Christmas Fairs & Festivals In & Around Central Mass

The crisp Central Massachusetts air is filling with the scent of pine and gingerbread, and the lights are ready to twinkle across our town commons—it’s officially time to dive into the region’s Christmas fairs and festivals! This year, Central Mass is bursting with incredible local markets, historic celebrations, and festive gatherings.

Multi-Date Holiday Wonderlands
These festivals run for multiple weeks, giving you plenty of chances to soak up the cheer!

Snowport Boston (Boston, MA)

• Dates: November 7th-December 28th, 2025, and is closed on Thanksgiving Day and Christmas Day.
• Hours:Monday – Thursday 3:00pm – 8:00pm, Friday & Saturday 11:00am – 9:00pm,            Sunday 11:00am – 8:00pm
• Holiday market and winter wonderland located in the Seaport, featuring over 120 vendors, food and drink, themed bars, live music, and attractions like an iceless curling rink and a heated tent. 

Christmas By Candlelight (Old Sturbridge Village, MA)

• Dates: Nov 28-30, Dec 5-7, 12-14, 19-23, and 27-30.
• Times: 2:00 PM – 8:00 PM.
• Step back in time to experience classic Christmas traditions. Enjoy demonstrations, stroll the decorated Village and Christmas Tree Trail, listen to live music and stories, and sample sweet treats. A truly historic and heartwarming celebration.

SOWA Winter Festival (Boston, MA)

• Dates: November 28th – December 28th (Closed Mondays).
• Details: Admission is $10 (children 12 & under are free), $10 onsite parking.
• 25+ local vendors, handmade art + holiday gifts, specialty foods + cocktails! Enjoy it all indoors—warm, festive, and heated! On-site Parking Is Available for $10; admission is $10. Children 12 and under are free!

Festival of Trees Elm Bank (Wellesley, MA)

• Dates: November 28th – December 28th, 2025
• Times: Wed & Thu 4pm-8pm, Fri-Sun 10am-8pm.
• Enjoy the lighted gardens at Elm Bank, visit the Snow Village with model trains, and see dozens of beautifully decorated holiday trees.  

Holidays at Oakholm Farm (Brookfield, MA)

• Dates: November 28th-December 21st, 2025
• Hours: Fri 3pm-6pm, Sat & Sun 10am-6pm.
• Not much beats the smell of fresh pine during the season, and Oakholm Farm is known for its wonderful selection of trees. Enjoy visits with Santa and horse-drawn wagon rides.

Festival of Trees (Methuen, MA)

• Dates: November 22nd to December 6th, 2025 (closed Thanksgiving Day and open 9 am to 9 pm on Friday, November 28) 
• Times: Open weekdays from 5pm-9pm and weekends from 9am to 9pm.
• Enjoy over 300 decorated trees, mini-trees and wreaths, a Holiday Gift Shop, a children’s scavenger hunt, and a visit with Santa.

Christmas at Castle Hill (Ipswich, MA)               

• Dates: December 5th to December 28th, 2025
• Times: Friday, Saturday, and Sunday
• Explore the Castle Hill estate, decorated for Christmas. Enjoy cookies and hot chocolate, check out the gift shop, and try the eye spy activity.

Market On Brussels Holiday Market (Worcester, MA)

• Dates: On Sundays 12/7, 12/14, and 12/21
• Time: 11am to 2pm

• The Market On Brussels 2025 Holiday Market is designed to be an alternative to a traditional market, with a strong focus on curated vendor selection to support the success of our participants. This market is OUTDOORS at the same location as the Market On Brussels farmers market.

Holiday Shows at The Hanover Theatre (Worcester, MA)

• Dates: Various dates and times.
• Enjoy holiday shows like  “A Christmas Carol” and “The Nutcracker.” Bring the whole family and make it a lasting memory.

Single-Day Festivals & Events Holiday Planner

November

Sat, Nov 15th

• Christmas Craft Fair (Fiskdale at 9am): Discover unique handmade gifts, decorations, and local products.
• Winterfest & Kids Maker Market (The Wildwood Farm and Forest School in West Brookfield, from 12pm-4pm): A cozy event with food, drinks, a bonfire, shopping, and a special market for young entrepreneurs.

Sun, Nov 16th

• Holiday Artisan Fair (Bolton Spring Farm, 10:30am-3:30pm): Shop over 65 local artisans, enjoy Victorian carolers, food trucks, wine, and a visit from a strolling Santa. ($5 admission for 18+).

Sat, Nov 22nd

• Shepherd Hill Festival of Crafts (Dudley, 9am-4pm): Annual festival with over 200 crafters and multiple food trucks.

