Holiday events throughout the region Tree sales and lightings, musical events, shopping, craft workshops, visits with Santa and much more

By Stacia Spaulding
©2024 Telegraph Publishing LLC

Do you need a Christmas tree or some hand-crafted gifts? Are the kids excited to meet Santa? How about a relaxing evening filled with holiday music?

The Telegraph has brought all the holiday events in the region together in one place. Our Calendar of Events contains additional information about several listings.

Do you have a Hanukkah, Christmas, Kwanzaa or other winter celebratory event that you would like to publicize? Email your events — as editable text only  — to Events Editor Stacia at calendar@chestertelegraph.org. Include a festive image as a jpeg or pdf. 

We’ll update these events as they come in, so be sure to check back!

Friday, Dec. 6

• Springfield Garden Club’s Holiday Market, 10 a.m. to 7 p.m. First Congregational Church, 77 Main St., Springfield. For sale will be handmade holiday arrangements, wreaths and other decorations.
• Springfield’s Annual Downtown Holiday Program, 4 to 8 p.m. Beginning at the Chamber of Commerce office, 56 Main St., with Sticker Map. Food will be sold from 4 to 6:30 p.m. at the entrance to Comtu Cascade Park. At 6 p.m. at Springfield Co-op lot, Santa will make his grand entrance for the community tree lighting and will be in his special house until 8 p.m. to visit with all of the children.
• Londonderry Tree Lighting and Open House with Santa, 6 p.m. Mountain Marketplace, 5700 VT-100, Londonderry. Cookies, hot chocolate and children’s activities.
• Weston Winter Cabaret, 7:30 p.m. Weston Theater Company at Walker Farm, 703 Main St., Weston. SOLD OUT.

Saturday, Dec. 7

• Christmas Bazaar, 9 a.m. to 3 p.m. Second Congregational Church, 2051 VT-11, Londonderry. Crafts, lunch and cookie walk. Click here for more information.
• Christmas Tree Sale, 9 a.m. to 4 p.m. Route 103 across from Marshall Road in Chester. Vermont balsam trees $47. To benefit the Chester Fire Department. The lot is staffed on weekends only. All other times, please leave payment in the mail slot or use the QR code for Venmo.
• Grafton Village Holiday Celebration takes place from 10 a.m. to 6 p.m. throughout the town. Other events include a Dog Parade, Santa’s Arrival at 11:30 a.m., Wagon Rides, Gingerbread House Extravaganza, Cookie Decorating, Community Fire w/S’mores, Holiday Shopping, Sugar House Tours and THE BIG RAFFLE. Click here for more information.
• Customer Appreciation Weekend, 11 a.m. to 4 p.m., Main Street, Chester. Several businesses on the Village Green will be offering specials and discounts.
• Holiday Open House, 11 a.m. to 5 p.m. Gallery at the VAULT, 68 Main St., Springfield.
• Christmas in Weston, 11 a.m. to 5 p.m. Visits with Santa and Mrs. Claus, horse-drawn wagon rides, Christmas caroling, cookie decorating, children’s crafts and face painting. At dusk, there will be a tree lighting on the Village Green and fireworks. Click here for more information.
• INNdulgence Tour, noon to 5 p.m. Self-guided tour of nine inns located in the region. Each is decked out for the holidays and offering an INNdulgent treat. All proceeds go to Vermont Foodbank. Click here for more information or to purchase tickets.
• Tree Lighting and Visit from Santa, 4 to 6 p.m. Village Green, Main Street, Chester.
• DaVallia’s Arts and Interiors Holiday Open House, 4 to 6 p.m. 39 North St., Chester. Bonfire, refreshments and special offers.
• Springfield Community Band Holiday Concert, 6 p.m. Riverside Middle School, 13 Fairground Road, Springfield. Click here for more information.
• Weston Winter Cabaret, 7:30 p.m. Weston Theater Company at Walker Farm, 703 Main St., Weston. SOLD OUT.

Sunday, Dec. 8

• Christmas Tree Sale, 9 a.m. to 4 p.m. Route 103 across from Marshall Road in Chester. Vermont balsam trees $47. To benefit the Chester Fire Department. The lot is staffed on weekends only. All other times, please leave payment in the mail slot or use the QR code for Venmo.
• Customer Appreciation Weekend, 11 am. to 4 p.m., Main Street, Chester. Several businesses on the Village Green will be offering specials and discounts.
• INNdulgence Tour, noon to 5 p.m. Self-guided tour of nine inns located in the Okemo Valley. Each is decked out for the holidays and offering an INNdulgent treat. All proceeds go to Vermont Foodbank. Click here for more information or to purchase tickets.

Tuesday, Dec. 10

• Christmas Celebration, 6:30 p.m. Perkinsville Community Church, 35 Church St. in Perkinsville. Music, caroling and reading of The Christmas Truce.

Thursday, Dec. 12

• Gift-Making Workshop for Adults: Old World Ornaments, noon to 2 p.m. Wilder Memorial Library, 24 Lawrence Hill Road, Weston. This program is inspired by art teacher Casey Junker Bailey’s trips to the holiday markets in Europe. The workshop is free, and all materials are provided.
• Green Mountain Middle/High School Holiday Concert, 7 p.m. Auditorium of the high school, 716 VT-103 in Chester. This holiday program features the school’s middle/high school band and chorus performing a variety of songs for the season. Free and open to the public.

