Wellesley Holiday Happenings 2025-26

Sign up now to ring the Red Kettle—over 100 time slots left! YOU are needed!

EVENT: Sign up here to ring Wellesley’s Salvation Army Red Kettle Bell
DATE/TIME: Launches Dec. 8 and runs through Dec. 24th
LOCATION: In front of Roche Bros. in Linden Square
SIGN UP here
DESCRIPTION: Volunteer bell ringers are needed to support this community effort. The Wellesley Red Kettle is a critical source of funding for those experiencing medical, housing, food and other needs. Red Kettle Drive donations are distributed to those in need by the Wellesley Council on Aging, Wellesley Department of Health, Wellesley Friendly Aid, and Veterans Services. The Wellesley Kiwanis Club has hosted the Salvation Army Red Kettle nearly every December since 1994.

Wellesley Theatre Project presents How the Grinch Stole Christmas, Jr.

DATES: December 11, 12, 13, & 14 (rated PG, 60-min. run time.
LOCATION: Sorenson Center for the Arts, 19 Babson College Drive Wellesley, MA
TICKETS HERE
DESCRIPTION: With a heart “two sizes too small,” the Grinch despises the annual Christmas festivities of Who-ville from a solitary distance. Fed up, he carries out a plan to stop them once and for all, only to learn a lesson about opening his heart to the real meaning of Christmas.

Winter Market of Newton at 275 Grove

DATES/TIMES: Friday, Dec. 12, 5pm-8pm and Saturday, Dec. 13, 10am-3pm
LOCATION: 275 Grove St. Auburndale, MA 02466
DESCRIPTION: A festive Winter Market featuring 20+ local vendors with handmade crafts, artisanal treats, live music, food, and a raffle. Raffle ticket proceeds benefit the Newton Food Pantry. Free entry.

 Linden Square Holiday Stroll

DATE: Saturday, Dec. 13
TIME: 1pm-3pm
LOCATION: Linden Square, Wellesley
DESCRIPTION: Celebrate the season at Linden Square’s annual Holiday Stroll—now with a fun new twist! This year, families are invited to begin in the Courtyard, pick up a stroll map, and make their way to participating storefronts for festive treats and holiday surprises.
RSVP here

Enjoy an afternoon filled with seasonal cheer including:

• Free hot cocoa, holiday treats, and kids’ crafts with the Wellesley Lions Club in The Courtyard.
• Special visit from Christmas Minnie Mouse and Rudolph
• Touch-a-Truck with the Wellesley Fire Department
• Holiday freebies and giveaways from select businesses
• Holiday tunes with Bach to Rock

Wreaths Across America

DATE: Saturday, Dec. 13, 2025
TIME: 11am
LOCATION: Wellesley Village Church, 2 Central St.

DESCRIPTION: Join the Amos Mills-Lucy chapter of the DAR during the patriotic groups annual Wreaths Across America event. Wreaths will be placed on 36 veterans’ graves in the church’s historic cemetery. Many veterans will be in attendance, and Wellesley High School trumpeters and a local bagpiper will be a part of the ceremonies. Local Historian Bradford Harding will present an engaging historic story of a local Patriot!  The cemetery, along with the church building, is listed on the National Register of Historic Places.

Please sponsor a wreath today to be placed on a Wellesley veteran’s grave.

Metrowest Dance Academy presents The Nutcracker: Clara’s Dream

DATE: Saturday, December 13
TIME: Two performances, 1pm and 6pm. Tickets here.
LOCATION: Wellesley High School, 50 Rice St.
DESCRIPTION: A beautiful family-friendly performance of this holiday classic performed by students of Metrowest Dance Academy. Journey with Clara from her dream of a battle between mice and soldiers and then through a Land of Snow and Sweets in this abridged holiday classic.

UU Wellesley Hills Community Messiah Sing

DATE: Sunday, Dec. 14
TIME: 1:30pm
LOCATION: UU Wellesley Hills, 309 Washington St., Wellesley Hills, ample parking
COST: Free & family friendly
DESCRIPTION: A joyous annual event hosted by UU Wellesley Hills. The performance features professional soloists and a chamber orchestra performing G.F. Handel’s Messiah, part 1, with the audience singing along on the choruses. People of all ages are invited to enjoy this seasonal classic, whether singing along or listening.

