Williamsburg’s Occasion for the Arts Returns October 4–5, 2025
WILLIAMSBURG, VA – October 4–5, 2025
Downtown Williamsburg will once again transform into a vibrant open-air gallery for the 52nd Annual Occasion for the Arts. Every block of Duke of Gloucester Street will be filled with color, sound, and creativity — from fine art exhibits and live music to dance, theater, and interactive demonstrations.
What makes this festival truly special is its unique blend: nationally recognized artists from across the country alongside performers and creators who are deeply rooted in Williamsburg’s cultural community. Over more than five decades, it has grown into one of Virginia’s premier cultural events, drawing thousands of visitors while directly supporting local arts education.
Art, Music, and More
🎨 The Visual Arts
Stroll Duke of Gloucester Street and explore booths featuring an extraordinary range of work — sculpture, painting, photography, jewelry, fiber arts, glasswork, and ceramics. Each artist brings a unique perspective, turning Williamsburg into a giant gallery beneath the autumn sky.
🎶 Live Performances
Multiple stages will showcase music and performances throughout the weekend. Here’s the full lineup:
Saturday, October 4
Morning
10:30 am – Christoff & Pedigo (Mainstage) 10:30 am – En Pointe Dance Academy (Prince George Stage) 11:15 am – Flute Frenzy (Prince George Stage) 11:30 am – Doug Wilcox (Mainstage) 12:15 pm – Daniel Scruggs (Prince George Stage) 12:30 pm – Poisoned Dwarf (Mainstage)
Afternoon
1:15 pm – Teacher Symposium (Prince George Stage) 1:30 pm – Sammy Lee (Mainstage) 2:15 pm – Williamsburg Youth Harp Society (Prince George Stage) 2:30 pm – Skip Friel and the Resonators (Mainstage) 3:00 pm – Daniel Scruggs (Prince George Stage) 3:30 pm – Joe’s Day Off (Mainstage)
Sunday, October 5
Morning
10:00 am – Colonial Williamsburg Fifes and Drums (Duke of Gloucester Street) 10:30 am – Rainbow Puppets (Prince George Stage) 11:30 am – Winsome (Mainstage) 11:30 am – William the Conjurer (Prince George Stage) 12:15 pm – Virginia Regional Ballet (Prince George Stage) 12:45 pm – Clan McCool (Mainstage)
Afternoon
1:15 pm – Ron Fetner (Prince George Stage) 2:00 pm – Higher Ground Jazz Band (Mainstage) 3:00 pm – Phil Casey (Mainstage) 4:00 pm – Runaway String Band (Mainstage)
👨👩👧 Family Activities
The festival is family-friendly, with art projects, demonstrations, and hands-on experiences designed to inspire the next generation of creators.
🍴 Food & Drink
Festival-goers can enjoy a wide array of local eats, from savory bites to sweet indulgences, provided by Williamsburg restaurants and food vendors.
Why It Matters
The Occasion for the Arts isn’t just about art shows and music. It’s about community. It’s a chance for Williamsburg residents and visitors alike to come together and celebrate creativity in all its forms. And it’s an important fundraiser, helping to support arts programs and education throughout the region.
Event Details
📅 Saturday, October 4 – Sunday, October 5, 2025
📍 Duke of Gloucester Street, Colonial Williamsburg
🌐 Festival Guide: Occasion for the Arts
A Note from Mr. Williamsburg
As someone who has lived, worked, and raised a family in Williamsburg, I love sharing stories like this. Events such as the Occasion for the Arts highlight the best of our community — its creativity, hospitality, and spirit of togetherness. Whether you’re a long-time resident or visiting for the first time, this festival is a reminder of why Williamsburg continues to be such a special place to call home.
I hope to see you on Duke of Gloucester Street this weekend — surrounded by art, music, and neighbors.
— John Womeldorf, a.k.a. Mr. Williamsburg