October 2026 Events Guide: Williamsburg, Yorktown & Jamestown

October is when Williamsburg shows off. It is the month people visit, fall for the place, and start browsing homes on the drive back. If you are already here, this is the calendar to keep.

Below is everything happening across Williamsburg, Yorktown, and Jamestown this October — organized the way the month actually unfolds.

The Opening Weekends — October 2–11

The month kicks off with art, oysters, football, and music all landing in the same stretch of days.

• Friday, Oct 2: Pressing Strings, Free Concert — 6 PM · Merchants Square · Arts Kickoff

• Sat–Sun, Oct 3–4: An Occasion for the Arts — 10 AM–5 PM · Duke of Gloucester St

• Sat–Sun, Oct 3–4: Yorktown Wine & Oyster Festival — Riverwalk Landing

• Saturday, Oct 3: W&M vs. Holy Cross White Out — 3:30 PM · Zable Stadium

• Saturday, Oct 3: Williamsburg Bluegrass Festival — Copper Fox Distillery

• Fri–Sat, Oct 9–10: African Baptist Meeting House Dedication — Colonial Williamsburg

• Sat–Sun, Oct 10–11: Yorktown Fall Festival — 9 AM–3 PM · Riverwalk Landing

• Sunday, Oct 11: 2nd Sundays Art & Music Festival — 11 AM–4 PM · Downtown Williamsburg

The Main Event — Victory Weekend, October 16–19

Four days on the river marking the 1781 victory. If you only make one weekend this month, make it this one.

• Friday, Oct 16: Michael Ray in Concert — 7 PM · Riverwalk Landing

• Saturday, Oct 17: Victory Market — Riverwalk Landing

• Saturday, Oct 17: ECW AutoFest Car Show — 10 AM–2:30 PM · Waltrip Executive Airport

• Sat–Sun, Oct 17–18: Yorktown Victory Celebration — Artillery at 11 & 3 · American Revolution Museum

• Monday, Oct 19: Yorktown Day — Wreath-Laying & Parade · Historic Yorktown

The Final Stretch — October 22–31

The month finishes strong with W&M's 100th Homecoming, family-friendly frights at Jamestown Settlement, and a run of weekend events at Riverwalk.

• Thu–Sun, Oct 22–25: W&M Homecoming, the 100th — All Weekend · Across Campus

• Friday, Oct 24: Homecoming Parade — 4 PM · Richmond Road

• Saturday, Oct 25: Tribe vs. Georgetown — 3:30 PM · Zable Stadium

• Fri–Sat, Oct 23–24: Family Frights — After Dark · Jamestown Settlement

• Saturday, Oct 24: Market Days: Paws at the River — Pet Adoptions · Riverwalk Landing

• Sunday, Oct 25: Yorktoberfest — 12–5 PM · Riverwalk Landing

• Wed–Sat, Oct 28–31: Halloween Afternoon Tea — 2–3:30 PM · The Williamsburg Inn

All Month Long — The Standing Lineup

These run every week, no reservation required.

• Saturdays: Williamsburg Farmers Market — 8 AM–Noon · Merchants Square

• Fridays (Oct 9, 16, 23 & 30): Letters from the Archives — Colonial Williamsburg

• Select nights through Nov 1: Howl-O-Scream — Busch Gardens

• Weekends: Halloween Spooktacular (for the little ones) — Busch Gardens

• Nightly: Haunted Williamsburg Ghost Tours by Candlelight — Colonial Williamsburg

For families: Yorktown Fall Festival (Oct 10–11), Family Frights (Oct 23–24), Paws at the River (Oct 24), and Spooktacular every weekend at Busch Gardens.

Thinking About Making This Home?

October is the month people visit and start browsing on the drive back. If you are curious about what it is like to live here — not just visit — I would love to show you the neighborhoods that fit how you actually spend your weekends.

Reach out at brandonchildress.com or call (910) 352-7468. I grew up here, and I am happy to show you around.