• Holiday Fair (St. Bernard’s Elementary School, Fitchburg, 8am-3pm): Vendors, games, raffles baskets, bake sale, chance auction, and pictures with Santa.

Fri, Nov 28th (Black Friday Fun)

• Country Folk Art Show Christmas Market (Sturbridge, 9am-5pm): Christmas decor, unusual gifts, framed art, farmhouse style, vintage finds, Boho chic, primitive’s, jewelry and apparel, gourmet goodies, and so much more!
• Holiday Shopping, Toy Drive and Santa Visits (Wojcik’s Farm, Blackstone, 10am-3pm): There will be a variety of artisan vendors, a few food trucks, kids’ activities, and of course, Santa! Please bring an unwrapped toy to donate to those less fortunate kids in our area! And this grants you a free visit with Santa!
• Holiday Festival of Crafts (Worcester, 10am-5pm): The Worcester Center for Crafts will be transformed into a European-style holiday marketplace complete with twinkly lights and the sweet smell of evergreens. This juried marketplace celebrates American handmade craft and is our antidote to the big-box madness of holiday shopping. $5 admission.

Sat, Nov 29th (Small Business Saturday)

• Country Folk Art Show Christmas Market (Sturbridge, 9am-4pm): Beautiful Christmas decor, unusual gifts, framed art, farmhouse style, vintage finds, Boho chic, primitive’s, jewelry and apparel, gourmet goodies, and so much more!
• Holiday Sip & Shop (The Mill, Webster, 10am-2pm):  Shop local Artisans and Vendors on Small Business Saturday! There will be a cash bar and food available.
• Holiday Festival of Crafts (Worcester, 10am-5pm): Day two of the juried craft marketplace. ($5 admission).
• Holiday Tree Lighting (Douglas Common, 5:15pm-7pm): Santa, tree lighting, carolers, and refreshments.
• Christmas at Hardwick Crossing (Hardwick Crossing Country Club, Gilbertville, 12pm-4pm): They have craft vendors, merchandise vendors, food, cocktails, free photos with Santa, the Grinch and Mrs. Claus, free cookie making, ornament decorating, music, and more!

Sun, Nov 30th

• Holiday Festival of Crafts (Worcester, 11am-4pm): Final day for the Worcester Center for Crafts market. ($5 admission).
• Christmas at Hardwick Crossing (Hardwick Crossing Country Club, Gilbertville, 12pm-4pm): They have craft vendors, merchandise vendors, food, cocktails, free photos with Santa, the Grinch and Mrs. Claus, free cookie making, ornament decorating, music, and more!

December

Thurs, Dec 4th

• Dudley Tree Lighting (Municipal Complex, 6pm-7:30pm): Holiday music and warm cheer will greet all for the seasonal celebration that will include crafts, pizza, hot cocoa, and sweet treats. A little Christmas magic is expected when Santa arrives atop his big, red fire truck sleigh to visit with the wee ones.

Fri, Dec 5th

• 9th Annual Santa Parade, Tree Lighting, and Fireworks Celebration (Founder’s Park in Mendon starting at 6pm): Come join us for a magical evening filled with a spectacular parade of Christmas and holiday-decorated floats, including multiple firetrucks, local businesses, and the Brothers’ own float leading the pack, delivering Santa Claus himself to the party, so much more, plus an absolutely stunning fireworks display to end the night.

Sat, Dec 6th

• Peppermint Christmas Craft and Vendor Fair (Quaboag Church, Brookfield, 9am-2:30pm)
• Mountainside Holiday Vendor Fair (Princeton, 9am-3pm)
• Christmas Bazaar (Leicester from 9am-3pm): Raffle tables, scratch ticket raffles, baked goodies, and lunch available. Crafts for the kids, and face painting, with a special visit from Santa!
• Annual Holiday Fair 2025 (Townsend Public Library, 10am-3pm): Crafters, homemade food, cookies by the bag, children’s games, child only shopping room (items under $5), and Santa until 12pm.
  
