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Holiday Happenings

From tree lightings to menorah lightings, Holiday Strolls to holiday markets, there is a ton of fun to be found this December in MetroWest! All events are FREE unless otherwise noted. (Plus, be sure to check out our gift guide to interesting, unique, and made-in-MetroWest gifts this holiday season!) Grab the fam or some friends and head to…

Dec 1:

Framingham’s 32nd Annual Tree Lighting Ceremony and Outdoor Holiday Block Party from 5 pm – 7:30 pm. Holiday Block Party from City Hall Plaza Down Union Avenue to Include Free Digital Pictures, Hot Chocolate and Treats, Music, a Story Walk, Free Books, and More. All are welcome to watch as Santa and Mrs. Claus arrive in grand style atop a Framingham Fire Engine before lighting the tree.

Milford Christmas Tree Lighting starting at 5:30 at Draper Memorial Park. Enjoy some hot cocoa and chili courtesy of Red Heat Tavern of Milford and fresh baked cookies courtesy of the Milford Public Schools food service! The Greater Milford Community Chorus will be there with a festive holiday sing-along beginning at 6:00 p.m. And of course…..SANTA will be there at 5:45 p.m. to hear all those early Christmas wishes from the kids!!

Marlborough’s Home for the Holidays and Tree Lighting at Union Common (intersection of routes 85 & 20) from 6pm – 8pm. Santa will make a special appearance with Mayor Vigeant and will arrive by a Marlborough Fire Engine to commence the 2023 tree lighting. All are welcome to attend! Complimentary hot chocolate, popcorn, and candy canes will be available. Guests will be able to view and visit a variety of barn animals. The Marlborough High School Choir directed by Caleb Whelden will entertain attendees with Christmas carols. The festive musical portion of the event will continue at the First Congressional Church.

Dec 2:

Hopkinton Chamber of Commerce Holiday Stroll from 10am – 3pm in downton Hopkinton, around 18 Main St–a great way to get all of your shopping done, get a chance to win a $300.00 cash prize and have a fantastic time doing it! Join the Hopkinton Girl Scouts from 4 – 6pm after the Holiday Stroll for this annual event to celebrate the season with community, cocoa, gift vendors, kids crafts, Santa photos and caroling! Plus, Hopkinton Center for the Arts is hosting their Holiday Marketplace from 10am – 3pm, where you can get in the festive spirit and find the perfect gifts for your loved ones or yourself! Santa Claus will be available for pictures and visits between 11 a.m. and 2 p.m., so be sure to bring your camera and Christmas list.

With over 25 local artisans selling their handmade wares, you’ll find unique and beautiful gifts ranging from pottery, jewelry, gift baskets, home decor and more.

Town of Sudbury Holiday Village will feature live music, winter gift market, food and fun. 11am-2pm around 5 Hudson Rd, Sudbury.

Ashland Holiday Stroll from 12 – 4pm is more than just shopping! Check out the activities at The Corner Spot: Roast marshmallows at the fire pit, buy a wreath from the Boy Scouts, grab some cookies from the Girl Scouts, tell Santa what you want for Christmas, and enjoy hot chocolate, cider, and noodles from Doragon Ramen. Don’t forget to collect stamps as you shop! Every unique shop you make a purchase from earns you a stamp. Once you’ve gathered five or more stamps, you can enter to win their Holiday Stroll Raffle.

Hopedale Downtown Winter Stroll from 12 – 7pm. NEW THIS YEAR! They have added a Shop Hop to the event to include any Hopedale businesses & organizations that would like to take part but are not located downtown. The stroll takes place at many stops along Hopedale Street and Dutcher Street including many historic buildings such as the Draper Gym, Hopedale Community House, Bancroft Memorial Library, Hopedale Unitarian Church, Union Evangelical Church and the Little Red Shop Museum. The Shop Hop list will also include stops all over Hopedale for you to visit, shop, eat and enjoy! Multiple vendor locations will showcase work from local vintage vendors, hand makers, artisans, food vendors and mobile shops. Many businesses will take part in the Stroll and Shop Hop with special offers for customers. Past years have included performers setup along the route like live music at the park, costumed characters, outdoor movies and carolers roaming the route while guests stroll from stop. All of this ending in the long standing and popular town tradition of the tree lighting and Santa visit at the Hopedale Community House.

