Summer may be over but fall fun in Williamsburg is just getting started. Start planning the perfect autumn weekend with these upcoming festivals, live music shows, and events in the Hampton Roads and Historic Triangle area. 

October is right around the corner which marks the start of autumn activities like apple picking, pumpkin spice latte sipping, and corn maze exploring. Immerse yourself in the spirit of the season by attending these fall-themed events in Williamsburg, VA all happening this weekend. From family-friendly fall festivals to boozy brewery crawls, there’s something going on for everyone in the Historic Triangle. 

Karaoke Night at Aleworks Brewery 

Date(s): Friday, October 1
Time: 6:00 PM to 8:30 PM
Location: 189B Ewell Rd, Williamsburg, VA 23188 Cost: Free Admission 

Aleworks Brewery is bringing their karaoke events back with a bang. Live out your rockstar dreams at the open mic night accompanied by SueRay Deejay. Liquid courage in the form of craft beer will be readily available and munchies will be supplied by the Foodatude food truck. Head to Alewerks Friday night for your time in the spotlight, or to just sit back and enjoy the show. Click here for more information about the event and check out our Live Music Finder to discover other live music events happening in Williamsburg. williamsburg virginia live music finder alewerks outdoor beer garden

An Occasion For The Arts 

Date(s): Saturday, October 2 and Sunday, October 3.
Time: 10:00 AM to 5:00 PM. View the full schedule here.
Location: Merchants Square | 134 N Henry St, Williamsburg, VA 23185 Cost: Free Admission 

For over fifty years, An Occasion for the Arts has been a cultural staple in Williamsburg’s art scene. The festival, also described as an “arts extravaganza”, provides space for emerging artists and musicians to showcase their work. Attendees are welcome to browse art galleries, listen to live music, and indulge in culinary creations from the festival’s food court. With a jam-packed schedule of events, and the opportunity to create your own masterpieces, this year’s festival is worth checking out. Click here to learn more about the festival.

Williamsburg 2021 Book Festival 

Date(s): Saturday, October 2
Time: 10:00 AM to 4:00 PM
Location: Stryker Center | 412 N Boundary St, Williamsburg, VA 23185 Cost: Free Admission 

Need even more culture? In addition to the art festival, there will also be a celebration in Colonial Williamsburg for literature lovers. Some of the festival’s notable events include a Book Fair featuring more than 40 authors across a wide variety of genres, a presentation by the Poetry Society of Virginia, and a Publisher’s Alley where Virginia publishing companies will be showcasing their books and authors. There will also be workshops for readers and writers alike that shine light on the local library’s resources. Click here to learn more. 


Billsburg Brewery Oktoberfest 2021 

Date: Saturday, October 2
Time: 12:00 PM to 4:00 PM
Location: Billsburg Brewery | 2054 Jamestown Rd, Williamsburg, VA 23185 Cost: $40 in Advance or $45 at the door. VIP packages available for $60. 

Beer lovers rejoice, Billsburg Brewery is holding its annual Oktoberfest with a lineup of 19 local breweries. Their waterfront parking lot will be transformed into a festbier where attendees can enjoy the best german-style lagers in the 757 while listening to live music performed by the DOG Street Boys. Bring an appetite because The Hungry Pug, Old City BBQ, and Chez Ray Mobile food trucks will be serving some great bites. The $40 admission ticket includes a Oktoberfest Beer Stein Glass. Click here to buy tickets and to learn more about the event. 

Yorktown Wine Festival 2021 

Date: Saturday, October 2
Time: 12:00 PM to 6:00 PM
Location: Riverwalk Landing, 400 Water Street, Yorktown, VA 23692 Cost: $30 in Advance or $35 at the door. 

Prefer wine to beer? Head to the Yorktown Wine Festival to taste the finest globally-inspired vino in the state. 13 wineries will be in attendance all serving a variety of wines – from crisp Rieslings to velvety Merlots – you might find your new favorite bottle. In addition to wine tasting, there will be vendors from local restaurants serving food and musicians providing live entertainment. This year, there will also be beverages from local distilleries to sample as well. Learn more about the festival and purchase tickets here. 

