Saturday December 6, 2025 10am - 4pm
2025 Routes
Route 1
1. Sutton High School - Trolley Hub - Park here and take the trolleyto Route 1, Route 2 and Route 3 stops!
383 Boston Road
R/H/F/P
Kick off your trolley adventure at the Sutton High School Trolley Hub! 🎄 Browse unique creations from local crafters and artisans, then treat yourself — grab a fresh coffee, hot chocolate, or warm donut from the DonutNV Food Truck, or enjoy a tasty lunch from Joe’s Snack Shack before you roll out!
2. First Congregational Church
307 Boston Road
R/P/H/F
Start the festivities here! Visit our beautifully decorated Sanctuary and learn about the history of our church. Downstairs we offer a savory hot lunch from 10-3: homemade soups and grilled cheese sandwiches. Gluten free available! Buy uniquely handcrafted gift from local vendors, bountiful raffle baskets and delicious homemade bakedgoods. Holiday cookie decorating and free face painting in our kid’s room!
3. Pleasant Valley Crossing
29 Galaxy Pass
P/H
Meet Frosty and make memories! Enjoy FREE family fun with games, a Photo Booth, and Face Painting - from 10 to 3!
Join us and celebrate a day in our "Whoville" town. Who's in, who's out, who's up, who's down? We welcome you to spreading holiday cheer with our very own Grinch!
Tis the season for samples, games, giveaways and more at the Sutton Market 32! From 11am-2pm, stop by for samples, giveaways and more.
Join us for a Charlie Brown Christmas! Our guest visitors include Charlie Brown and Woodstock. Our little visitors will have plenty of opportunities to mingle and take photos with the Charlie Brown crew! Make your own smores atour firepits, equipped with cozy warm blankets! Grab a Hot Dog and a Gourmet Hot Chocolate! Warm up & Relax at the fire with Christmas Tunes, friends, snacks and play a game of Corn Hole! Gift ideas for everyone in Mickey’s store! Check out the finest DIY products & supplies, Gift Bundles, Stocking Stuffers and more! Please join us as the Town of Sutton and Mickey’s Car Wash & Detail Shop welcome you to a memorable holiday event!
4. Holy Spirit Episcopal Church
3 Pleasant Street
R/P/H/F
Welcome to Holy Spirit Episcopal Church! Come in out of the cold for a warm and welcoming lunch. Check out our various raffle prizes and enjoy shopping assorted crafts made by talented locals. Check out our Cookie Walk and Attic Treasures store. Come build a collection of your favorite cookies and discover treasures for your Christmas stockings and small gift exchanges. A perennial favorite, live music in the sanctuary will feature vocals and instrumentals. Come join us!
5. Al’s Rubbish and Container Service
77 Providence Road
P/H/F
Step into a winter wonderland of sparkling lights and festive cheer! Stroll through winding pathways lined with glowing trees, shimmering tunnels, and dazzling light sculptures that bring the magic of the season to life. Every corner reveals something new — from twinkling snowflakes to whimsical holiday scenes and animated displays. Shop with our select vendors or grab a bite to eat at the Hog Wash BBQ from 10a-2p. Whether you come with family, friends, or someone special, this immersive walk-through light experience is sure to fill your heart with the wonder and joy of the holidays.
6. Dudley Gendron
156 Boston Road
R/P/H/F
Join us for the Polar Express experience with games, crafts, raffles, snacks and cookie sales.
356 Boston Road
R/P/H/F
Welcome back to St. Mark’s Gingerbread Fair! At our warm and welcoming church, you will find tables filled with delicious home-made treats and “decorate your own” gingerbread cookies packaged with icing and sprinkles to take home and our famous chili spice mixes. Also back this year are wonderful sewing and craft items, lots of treasures and collectibles which will benefit the Haiti ministry and tables filled with raffle baskets. While our kitchen will not be open this year, the Knights of Columbus will be serving fried dough, clam fritters and more from their trailer.
Route 2
8. Manchaug Village
356 Manchaug Road
R/H/F/P
For the Chain of Lights, our favorite season of all, the House will be transformed into a gingerbread wonderland—a place where dreams, magic, and nostalgia swirl together in the glow of Christmas delight. Wander through whimsical displays, meet playful gingerbread characters, and be swept away by the sweet harmonies of the Very Merry Dickens Carolers. Hop off and step right into our winter wonderland as part of your Chain of Lights adventure.
Outside, enjoy festive bites from the Roadhouse Grille and cozy drinks from the 20 Hudson Street beverage trailer, all while soaking up the joyful holiday spirit.
Annmarie Harrity Ryan will be performing live piano from 11 AM – 1 PM
Gingerbread characters will be greeting little ones from 11 AM – 2 PM
(don’t forget to take your own photos!)
The Very Merry Dickens Carolers will perform from 2 PM – 4 PM
Come celebrate with us—where history, community, and Christmas magic meet.
