3 Fun Outdoor Events in Williamsburg

Colonial Williamsburg Va is known for it’s history. Thousands of guests come to enjoy the sites of Thomas Jefferson, Patrick Henry, the Capitol and the Governors Palace in our Colonial Capitol. Here are some suggestions if you would love to combine some outdoor fun with history. Enjoy our 3 Fun Outdoor Events in Williamsburg.

The main road that runs through Colonial Williamsburg is Duke of Gloucester Street. This pedestrian street allows for some amazing opportunities for outdoor venues.

From concerts and Street fairs to Farmers Markets, you will find wonderful outdoor events happening in the Merchant Square area, just a 4 block walk down the street from our Williamsburg Bed and Breakfast.


Williamsburg Farmers Market

woman at the market

Every Saturday. March through December, farmers and local merchants bring their goods to the heart of Colonial Williamsburg and set up an amazing Farmers Market from 8am-noon.

Farmers offer ripe delicious vegetables and fruits, fresh cut flowers and homemade goodies. Local Bake Shops, coffee shops and specialty stores offer their selections of  breads, bagels, pies, scones other pastries.

Maybe you are more interested in fresh honey or local wines? Or maybe you just want to grab a cup of coffee to sit and enjoy the music performed by a variety of artists every weekend.

After a morning of enjoying the Williamsburg Farmers Market, you can enjoy strolling the local store fronts in Merchants Square that have everything to offer from jewelry to Scottish Sweaters. If you work up an appetite you can enjoy lunch at one of our local restaurants with outdoor seating, ranging from a casual sandwich shop to a French Bistro around the corner.

What will you miss if you don’t attend one of our Fun Outdoor Events in Williamsburg?

                                                                                                     Delicious fruits and vegetables

Fresh Cut Flowers

Bakery Items

Wine and Homemade Honey


Fresh Air



Williamsburg Second Sundays

food truck food

Walk down the street from your room at our Williamsburg Inn and you will find our Williamsburg downtown filled with tents of over 150 unique artisans, food vendors, musicians and street performers.

  The Outdoor fun is spread out over 6 blocks of downtown Williamsburg streets on the second Sunday of every month, March through December.

From 11am-5p, you will find amazing unique art, handcrafts and live music in a wonderful friendly atmosphere. Food trucks are scattered around the event as well as dessert trucks and adult beverages.

You may find local authors on hand for signings and pictures as well as local musicians and dancers performing live.

This is truly an Outdoor event that can be enjoyed by any age.


Occasion for the Arts 

young people looking at art

October 6-8, 2023

Now in its 55th year, An Occasion for the Arts, is Williamsburg’s premier fine art and music festival.

This amazing event features over 150 artisans from across 22 states to showcase their art in Williamsburg, Va.

This is no ordinary art show. There is live music on stage, dancing, cultural performances and a youth art exhibition.

Of course what would a festival be without food trucks, wine, beer and bands.

An Occasion for the Arts has expanded to become a three-day festival that also includes a Friday evening event, An Evening for the Arts.

This ticketed Friday event is a fundraiser to support an “Artist in Residence” program supporting the arts in Williamsburg / James City County Public Schools.

Purchasing a ticket to this event will support art education in the schools as well as offer you an artist preview, allowing you an early peak at that perfect treasure as well as enjoying music for the fantastic band, Good Shot Judy. There will be an eclectic mix of local Merchant Square restaurants providing food for the evening.

An Evening for the Arts will begin at 5 p.m., with a private shopping event of artwork from the talented festival artists and a chance for guests to mingle with the artists at the party. The full reception will begin at 7 p.m., with food stations featuring the best small bites in Merchants Square.

With wonderful outdoor venues in Williamsburg, be sure to reserve your stay in advance as rooms will book quickly. Just a short walk down the street you will find great accommodations at A Williamsburg White House Inn with a full complimentary breakfast each morning to start your day!