Best Things to Do in Williamsburg and Yorktown in September 2025
Best Things to Do in Williamsburg and Yorktown in September (& Hampton Roads) 2025 Edition
If you live in Williamsburg, you probably know that we have an amazing number of cultural and entertainment events for such a small town, but maybe you are new here…or maybe you are coming to visit…and you are looking for things to do in and around Williamsburg, VA.
So the folks at The Burg Weekender & WilliamsburgFamilies.com have put together a big list of some of the best events in Williamsburg for September. There are a lot of them and even more on our Williamsburg Events Calendar.
We keep updating this list of great things to do all month long so be sure to check back.
Rhythms on the Riverwalk in Yorktown – FREE Outdoor Concerts
Bring a lawn chair, blankets, your dancing feet and your favorite peeps. And there will be food trucks at each event. Six back-to-back concerts on Thursdays from 6:30-8:30pm from September 4 through October 9. See all the details and info on each band here.
- September 4 – Runnin’ Shine
- September 11 – The KOS Band
- September 18 – Anthony Rosano and the Conqueroos
- September 25 – WonderLand
- Additional dates in October here
Fall Sidewalk Sale in Merchants Square, Williamsburg
Fall Sidewalk Sale in Merchants Square is September 5 – 7 from 10 am – 6 pm. Come support your favorite merchants during the Fall Sidewalk Sale! With offers ranging from 20% -75% off select merchandise, you’ll find unique gifts, accessories & fashions for everyone in the family. More information
Merchants Square Summer Concert Series featuring Jenny Don’t and the Spurs
On Friday, September 5 from 6 pm – 8 pm come out to the finale Summer Concert Series of the summer. For over a decade, Jenny Don’t and the Spurs, have been making waves in the alt-country scene with their high-energy performances and infectious enthusiasm. Their extensive discography includes three albums, an EP, and multiple singles, with their latest release, Broken Hearted Blue, debuting in June 2024. Expect a show filled with honky-tonk spirit, twangy guitars, and captivating stage presenceFood and drink available for purchase, make sure to bring a lawn chair or blanket. Family friendly and fun way to wrap up the summer! Learn more about this series!
Homeschool Days at the American Revolution Museum at Yorktown & Jamestown Settlement
Homeschool Family Days return from September 6 – 14, a special ticket offers families unlimited admission to both museums, plus a Homeschool Family Guide to dig into aspects of early American history. On select dates, education stations invite families to take a deep dive into historical topics through language arts, primary sources, historical narratives and critical thinking. Tickets can be purchased online or in-person at the museums. More information
Homeschool Days in Colonial Williamsburg
September 7 – 22 homeschoolers and their families can discover history brought to life in Colonial Williamsburg at a special discounted rate. Visit the historic sites where Revolutionary ideas were shaped, meet the tradespeople whose craftsmanship supported the War for Independence, and more. Additional information.
Yorktown Market Days – Special First Responders Market
Yorktown Market Days Special First Responders Market is on Saturday, September 6 from 8 am-noon. Emergency vehicles and personnel will be on-site to educate and answer your questions about what it’s like being a first responder. While you’re there, be sure to express your gratitude to the firefighters, sheriff’s deputies, emergency communications dispatchers, and public works officials who protect our community. This family-friendly event is a perfect way to spend a Saturday morning (balloon artist will be there starting at 9 am). Be sure to check out the York County Fire & Life Safety’s fire truck and safe house, the York-Poquoson Sheriff’s Office’s patrol cars, crime prevention trailer, SWAT team & K-9 unit, and the U.S. Navy’s Naval Weapons Station Bomb Squad. Shop for seasonal produce; meats; breads; fresh-cut flowers; handmade soaps and candles; honey; gourmet dog treats; and a beautiful display of work from local artists and artisans.
Yorktown Market Days regular market will take place Saturday, September 13, 20 & 27 from 8 am- noon. Head down to the beautiful waterfront in Historic Yorktown and visit produce, bread, meat and artisan booths. They have food trucks and free parking. There are restaurants and local stores to visit as well. This is a must visit weekly market. Learn more.
