Welcome to your local update! Here's everything happening around Southern Vermont this month.

Reminder: For weekly and monthly recurring events, check out our recurring events post here.

Here is your updated draft for the December 2025 newsletter. I have separated the Manchester Merriment events, added the specific Local Maverick market (taking place just as the season kicks off), and included the full slate of December events for the Bennington Theater.

Jump to: Manchester Merriment | Bennington Theater | Live Music & Nightlife | Food, Bev, & Trivia | Outdoor & Family Friendly

Southern Vermont Events: December 2025

Your Guide to Holiday Happenings in Windham & Bennington Counties

December in Southern Vermont is packed with community spirit, from lighted tractor parades to cozy trivia nights. Here is a curated list of events taking place across the region to help you plan your month.

🎄 Manchester Merriment & Holiday Festivals

Manchester Merriment: The Main Event Series

• When: throughout December 2025

• Where: Manchester, VT

• Description: The signature holiday celebration of the Northshire. From shopping and dining specials to community gatherings, the entire town transforms into a winter wonderland.

• Link: Manchester Merriment Schedule

Local Maverick’s Holiday Market at The Equinox

• When: Saturday, November 29, 2025 | 11:00 AM – 3:00 PM

• Where: The Equinox Golf Resort & Spa, Manchester, VT

• Description: Kick off the season on Small Business Saturday! Shop a curated collection of over 20 Vermont vendors, makers, and food producers in the historic Colonnade Ballroom.

• Link: Local Maverick Event Info

Holiday Lighted Tractor Parade

• When: Saturday, December 6, 2025 | 5:30 PM

• Where: Manchester, VT (Main Street)

• Description: A local favorite! Watch antique and modern tractors draped in thousands of lights roll through Manchester Center. It’s a festive, one-of-a-kind display of Vermont ingenuity and holiday cheer.

• Link: Manchester Merriment Schedule

Shires Holiday Inn Tours

• When: Saturdays, December 6 & 13, 2025 | 11:00 AM – 3:00 PM

• Where: Various Inns from Manchester to Bennington

• Description: A self-guided tour of the region’s most beautiful inns, decked out in their holiday finest. Ticket proceeds often benefit local food cupboards.

• Link: Manchester Merriment Schedule

Market on Main (Brattleboro)

• When: Weekends in December (Dec. 5-7, 12-14, 19-21)

• Where: 74 Main Street, Brattleboro, VT

• Description: This pop-up holiday market transforms a downtown storefront into a winter wonderland featuring over 30 local vendors, artisans, and makers.

• Link: Brattleboro Events Calendar

Bennington Museum "Dreamscapes" Winter Gala

• When: Saturday, December 13, 2025 | 5:00 PM – 9:00 PM

• Where: Bennington Museum, Bennington, VT

• Description: An elegant evening featuring dinner, music by Midnight Choir, and a silent auction.

• Link: Bennington Museum Events

🎭 Bennington Theater: December Lineup

• Kids on Stage - A Workshop

  • When: Dec 3 & Dec 10, 2025

  • Description: Interactive theater workshops for youth.

• Trivia Night Live!

  • When: Thursday, December 11, 2025

  • Description: Test your knowledge in a fun, live trivia environment.

• Wine & IMPROV

  • When: Thursday, December 18, 2025

  • Description: An evening of comedy and fine wine—perfect for a lighthearted night out.

• A Cozy Christmas Cabaret

  • When: Saturday, December 20, 2025 | 7:00 PM

  • Description: A heartwarming evening of holiday songs and stories featuring local favorites.

• Reed Foehl & Friends

  • When: Saturday, December 27, 2025 | 7:30 PM

  • Description: A post-holiday musical celebration with the acclaimed singer-songwriter.

• Link for all events: Bennington Theater Tickets

🎸 Live Music & Nightlife

The Stone Church Concerts

• Where: The Stone Church, Brattleboro, VT

• Events:

  • Armchair Boogie: Saturday, December 6, 2025

  • Cursive: Saturday, December 13, 2025

• Description: Catch live performances at one of Southern Vermont’s most iconic venues.

• Link: Stone Church Events

Vermont Jazz Center Big Band with Peter Eldridge

• When: Friday, December 12, 2025 | 7:30 PM

• Where: Vermont Jazz Center, Brattleboro, VT

• Description: The VJC Big Band celebrates its 21st year with a special swing performance.

• Link: Vermont Jazz Center Concerts

Maxine Linehan: "This Time of Year" Holiday Concert

• When: Saturday, December 6, 2025 | 7:30 PM

• Where: Southern Vermont Arts Center (SVAC), Manchester, VT

• Description: An enchanting holiday concert performance at the beautiful Arkell Pavilion/SVAC campus.

• Link: SVAC Calendar

🍔 Food, Drink & Trivia

Trivia Night at Snow Republic Brewery

• When: Thursdays (Dec. 4 & 11, 2025) | 6:30 PM

• Where: Snow Republic Brewery, West Dover, VT

• Description: Gather your smartest friends for weekly trivia hosted by Laura. Prizes are awarded for the top three teams!

• Link: Snow Republic Events

SoVTYPs Gathering & Craft Fair

• When: Saturday, December 13, 2025 | 11:00 AM

• Where: Valley Craft Ales, Wilmington, VT

• Description: The Southern Vermont Young Professionals meetup coincides with local holiday craft festivities.

• Link: BDCC Events

Brattleboro Sunrise Rotary Trivia Night

• When: Monday, December 15, 2025 | 6:30 PM

• Where: American Legion, Brattleboro, VT

• Description: Monthly charity trivia night that includes dinner with your entry fee.

• Link: Sunrise Rotary Trivia

🏔️ Outdoor & Family Friendly

Kids Ski Free Week at Stratton

• When: December 6 – 12, 2025

• Where: Stratton Mountain Resort

• Description: Children 17 and under ski and ride for free during this special early-season week.

• Link: Stratton Kids Ski Free

Rudolph the Red-Nosed Reindeer Jr.

• When: Dec 5-7 and Dec 12-14, 2025

• Where: Dorset Playhouse, Dorset, VT

• Description: The Dorset Players present this family-friendly musical adaptation.

• Link: Dorset Players 2025 Season

Sun Mountain S'mores

• When: Saturday, December 27, 2025

• Where: Bromley Mountain, Peru, VT

• Description: Warm up by the fire pit with free s'mores after a day on the slopes.

• Link: Bromley Mountain Events

Thanks for Reading!