Wellesley Holiday Happenings 2023

Our roundup of holiday activities taking place in Wellesley:

Don’t see your low-cost or free community-oriented holiday event here? Contact Deborah at deborahcb100@gmail.com for inclusion.

Wellesley Marketplace—Nov. 18

The 45th annual Wellesley Marketplace will be held Saturday, Nov. 18, 9am-4pm, at Wellesley High School, 50 Rice St. Tickets here. More than 200 local artisans, boutique owners, and craftspeople will help you mark the start of the holiday shopping season at this fine arts and holiday fair.

Wellesley Marketplace

Wellesley Turkey Trot—Nov. 23

The Wellesley Turkey Trot returns to Linden Square on Thanksgiving morning with a 5K run, plus a fun run for kids 10 and under, all in support of good local causes. Register here.

This Wellesley tradition kicks off at 8am on Thursday, Nov. 23, with 5K race participants following a course from Linden Square that traverses through Wellesley Square and the Wellesley College campus before returning to Linden Square. Awards are given to individuals and teams, with special awards to the fastest Wellesley High students and alums.

The Hannah Randolph Fun Run for kids starts at 8:45am in the back of the parking lot near CVS.

The event is always a great way to see friends and burn off a few calories before filling up on Thanksgiving Day.

wellesley turkey trot
Wellesley Turkey Trot 2022.

Mass Hort Festival of Trees—Nov. 24-Dec. 29


Mass Hort, Festival of Trees
Festival of Trees 2022. Photo by Marco Kaltofen.

Massachusetts Horticultural Society‘s 15th Annual Festival of Trees showcases dozens of decorated trees, the Snow Village, and a festive model railroad display, Nov. 24-Dec. 29, at the Garden at Elm Bank, 900 Washington St., Wellesley.

Visitors vote with their raffle tickets for trees they would like to win and take home at the end of the event. Trees range from one foot to nine feet tall, and many have gifts in addition to beautiful decorations.

Don’t miss the Snow Village, an indoor model train exhibit, or the holiday lights and decorations that fill the Garden. Paid tickets include a cup of hot chocolate at admission and a s’mores kit for the fire pit at the end of your visit.  Tickets are on sale now. 

Please note: Advanced purchase of timed tickets is required for both MHS members and general admission. Tickets will not be sold on site.

Wellesley Square Holiday Stroll—Dec. 3

The Wellesley Square Merchants’ Association is getting ready for the always festive Holiday Stroll on Dec. 3. Free parking, fun traditional activities, and Scavenger Hunt. More info to follow.

Wellesley Square Holiday Stroll


Wellesley Symphony Orchestra Holiday Concert—Dec. 3

The Wellesley Symphony Orchestra will perform their annual Holiday Concert on Sunday, Dec. 3, 3pm, at MassBay Community College, 50 Oakland Street, Wellesley Hills. Tickets here.

Wellesley Symphony Orchestra


Featuring the Fireside Barbershop Quartet performing music arranged by Mark Latham, and Chris Ten Eyck, principal trumpet, in an arrangement of “What a Wonderful World.”

Also, music by Tchaikovsky, Coleridge-Taylor, Anderson, Prokofiev, Strauss and Corelli, plus the traditional sing-along.

Linden Square Holiday Stroll—Dec. 10

Tis the season to celebrate at the Linden Square Courtyard with its beautiful holiday decor and stunning tree, Sunday, Dec. 10, 11am-1pm.

Linden Square, Wellesley

The Wellesley Food Pantry will be collecting of unopened boxes of mac & cheese, raisins, and canned tuna.
Cradles to Crayons will be collecting new or gently used infant and kids coats.

H.O.M.E. Store at Wellesley Village Church—Dec. 2 & Dec. 3

H.O.M.E. Store is back! Support a good cause and do some holiday shopping on Dec. 2 & 3, 9am-5pm, at Wellesley Village Church, 2 Central Street. H.O.M.E., Inc. enhances the quality of life of people who have fallen on challenging times by honoring their dignity, attending to such basic needs as food and shelter, supporting their long-term health and development, and fostering a vibrant and mutually supportive community. Whether you are looking for a Maine souvenir or an interesting craft, the Home Store has something for everyone. Quilts, knit/crochet items, birdhouses, jams and jellies, pottery, and stained glass.

Wellesley High School Winter Choral Concert—Dec. 14

The talented members of the Wellesley High choral ensemble will perform for the community at the annual Winter Choral Concert, Thur., Dec 14, 7pm-8:30pm, at the WHS Katherine L. Babson Auditorium.

Beyond Wellesley: Nutcracker Ballet performances

Commonwealth Ballet’s production of The Nutcracker (Weston, MA)—Nov. 24-Dec. 17
Share the merriment of the holiday season as the accomplished dancers of Commonwealth Ballet and guest artists frolic, battle and dance through Clara’s holiday dream. The performance lasts approximately 2 hours, including one intermission. Recommended for ages 4 and older.

A special sensory/family friendly performance will take place on Friday, Nov. 24, 1pm, featuring a shortened version of the ballet at reduced prices.

LOCATION: Eleanor Welch Casey Theater, Regis College, 235 Wellesley St, Weston, Mass.

Studios Dance Academy’s The Nutcracker Ballet (Wayland, Mass.)—Dec. 9
Enjoy the magic of the holiday season at this beautiful presentation on Saturday, Dec. 9, 4pm, at Wayland High School auditorium, 264 Old Connecticut Path, Wayland, Mass. The role of Sugar Plum is being played by Brooke Bovie, a senior from Wellesley.

Call the studio 781-235-3638 or email to reserve tickets studios@comcast.net Limited tickets available at the door.

Calling all Girl Scouts, Brownies and Daisy—call for discounted tickets, and attend the performance to earn a fun badge.

Walnut Hill’s Nutty Nutcracker (Natick, MA)—Dec. 9 & Dec. 10
The Community Dance Academy at Walnut Hill has teamed up with local children’s author David Ira Rottenberg to bring his well-loved children’s book Gwendolyn’s Nutty Nutcracker to life. The fun 1-hour kid-friendly performance features the most loved music from the Nutcracker and intermission meet-and-greets with the characters and the author.

LOCATION: Perrin Theater, Keiter Center for the Performing Arts
PARKING: 146 Bacon Street, Natick MA 01760