Woodstock, VT artwork
The Family Vacationer

Woodstock, VT

  • S1E168
  • 10:34
  • November 1st 2024

Episode 168 Highlights:

  1. Introduction to Woodstock, Vermont
  • Discover this charming town in central Vermont, near Lebanon, NH, and Rutland, VT.
  • A brief history of Woodstock’s New England character and why it’s a great holiday destination.
  1. Wassail Weekend Preview
  • A glimpse at the 40th Annual Wassail Weekend, held December 13–15:
  • Wassail Scavenger Hunt: Start your holiday adventure at the “Town Smiler” with a town-wide scavenger hunt.
  • Christmas at Billings Farm & Museum: Enjoy Victorian holiday traditions, including candle-dipping and sleigh rides.
  • Rare & Vintage Book Sale and Story Hour at Norman Williams Public Library.
  • Woodstock Town Hall Theatre: Live performances and holiday music in a historic setting.
  1. Saturday’s Main Events
  • Artisan and Food Market on the Village Green: Local crafts and treats.
  • Wassail Parade: Horses decked out in festive regalia for an iconic holiday parade.
  • Luminary Lighting and Caroling: Caroling, tree lighting, and a cozy bonfire to end the day.
  1. Family-Friendly Sunday Activities
  • Billings Farm Victorian Traditions: Another chance for old-time holiday charm.
  • Skate with Santa at Union Arena: A holiday skating experience with Santa.
  • Snow Maiden Puppet Show at Town Hall Theatre.
  • Messiah Sing at Our Lady of the Snows: A community sing-along of Handel’s Messiah.
  1. Tips for a Great Visit
  • Dress Warmly: Layers are key for Vermont’s cold winters.
  • Plan Ahead: Reserve tickets and dinner reservations early.
  • Shuttle Service: Park at Woodstock Union High School and take the free shuttle.
  1. Dining and Lodging Suggestions
  • Dining: Enjoy a cozy meal at local spots like Worthy Kitchen and Mon Vert Café.
  • Accommodations: Stay at The Woodstock Inn & Resort for a memorable holiday getaway.
  1. Year-Round Attractions and Festivals
  • Woodstock is great all year! Explore other events, outdoor activities, and arts festivals that make this town a family-friendly destination.

Social Media & Hashtags:

Share your Wassail Weekend photos with #WoodstockVT and tag @TheFamilyVacationer to be featured!

Links and Resources Mentioned:


The Family Vacationer

A podcast dedicated to families that travel. So many of our memories come from time spent with our family. We want to help you make the most of your family vacations. We do that by covering travel destinations, travel apps, and gadgets, and talk to travel experts for ways to make family travel less stressful. Who doesn't want that?

Meet the Hosts

Rob Jones avatar
Rob Jones
Co-Host

Growing up, Rob Jones mainly traveled to Florida for vacation. Those family trips to Orlando and the Gulf Coast are cherished memories that influence him to this day. His entire professional career has involved travel. From working in the music business to event marketing, Rob has traveled to 46 states and five countries. Rob has been married to his wife, Traci, for 16 years and they love to travel with their three children: Ruthie, Nash, and Chase.

Traci Jones avatar
Traci Jones
Co-Host

    Traci's been shaking up the Dawson County School System for four years now, injecting it with her unique brand of energy and enthusiasm. When she's not molding young minds, you'll find her co-conspiring with her sister at Seasonal Events and Design—because who doesn't love a good party?

    She's a self-proclaimed beach aficionado, never meeting a sandy shore she didn't instantly click with. And let's not forget her partner-in-crime for the past eighteen years, Rob, who's been keeping up with her antics and their three beautiful troublemakers—Ruthie, Chase, and Nash. Together, they're a whirlwind of chaos, laughter, and love.

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