1781 Yorktown Before the Siege
On Saturday & Sunday, September 6 & 7 from 10 am – 3:30 pm, take a step back in time to see what life was like in the British Camp before the arrival of the American and French forces on September 28, 1781. Learn how Lord Cornwallis and his troops invaded the town and set up camp. There will be artillery demonstrations, cooking and laundry lessons, a blacksmith display, military re-enactments on the Yorktown Battlefield, and more! Additional info
Watermen’s Museum Oyster Roast
Shell-ebrate your love for seafood during this annual fundraiser on Saturday, September 13 from noon -3 pm! Enjoy fresh-roasted or raw oysters from various local sources, regular and gluten-free clam chowder with or without bacon, hot dogs, sides, and more. For tickets, call (757) 887-2641 or email admin@watermens.org. Active military and museum members receive a $5 discount. Kids 5 and under may join for free. More info
Colony Auto Enthusiast Annual Car Show
Come check out this year’s Colony Auto Enthusiast Annual Car Show on Sunday, September 8 from 10 am – 2 pm. 50 Roadsters will be on display from Duke of Gloucester Street at Henry Street to Nassau Street in Merchants Square. The vehicles represent a wide variety of makers and are from the 1920’s to the 2020’s. This is free and open to the public. More info
2nd Sundays Arts & Music Festival
2nd Sunday Art & Music Festival will be on Sunday, September 14, from 11 am – 4 pm. Just as the title indicates this is a monthly event that includes unique handcrafts from more than 180 artisans, live music, performing arts and food trucks in a fun and family-friendly atmosphere. Wide range of handcrafts and continuous live music & performances. There’s something to be enjoyed by all! ADMISSION IS FREE. Great way to spend the Sunday in the Burg! For a list of vendors click here.
Drool in the Pool at Chickahominy Riverfront Park
Drool in the Pool at Chickahominy Riverfront Park is being held on a Sunday, September 8, from 11 am – 3 pm. All well-behaved dogs are welcome to the close-out of summer swimming. Pups can also run through the splash pad. Music, refreshments and goodies featured! $10/per dog – learn more
ADULTS: MEET & MAKE- Embroidered Crew Neck Sweatshirt with Tabitha Sewer Studio
Sunday, September 15 at 3 pm – More info and get your spot
Join in this Adults: Meet & Make in the a bright, fun environment of Tabitha Sewer Studio – it is a great place to connect and create! Ladies, you are going to love this project. Together you will use simple embroidery stitches to create a fun embellished fall-themed sweatshirt. Light refreshments and beverages are provided. Just bring a sweatshirt to embroider and will provide the floss and instruction. Bring your friends or make some new ones! More info and get your spot
BurgQuest – Tabletop Gaming Festival
A three day, September 20-22, tabletop gaming festival featuring board game and RPG free play, panels, guests, game demos, field trips, game design workshops, and more at the Woodlands Conference Center in Colonial Williamsburg. For all ages and interest levels. Ticket gives you access to all three days. Additional information and purchase tickets.
Movies in the Park: The Goonies (1985) PG
Saturday, September 21 at McReynolds Athletic Complex in Yorktown. Movie begins roughly 15 minutes after sunset (around 7:45 pm). Full concessions will be available for purchase. You are encouraged to bring blanket and/or chairs for the showing. More info
Opera in Williamsburg presents: Donizetti’s Lucia Di Lammermoor
Opera in Williamsburg presents: Donizetti’s Lucia Di Lammermoor. Live fully-staged opera with world-class cast. Concessions offered at the venue. In the original Italian, with English supertitles. Reserved seats. Performances are Wednesday, September 18 at 7:30 pm, and Friday, September 20 at 8:30 pm, and Sunday, September 22 at 2:30 pm at the Crosswalk Auditorium at the Kimball Theater in Merchant Square. Tickets and details at www.operainwilliamsburg.org.
