Three historic buildings decorated with true New England charm

Marvel at the charm and elegance of the historic building as they come a glow during the holidays

Tree Dispays and Raffle Items

Tree Raffle
The event opens November 24 at 10 a..m. and closes December 2 at 8 p.m. and will be accessible to all who wish to participate.


The 2023 Festival of Trees raffle will showcase:

  • Beautifully adorned 7’-10’ Trees

  • Beautifully adorned 4’-6’ Trees

  • Wreaths

  • Centerpieces

    Raffle

  • Take a chance on one of the 100+ raffle items, giftbaskets and services.

Live Holiday Performance

Join us for an afternoon fillled with live holiday perfomances, free of charge! Kick off the season with a cup of Hot Cocoa from the Cafe and settle into a pew and be entertained for hours! Something to please every attendee! 216 Meeting House 2PM-7PM Schedule

Holiday Market Boutique

It’s not just about the trees, the 2023 Festival of Trees will also showcase a holiday market place featuring 100% handcrafted items for sale. Local vendors have displayed their wares for completeing those holiday gift lists. Be sure to stop by the Littlefield Library to pick up some one-of-a-kind items.

Stroll up the walkway through the mini holiday decorated houses in the Littlefield Village to find your way to the market.

Be a vendor.

Laser Light Holiday Spectacular

November 26 - 4:30PM; 5:10PM; 5:50PM; 6:30PM; 7:10PM; 7:50 PM, 8:30PM (216 Meeting House): LASER LIGHT HOLIDAY SPECTACULAR! Multiple showtimes. Reserved seating only. Buy tickets starting October 27, 2023. $7.50pp (child or adult). Sponsored by: Metro Mass Entertainment and Tyngsborough Recreation and Parks

Click here to buy tickets

Sip and See Senior Tea

Sip & See Registration Thursday, November 30, 2023 1-2PM Our Seniors 55+ are invited to join us at the 216 Meeting House to hear the sounds of live singers "The Crescendos", will be singing a cappella for our Senior Citizen Tea event. They’re doing a mix of holiday songs and a little contemporary pop.They are a treble-voiced contemporary a cappella group from Chelmsford High School under the Direction of Amanda Roeder. perform while sipping tea and enjoying some sweet treats. It’s sure to a highlight of the season! Register

Specialty Events

Many opportunites are avaible to during the two weekend event. Feeling creative? Learn how to arrange a beautiful festive holiday arrangement, paint a sleigh or tree box for your holiday decorating. Brings the kids to decorate their own holiday cookie. Have a visit with Santa on scheduled dates. Enjoy live entertainment in the Meeting House, the holiday spectacular Laser Show, Sip & See Senior Tea, and more.

See the Event page for detailed information

Book Author Signings

Local Book authors read excerpts from thier published works. Old Littlefield Library. Every day 11AM- 3PM and 3PM to 7PM. See schedule of Authors

Children’s Cookie Decorating

Short & Sweet Bakery will be hosting a kids cookie decorating event from Friday, Dec 1 4-4:30. Old Town Hall

GROUP 2 - from Friday, Dec 1 4:30-5. Old Town Hall

Additional walk in times are held at 216 Meeting House on November 30 and December 1 and morning of December 2. Based on avaiblilty.

Register for a session

Floral Workshop with Anne’s Country Florals

Make a holiday greens arrangement to display in your home or give as a gift. All materials provided to make and take a Mason Jar arrangement, November 26.Old Town Hall $60 Register

Bow Making Workshop with Anne’s Country Florals

Do you struggle trying to twist ribbon into a presentable bow? Come learn some tips and tricks from the professionals. Bring 3 your own coordinating full ribbon spools and learn to create a perfect bow! Just in time for holiday decorating. November 26. 2:15PM Old Town Hall $5 Register

Holiday Decor Night

Make a holiday item to display in your home or give as a gift with The Canvas Road Show. Pre registration required. Choose from 3 differnt crafts. Thursday, November 30th, 6PM

Register

Winslow Wonderland.

Wooden cutouts of trees and snowman are decorated by residents annually for the “Winslow Wonderland” stroll. Walk through the decorated cutouts and make note of your favorites! Vote on our Facebook page which is your favorite. The competition is fierce! Be sure to cast your vote. REQUEST A CUT OUT

Little Village

It all begins with an idea of having a market place in the historic Littlefield Library. To bring people over to the building we wanted a welcoming and exciting entrance. This mini village is decorated in various holiday themed house, on a miniture scale. It’s sure to delight!

Elf Challenge

Do you have what it takes to be one of Santa’s helpers? Take the challenges of the Ice House to see how you fair! Complete the fun challenges, check off your “in training” sheet and return to see if you pass!

While you are there enjoy make and take Holiday Crafts, "Letter-To-Santa"area, complete with express North Pole mailbox. Face Painting w/ Fancy Faces

Elf Dance Party w/ DJ Steve from metro mass entertainment

THS Band Ensemble performs in 216 Meeting House.

THS Choir performs to usher the famous couple in red to our door.

5:00PM ish: Santa’s Grande Arrival ("-ish" due to cross winds and unpredictable air traffic patterns)

Saturday, December 2. 2-5PM