Relay for Life 

Date: Saturday, October 2
Time: 5:00 PM to 9:00PM
Location: Palace Farms | 100 Visitor Center Drive Williamsburg, VA Cost: $10 registration fee to join or create a team. 

Feeling charitable? Grab some friends and create a team or join an existing team to help raise money for the American Cancer Society in this year's Relay for Life at Palace Farms. Get your steps in and help fundraise for a good cause. The event starts off with an Opening Ceremony before segwaying into the Cancer Walk. The relay ends with a Luminaria Ceremony honoring those impacted by cancer and a Closing Ceremony celebration. Participants are encouraged to raise money for the American Cancer Society. Click here to register for the relay. 

We make it easy to find where food trucks will be in Williamsburg. Here is a round up of the locations of where you can find the best meals on wheels in the area this weekend. Check out our Williamsburg Food Truck Finder for a complete calendar of food truck pit stops around town. 

Don Chido 

Date: Friday, October 1
Time: 12:00 PM to 5:00 PM
Location: Alewerks Brewery | 189B Ewell Rd, Williamsburg, VA 23188 Cuisine: Latin Fusion 


Date: Saturday, October 2
Time: 12:00 PM to 7:30 PM (Open until 8:30 Friday - Saturday) Location: Billsburg Brewery | 189B Ewell Rd, Williamsburg, VA 23188 Cuisine: Soups, Small Bites, Smoked Meats 

The Hungry Pug 

Date: Daily
Time: 12:00 PM to 5:00 PM
Location: Alewerks Brewery | 2054 Jamestown Rd, Williamsburg, VA 23185 Cuisine: American, Grilled Cheese 

Live Music 

Sit back and relax with these live music events happening in Williamsburg this weekend. Experience Hampton Roads’ vibrant music scene and rock out to sounds produced by the area’s premier musicians. There’s more where these came from, head to our Live Music Finder for a full calendar of live music in Williamsburg.

Travis Morrison 

Date: Friday, October 1
Time: 6:00 PM to 9:00 PM
Location: Virginia Beer Company | 401 Second Street, Williamsburg, VA 23185 Genre: Indie Rock 

The Virginia Beer company is partnering with Here for the Girls to host a fundraiser for breast cancer awareness all day on October 1, the first day of breast cancer awareness month. Indie rocker Travis Morrison will be performing in the Beer Garden starting at 6:00 PM. The “You Make Me Feel Like A Freak” singer is also known for his affiliation with the band The Dismemberment Plan. 

Enjoy his live performance while sipping the brewery's new pink-hued Golden Ale which will be released at the event. 20% of its sales, along with a percentage of the full taproom sales will be donated to those who are affected by breast cancer. Learn more about the event here. 

Troy Breslow 

Date: Friday, October 1
Time: 6:30 to 10:00 PM
Location: Jolene’s Bar and Grill | 3032 Richmond Rd Williamsburg VA 23185 Genre: Country, Blues, and Western 

Williamsburg local Troy Breslow is known for his country and folk sounds. He won Country Artist of The Year at the 2018 Veer Music Awards and has played over 900 shows in the south and southwest areas of the United States. Slip on your cowboy boots and head to Jolene’s to listen to the “I Wish” singer perform a live show. Add this show to your calendar and learn more about Breslow here. 

Tony Mata 

Date: Sunday, October 3
Time: 11:00 AM to 2:00 PM
Location: Craft 31 | 3701 Strawberry Plains Rd, Williamsburg, VA 23188 Genre: Jazz 

Guitarist and composer Tony Mata is based in the Greater Williamsburg area and produces smooth jazz sounds. Along with performing live shows, he also offers guitar lessons to students in Virginia. Read more about him here and don't forget to mark his Sunday afternoon show in your calendar. 

Thanks for reading. All WilliamsburgVisitor.comcontent, articles, news updates, event calendars, Food Truck Tracker and Live Music Finder are always free!

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