Gwendolyn’s Nutty Nutcracker—Dec. 3

Based on the book by David Ira Rottenberg, Walnut Hill Community Dance Academy’s production of Gwendolyn’s Nutty Nutcracker brings together the world s greatest dancing pigs, Gwendolyn and Omar, who are are eager to rehearse. All is excitement, hard work, and fun as the Nutcracker’s artistic director and her former ballet partner are on hand to help their students learn the steps and a little bit about life. Don’t miss out on all the drama, laughter, and applause. Hurry inside. The curtain is about to rise.

Saint John School’s Trees & Trimmings Christmas Market—Dec. 3

The annual St. John School Trees & Trimmings Christmas Market will take place on Saturday, December 3rd, 8am-1:30pm, at Saint John School, 9 Ledyard St. Trees & Greens sales starts at 8am. Custom decorated wreaths sales begin after 8:30am.

*The event keeps going until  supplies last. Times are subject to change.

 Wellesley Square Holiday Stroll—Dec. 4

The Wellesley Square Merchants’ Association is getting ready for the always festive Holiday Stroll on Sunday, December 4, noon – 6pm. All of the traditional activities will be part of the fun, from the carolers and sleigh ride with Santa, to the Scavenger Hunt. Free parking, too.

Wellesley Symphony Orchestra Holiday Pops Concert—Dec. 4

The WSO will perform a Holiday Pops concert on Sun., Dec. 4, at 3pm, at MassBay Community College, 50 Oakland Street, Wellesley Hills.

Music Director Mark Latham has put together a great program of favorites, some with an unusual twist. You do not want to miss a rendition of Tchaikovsky’s “Trepak”from the Nutcracker, complete with some crazy electric guitar players. Serenading you will be Rebecca Hains, soprano, with some lovely songs for the season. She will also narrate a famous Christmas poem and will lead the audience in a fun and uplifting sing-along.

Tickets here. Or email info@wellesleysymphony.org

Covid policy: all audience members must present proof of vaccination and wear masks in the auditorium. Seats are assigned with three feet of social distancing. Orchestra members are fully vaccinated and are masking where possible.

Wellesley High School Winter Band Concert—Dec. 7

The talented members of the Wellesley High concert band will perform for the community at the annual Winter Band Concert on Wed., Dec 8, 7pm-9pm, at the WHS Katherine L. Babson Auditorium.

Linden Square Holiday Stroll—Dec. 11

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

• Meet costumed characters Anna and Olaf from FROZEN
• Take home your specially created FREE balloon from the Balloon Twister
• Enjoy the FREE donut bites and hot chocolate from the food truck
• Revel in the beautiful voices from the Wellesley High School carolers
• Please bring an item for the Wellesley Food Pantry.

At 10am-noon, make your own tie-dye creation in the Tyed with Love Igloo. There will be a cost (details to come).

 H.O.M.E. Store—Dec. 10 & 11

H.O.M.E. Store is back! Support a good cause and do some holiday shopping on Saturday, December 10, 9-4 and Sunday, December 11, 9-noon, 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. 15

The talented members of the Wellesley High choral ensemble will perform for the community at the annual Winter Choral Concert, Thur., Dec 15, 7pm-9pm, at the WHS Katherine L. Babson Auditorium.

 4th annual Dreidel Dash—Dec. 18

Temple Beth Elohim will hold its fourth annual Dreidel Dash 5k on Sun., Dec. 18, 8:15am-noon. The race is a great opportunity to connect as a community and celebrate Chanukah, and is open to all.

Following the race, food trucks options will be available for purchase. There will also be interactive stations with fun activities for children of all ages available from 9:30–11:30 am, including stations hosted by TBE’s partner Jewish overnight camps and Jewish day schools.

Please bring reusable water bottles that will be donated to JFCS, Brookline Food Pantry, and Wellesley Food Pantry.

Race options are Kiddie Dash, Junior Dash, and two age categories of the Dreidel Dash. Information about the race is available here. 

At 4pm, enjoy the Voices of TBE Chanukah Concert, a musical celebration of the Chanukah holiday featuring the sounds of TBE’s musical groups and leaders.

The gift of free parking—through Jan. 2, 2023

Shop and dine locally and park for free at all 2-hour street meters in Wellesley during the holiday season.

Running through Monday, January 2, 2023, drivers are permitted to park free of charge for up to two hours at all street meters. The Select Board offers this opportunity during the holiday to support our local merchants.

Please adhere to the two-hour time limit. Cars parked for more than two hours will be ticketed.

Free parking meters are marked with bags. Parking fees are still in effect during the holidays at all 4-hour and 10-hour meters, and in all municipal parking lots.

Visit the Parking Clerk webpages for more information.