Southborough Kindergroup Santa Day from 12 – 3pm. Santa has an exciting arrival in a helicopter (or fire truck) on St. Mark’s Field in the center of town and then makes his way to the Southborough Community House to greet children and take pictures. Santa, Mrs. Clause, and the Elves will be hosting crafts, stories, chocolate, cookies, character visits, and more.

Natick Holiday Lighting Festival on the Common (12 S. Main St) from 2 – 5pm. Enjoy free crafts, caroling and more and a visit from Santa himself! Santa will still be touring town courtesy of Natick Fire Department.

Hudson Holiday Stroll from 3 – 7pm. Come visit Santa, toast marshmallows, visit the petting zoo, listen to live music, wander the shops, and much more!

Dec 3:

Wayland Center Holiday Events for All from 2 – 5pm starting at 4 Elissa Ave. Wayland Center will come alive with holiday festivities, as the Grout-Heard House Museum, the Wayland Free Public Library, the Depot, and the First Parish present an assortment of seasonal music and fun. The Grout-Heard House Museum, adorned with greenery provided by the Wayland Garden Club, will serve refreshments and host several events from 2 p.m. to 5 p.m. Girl Scouts will decorate the alcove of the Stone Room with themed creations, and children will be invited to join in a playful scavenger hunt. At 2:30, a string quartet of Wayland High School musicians will perform, followed by another select group of High School musicians. Visitors will be encouraged to tour the historic house. The Wayland Free Public Library, next door to the Grout-Heard House Museum, will also serve refreshments, and at 3 p.m., local musician David Polansky will lead a sing-along for guests of all ages upstairs in the Round Room. Polansky will also play the keyboard and trumpet. First Parish will host an outdoor sing-along caroling fest at 4:30 p.m. with music provided by the Sudbury Valley New Horizons Band under the direction of Diane Muffitt and carol singing led by veteran carol leader Maddie Sifantus. All are welcome to sing, or just enjoy hot cocoa and cookies after the event. The Depot will be open and will offer a unique selection of items as well as Booster apparel.

Dec 7:

Holliston Menorah Lighting at 6pm at 703 Washington St. Join Chabad House for lively music, Israeli-style donuts, Chanukah chocolate gelt, hot apple cider, dreidels for the kids, and more!

Hanukkah Party at the Verve from 6 – 8pm. Dreidels, Latkes and Dancing – celebrate the miracle of Hanukkah at The VERVE Hotel, Tapestry Collection by Hilton. Join them for dreidel spinning contests, photos with the “Dreidel”, chocolate gelt, sufganiyot and more! BYOD (Bring your own Dreidels) Tickets are $18 and can be purchased here.

Dec 8:

Milford Chanukah Shabbos Party, followed by outdoor Menorah Lighting at 3:45pm at the Milford Chabad House.

Dec 9:

Hopkinton Elf on the Shelf Scavenger Hunt from 12 – 2pm at 6 Hayden Rowe St. Join the Hopkinton Community Partnership as they collaborate with local businesses in town.  They are teaming up to raise money for community families for the holiday. They will be hiding an Elf in local businesses, and all you have to do is find the elf and have the map stamped.  Find as many as you can! Everyone wins a goodie bag and some local businesses will be giving out coupons too! Cost: $10 per child, $5 for additional children in same family. Buy tickets in advance here.

