Top Things to Do in Williamsburg in May 2025
Top Things to Do in Williamsburg in May 2025
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 2025. 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
Merchants Square Free Concert Series Kicks Off
Mark your calendars for the grand inaugural event on Friday, May 2 from 6 pm – 8 pm with Cam Clark. A musician, artist, and producer from Paris, KY, whose Appalachian-inspired sound explores themes of love, time, and acceptance. His debut album, The Outer Reaches, blends soulful, boundary-pushing music shaped by touring experience and collaborations with Grammy-winning producer Al Sutton. This concert opens the 2025 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
Bikes Out of Hibernation
Get that neglected bike out of your garage and get it ready for Spring, on Saturday, May 3 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!
Indigenous Arts Day – Jamestown Settlement
Bring the family to Indigenous Arts Day on Saturday, May 3 from 11 am to 5 pm. It celebrates the enduring legacies of Indigenous cultures with traditional and contemporary art forms by Indigenous artists, including special outdoor performances of music and dance. Clark Stewart (Chickahominy) will emcee performances on Jamestown Settlement’s mall, where a variety of Indigenous artists and craftspeople will….more info
Burning of the Socks/Canoe & Kayak Season Kick-Off
Begin your canoe and kayak adventure with a rite of Spring on the Chesapeake Bay on Saturday, May 3 from 10 am – 1 pm at York River State Park. Burning socks is a tradition among sailors near Annapolis. Participants are asked to bring a pair of natural fiber socks to add to the ritual fire. Continue reading
Blues, Brews & BBQ Festival
On Saturday, May 3 from 12 pm – 6 pm, come and sample more than 30 different craft beers, dig into some amazing BBQ (available for purchase), and listen as some of the best Blues musicians in Hampton Roads and beyond take the stage at Riverwalk Landing. More info
The Sleeping Beauty Presented by The Movement Ballet
Join the dancers of Williamsburg’s youth ensemble as they bring this beloved fairy tale to life in a lavish production featuring professional guest artists on Saturday, May 3 (Fairytale Matinee at 1 pm and Evening Classical Performance at 4:30 pm) at the Kimball Theater. Families with young children should plan to attend the Fairytale Matinee — an abbreviated performance that includes a meet and greet with the cast afterward! The 4:30 pm performance is the full 4-act classical ballet, with a run time of approximately 2.5 hours. More info
Lighting of the Cressets in Colonial Williamsburg
Head to Colonial Williamsburg at night, May 3, 10, 24, 31 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 12th Annual Art on River on Sunday, May 4 from 10am – 4pm 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 7 – The Fuzz Band
May 14 – London and WOAH – 2 Bands One Night
May 21 – Wolph
May 28 – Slapnation
June 4 – Wilder Horses
June 11 – The Nashville Nights Bands
Edgar Meyer, Tessa Lark & Joshua Roman Perform LIVE
Experience a night of genre-defying brilliance as legendary bassist Edgar Meyer joins forces with violinist Tessa Lark and cellist Joshua Roman for an unforgettable performance. Co-sponsored by the Virginia Arts Festival, this all-star trio blends classical mastery with boundary-pushing creativity. More info
Mother’s Day Weekend Tea – Williamsburg Inn
Treat Mom, friends, and loved ones to the fine tradition of Afternoon Tea at The Williamsburg Inn on May 8, 9 & 10 from 2 – 3 pm with an exciting Mother’s Day spring-themed tea. It’s not on Mother’s Day but starts the Thursday leading up to it and then again on Friday & Saturday! More Info
Sentara Cap2Cap presented by Dominion Energy
Gear up for the 20th annual Sentara Cap2Cap presented by Dominion Energy, one of the region’s premier cycling events on May 9 and 10. This exciting event welcomes riders of all ages to experience. Whether you’re looking for a fun outing or a thrilling challenge, there’s a distance for everyone, from a fun filled 7-mile family ride to a 100+ mile adventure! Family-friendly party zone with music, activities, and local vendors…Continue reading
Vintage Market & Car Show
Stroll through our Vintage Market at Riverwalk Landing on Saturday, May 10 from 8 m. 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
