Top Things to Do in Williamsburg in May 2026
Top Things to Do in Williamsburg in May 2026
Here are a list of top things to do in Williamsburg with kids, teens or adults on a date night or afternoon out. May is an exciting time of year, the weather is warming up, the thrill of summer approaching is igniting and the beauty of Spring is on full display, this is a great time to get out and explore!
Top Things to Do in Williamsburg, Yorktown and surrounding towns in May 2026. In this big list we actually have a couple of other posts like our “Things to Do on Mother’s Day Weekend in Williamsburg” and our “Things to Do Memorial Day Weekend” that will give you another set of events!
Events are in date order so you can plan your month:
Food & Wine Festival at Busch Gardens
Flavors are in full bloom this spring as Busch Gardens’ Food & Wine Festival is going on now through June 22 on Thursday – Sundays (plus Memorial Day). Explore more than 150 international flavors at 18 themed food and beverage locations throughout the park, including new menus inspired by China and Poland. 80 NEW tastes and exclusive wine and liquor tastings, every visit offers a new adventure for culinary explorers. Read our review of this year’s Food & Wine Festival here
The Busch Gardens Concert Series also returns this summer with an exciting lineup scheduled with popular artists from Christian to Pop, select nights from April 25 – September 5, 2026. Concerts are included with park admission, seating is on a first come, first served basis. However, reserved and VIP seating is available for an additional fee.
Concerts:
Saturday, May 2 – Hanson
Saturday, May 16 – Pop 2000 Tour with Chris Kirkpatrick, O-Town, Ryan Cabrera & LFO
Saturday, May 30 – Hoobastank…
More info
The Lion King
Watch as giraffes strut, birds swoop, and Pride Rock rises right before your eyes. Whether it’s your first time or your fifteenth, there is nothing quite like the goosebumps you get when that first note of “The Circle of Life” hits. SevenVenues and Broadway in Norfolk are proud to announce the return of Disney’s THE LION KING to Chrysler Hall for a limited three-week engagement from April 30 through May 17, 2026. More info
Williamsburg Artists Group Spring Art Show
Come and shop original paintings, jewelry, and notecards and a plethora of other fine arts and crafts at Bruton Parish House in Colonial Williamsburg. The Williamsburg Artists Group returns for its popular fall sale. This is a great opportunity to meet the artists behind the art and learn the stories of the paintings and works that you are buying! The event, to be held on Friday, May 1, from 4-8 p.m.; and Saturday, May 2, from 10 a.m.-3 p.m., at Bruton Parish House at 331 Duke of Gloucester Street, will feature the work of about 20 local artists. More information
Merchants Square Free Concert Series Kicks Off
Mark your calendars for the grand inaugural event on Friday, May 1 from 6 pm – 8 pm with West Texas Exiles. Known for their roots-driven sound, rich harmonies, and electrifying live performances, the West Texas Exiles blend Texas country, rock, and Americana into a show that is both authentic and crowd-pleasing. Based in Austin and drawing inspiration from across the Lone Star State, the West Texas Exiles feature seasoned musicians with deep ties to Texas music traditions. This concert opens the 2026 Season of the FREE Merchants Square Concert Series! Concerts are on the First Fridays of the Month! … See the full list of bands – More Info
Colonial Williamsburg Military Encampment Weekend: The Most Fatal Widow-makers; Virginia riflemen arrive in Williamsburg
Colonial Williamsburg Military Encampment weekends are May 2 & 3 from 10 am – 5 pm. During this two day event, Colonial Williamsburg will capture a pivotal moment in the history of Virginia’s and America’s revolution; the 250th anniversary of the riflemen of the 7th Virginia Regiment arriving in Williamsburg. These troops, largely raised beyond the Blue Ridge Mountains, would go on to fight in some of of the most important battles of the Revolution, including Gwynn’s Island, Brandywine, Saratoga, Germantown, and Monmouth. More info
Bikes Out of Hibernation
Get that neglected bike out of your garage and get it ready for Spring, on Saturday, May 2 from 9 am – 1 pm at Jamestown Settlement! Free tire pumping and minor adjustments will be given by several local bicycle shops. FREE helmets and helmet fittings! FREE refreshments! Then take your bike for a spin on the adjacent Virginia Capital Trail or the Colonial Parkway!
