If you have family coming for the holidays and hoping to tour the house, check the Historical Society's schedule for Thanksgiving weekend before the Nov. 30 closing. After that, Cary Hall's lineup and LexArt's gift shelves take over as the places to bring guests.

Two weeks, one stage

From Nov. 29 to Dec. 12, Cary Hall's calendar and the Lexington Symphony's season page list eight holiday performances. They fall on six of those 14 days.

The lineup covers a wide range. The Vienna Boys Choir on a Wednesday night and The Irish Tenors on a Friday bring touring holiday shows to a hall in the middle of town. The Dance Inn's two shows on Dec. 12 offer an afternoon and an early-evening option. Their listing on Cary Hall's calendar doesn't name a venue in the event entries, so check the details on the Cary Hall events page before you head out.

The Dec. 5 and 6 weekend is the busiest

If you can only keep one weekend free, make it the first weekend of December. The Lexington Symphony's 2026–2027 season puts three holiday performances into about 24 hours, and Cary Hall is the season's venue.

1. Kids Pops! at 4 p.m. on Saturday, Dec. 5, an earlier show with younger listeners in mind.
2. Holiday POPS! at 7:30 p.m. the same evening.
3. Holiday POPS! again at 3 p.m. on Sunday, Dec. 6.

With three times to choose from, families can pick the show that fits their weekend. Grandparents visiting for the holidays have an afternoon option, and parents of young children can go to the 4 p.m. show and still get everyone home for dinner. These three shows sit between the Vienna Boys Choir on Dec. 2 and the Cary Library event on Dec. 7, so this is the most crowded week of Lexington's holiday calendar.

Quieter evenings near the main stage

Some of the season happens in smaller rooms. On Monday, Dec. 7, from 7 to 8 p.m., Cary Memorial Library hosts "The Art of Gathering: Setting Your Holiday Table with Beatrice Sannino" in the Large Meeting Room at 1874 Massachusetts Avenue. It comes just after the busy Symphony weekend, and the timing works well if you're hosting this month. The library's December calendar has the listing.

On Thursday, Dec. 10, from 6 to 7 p.m., the town calendar lists "Celebrate the Festival of Lights in Lexington." Its description says the evening lights the seventh candle of the menorah and welcomes the whole community. The full listing is on Visit Lexington. It's a short, one-hour evening event, the night before The Irish Tenors and two nights before The Dance Inn's shows close out the busy stretch.

After Dec. 12, LexArt carries the season

When the stage schedule winds down after Dec. 12, one event still has nearly two weeks to go. The LexArt Holiday Marketplace runs from Nov. 29 through Dec. 24 and sells work by LexArt's artisan members. The organization calls the sale the result of a year of making and crafting. Its list includes handmade silver jewelry, finely crafted wooden toys, and woven clothing and housewares.

The hours change by day and stretch a little near the end, so they're worth saving:

• Tuesday and Wednesday: 11 a.m. to 6 p.m.
• Thursday: 11 a.m. to 7 p.m.
• Friday through Sunday: 11 a.m. to 6 p.m.
• Dec. 21, 22 and 23: 11 a.m. to 7 p.m.
• Christmas Eve, Dec. 24: 11 a.m. to 3 p.m.

The regular schedule has no Monday hours. The extra evening hour on Dec. 21 through 23 helps if your last-minute shopping has to wait until after work. Because the marketplace is open through the whole season, it pairs easily with other plans. You could stop by LexArt on a Thursday and come back for a Friday concert, or make it part of the Dec. 5 Symphony weekend.

Planning around the handoff

Put together, the calendar has a clear shape. Thanksgiving weekend opens the season with a 5K, a marketplace opening and the first Cary Hall show, and the Hancock-Clarke House closes the next day. The two weeks that follow hold nearly all of the stage performances, with Dec. 5 and 6 as the peak. After that, LexArt stays open until early afternoon on Christmas Eve.

For households expecting guests, here are three dates to plan around:

• Saturday, Nov. 28 and Sunday, Nov. 29, the last weekend before the Hancock-Clarke House's Nov. 30 closing, plus the Legacy 5K and LexArt's opening day.
• Saturday, Dec. 5 and Sunday, Dec. 6, for the three Lexington Symphony performances at Cary Hall.
• Dec. 21 through Dec. 23, for LexArt's extended hours before the Christmas Eve close at 3 p.m.

Our team supports the Cary Library Foundation, and we love seeing the library's December lineup next to everything else happening in town. If you'd like help sorting out which weekend works best for family visits, or you have questions about the town as you think ahead to the new year, the team at Murphy Group Lexington is happy to talk it through over coffee. Contact us anytime.