9 Main Street
R/F/H/P
Step into Vaillancourt’s to shop fine art chalkware and holiday collections, explore festive decorations, and enjoy the outdoor Yuletide Wine Garden with a Christmas-themed cash bar, Frauleins Bakery’s German treats, and George’s Coney Island’s hot dogs. Adding to the celebration,
Sam James—featured on The Voice and The Kelly Clarkson Show—will perform live from 11:00 am
to 1:30 pm, making the Vaillancourt studios a destination where fine art, tradition, and community
celebrate together.
9. Blackstone National Golf Course
R/P/H/F
227 Putnam Hill Road
Aloha Sutton! Transport away to a magical island... or at least to a warm place with food and drinks!
489 Central Turnpike
R/H/P
Stop in to make an ornament to bring home or put on our station tree. Take a chance on our beautiful raffle prizes. We also may have a surprise guest to take pictures with!
Route 3
11. Waters Farm
53 Waters Road
P/ F
Visit Sutton's Waters Farm, a living history site on the National Register of Historic Places to experience nostalgic charm of the holiday season. The Darling Barn will host fun for all beginning with a free, ticketed Breakfast with Santa (9-10:30am). Doors will then open to all Chain of Lights participants to take family pictures with the Jolly Fellow until 2pm. Enjoy arts and crafts planned for kids of all ages until 3pm. You will find Holiday Pickers Paradise and crafters to discover unique gifts and our famous apple crisp (until it runs out). While there is only ticketed seating for the full breakfast, pancakes will be served until 2pm. Outside, (weather permitting) be sure to stop by the Sutton Agricultural Trust for that special holiday photo in a Festive Farm Animal setting (10-12pm - $20 donation fee), visit the Captain Cornelius Putnam Blacksmith shop demonstration, take a "sleihay" wagon ride (also weather permitting) through the beautiful property, or find your perfect Christmas tree sold at the old fashioned tree lot (5 &7-8 footers). Discover the simple pleasures of a country Christmas!
12. Whittier Farms
90 Douglas Road
R/P/F/H
Celebrate Christmas on the Farm with tractor-drawn wagon-ride tours, plus holiday samples and shopping featuring Boar's Head Meats, Lake Champlain Chocolates, Cabot Creamery Cooperative, and more. The New England Dairy Milk Bar returns to Sutton to raise a glass of milk with you to local dairy. Our popular family favorite, Santa and his Reinsteins will be set-up for photos. New this year: Fast Dog Cafe will be open serving hot (and iced) coffee, breakfast sandwiches, chicken tenders, hot dogs, and more! From 12p-2p, come enjoy the music from St Joe and The Dorms.
13. Singletary Rod and Gun Club
300 Sutton Ave, Oxford
R/P/F/H
Visit local artisans and crafters, enjoy a bowl of chicken noodle soup or chili, or a hamburger and hot dog or have a hot beverage while shopping for that one of a kind item. While you shop, have your kids make an ornament at our crafts table!
14. Legacy Church
657-659 Central Tpk
R/P/F/H
Come join us at Legacy church. Take a walk through Santa’s village get into the Christmas spirit as music fills the air. Stop in at Mrs. Clause Christmas Cafe and buy lunch gourmet hotdogs, drinks and chips. Start shopping early with our vendors. Take a family selfie. Kids enjoy decorating cookies, buy one of our raffles, Grab a Delicious snack from Melissa’s cupcakes, fun for whole family!
R=Restroom
P=Parking
F=Food
H=Ada Accessible
Be sure to visit these not to be missed sites that are not on a trolley route:
6 Singletary Avenue
Watch our resident blacksmith at the M.M. Sherman Blacksmith Shop
54 Eight Lots Road
Although the trolley will not stop at this historic gem, it is worth the drive to 54 Eight Lots Road to tour this one-room school house built before 1773 and believed to be one of the oldest one-room school houses in the U.S.A. still standing on its original foundation. The school serviced children of some of the more famous Sutton forefathers of the Eight Lots region, so named for the eight 40-acre tracts of land apportioned to original settlers. Stop in and imagine what it was like to attend school over 200 years ago.
4 Uxbridge Road
The Friends of the Sutton Library will be selling merchandise, raffles, crafts for kids and of course all of our holiday books, movies and music will be out for you to borrow and enjoy!
130 Whitins Road
Catch some holiday spirit at Sleighbell Farm! While the trolleys will not be stopping at the farm, our Gift Barn will be stocked with ornaments, handcrafted Santas and snowmen, locally made pottery, wreaths and other greenery.
113 Singletary Avenue
Celebrate the winter holiday spirit... with the Snow Queen herself! Drive on over to O'Shea's from 11 to 2 for a magical visit with Elsa, and photos in Kristoff's sleigh. From 10 to 3 enjoy shopping handcrafted holiday decor, toasty hot chocolate, crafts and coloring. We're excited to meet you! Warm hugs!