October Festivities in Williamsburg, VA: Your Guide to Fall Fun!

by Jackie Berberabe

 

As the leaves change and the air turns crisp, Williamsburg comes alive with vibrant fall events perfect for gathering with friends and family. From pumpkin picking to art festivals, there’s something for everyone this October. Grab your flannel, sip on some pumpkin spice, and let’s dive into the exciting happenings around town!


🎉 FALL 2024 Strictly Business

When: October 2

Join the vibrant community at the Strictly Business event, hosted by leading media companies. This gathering is all about bringing local newsmakers together, with over 1,200 attendees expected! Connect, network, and engage with like-minded individuals while enjoying the company of fellow community advocates.


🎃 Get Your Pumpkins! – Holly Fork Farm Open for FALL

When: Daily from October 1 to October 31

Holly Fork Farm is your go-to destination for fall fun! Enjoy the Scarecrow Slide, jump castles, and hayrides. With a variety of activities like pumpkin picking and an adorable petting farm, there’s no shortage of excitement for kids and adults alike. Admission is only $6.50, and it’s free for kiddos 2 and under or seniors 60 and older!


🎶 New Town News: GRAND FINALE CELEBRATION

When: October 4

Bring your lawn chairs and picnic baskets to Sullivan Square for a night of music with Landslide – A Tribute to Fleetwood Mac! This outdoor concert series, in partnership with local food trucks and breweries, promises a delightful evening of great tunes and community spirit.


🎨 An Occasion for the Arts Festival

When: October 5-6

Celebrate creativity at the 56th Annual An Occasion for the Arts Festival! Featuring local musicians, a Youth Art Show, and fabulous original art, this festival showcases the incredible talent in Williamsburg. Bring your family and friends for a weekend filled with culture and community connection.


👻 Hallowscream at Busch Gardens

When: September 6 to November 3

Prepare for a spine-chilling adventure at Busch Gardens® Howl-O-Scream®! This event features haunted houses, terror-tories, and thrill rides under the moonlight. Parental discretion is advised after 6 PM, so bring your bravest friends for a night of thrilling scares!


🎸 Annual PIPE Concert

When: October 5

Rock out with The Deloreans at the Annual PIPE Concert, a fantastic fundraiser for Housing Partnerships, Inc. Celebrate the 80s with good music while supporting a great cause that helps neighbors in need. Bring your own chair and enjoy a fun night out!


👻 Trunk or Treat N Play

When: October 12

Join the fun at Catalillies Play Cafe for a morning of play followed by a delightful Trunk or Treat event! Kids can enjoy safe trick-or-treating while parents can relax and mingle. Don’t forget to book your play session in advance!


🛍️ Fall N’ Leaves Artisan Market – Williamsburg Premium Outlet

When: October 13

Support local artisans at the Fall N’ Leaves Artisan Market! With over 100 vendors, food trucks, and live entertainment, it’s the perfect opportunity to get into the holiday spirit while enjoying delicious treats and finding unique crafts.


🎨 2nd Sundays Williamsburg – Art & Music Festivals

When: October 13

Explore the lively streets of Williamsburg during the 2nd Sundays Festival! Enjoy art, live music, and delicious food while supporting local artisans. Bring the whole family for a day filled with creativity and fun!


🎃 Halloween Market at Strangeways Brewing

When: October 26

Join the spooky festivities at Strangeways Brewing for a Halloween Market! Enjoy safe trick-or-treating for the kids and a selection of unique vendors for the adults. Costumes are encouraged for all ages!


🍻 Field Dayz 2024

When: October 26

Get ready for a spooktacular celebration at the 6th Annual Field Dayz! Featuring over 25 craft breweries, delicious bites, and live music, this event promises a fun-filled evening for all. Don’t miss the 90s costume contest and help raise funds for CHKD!


This October, embrace the season and create lasting memories at these fantastic events around Williamsburg. Whether you’re indulging in the fall flavors or discovering local art, there’s no shortage of fun this month. Happy October! 🍂✨

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Jackie Berberabe

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