Want to Attend a Working Rehearsal of an Opera for FREE? Ever wanted to see the behind the scenes work that goes into putting together an opera? Now is your chance on Monday, September 16 at 2:30 pm. Opera in Williamsburg’s dress rehearsals are open for free to K-12 students with chaperone. Register (free) to attend a working rehearsal of Opera in Williamsburg’s upcoming production of Donizetti’s Lucia Di Lammermoor (not a full run of the opera). Please sit at the assigned areas — do not sit in front of the stage director. Once you register please check your email for possible updates before heading for the rehearsal. Register here
Picnic on the Pier – After Hours at the Jamestown Settlement
Blues, Barbecue & Stunning Views at Jamestown Settlement on September 20 from 6 – 8 p.m. Shake out your picnic blankets and make plans for an evening of blues, barbecue and stunning sunset views during this year’s Picnic on the Pier at Jamestown Settlement. Set along a picturesque backdrop of the James River waterfront, spend time with friends savoring delicious barbecue and beverages from Williamsburg favorites Old City BBQ and The Virginia Beer Company. Live music from Virginia’s Blues Ambassador will have your toes tapping, fingers popping and hips shaking to the sounds of The Bobby BlackHat Band. More info and tickets
Annual Watermen’s Museum Yorktown Folk Festival
Annual Watermen’s Museum Yorktown Folk Festival is on September 21 from 10 am – 6:30 pm & September 22 from 12 – 6:30 pm. This annual family friendly festival features musicians and dancers from all over Virginia. Music is hosted on multiple stages including Folk, Blues, Maritime, Rock and Roll, Celtic, and Sea Shanteys, and even more genres. Performances are free and open to the public. Music schedule and more info here.
Harvest Festival- Chickahominy Riverfront Park
The Harvest Festival is back on Saturday, September 21 from 11 am – 3 pm! Join James City County Parks & Recreation for this fun, fall annual family tradition! The festival features free activities for the kids including face painting, arts and crafts, a petting zoo, inflatables!
Scarecrow Stuffing is back too by popular demand, so come make the biggest, the best, and maybe the only scarecrow in your neighborhood…more
Call all dog lovers…don’t miss this event at Zoom Room Williamsburgon Sunday, September 22 from 5 – 7:30 pm! Turn a photo of your pup into a hand painted masterpiece! Price includes instruction, all supplies and light snacks. This is a parents night out event, so pups will stay at home. Space is limited, visit www.zoomroom.com/location/williamsburg/ to register.
Fall Afternoon Tea at the Williamsburg Inn
Enjoy a lovely afternoon with friends and loved ones with the fine tradition of Afternoon Tea, in the Goodwin Room at The Williamsburg Inn, September 26 – 28 from 2 – 3 pm. Relish in a selection of handmade freshly baked scones, tea sandwiches and pastry delights served with a signature tea from the Chef, in collaboration with the Tea and Spice Exchange. Make your reservation!
25 Years of Fear: Busch Gardens Williamsburg’s Howl-O-Scream
Howl-O-Scream at Busch Gardens returns to take over the night starting select nights September 6 to November 9. – Once the day turns to night, Busch Gardens® Howl-O-Scream® returns in full force, taking over the entire park with five haunted houses, six terror-tories, four sinister shows, and unsuspecting horrors awaiting their victims at every turn. Beyond the haunts, guests can take their horror to new heights with nighttime rides on world-class coasters, including the all-new Loch Ness Monster: The Legend Lives On.
The Halloween Spooktacular for Kids at Busch Gardens
Halloween Spooktacular for Kids at Busch Gardens – Saturdays & Sundays starting September 24-October 29. A Sesame Street® Halloween Event Celebrate not-too-spooky daytime family fun at Busch Gardens’ Halloween Spooktacular in the Sesame Street® Forest of Fun™. On Saturdays & Sundays, kids (ages nine and under) are invited to dress up in their favorite costumes and enjoy our ALL-NEW Trick-or-Treat Trail in the Wild Reserve. Plus, join in the fun with the Countdown to Halloween Show, dance parties, a festive hay maze and a costume parade alongside favorite Sesame Street friends. New themes every weekend, unique activities and special photo opportunities offer a different experience with every visit.
Yorktown Art Stroll
The 13th Annual Yorktown Art Stroll is on Sunday, September 29 from 10 am – 5 pm at the Freight Shed & Riverwalk Landing in Yorktown. Visitors will find a wide range of art for sale at including paintings, pottery, photography, jewelry, sculpture, mosaics, painted furniture, and mixed media. Don’t miss the opportunity to participate in a community painting project and listen to acoustic harmony trio, Audio Portrait, from 11 a.m. to 3 p.m. This event is free and open to the public. Presented by the Yorktown Arts Foundation and York County with support from the York County Arts Commission. More info
Bookmark this post so you can check back – because when new events come up we will add them below! We have also included a few events from the Hampton Roads area because they are less than an hour drive and completely worth it!
We have these Best things to Do in Williamsburg monthly guides of events to help you plan your fun time. Check them all out here, and check make sure to check out the pages we have below!
