Farm with red barn, green fields, and trees under blue sky.

May in Woodstock, Vermont

A Season of Delight

May in the heart of Vermont brings excitement, renewal, and beautiful spring days. With outdoor experiences resuming, flowers and fresh garden produce flourishing, and some of our favorite events of the year on the horizon, this month feels like a crescendo of enjoyment. Nevertheless, there is always time to slow down and savor the fresh air, wellness at The Spa, and seasonal flavors in our restaurants. Whether you’re exploring a local trail or lingering over a leisurely afternoon in the village, you’re invited to strike a perfect balance between discovery and stillness. Join us and delight in springtime in Woodstock, Vermont.

Golf course surrounded by forested hills under a blue sky with clouds.

Legendary Vermont Golf

Our 18-hole championship golf course is open for its 131st season! The scenic Woodstock Country Club sits less than a mile from the main Inn and offers premier play as the course winds across the Kedron Brook and along the base of Mt. Peg. Beyond the fairways, the course includes a driving range and practice putting greens. The welcoming clubhouse features a friendly Golf Shop with apparel and club rentals, event spaces, and the Fairway Grill, set to open later in the month with delicious lunch options and your favorite drinks.

Join us this spring, summer, and fall for legendary Vermont golf!

Chef’s Table Experiences

Reserve your seat at our specialty Red Barn Dinner events, where our chefs prepare ingredients picked right outside the dining room doors from our organic Kelly Way Gardens. Thursday Dinners feature 4 courses with local farm partners, and family-style Sunday Suppers showcase 3 courses of fresh, seasonal cuisine. Dig deeper into our culinary story with the video below!

View the 2026 Red Barn Dinner Series

White barn with open doors, bicycles outside, green lawn, pink flowers in foreground.

Introducing the Outdoor Hub

Just beyond the South Garden at the Inn, sits our center for all things outdoor adventure! The newly reimagined Outdoor Hub is here to:

-- Create an itinerary of the best regional outdoor activities for you!
-- Take you fly fishing with our Orvis Endorsed Guides.
-- Offer mountain bike rentals and knowledgeable guidance on the best local trails for you.
-- Plan your day hikes! From short local jaunts to longer treks, our experts will help you pick what trails to take on.
-- Curate fly fishing gear essentials in the shop.

Explore the Outdoor Hub

Pride Weekend in Woodstock

The 3rd annual Pride of Woodstock festivities kick off Thursday, June 4! This year, new events have been added to the weekend alongside favorites like the High Heel Race and Drag Brunch at the Woodstock Inn.

Celebrate Pride in Woodstock!

Join us to kick off the annual Pride of Woodstock, Vermont weekend on the Front Lawn! Sip cocktails while you meet others and get the celebration started.

Cheer on racers as they sprint, strut, and stumble their way through this crowd-favorite Pride tradition.

Movie Screening of Claim The Lane: Becoming Roxy

Settle in for a curated film that celebrate LGBTQ+ stories, voices, and creativity. This documentary tells the brave story of Roxy Bombardier, an Iraq veteran amateur cyclist who risks losing her closest relationships to be her true self and transition at age 51.

Take in scenic views and fresh air on a relaxed group ride through the beauty of Woodstock and the surrounding countryside. Enjoy a gravel ride with Roxy Bombardier and the team at Ranch Camp in Woodstock.