Illuminate Downtown Ashland from 4:30 – 7:30pm. This community event aims to shine a light on the important role art plays within a community. Annemarie’s Dance Centre alongside the town of Ashland and Arts! Ashland Alliance partner local art and artists with community spaces both public and private. Live audiences are welcome in the several locations around downtown to view the art, hear the music and experience the dancing. Annemarie’s Dance Centre, The Corner Spot, Ashland Historical Society, Blush Bouquet, Needham Bank and Ashland Reiki & Wellness will host live performances and art works for the community to enjoy. Ashland High School Chorus, Neayong Cho, The Drum Nomads, International Trio, The Cardinal Joe Stillitano & The Movement Project Performance Company will occupy the spaces for a night of free performance and luminaries.

Wayland Holiday Stroll & Tree Lighting from 3 – 5pm. Join the local businesses at Wayland Town Center for some holiday fun, giveaways, tree lighting on the green courtesy of Russell’s Garden Center, and SPECIAL GUEST APPEARANCES by Santa, our friends at Wayland Police & Wayland Fire and more! Line up on the green at 3pm with Elsa & friends, and see Santa arrive by firetruck with our friends at Wayland Police & Wayland Fire. Gather around the Green for their annual tree lighting at 4:45pm as we sing a song with Santa and countdown to the tree lighting with Santa and all his friends!

Claflin Hill Holiday Pops2

Claflin Hill Symphony Holiday Pops Concert from 7:30 – 10:15pm at the Milford Town Hall. Come celebrate winter’s magic with the CHSO and Greater Milford Community Chorus where The Grand Ballroom is transformed into a winter wonderland!  The warm sounds of the holidays will fill the hall with festive seasonal favorites, including a holiday sing-along and a visit from jolly ol’ St. Nick! Let’s ring in the Holidays together with The Greater Milford Community Chorus, under the direction of Mark Schiappucci, joining CHSO for their sixth year! Tickets from $29-47 can be purchased here.

Santa Visit & Gingerbread Workshop at Lookout Farm. Santa is visiting The Lookout Farm Greenhouse (89 Pleasant St, South Natick) from 3 – 7pm! Experience includes meet and greet with Santa, photos, and special gift bag for each registered child. Cost is $35 per child. You can also sign up for their Eat, Sip and Create Gingerbread House workshop to create your very own yummy masterpiece. Workshop is from 1 – 3pm (All Ages). Cost is $45 per house kit which includes 1 Gingerbread House and all the tasty decorating supplies! Book tickets here.

Dec 10:

Medway Menorah Lighting at 3:30pm at Choate Park (7 Oak St, Medway) Join Chabad House for lively music, Israeli-style donuts, Chanukah chocolate gelt, hot apple cider, dreidels for the kids, and more!

Franklin Menorah Lighting at 4:15pm at the Franklin Town Common (Intersection of Main St & High St., Franklin) Join Chabad House for lively music, Israeli-style donuts, Chanukah chocolate gelt, hot apple cider, dreidels for the kids, and more!

Dec 15:

The Grinch community movie viewing at atac downtown arts + music (160 Hollis St, Framingham) from 6:30 – 9pm. A grumpy Grinch plots to ruin Christmas for the village of Whoville in this 2018 animated adaptation of the Dr. Seuss classic. Free with RSVP.

Ayla Brown Christmas concert at Hopkinton Center for the Arts from 7:30 – 9pm. Jingle all the way to our festive holiday concert featuring the talented Ayla Brown, country music star and Country 102.5 morning show host! Get ready to rock around the Christmas tree as Ayla performs your favorite holiday classics and a special original Christmas song. From toe-tapping covers to heartwarming originals, Ayla’s music will have you feeling merry and bright So don’t be a Grinch, join us for a magical evening of music and storytelling that will sleigh your holiday season! Tickets are $25 and can be purchased here.

Grinch Visit at Lookout Farm. The Grinch is visiting The Lookout Farm Greenhouse (89 Pleasant St, South Natick) from 3 – 7pm! Experience includes meet and greet with the Grinch, photos, and special gift bag for each registered child. Cost is $30 per child. Book tickets here.

Don’t miss our gift guide to MetroWest too!

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