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.
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.
Mass Hort Festival of Trees—through Dec. 31
Massachusetts Horticultural Society’s 14th Annual Festival of Trees showcases dozens of decorated trees, the Snow Village, and a festive model railroad display, Nov. 25-Dec. 31, at the Garden at Elm Bank, 900 Washington St., Wellesley.
Don’t miss the Snow Village, an indoor model train exhibit, or the holiday lights and decorations that fill the Garden. The firepits will be going strong, and s’mores and hot chocolate will be available. Tickets are on sale now.
Beyond Wellesley: Commonwealth Ballet’s production of The Nutcracker—through Dec. 18
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 at Eleanor Welch Casey Theater at Regis College, 235 Wellesley Street, Weston. Join the family party set before a magical tree and enjoy the laughter, magic, and wonder of this holiday classic accompanied by the beloved Tchaikovsky score.
Performances are Thanksgiving weekend, Nov. 25-27, and the weekend of Dec. 16-18.
A special sensory/family friendly performance will take place on Fri., November 25, 1pm, featuring a shortened version of the ballet at reduced prices.
The Nutcracker lasts approximately 2 hours, including one intermission. Recommended for ages 4 and older.
Grand Menorah Lighting: Town hall-Dec. 21
The community will have a chance to unite for the Chanukah on Wednesday, Dec. 21 at 5:30pm outside of Town Hall for a grand menorah lighting.
Wellesley Weston Chabad, the Wellesley Police Department, and Wellesley Fire Departments will join forces for the event, which will feature a gelt drop, hot chocolate, Chanukah songs, jelly doughnuts, and various prizes.
Wellesley Town Band Concert—Dec. 18
After scattering to the winds for a few years, it looks like the Wellesley Town Band has finally gotten back together. You can catch them in a free concert on Sun., Dec. 18, 3pm, at Wellesley High School.
Interested in joining this dedicated and fun group of musicians? Email info@wellesleytownband.org
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.
Cookie decorating at Magic Beans—Dec. 17
Kids ages 2 to 10 come on out to Magic Beans in Linden Square on Sat., Dec. 17, 9am-10am for 
a special holiday cookie decorating event. So much fun.
Wreaths Across America—Dec. 17
Join the Amos Mills-Lucy chapter of the DAR during the patriotic group’s annual “Wreaths Across America” event, Sat., Dec. 17, 11am, at the Wellesley Congregational Village Church, 2 Central Street. Wreaths will be placed on over 30 veterans’ graves in the church’s historic cemetery, which along with the church building is listed on the National Register of Historic Places.
Each December DAR chapters nationwide place remembrance wreaths on veterans’ graves at over 3,000 locations in the United States, at sea, and abroad.
Can’t make it to the wreath-laying? You can sponsor a wreath today to be placed on a Wellesley veteran’s grave on Dec. 17.
Annual Holiday Toy Drive & Light Show at 10 Falmouth Circle—through Dec. 16
You can watch the show through Dec. 16, 5pm-9pm, from your car by tuning into 98.9 on your radio or feel free to walk up the driveway. Last year the Burkhead kids collected over 500 toys that went directly to kids at Boston Children’s Hospital. The Toy Drop Box is out during the day as well as at night. Please help collect them UNWRAPPED toys this holiday season.
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.
Heaven and Nature—an evening of Yuletide carols—Dec. 12
Community Messiah Sing—Dec. 11
The Unitarian Universalist Society of Wellesley Hills will present a free Community Messiah Sing on Sun., Dec. 11, 1:30pm, 309 Washington St. The event will feature professional soloists and an orchestral. Attendees are invited to join in singing the choruses of G.F. Handel’s Messiah oratori0 (part 1). But no pressure on that count. Scores available; please bring your own if you can.
Vaccinations and masks required. Dress warmly—windows and doors will be thrown open for maximum ventilation.
Contact music@uuwellesley.org or call 781-235-7423 for more information.
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.
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 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.
See Santa at Wellesley Hills Congregational Church—Dec. 10
Santa’s sleigh will glide into Chapel Place on Sat., Dec. 10. 9am-11am, when the Jolly Old Elf makes his annual visit to Wellesley Hills Congregational Church, 207 Washington St. Once you arrive, just follow the signs that lead the way. Santa will meet you at the Wallace Chapel (located on the east side of the church).
Visit, invite friends, write Santa a letter, bring a camera to take your own photos (or helpful volunteer elves will take them for you). All ages are welcome to decorate and share a cookie with the big guy at this free event.
Christmas with the Back Bay Ringers—Dec. 3
Do you hear what we hear? From Bach to Blue Christmas, the Back Bay Ringers handbell ensemble’s season will feature both classical and contemporary favorites Dec. 3, 2pm-3:30pm, at the Wellesley Hills Congregational Church, 207 Washington Street. The seasonal tunes will be brought to life on a dazzling array of handbells, chimes, percussion and of course, sleigh bells. The concert will encompass many moods, from baroque precision, to contemplative calm, to joyful celebration. This year’s program will include some audience favorites including a new arrangement of “Carol of the Bells” and our beloved and familiar transcription of Leroy Anderson’s “Sleigh Ride.”
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.
DATE: Saturday, December 3, 2022
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.
Small Business Saturday, all over Wellesley—Nov. 26th
Shop local all over Wellesley on Small Business Saturday, November 26, a day to celebrate and support small businesses and all they do for their communities. You’ll find a unique range of stores, brands, services, and restaurants throughout town, along with free meter parking and smiling faces all around. Get inspired to shop small, and shop local.
Wellesley Turkey Trot—Nov. 24
Registration is still open for the annual Wellesley Turkey Trot, which features both a 5K race that courses through town as well as a the 1-mile Hannah Randolph Kids Fun race that stays closer to Linden Square.
The 5K race begins at 8am in Linden Square and raises funds for local charity partners.
The 1-mile race begins at 8:45am, in the back of the parking lot near CVS. This race is for children ten years old and younger. All registration proceeds go to the Hannah Randolph Foundation, which supports students.
The annual Turkey Trot was founded by the late Carol Chaoui, who is honored with a plaque near the race start/finish.
Thanksgiving game, Wellesley vs. Needham—Nov. 24
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