42nd Annual Williamstown Holiday Walk!
This festive and family-friendly weekend of events includes the ever popular Reindog Parade on Saturday, as well as a visit with Santa Claus, old-fashioned caroling and tree lighting, horse-drawn carriage rides, a soup-tasting competition, Holiday Musical Bingo, and so much more!
For a complete schedule of holiday fun, visit DestinationWilliamstown.org.
Williamstown Holiday Walk – FRIDAY!
December 5, 2025
4pm TREE LIGHTING at Sweetwood of Williamstown.
6pm CONCERT: JENNY HERZOG* at The Clark Art Institute Auditorium. Berkshire County part-time resident, jazz singer, and tap dancer Jenny Herzog kicks the season off in style with a spirited concert blending the Great American Songbook, tap dance, and holiday classics. Herzog celebrates the long relationship between improvisational tap dance and jazz. Joined by long-time collaborator, interdisciplinary pianist Jacob Hiser, this duo promises to get your toes tapping and your spirits lifted, just in time for the holidays!
Reserve your spot! Tickets cost $20 ($16 members, $14 students, $10 children 17 and under).
Williamstown Holiday Walk – SATURDAY!
December 6, 2025
8am-12pm BREAKFAST WITH SANTA* at Ioka Valley Farm.
10am HOLIDAY CALM YOGA* at Tasha Yoga. Registration required at tashayoga.com/classes.
11am & 3pm SCREENING OF ELF at Paresky Center Auditorium. Sponsored by Williamstown Cultural District. Hosted by Images Cinema
12-1:30pm FACE PAINTING at ROAM Gallery. Get ready for the ReinDog Parade! Become a dog, reindeer, or other animal to march in the parade.
12-2pm WUPE-FM LIVE BROADCAST
12-2pm CRAFTING FOR KIDS at The Log by Ramunto’s. Sponsored by Pine Cobble School.
12-2pm COOKIE DECORATING at The Williams College Bookstore. Sponsored by Buxton School.
12-2pm SOUP-ER BOWL COOK-OFF* at Williams College Lasell Gym (enter from Main Street). Sponsored by MountainOne.
12-4pm PENNY SOCIAL* & NONPROFIT FAIR at Williams College Lasell Gym (enter from Main Street). Benefiting Williamstown Community Chest. Enjoy music with the Flatbed Jazz Band 2:30 – 4pm.
1-3pm HOT CHOCOLATE & COOKIES at The Williams Inn. Sponsored by The Williams Inn
1-3pm HOLIDAY MUSIC at Tea & Boba Lounge with violinist Suzy Homan.
1-4pm ROXIE’S BARKERY POP-UP SHOP* on Spring Street.
1-4pm LIVE A CAPELLA MUSIC outside Tasha Yoga.
1-4:30pm HOLIDAY SHOWCASE* at First Congregational Church. Benefiting Northern Berkshire Habitat for Humanity.
1-4:30pm GINGERBREAD HOUSE COMPETITION AND RAFFLE at First Congregational Church. Sponsored by Sweetwood of Williamstown. Benefiting Northern Berkshire Habitat for Humanity.
1-4:30pm YULETIDE TREASURES POP-UP SHOP* at First Congregational Church. Shop vintage & handmade tree ornaments, jewelry, and small gifts for sale.
1-4:30pm WES CLOTHING SALE POP-UP SHOP* at First Congregational Church. Find winter coats, snow pants, sweaters, and seasonal items for kids.
1:30pm REINDOG PARADE LINE-UP & JUDGING on the Falk Science Quad. Dog owners are welcome to deck their hounds and join the fun. Enter: Small, Medium, Large & Family Troupe. Prizes provided by: Goodwill, Chapter Two Books, and Roxie’s Barkery.
2pm REINDOG PARADE down Spring Street!
2-3:30pm WILLINET TV LIVE
2:30pm VISIT WITH SANTA CLAUS at The Williams Bookstore. Sponsored by Greylock Federal Credit Union.
