Best Things to Do in Williamsburg, Virginia in October 2026
Fall is a wonderful time of year to live or visit Williamsburg, VA and its surrounding towns. There are a ton of fun activities for you and your family to do in October, the weather is nice so its enjoyable to be outside and the leaves are changing which is a beautiful experience. Don’t miss the highlighted events below.
King of Glory’s Children’s Consignment Sale
King of Glory on Friday, October 2 from 9 am – 6 pm and Saturday, October 3 from 8 – 11 am
The King of Glory Children’s Consignment Sale features high-quality children’s clothes, toys, books, and equipment ranging from infants to juniors at a fraction of their retail costs. This is a huge sale so get ready to shop! More info including how to consign
Merchant Square Concert Series featuring Pressing Strings
Merchant Square on Duke of Gloucester Street on Friday, October 2 at 6 pm
Pressing Strings wraps up the Merchant Square Concert Series. Known for blending indie folk, soul, and rock into an emotionally rich and compelling live performance. With soulful vocals and thoughtful songwriting, Pressing Strings create a sound that is both powerful and deeply engaging. Based in Annapolis, Maryland, Pressing Strings have earned national attention through extensive touring and a growing catalog of recordings that showcase their genre-blurring style and strong musical identity.
Bring a lawn chair and your friends. Concerts are FREE and open to the public!
Yorktown Wine & Oyster Festival
Riverwalk Landing Yorktown on Saturday, October 3 from Noon – 4 pm and Sunday, October 4 from Noon – 4 pm
The Yorktown Wine & Oyster Festival returns for two days of fine wine, fresh seafood, and waterfront views that can’t be beat. Yorktown’s Wine & Oyster Festival pairs the finest Virginia wines with the freshest local seafood—including succulent oysters served raw, roasted, and steamed. More info.
Boo Bash at the Beach
Jamestown Beach Event Park on Saturday, October 3 from 1 – 4 pm
Enjoy a day at the beach with a Halloween twist! Enjoy Trick-or-Treating, hands-on activities, music, games, food for purchase and more! Choose a pumpkin from the patch on the beach to carve and decorate available first-come, first-served while supplies last. Costumes welcome; please, no costume masks. Children must be accompanied by an adult. For more info on this event go here.
Parking Fee: $5/car (cash or check only)
Counts Spooktacular and Howl-O-Scream
Busch Gardens Williamsburg select nights through November 1
During the daytime there are lots of fun kid-friendly activities. These include trick or treating, a hay maze, character fun, and more. Be sure to head out by 5 pm, the park will begin to transform into its haunted self. Counts Spooktacular runs on Saturday’s and Sundays and is made for kids.
Howl-O-Scream begins at 6 pm. Get ready for 5 haunted houses, 5 terror-tories™, 4 sinister shows, and plenty of creepy surprises lurking around every corner. Plus, test your thrill threshold with 10 world-class coasters at night, offering a completely different ride experience. Learn more
New Town Tunes Concert Series
October 7 – DOUBLE HEADER Channel 90, high-energy 1990s tribute band AND Three Hour Tour, Yacht rock and classic AM gold
October 14 – U2TOPIA – Washington D.C. based U2 Tribute Band
The New Town Tunes Concert Series wraps up with the last two concerts in October. Bring your lawn chair or blanket and enjoy the outdoors while you take in the tunes from some of our top area bands. Dogs welcome! Food and beverages available for purchase from New Town Restaurants, Local Food Trucks & Breweries! For more information, visit New Town Special Events.
Lighting of the Cressets in Colonial Williamsburg
Colonial Williamsburg on Fridays & Saturdays from October 9 – 31 from 6 – 9 pm
FREE and open to the public. Head to Colonial Williamsburg at night on the historic Duke of Gloucester Street – they will be Lighting of the Cressets this fall! The 18th-century lighting brings the streets to life at night – so don’t miss the strolling musicians and make sure to take in an evening program like To Hang a Trial of a Patriot, Cry Witch, or Haunted Williamsburg. Enjoy the fall evenings – the cressets make the streets glow and it is a beautiful sight! Learn more here.
Yorktown Fall Festival
Riverwalk Landing on Saturday, October 10 & Sunday, October 11 from 9 am – 3 pm
During this special, extended farmers market at the beautiful Historic Yorktown waterfront—Shop more than 40 local vendors and artists selling autumn favorites, from caramel apples to cozy décor. Kids will love the petting zoo, face painting, and hay maze while parents enjoy a pumpkin spice moment or two. Get the rundown on the days events at VisitYorktown.
2nd Sundays Art & Music Festival
Colonial Williamsburg on Sunday, October 11 from 11 am – 4 pm
Take in unique handcrafts from more than 200 artisans, live music, performing arts and food trucks in a fun and family-friendly atmosphere. There’s something to be enjoyed by all! ADMISSION IS FREE. MORE
Victory Weekend Kick-Off Concert with Michael Ray
Riverwalk Landing in Historic Yorktown on Friday, October 16 from 7 -8:30 pm
Kick off Yorktown’s Victory Weekend in style with a patriotic concert featuring certified Platinum country artist Michael Ray. Expect an evening full of chart-topping hits and patriotic pride you won’t want to miss — plus a special surprise finale to send the weekend celebration off right.
Yorktown Victory Market
Riverwalk Landing October 17 from 9 am to 3 pm
The red, white, and blue will be on full display as local artists will be selling patriotic handiwork such as glassware, paintings, and woodwork. If the celebrations have you craving an all-American meal or one with a French flair, you can shop our vendors for apples, cookies, meats, oysters, honey, macarons, and more! The free, accessible Yorktown Trolley will be in operation beginning at 11 am during this event! View the schedule of events.
