I recently returned home from my first trip to Williamsburg, Virginia, and couldn’t wait to share with you how I spent my three days there. Since my trip consisted of a few seasonal experiences, I’ve decided to make this post a list of things to do in Williamsburg, VA, in October.

Stay at Kingsmill Resort

Kingsmill Resort front entrance
Photo credit: Kingsmill Resort

First things first, you will need a place to stay while in Williamsburg, assuming, of course, that you are coming from out of town. I spent my extended weekend at the Kingsmill Resort, a 400-acre property known as a top golf and spa destination. Here’s what you need to know:

  • 45-minutes from the Richmond International Airport
  • Williamsburg, Virginia’s only AAA Four Diamond condominium golf resort
  • 350 rooms available with a wide variety of accommodations – Kingsmill Vacation Homes, Cottages on the James, Guest Rooms and Condos, the Estate at Kingsmill
  • Pet-friendly rooms are available
  • 4 Restaurants – Breakfast (Elements 1010, The Mill), Lunch (The Mill, Eagles), Dinner (Eagles, James Landing Grille)
  • 3 Pools – Indoor, Outdoor, and The River Pool
  • 15 tennis courts – 13 clay, two hard, with six Hydro Courts® and two lit courts
  • 2 renowned 18-hole golf courses – The River Course and The Plantation Course

Stay tuned for a more thorough review of Kingsmill Resort soon, where I’ll cover all of their restaurants, activities, and more!

Get Scared at Busch Gardens’ Howl-O-Scream

I love a good Halloween-themed park, so it was only natural for me to be excited to check out Busch Gardens’ Howl-O-Scream on one of the evenings I was in Williamsburg. Best of all, it was only a 15-minute Uber from my hotel at Kingsmill.

The last Halloween event I attended pre-pandemic was when I lived in Los Angeles and went to Knott’s Scary Farm. It was good, but not quite like this.

Here are a few things you can look forward to at the Williamsburg, VA Busch Gardens from September 10 – October 31.

  • 5 Haunted Houses
  • 4 Terror-tories
  • 4 Sinister Shows
  • 4 Booze Bars
  • 2 Party Zones

Dine and Shop at Merchants Square

Located adjacent to Colonial Williamsburg, Merchants Square is an 18th-century style retail village with over 40 shops and restaurants. Also just a short 15-minute drive from Kingsmill Resort.

Visit Merchants Square in Williamsburg, VA

During the month of October, Merchant Square hosts a Halloween window display contest between the local shops. If I had more time, I would have spent the entire day there eating and drinking my way through the square while admiring the window displays.

Since my time was limited, I decided to visit The Williamsburg Winery Tasting Room & Bar for a wine flight and The Amber Ox Public House for some insane poutine and beer.

Amber Ox Poutine - Williamsburg, VA
Public House Poutine – pulled pork shoulder, pickled red onions, smoked curds, soft poached egg, fried chili, golden raisin salsa macha

Wine Tasting at Williamsburg Winery

There’s a 100% chance I will seek out the local winery if the destination I’m in has one.  I don’t make the rules.

Just a short drive from their tasting room in Merchant Square, the Williamsburg Winery vineyards span over 50 acres, growing a wide variety of grapes. I had the pleasure of sampling the Wessex Hundred Flight featuring the 2018 Wessex Hundred Viognier, 2018 Wessex Hundred Chardonnay, 2020 Wessex Hundred Dry Rosé, and 2019 Wessex Hundred Petit Verdot.

Wessex Hundred Flight - Williamsburg Winery
Credit: @JoesDaily

I absolutely love visiting vineyards and tasting rooms during the Fall season. There’s just something magical about the change in colors and weather to set the mood for a long day sampling wine.

If you don’t have time to tour the vineyard but still want to sample their wine, definitely head over to the Merchant Square tasting location and try a flight.

Three days in Williamsburg, VA is simply not enough. I could have spent two days in Merchants Square alone, shopping and trying the various restaurants. Stay tuned for more articles about my stay in Williamsburg coming soon.