Boots, Brews & BBQ Festival
On Saturday, May 2 from 12 pm – 6 pm at Riverwalk Landing in Yorktown, come and sample more than 30 different craft beers, dig into some amazing BBQ (available for purchase), and live country music to keep toes tapping all afternoon. More info
Lighting of the Cressets in Colonial Williamsburg
Head to Colonial Williamsburg at night, May 2, 9, & 23 from 8–10 pm on the historic Duke of Gloucester Street – they will be Lighting of the Cressets this spring! The 18th-century lighting brings the streets to life at night – so don’t miss the strolling musicians…More info
Art on the River – Riverwalk Landing
Come to the wonderful 13th Annual Art on River on Sunday, May 3 from 10 am – 4 pm at Riverwalk Landing, Historic Yorktown. This juried art show at the waterfront features the work of more than 35 local artists. You and your family can stroll down the Riverwalk and check out incredible one-of-a-kind works on display and for sale – including paintings, pottery, jewelry, glass arts, photography, woodwork, metalwork, and much more! Live music and great food will round out the day. More info
New Town Tunes – Free Concert Series
Bring a lawn chair or a blanket to Sullivan Square in New Town (grassy area behind Legacy Hall in New Town). Concerts run 5:30 – 8 p.m.; gates open at 5 p.m. Family and dog friendly. Enjoy food and drink for purchase from local restaurants, food trucks and breweries. Dogs welcome. FREE Concerts! Learn more
May 6 – Elton vs. Billy (Tribute to Elton John & Billy Joel)
May 13 – The Roadducks (Classic, Southern Variety Rock Band)
May 20 – The English Channel (America’s Premier British Invasion Band)
May 27 – Cari Lacey (Country Folk and Blues)
June 3 – Runaway String Band (Bluegrass Oldtime Swing) & Cooler Heads (Jam Band)
June 10 – Klaxton Brown – Motown Dance Band
Mahjong Nights at Paint on Pottery
Join Paint on Pottery for Mahjong Nights on May 7 & 14 from 6 PM – 8:30 PM, designed for every skill level! Whether you’re brand new to the game or looking to sharpen your strategy, there’s a session for everyone.Start with the 101 Lesson to learn the basics of American Mahjong, build confidence in the 201 Lesson with helpful winning strategies, or enjoy Open Play & Paint–where participants receive guided gameplay tips while creating their own custom dice trinket dish. All supplies are provided–just come ready to play, learn, and have fun! Sign up here.
Vintage Market & Car Show
Stroll through our Vintage Market at Riverwalk Landing on Saturday, May 9 from 8 am to 12 pm to hunt for upcycled treasures and beautiful collectibles, then head up the hill to Historic Main Street–our showplace for more than a dozen fully restored classic cars. Live music by the Liberty Dolls…More info
Jamestown Day – Jamestown Settlement
Mark the anniversary of the 1607 founding of Jamestown with family friendly programs, military salutes, maritime and interpretive demonstrations at Jamestown Settlement on Saturday, May 9 from 9 am – 5 pm. Visitors can board the Discovery and learn how sailors navigated the seas in the 17th century….More Info
Water Country USA opens for the 2026 Season
Get ready to take on the park’s thrilling slides, refreshing pools, and lazy rivers on Saturday, May 9. The park will be open May 10, 16 & 17, and open daily starting May 22! More info
KidLit Fest: Anniversary Edition
The Williamsburg Regional Library is celebrating the joy of children’s books at the fifth annual KidLit Fest on Saturday, May 9 from 12:30 – 4 pm at the Williamsburg Library! This year’s theme takes kids on a journey through time, spotlighting historical fiction with special connections to Williamsburg’s own past. Designed for all ages, the festival features engaging activities that explore the world of children’s historical stories while also commemorating the 250th anniversary of the Declaration of Independence. Highlights include an in-person author visit and book signing with Valerie Tripp, along with special guests from Colonial Williamsburg and the Jamestown-Yorktown Foundation, plus more to enjoy. More info
Mother’s Day at Zoom Room
Calling all dog moms! Celebrate Mother’s Day with a special event at Zoom Room Dog Training Williamsburg on May 9 from 6 PM – 8 PM, designed just for you and your furry friend.
Local artist The Simplistic Peach will be on site to create a custom sketch of your pup, making this a keepsake-worthy celebration. The event will be catered by Publix and will feature a fun BINGO game with exciting giveaways
Admission is $35 per person, and spots are limited, so be sure to sign up today!
Register online, or stop by the store with questions, or call (757) 808-5657 for more information.