St. John – St. Paul Collaborative Choir, Lessons and Carols

DATE/TIME: Sunday, December 14, 2pm
LOCATION: St. Paul Church, 502 Washington St., Wellesley
COST: Free
DESCRIPTION: All are invited to a Service of Lessons and Carols presented by the Parish Choirs of St. Paul and St. John. Come and hear the Christmas story in words and music during this season of preparation.

Wellesley Town Band Winter Concert

DATE/TIME: Sunday, December 14, 3pm
LOCATION: 50 Rice Street, Wellesley, MA 02481
COST: Free
DESCRIPTION: Seasonal songs to get you in the spirit.
PROGRAM: Classic band works and holiday favorites, conducted by Pam Choinski

Wellesley Menorah Lighting

DATE/TIME: Sunday, Dec. 14, 5pm
LOCATION: Linden Square Courtyard
SPONSOR: Linden Square, Wellesley Weston Chabad, Temple Beth Elohim,
DESCRIPTION: The Wellesley Fire Department will be there to help entertain the kids; festive music; light-up prizes; hot chocolate; live fire show; grand gelt drop.

 Religious activities and services, Hanukkah

Hanukkah begins on Sunday, Dec. 14, and ends with nightfall on Monday, Dec. 22, lasting for eight days.

Check in with Temple Beth Elohim and Wellesley Weston Chabad for their full roster of activities and celebrations.

LEGO Winter Village arrives

DATES: Monday, December 15 to Friday, January 2
LOCATION: Wellesley Free Library, 530 Washington St.
DESCRIPTION: Created by Nick Tatar, the LEGO Winter Village makes its annual return to the Wellesley Free Library. Come see Santa’s workshop, the Clock Tower, and exciting winter scenes all made of LEGO! This remarkable festive display always delights families with children of all ages. Sponsored by the Friends of the Wellesley Free Libraries.

Wellesley High School Winter Choral Concert

DATE: Wednesday, Dec. 17, 2025
TIME: 7pm
LOCATION: Wellesley High School, 50 Rice St.
COST: Free

Arrais Ballet’s The Nutcracker

DATES: Dec. 19, 20, & 21, 2025
LOCATION: Dwight Performing Arts Center, Framingham State University
TICKETS HERE
DESCRIPTION: Enjoy the Arrais Ballet students preforming in the second annual production of the Arrais Ballet Nutcracker.

Handbell Christmas Concert

DATE: Dec. 20
TIME: 4pm
LOCATION: Wellesley Hills Congregational Church, 207 Washington St.
DESCRIPTION: Featuring The Hills Bells, The Village Ringers, Chancel and Children’s Choir

Commonwealth Ballet’s production of The Nutcracker

DATE: through Dec. 21, 2025
LOCATION: Eleanor Welch Casey Theater, Regis College, 235 Wellesley St, Weston, Mass.
TICKETS HERE
DESCRIPTION: 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! 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. This fully staged production is sure to captivate and entertain all ages. 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. 28, 1pm, featuring a shortened version of the ballet, mostly Act I, and suitable for younger audiences including children of all ages.

EVENT: Holiday concert with Meatloaf and the Boys
DATE/TIME: Sunday, Dec. 21, 3pm-4pm
LOCATION: Wellesley Free Library
DESCRIPTION: This program is a musical performance of a small group of musicians with roots in jazz, all having recently graduated from Wellesley High School. The performance will contain various genres of music, including jazz, holiday music, and some Japanese fusion. No registration required.

 Art and Ornament Sale

DATE: through Dec. 23
LOCATION: Wellesley History and Exhibit Center, 323 Washington Street (and online)
DESCRIPTION: The Wellesley Society of Artists (WSA) is partnering with the Wellesley Historical Society to celebrate the new Wellesley History and Exhibit Center with an Art and Ornament Sale, November 28–December 23.