Saturday, Dec. 14

• Christmas Tree Sale, 9 a.m. to 4 p.m. Route 103 across from Marshall Road in Chester. Vermont balsam trees $47. To benefit the Chester Fire Department. The lot is staffed on weekends only. All other times, please leave payment in the mail slot or use the QR code for Venmo.
• Holiday Fiesta, 10 a.m. to noon. Cavendish-Fletcher Community Library, 573 Main St., Proctorsville. Pages from old hymnals can be used to make a variety of ornaments, such as angels, birds, paper chains, stars and more. Free; all materials are provided, and there will be projects suitable for all ages. Treats for tasting and a piñata for children. Click here for more information.
• Gift-Making Workshop for Children, 10:30 a.m. to noon. Wilder Memorial Library, 24 Lawrence Hill Road, Weston. Art teacher Casey Junker Bailey will help children use printmaking, drawing and collage to make a variety of small gifts and ornaments for the people they love. The workshop is free and appropriate for all ages. All materials are provided.
• Christmas Tree Sale, 10 a.m. to 3 p.m. Next to the Grafton Inn, 92 Main St., Grafton. Proceeds benefit the Grafton Fire/Rescue Scholarship Fund.
• Meatball Saturday Open House, 11 a.m. to 3 p.m. Erskine’s Grain & Garden, 54 Grain Store Road, Chester Depot. Wagon rides until 2 p.m., meatballs served until 3 p.m. Donations for wagon rides benefit Whiting Library.
• Gingerbread House Decorating Party & Visit with Santa, 11 a.m. to 3:30 p.m. Stone Hearth Inn & Eatery, 689 VT Route 11W, Chester. Call 802-875-2525 to reserve your kit ($25), which includes pieces for 1 house, 2 gingerbread people, royal icing and candy for decorating.
• Chester-Andover Senior Christmas Dinner, noon. Green Mountain Union High School, 716 VT-103, Chester. The menu includes turkey and all of the fixings. Reservations for dining in and takeout are recommended; call Pat Budnick at 802-376-6643 or Chester Town Hall at 802-875-2173. Click here for more information.
• Holiday Sip ‘n Shop, 4 to 7 p.m. Smokeshire Design, 3630 VT-103 North, Chester. Live music, local vendors, a chance to win Simon Pearce items in a raffle and plenty of holiday cheer.
• VSO Brass Quintet and Counterpoint Concert, 5 to 7 p.m. Grafton Community Church, 55 Main St., Grafton. Enjoy a mix of sacred and holiday music. Admission  is free, but reservations are required. Send an e-mail that includes your name, telephone number and the number of tickets required. Click here for more information. 
• Springfield Community Chorus Christmas Concert, 7 p.m. Chester Baptist Church, 162 Main St.
• The Dance Factory’s ‘The Nutcracker,’ 7 p.m. Springfield High School, 303 South St., Springfield. Tickets are $15 for adults and $10 for children/students.  Click here for more information.

Sunday, Dec. 15

• Christmas Tree Sale, 9 a.m. to 4 p.m. Route 103 across from Marshall Road in Chester. Vermont balsam trees $47. To benefit the Chester Fire Department. The lot is staffed on weekends only. All other times, please leave payment in the mail slot or use the QR code for Venmo.
• The Dance Factory’s ‘The Nutcracker,’ 2 p.m. Springfield High School, 303 South St., in Springfield. Tickets are $15 for adults and $10 for children/students. Click here for more information.

Saturday, Dec. 21

• Christmas Tree Sale, 9 a.m. to 4 p.m. Route 103 across from Marshall Road in Chester. Vermont balsam trees $47. To benefit the Chester Fire Department. The lot is staffed on weekends only. All other times, please leave payment in the mail slot or use the QR code for Venmo.
• Holiday Express, 563 Depot St., Chester. Trains depart Chester Depot station (9 and 11 a.m. and 1, 3, and 5 p.m.) for a one-hour magical train ride. Meet Santa and his elves and enjoy hot cocoa and cookies. Click here for more information and to purchase tickets.
• Solstice Celebration, 10:30 a.m. to noon. South Londonderry Free Library, 15 Old School Road, South Londonderry. Children will be working with a variety of materials to create keepsake presents and ornaments for friends and family. Adults can join in the workshop or browse Solstice Book Sale. Refreshments will be served. The workshop is free of charge and appropriate for all ages.
• Santa Returns to His Special House at 6 Main St. in Springfield, noon to 3 p.m.
• Starry Starry Night, 4 to 7 p.m. Village Green, Main Street in Chester. A night lit by luminaries, with more than 18 participating businesses. Refreshments and events throughout town.
• A Seraphic Fire Christmas concert, 7:30 p.m. Brick Meeting House, 2 Main St., Grafton. Admission fee. Click here for more information or to purchase tickets.

Sunday, Dec. 22

• Christmas Tree Sale, 9 a.m. to 4 p.m. Route 103 across from Marshall Road in Chester. Vermont balsam trees $47. To benefit the Chester Fire Department. The lot is staffed on weekends only. All other times, please leave payment in the mail slot or use the QR code for Venmo.
• Holiday Express, 563 Depot St., Chester. Trains depart Chester Depot station (9 and 11 a.m. and 1, 3 and 5 p.m.) for a one-hour magical train ride. Meet Santa and his elves and enjoy hot cocoa and cookies.  Click here for more information and to purchase tickets.
• Yuletide Sing-Along, 1 p.m. Rockingham Meeting House, 11 Meeting House Road, Bellows Falls.

Tuesday, Dec. 24, Christmas Eve

• Christmas Eve Service of Lessons, Carols and Candelight, 5:30 p.m. Second Congregational Church, 2051 VT Route 11, Londonderry. Watch live via YouTube.
• Christmas Eve Candles & Carols Service, 6 p.m. United Church of Ludlow, 48 Pleasant St.