Victory at Yorktown Celebration
American Revolution Museum at Yorktown on Saturday & Sunday, October 17 & 18 from 9 am – 5 pm
Celebrate America’s momentous 1781 Revolutionary War victory at Yorktown with artillery firings, exhibits and interpretive programs. Visitors can interact with Revolutionary War re-enactors and take part in interpretive demonstrations. On Yorktown Day, the American Revolution Museum at Yorktown offers free admission to active duty, reserve and retired military personnel and up to three direct family members with military identification. See the full schedule of the days events here.
Hamilton with Hamilton
Yorktown Victory Monument on Saturday, October 17 from 6:30 – 9 pm
Watch the film of the musical Hamilton on the actual ground where Cornwallis surrendered and America won its independence, the foot of Yorktown Victory Monument. Meet Alexander Hamilton himself and ask him your burning Revolutionary War questions. Then, settle in for the award-winning musical on the very land where the real story ended — and America’s began.
Yorktown Day
Yorktown, Monday, October 19 from 9 am – 5 pm
The festivities begin with a wreath-laying ceremony and patriotic parade down Main Street, featuring The Fifes & Drums of York Town. Then, explore Yorktown’s historic treasures like the Nelson House, Custom House, Watermen’s Museum, and more. Walk the very grounds where America secured her independence. …read more here.
Family Frights at Jamestown Settlement
Jamestown Settlement on Friday and Saturday, October 23 and 24
“Family Frights,” a Halloween-theme, “must-do” museum night for the entire family, returns to Jamestown Settlement with “Stories, Myths and Legends” featuring trick-or-treating, creative crafts and games, festive music and face painting, haunted houses and spooky ships. Tickets must be purchased online, tickets not sold at the door. More info
Paws at the River
Riverwalk Landing on Saturday, October 24 from 9 am to 3 pm
This awesome market has a pet parade (costumes…YES!) a spot on the waterfront where you can get your pet portrait or family picture with the pet! There is a wonderful market that day and many activities for the whole family. Children activities include Trick-or-treating at Historic Yorktown businesses and a dog bandana craft. Vendors selling seasonal produce; fresh baked goods; meats; fresh-cut flowers; honey; and more! You don’t want to miss this themed market. More info
Precarious Beer Project Field Dayz
Lawn of the Art Museums of Colonial Williamsburg on Saturday, October 17, from 12–6 pm
8th annual Field Dayz, enjoy craft beer, local food vendors, live music, activities for all ages, and a full afternoon of fall fun! This year they’ve added fun for kids to include face painting, a ballon artist, a petting zoo, a giant inflatable side, and crafts! Tickets are $10 each and include one token redeemable for food or a beverage at the event. Kids 12 and under are free! Learn more and get your tickets for Precarious Field Dayz Big event
Yorktoberfest Riverwalk Landing Yorktown
Riverwalk Landing on Sunday, October 25 from 12 – 5 pm
Sample more than 40 beers (unlimited tastings), ciders, and more, from Coastal Virginia at this annual event hosted by the York County Chamber of Commerce. With live music, beer classes, and vendors, you’ll definitely have something to yodel about! This is a tented event and will be held rain or shine. Get your tickets.
William & Mary’s Trick or Treat on the Row
William & Mary Community Building, Tuesday, October 27 from 5:30-7:00 pm
The Fraternity & Sorority Community will be handing out candy to Williamsburg community members during Trick or Treat on the Row. FREE & Open to local families! The Fraternity & Sorority Community Building is at 650 Ukrop Way.
Halloween Afternoon Tea
Williamsburg Inn on Wednesday, October 28 – Friday, October 31 from 2 – 3:30 pm
Enjoy a spooky afternoon with your family and friends while indulging in the fine Afternoon Tea at the Williamsburg Inn with a Halloween-inspired menu. Expect handmade scones, tea sandwiches, pastries, and more with a signature tea from the Chef Collaboration with the Tea and Spice Exchange! More info
The Play That Goes Wrong
Williamsburg Players, select days beginning October 30
This 1920s whodunit has everything you never wanted in a show: an unconscious leading lady, a corpse that can’t play dead, and actors who trip over everything (including their lines). Nevertheless, the accident-prone thespians battle against all odds to make it through to their final curtain call, with hilarious consequences! Part Monty Python, part Sherlock Holmes, this Olivier Award-winning comedy is a global phenomenon that’s guaranteed to leave you aching with laughter! More info
Colonial Williamsburg Ghost Tours
Colonial Williamsburg, Nightly, October 1 -31 from 7 – 8 pm or 8:30 – 9:30 pm
Hopefully you’ve walked through the beautiful streets and buildings of Colonial Williamsburg (if you haven’t add that to your list). Try walking through CW at night with a ghost teller relaying authentic ghost stories from the 1700s. And perhaps they may mention a few creepy recent encounters too. Haunted Williamsburg is the official ghost tour experience of Colonial Williamsburg MORE.
Don’t forget to bring your Good Neighbors Pass if you are a local resident as you will get a 25% discount. Your Good Neighbor Pass offers discounts on food and beverage and shopping in Colonial Williamsburg stores and resort eateries. If you are a local resident or you teach or work in the area you may qualify for the Good Neighbors pass which gives you unlimited entrance to Colonial Williamsburg museums, historic trade house and discounts on tickets you purchase for friends and family. MORE on all the benefits of this pass!
Ongoing Events:
Fall Fun – It is our big list of all things fall – from festivals to hayrides to fall leaves – if it has to do with fall – it’s there!
Fall Fun – we just have too many great events in the area to fit in to one post so this page has tons of events that are linked to it – it is a BIG list of Fall Fun Events!
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