Where to take Mom to Celebrate Mother’s Day in Colonial Williamsburg
Mother’s Day Brunch at the King’s Arms Tavern
Sunday, May 10 from 11 am – 2 pm
Mother’s Day Brunch at Shields Tavern
Sunday, May 10 from 11 am – 3 pm
Regency Room Mother’s Day Brunch
Sunday, May 10 from 11 am – 1 pm
Mother’s Day Brunch Buffet at The Lodge
Sunday, May 10 from 11 am – 3 pm
More information and reservations.
2nd Sunday Art & Music Festival
On Sunday, May 10 from 11 am – 4 pm shop unique handcrafts with 200 unique artisan vendors, enjoy live music, street performances and food trucks, at this fun, family friendly event. Great artist & music lineup planned! There’s something to be enjoyed by all! ADMISSION IS FREE. See who is coming…HERE
Mother’s Day Weekend Events – May 9 & 10
Here is our BIG list of events going on on Mother’s Day Weekend. And you can also head to our Daily Calendar to find all the events.
The Flame of Revolution: 5th VA Convention
To mark the 250th anniversary, come for a groundbreaking live theatrical performance unlike anything the Foundation has produced before. Written and directed by Nation Builders Katharine Pittman (Martha Washington) and Kurt Smith (Thomas Jefferson), The Flame of Revolution is a multimedia experience blending live action with digital projections to tell the story of a new, independent Commonwealth and the origins of a new nation.” exerpt from a letter from Cliff Fleet, President of Colonial Williamsburg Foundaion. Friday, May 15 from 8:30 – 9:30 pm and Saturday, May 16 from 8:30 – 9:30 pm at Colonial Williamsburg Capitol Circle. Free & Open to the Public. More info
Yorktown Market Days
Spend a beautiful morning on the York River, around 50 vendors will be selling seasonal produce, fresh baked goods, meats, fresh-cut flowers, handmade soaps and candles, gourmet dog treats, and a work from local artists and artisans. Saturdays, May 16, 23 & 30 from 8 am – 12 pm.
Outlander Day
On May 16 from 10 AM – 5 PM, spend the day celebrating all things Outlander during the final weekend of the “Outlander: Costumes Woven in Time” exhibition at the American Revolution Museum at Yorktown! For more information, see here.
Wonder Fest
James City County Parks & Recreation welcomes families of all ages to Wonder Fest on Saturday, May 16, 11 a.m.-3 p.m. at Chickahominy Riverfront Park. Explore hands-on activities, thrilling performances and surprises around every corner. Bring your curiosity and imagination for a day full of unforgettable wonder! Parking is$10/car (cash or check only); however, most activities are FREE! More info.
Sounds of Summer Concert Series
Kick off the Sounds of Summer Concert series this month, with BJ Griffin on May 21st and The Embers on May 28th! Enjoy the sounds of summer at Yorktown’s beloved Thursday night concert series at Riverwalk Landing.
This free outdoor event, held from May through August, features live music from 6:30 to 9 p.m. with an eclectic lineup of Beach Music, Motown, Pop, and R&B. Guests are encouraged to arrive early to claim a favorite spot on the grassy field in front of the stage.
Bring chairs, blankets, coolers, and dancing shoes for a fun evening by the water. Alcohol is permitted within the designated concert area, and nearby restaurants and a rotating food truck offer plenty of delicious take-out options to enjoy during the show. For the full line-up and more information, see here.
Bodacious Bazaar
On May 22-24, grab your friends and head to the Hampton Roads Convention Center, to shop 250+ vendors, artists, crafters and several of Virginia’s finest wineries – there is something for everyone! It’s going to be a great weekend of shopping. More info & tickets
Fee Free Day at National Parks
Plan a park adventure this May! In honor of Memorial Day on May 25, all entrance fees will be waived at sites managed by the National Park Service. It’s a great opportunity to explore a new national park or revisit a favorite while enjoying the beauty, history, and outdoor experiences our parks have to offer. For more Fee-Free Days at National Parks, see here.
Drummer’s Call Weekend in Colonial Williamsburg
Colonial Williamsburg’s Fifes & Drums, along with fife and drum units from across the United States, will celebrate the tradition of military music during Drummers Call Weekend on Friday, May 29 – Sunday, May 31. Free and open to the public to enjoy! These are really cool events – see all three with times and locations here.
Memorial Day Events
In the Historic Triangle there are usually quite a few events going on for Memorial Day weekend also known as the unofficial start to summer. So many that we have a separate post for it. Visit here to see all the events going on for Memorial Day including Colonial Williamsburg offering free admission for veterans and military families, May 22-25, and special programming on Monday, May 25. Visit here
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