• Oxford Holiday Extravaganza (Oxford High School 10am-3pm): Do some Christmas shopping at our event and scoop up some handmade items from various local crafters. 
• Christmas on the Farm Sutton Chain of Lights (Whittier Farms Sutton from 10am-4pm): Featuring holiday samples and shopping from Lake Champlain Chocolates, Boar’s Head Meats, Cabot Creamery Cooperative, Whitt’s Wicks, and more. We will have FREE wagon-ride tours of our farm.
• GrotonFest Winter (Prescott Community Center from 12pm-4pm): Celebrate the magic of GrotonFest Winter with Santa, festive hayrides, carolers, and live music! Enjoy warm food, hot drinks, and sweet treats while browsing handmade gifts, holiday décor, winter clothing, jewelry, and artisan crafts. Capture the joy at our festive photo booth and experience the spirit of the season in a true winter wonderland!
• Kelly Square Tree Lighting (Worcester from 3pm-5:15pm): Main event located at Jersey Mike’s Kelley Square, with the addition of the participating businesses around the Square and at The Worcester Public Market. Burncoat High School marching band and Christmas carolers! Meet and greet with Santa Claus & Mrs. Claus, photo ops with Rudolph, Frosty, The Grinch, Mickey Mouse, Goofy, and Santa’s Elves, catch a horse-drawn wagon ride around the area, and antique firetruck rides!
• Winter Festival (Shrewsbury Town Common from 3pm-7pm): Discover dozens of local vendors offering holiday gifts, handmade crafts, art, jewelry, gourmet treats, and more in the Yuletide Market. Enjoy live music from choirs singing carols to lively bands and dance groups. Warm up with delicious bites from local food trucks, sip hot cocoa, and indulge in seasonal treats for the whole family. Play carnival games, capture memories at the photo booth, and enjoy activities designed to delight children and parents alike. Enjoy the breathtaking finale: thousands of twinkling lights illuminate Shrewsbury’s Town Common, creating a dazzling winter wonderland. A true community moment you won’t want to miss.
• Leicester Tree Lighting (Leicester from 4pm-6pm): Cocoa, cookies, crafts, face painting, pizza, letters to Santa, tree decorating contest, elf hunt, pictures with Santa and Mrs. Claus, and of course, the Tree Lighting!
• Journey to the King: A Christmas Drive-Thru (Charlton Baptist Church from 5pm-7pm): Journey through time and learn about Jesus the King and see the impact of his life on ours!

• 14th Annual Hopedale Winter Stroll & Shop Hop (Hopedale, 12pm-7pm): The stroll takes place at many stops along Hopedale Street and Dutcher Street, including many historic buildings. Grab a drink from the mobile Irish pub and a meal from one of our food trucks or Hopedale restaurants, and then shop multiple vendor locations that will showcase work from local vintage vendors, hand makers, artisans, food vendors, and mobile shops. 

• Uxbridge Craft, Vendor, & Holiday Fair (Uxbridge High School from 10am-2pm): Over 50 VENDORS with a vendor raffle, toy raffle (over 40 gifts), and a food truck.
• Uxbridge First Holiday Night (Parade Kickoff at 4:30PM): From dazzling floats to marching bands, local groups, and holiday lights, to fireworks, it’s a night of joy, community, and celebration you won’t want to miss.

Sun, Dec 7th

• White Christmas (West Brookfield, 10am-4pm): The 33rd annual event with Santa pictures, horse and carriage rides, open houses, and vendor fairs all over town.
• Millbury Chain of Lights (Canal St, 10:30am-4:30pm): Explore over 40 businesses, non-profits, and vendors for shopping, food, and entertainment.
• Grafton Celebrates the Holidays (Grafton Common, 10am-2:30pm): Includes a Craft Fair at Grafton High School and Frosty Stops around town, culminating in Santa’s visit.
• Holiday Market at the Mill (Westborough, 11am-4pm): Gifts & holiday goods from local artisans & small businesses.
• 2025 Welcome Santa Parade (Milford, MA, starting at 4:30pm)
• Journey to the King: A Christmas Drive-Thru (Charlton Baptist Church, 5pm-7pm): Day two of the drive-through experience.

Sat, Dec 13th

• Auburn Holiday Craft Fair (Auburn High School, 9am-4pm): 150+ Craft Vendors, food, face painting, and more. Santa will be making an appearance from 10 to 2, so bring the kids.
• Artisan Market Sip & Shop (Lilac Hedge Farm, Rutland, 11am-4pm): Santa visits, holiday shopping, delicious local beverages, live music, and food trucks.
• Douglas Holiday Stroll (Douglas Orchard & Farm, 3pm-6pm): An open house with over 30 local vendors, warm cider, hot chocolate, and cookies.
• Shrewsbury Holiday Fair (Shrewsbury Sportsman Club at 11am)
• Holiday Open House (Turn Back Time in Paxton from 1pm-3pm): Holiday Event on the farm! Winter crafts, forest walks, farm animals, TBT PTO will have food available to purchase and cook over an open fire!

Sun, Dec 14th

• Artisan Market Sip & Shop (Lilac Hedge Farm, Rutland, 11am-4pm): Santa visits, holiday shopping, delicious local beverages, live music, and food trucks.

Which of these incredible holiday markets or festivals are you planning to visit first? And if we missed your favorite, leave it in the comments so we can add it to this list!