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Four people smiling with pride flags at an outdoor event.

Pride of Woodstock VT 2026 Celebration and Hotel Offers

Publication Date

May 11th, 2026

Location

Vermont

Article Summary

Join the vibrant community of Woodstock, Vermont, from June 4–6, 2026, for the third annual Pride of Woodstock celebration. This weekend-long event features a colorful lineup of activities including the famous High Heel Race, a "Made with Pride" arts fair, and a signature Drag Brunch. In honor of the celebration, the Woodstock Inn & Resort is offering an exclusive Pride getaway package designed to promote equality and inclusion in one of New England's most picturesque destinations.

Celebrate Love and Diversity in the Heart of Vermont

Woodstock, Vermont, is known for its quintessential New England charm, but from June 4th through June 6th, 2026, the town will be painted with every color of the rainbow. We invite you to the third annual Pride of Woodstock, a weekend-long celebration of love, diversity, and community.

This year’s celebration continues the tradition of blending Woodstock’s historic atmosphere with the vibrant spirit of the LGBTQ+ community. Whether you are a local or a traveler visiting for the first time, Pride of Woodstock offers a unique and welcoming environment where love knows no labels and everyone is embraced.

Weekend Highlights: High Heels, Art, and Drag

The 2026 schedule is packed with high-energy events and community gatherings designed for all ages:

  • The High Heel Race on Elm Street: Watch (or join!) the most spirited race in Vermont as participants sprint through the heart of town in their finest heels.
  • "Made with Pride" Arts & Crafts Fair: Support LGBTQ+ creators and local makers at this curated market.
  • Drag Brunch at the Woodstock Inn & Resort: Experience world-class entertainment and delicious local cuisine at the resort's signature Sunday event.
  • Dance Parties & Nightlife: Keep the energy going with evening celebrations and community mixers held across town.

The Woodstock Inn & Resort Pride Getaway

In collaboration with Preferred Hotels & Resorts, the Woodstock Inn & Resort is proud to champion initiatives that advance equality and systemic change for the LGBTQI+ community. To celebrate Pride weekend, the resort is offering an exclusive Pride Package for guests looking to unwind in luxury.

The Pride Package includes:

  • The Best Available Rate for your stay.
  • A welcome bottle of wine (Red, White, or N/A) to toast the weekend.
  • A $50 Resort Credit to be used toward dining, spa services, or resort activities.

Plan Your Woodstock Pride Experience

Woodstock is often called the most picturesque destination in Vermont, and during Pride weekend, that beauty is matched by the town's inclusive spirit. This is more than just an event; it is an opportunity to getaway, unwind, and celebrate authentic self-expression in a stunning mountain setting.

To reserve your Pride Weekend package, please call the Woodstock Inn & Resort reservations team directly at 1-800-448-7900. Join us in the Green Mountains this June to celebrate a community where everyone belongs.