This sale features 52 paintings in a variety of mediums and styles, all done by WSA members. Hand-painted ornaments are also available to purchase for gift giving while supplies last. Artists are donating 100% of the proceeds from the ornament sale and 20% of the proceeds from the art sale to benefit the Wellesley Historical Society.

Religious activities and services, Christmas

Christmas Eve takes place on Wednesday, Dec. 24, and Christmas Day is Thursday, Dec. 25.

The Swellesley Report‘s Where to Worship page has information on many of the activities and services.

Don’t see your religious organization’s holiday information on our Where to Worship page? Contact deborahcb100@gmail.com for inclusion.

MassHort Festival of Trees

EVENT: Massachusetts Horticultural Society‘s annual Festival of Trees
DATE: through Dec. 28, 2025
LOCATION: 900 Washington St., Wellesley, MA
DESCRIPTION: Showcases dozens of decorated trees, the Snow Village, and a festive model railroad display.
COST: Adults in the $30 range. Other pricing options. Tickets here.

New Year’s Eve celebration on Cochituate Rail Trail

EVENT: New Year’s Eve celebration
DATE: Wednesday, Dec. 31, 2025
TIME: 4:30pm-7:30pm
LOCATION: Cochituate Rail Trail in Natick and Framingham
DESCRIPTION: Friends of Natick Trails and Friends of Framingham Trails will host the 5th New Year’s Eve celebration on the Cochituate Rail Trail in both towns. The always fun event is a family friendly way to say goodbye to 2025 and march on toward 2026. The event will feature numerous fire pit stations with snacks, beverages, food trucks, entertainment, and giveaways.

Select Board approves free parking—last day is Jan. 2, 2026

FREE PARKING: Shop local and enjoy free parking in Wellesley at all 2-hour bagged street meters during the holiday season.
START DATE: Monday, November 24, 2025
LAST DAY: Friday, January 2, 2026
REMINDERS: Look for bags designating specific free meters. Fees WILL be charged in all municipal parking lots, and at 4-hour, and 10-hour street meters. Parking attendants will ticket cars after 2 hours. Please do not move cars to a different meter; that will also result in a ticket.

THESE EVENTS HAVE PASSED

Wellesley Symphony Orchestra Holiday Concert

DATE: Saturday, December 6
TIME: 2pm-4pm
LOCATION: MassBay Community College, 50 Oakland St., Wellesley, Mass.
Get Tickets

DESCRIPTION: The Wellesley Orchestra Holiday Concert will feature the Fireside Barbershop Quartet and holiday favorites.

H.O.M.E. Store

DATE: Saturday, Dec. 6, 2025
TIME: 9am-5pm
LOCATION: Wellesley Village Church, 2 Central St., Wellesley
DESCRIPTION: Support a good cause and do some holiday shopping. H.O.M.E., Inc. enhances the quality of life of people who have fallen on challenging times. 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, stained glass, and more.

St. John School Trees & Trimmings Christmas Market

Wellesley Turkey Trot

DATE: Thursday, Nov. 27
TIME: 5K,  8am; Kids Fun Run, 8:45am (check for availability…these events may be sold out)
LOCATION: 181 Linden St., Wellesley
DESCRIPTION: 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. 5K race participants run 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.

Wellesley vs. Needham Football

DATE: Thursday, November 27
TIME: 10am–12:30pm
LOCATION: Wellesley High School field, 50 Rice St.
DESCRIPTION: The Wellesley Raiders will travel across the border to face the Needham Rockets during the oldest football rivalry in the country.

Wellesley Marketplace

DATE: Saturday, Nov. 22
TIME: 10am-4pm (9am for VIP ticket holders)
LOCATION: Wellesley High School, 50 Rice St.
TICKETS HERE
DESCRIPTION: Come shop with your besties! Now in its 47th year, Wellesley Marketplace is a beloved annual holiday market for those seeking unique gifts for family and friends. We bring some of the very best vendors to our corner of MetroWest Boston. Shop from local businesses and support the community in the process!

• 200+ local artists and vendors
• Handmade art, holiday gifts, gourmet foods, jewelry, clothing and more
• 100% of proceeds fund scholarships and grants supporting the local community