Virginia Living Museum Native Plant Sale
The Virginia Living Museum Annual Spring Plant Sale will be outdoors in the Museum’s Conservation Garden on May 3 & 4, May 10 & 11 from 9 am-4:30 pm. Choose from an array of beautiful and unusual museum propagated plants ready for planting. Many of these native plants are excellent for attracting wildlife to your yard and are a good choice for area gardeners because such plants tolerate the area’s weather. 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 10 from 9 am – 5 pm. Visitors can board the Discovery and learn how sailors navigated the seas in the 17th century….More Info
Peter Pan Jr. presented by Centerstage Academy
On Saturday, May 10 at 2 pm at the Kimball Theater, Centerstage Academy presents Peter Pan Jr. Soar to Neverland in this magical stage adaptation of the classic tale! Featuring beloved songs like “I’m Flying” and “I Won’t Grow Up,” this high-energy musical is eerfect for the whole family. Join Peter, Tinkerbell, and the Darling children on a whimsical adventure with pirates, fairies, and childhood dreams. Presented by special arrangement with Music Theatre International (MTI). Tickets
Water Country USA opens for the 2025 Season
Get ready to take on the park’s thrilling slides, refreshing pools, and lazy rivers on Saturday, May 10. The park will be open May 17 & 18, and open daily starting May 23! More info
Where to take Mom to Celebrate Mother’s Day in Colonial Williamsburg
Mother’s Day Brunch at the King’s Arms Tavern
Sunday, May 11 from 11 am – 2 pm
Mother’s Day Brunch at Shields Tavern
Sunday, May 11 from 11 am – 3 pm
Mother’s Day Brunch Traditions – Williamsburg Lodge
Sunday, May 11 from 4 – 8 pm
Mother’s Day Dinner in the Terrace Room – Williamsburg Inn
Sunday, May 11 from 5 – 9 pm
Mother’s Day Brunch in the Rockefellers Room – Williamsburg Inn
Sunday, May 11 from 5 pm – 9 pm
2nd Sunday Art & Music Festival
On Sunday, May 11 from 11 am – 4 pm shop unique handcrafts with 180+ 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
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 16 & Saturday, May 17. Events in the day and a Military Tattoo at night. Free and open to the public to enjoy! These are really cool events – see all three with times and locations here
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. Saturday, May 17 is a special Community Market and Saturday, May 24 & 31 are regular markets.
Family Fun Fest
James City County Parks & Recreation welcomes families of all ages to Family Fun Fest on Saturday, May 17, 11 a.m.-3 p.m. at Chickahominy Riverfront Park. The annual event is designed to entertain, enrich and educate the entire family! Some featured events include inflatables, games, Kiwanis Kids Train, petting zoo, costume characters, face painting and more! Parking is $10/car (cash or check only); however, most activities are FREE! More info
Colonial Heritage Model Railroad Display & National Train Day Celebration
On Saturday, May 17 from 10 am – 4 pm and Sunday, May 18 from 1 pm – 4 pm. The Colonial Heritage Model Railroad Club will be operating Yarmouth Creek and Western Railroad. Assembled from 20 different modules into a HO single display, their layout includes mountains, towns, and a new operating turntable and roundhouse. A challenge will be to locate hidden objects placed somewhere on the display. Be sure to stop by the Norge Depot to see rail artifacts with a Williamsburg connection. More Info
Riverwalk Landing 20th Anniversary Celebration
Riverwalk Landing is celebrating its 20th anniversary, and everyone is invited to join the fun. This is a five-day celebration extravaganza, Thursday May 22 – Monday, May 26. Enjoy live music, food, family-friendly activities, raffles, games, and even special discounts! See the full schedule of events.
Bodacious Bazaar – May 23, 24 & 25
Hampton Convention Center
Grab your friends and get ready to shop at over 250 vendors, artists, crafters and several of Virginia’s finest wineries at the Hampton Roads Convention Center – there is something for everyone! It’s going to be a great weekend of shopping. More info & tickets
Mother’s Day Weekend Events – May 10 – 11
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.
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 24-27, and special programming on Monday, May 26. Visit here
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