Williamsburg Fall Festivities: Art, Music, and Community Vibes Await You This September

Group of Friends enjoying festival, concert on summer set up with banners

As summer fades and fall sneaks in, Williamsburg comes alive with art, music, and vibrant community vibes. Whether you’re into creativity or just here for the fun, there’s something in town with your name on it! 


Community Art Day

Date: September 7, 10 AM – 4:00 PM
Location: Williamsburg Community Building, 401 N. Boundary Street

Sunshine, good vibes, and endless creativity—Williamsburg’s Community Art Day is back! Grab your crew and dive into the fun!

  • Chalk Art Competition: Got artistic flair? Show it off for a shot at $500! Register now or sign up on-site and let your creativity shine! Register here
  • Pop-Up Exhibition Tour: Step across the street to the Stryker Center for a guided tour of our powerful exhibition, “America in Black & White: Depression-Era Photographs from the Farm Security Administration.” It’s a moving look at history that’ll stay with you long after you leave.
  • Communal Quilt Unveiling: This is a moment of pure community pride. The Communal Quilt, now more than 150 feet long, will be unveiled, and if you’ve been part of this project, you’ll get to spot your square and see it in all its glory.
  • Art Activities & Student Vendors: The day wouldn’t be complete without some hands-on art activities for all ages, plus a chance to shop for unique handmade items crafted by William & Mary’s talented students.


Music In Midtown Concert: Good Shot Judy

Date: Thursday, September 12, 6-8 PM
Location: Midtown Row Village Green

You know that song that makes you dance? That’s Good Shot Judy! Grab your lawn chair, leash your pup, and enjoy a free, high-energy swing show at Midtown Row. Fun vibes guaranteed!


New Town Tunes

Date: Wednesdays in September, Gates open at 5 PM; Concerts start at 5:30 PM
Location: Sullivan Square, New Town

When midweek rolls around and you’re looking for a little escape, New Town Tunes has got you covered. These Wednesday night concerts are the perfect excuse to gather your favorite people, kick back, and enjoy some seriously good music. Each week brings a new band, fantastic food trucks, and the kind of atmosphere that makes you feel right at home.

  • September 4: The Dave Matthews Tribute Band
  • September 11: BJ Griffin
  • September 18: Bobby BlackHat
  • September 25: Good Shot Judy
  • October 4 (Grand Finale): Landslide – A Tribute to Fleetwood Mac


2nd Sundays Williamsburg Art & Music Street Festival

Date: September 8, 11am – 5pm
Location: Downtown Williamsburg

Six blocks of downtown Williamsburg buzzing with 175 artisans, live music, and mouthwatering food trucks. That’s 2nd Sundays—where creativity, good vibes, and all ages come together!


Oktoberfest at Precarious

Date: Saturday, September 21
Location: Precarious Beer Project

Dust off your lederhosen and get ready for a day of festive fun at Oktoberfest! We’re tapping exclusive beers, dishing out food specials, and bringing in the Oompah Oktoberfest Band to set the perfect mood. It’s the kind of celebration that’ll have you raising your glass and saying, “Prost!” before the night is through.


Harvest Festival

Date: Saturday, September 21, 11 AM-3 PM
Location: Chickahominy Riverfront Park

Ah, fall. The time of year when the leaves start to turn, and the air is crisp with the promise of cooler days. What better way to celebrate than at our annual Harvest Festival? Bring the family for a day of arts and crafts, games, food, and even laser tag! With live bluegrass from Code Blue and free hayrides, it’s a fall tradition you won’t want to miss.


Oysters, Crabcakes, and Cocktails: A Taste of Coastal Virginia

Date: Saturday, September 21
Location: Copper Fox Williamsburg

If your idea of a perfect afternoon involves fresh oysters, crabcakes, and cocktails, then you’ll want to head over to Copper Fox for this tasty event. Rappahannock Oyster Company is bringing the flavors, and we’ve got live music to keep the energy up. It’s the kind of laid-back, delicious day that reminds you why coastal Virginia is so special.


Jubilee XVIII

Date: Saturday, September 21, 12-10pm
Location: Alewerks Brewing Company

Time to raise a glass—Alewerks Brewing Company is turning 18, and you’re invited to the party! This isn’t just any birthday celebration; it’s an epic day of live music, delicious food, and of course, amazing beer. This year, Alewerks is teaming up with the Junior Woman’s Club of Williamsburg for a fundraiser that includes an artisan market and 50/50 raffles. Plus, 10% of the day’s sales will go back to support their community efforts.

  • Live Music Lineup: Felicia Hoyos at 12 PM, Patrick Ryan at 3:30 PM, and Barry Manilow’s Wardrobe keeping the party going from 7-10 PM.
  • Food Trucks: Satisfy your cravings with eats from Bald Guys Pies, Piha Aloha, and Flossed-Out Cotton Candy.
  • VIP Experience: For $50, snag a VIP ticket and enjoy exclusive perks like a specialty mug, a reserved area, two drink tickets, $10 off one of the food trucks, and access to two special brews. VIP access is from 12 PM-6 PM.


So, there you have it—a September full of events that’ll keep you entertained, inspired, and connected with our wonderful community. Grab your calendar and start planning, because you won’t want to miss a single moment!

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