2:30-4:30pm ART-MAKING WITH THE CLARK in the TD Bank Lobby. Sponsored by The Clark Art Institute.
2:30-5pm HORSE-DRAWN CARRIAGE RIDES on Spring Street. Sponsored by The Clark Art Institute.
3-5pm HOLIDAY STORIES at Chapter Two Books. Drop in for some holiday cheer—a Holiday-themed story will be read aloud every half hour!
3-5pm WILLIAMSTOWN FOOD PANTRY DONATION DRIVE outside Amy’s Cottage. Hosted by Girl Scout Troops 65391 & 65237. Donate $25 and receive a coupon for 20% off any one item from Amy’s Cottage.
3-5pm CROCHET, CORALS, AND CANDY CANES inside The Coffee Shop. Hosted by WCMA. Come warm up with the Williams College Museum of Art and the Berkshire Satellite Reef project. Try your hand at crocheting a coral to be part of the Coral Reef Project. No experience necessary. All ages are welcome to come enjoy a candy cane and learn about this community art project!
4pm & 7pm CHRISTMAS SERVICE OF LESSONS AND CAROLS at Thompson Memorial Chapel.
5pm TREE LIGHTING & CAROLING on The Williams Inn Lawn. Sponsored by The Williams Inn.
5:15pm LAS POSADAS: WELCOMING THE STRANGER Sponsored by Saint John’s Episcopal Church. Meet in front of Hopkins Hall to take part in celebrating Las Posadas. A candlelight procession with singing culminates with an indoor dinner and nut-safe piñata party at the Church. Bundle up for this fun event. Gilbert the donkey will join in if weather allows.
5:30-7:30pm BUILD-YOUR-OWN-WREATH WORKSHOP* at The Williams Inn. Take part in a great opportunity to gather, get creative, and enjoy the holiday spirit together. Tickets are $65 and can be purchased at https://breezyhillblooms.com/products/wreath-workshop
6pm SING IN DARIJA: MOROCCAN ARABIC SONG & HAVDALAH at Williams College Jewish Religious Center. Sponsored by the Williams College Jewish Association and the Jewish Federation of the Berkshires. Yona A. Elfassi, PhD, will lead an experience in the rich musical and linguistic heritage of Morocco’s Jewish community as we say good-bye to Shabbat, the Jewish Sabbath. Explore traditional and contemporary Moroccan songs, learn to sing in Darija (Moroccan Arabic), and discover the stories, rhythms, and cultural expressions behind the music. Take part in an immersive journey that bridges language, spirituality, and sound—a soulful way to end Shabbat and welcome the new week. For more information, please email Rabbi Seth Wax, College Chaplain and Director of Jewish Life, at smw4@williams.edu.
Williamstown Holiday Walk – SUNDAY!
December 7, 2025
8am-12pm BREAKFAST WITH SANTA* at Ioka Valley Farm
9am-2pm PANCAKE BREAKFAST, LUNCH, & BAKE SALE* at Williamstown Elementary School Cafeteria. Benefiting the 6th Grade Class.
1-3pm SHOP SMALL SUNDAY Explore the Williamstown Business District and find unique gifts and experiences at the following merchants:
Amy’s Cottage: Tea sampling
Chapter Two: Coffee Table Books Sale
The Coffee Shop Williamstown:
Neighbors: 10% Discount
Provisions Williamstown:
ROAM Gallery:
Where’d You Get That?!: Toy Demonstration
3pm COMMUNITY COLD PLUNGE at Sand Springs Pool.
5pm TREE LIGHTING at The Store at Five Corners. Hosted by South Williamstown Community Association. Enjoy caroling, food, drink, and a visit from Santa.
5-8pm KRAMPUS MUMMER’S BALL at 283 Cole Avenue. Hosted by Wild Soul River, Berkshire Cider Project, Rainy Day Coffee, Cricket Creek Farm. Adult fun! Wear your scariest Krampus mask, Mari Lwyd, or other costume. Hang out around the fire, hear ghost stories, and honor the land through ritual.
Shop small, support local, and make Williamstown your holiday getaway in December!
