My wife and I first started taking vacations in the fall because flights were cheaper and tourist sites were less crowded. But the changing colors of the season at Williamsburg, VA is what made it a tradition for our family. Between the busy summer and the bustle of the holidays, autumn (and the crisp, fresh air) is an excellent place for a family vacation!

We attend harvest festivals and visit seasonal attractions, such as Haunted Colonial Williamsburg. The fall is filled with special festivities, food events, and activities, and each of our vacations is a different experience. There’s no short of local happenings around our timeshare resort, Vacation Village at Williamsburg. 

If you have never taken a family vacation in the fall, below are some tips on what to expect and how to prepare.  

Tip #1 – Pack for all the Fall Fun

Before packing anything, check the weather at your destination first. Fall can be unpredictable, so pack your layers upon layers upon layers! I cannot stress this enough, especially with the kids. Make sure to plan outfits for a base layer, mid-layer, and outer layer. 

Thanks to the laundry facility at our resort, I use the Rule of Three. I pack three of everything, from socks to shirts. When we start to run low, I do a load of laundry to refresh our vacation wardrobe.

• 3 pairs sock and underwear
• 3 bottoms (2 long pants, 1 pair of shorts or skirt)
• 3 tops (2 short sleeves, 1 long sleeve – my kids hate sleeves)
• 3 middle layers (sweatshirt or sweater)

However, we don’t need three of everything. 

• 1 jacket or coat
• 1 head covering (beanies for the kids, a cute fall hat for me, and a baseball cap for my husband)
• 1 pair of gloves or mittens
• 1 back up pair of mittens for the kids

If you have young kids like me, an extra emergency hat and gloves is convenient when something eventually goes missing. 

One set of outerwear is sufficient, and, more often than not, it is what we are wearing when carrying our luggage out the door anyway. Wearing bulkier items is also a great way to save space when packing. If I’m bringing more than one set of shoes, for instance, I wear the larger pair for travel.

Don’t forget to pack clothes for the resort’s features, such as swimming pools (they have an indoor pool if it’s too cold out), a hot tub, a game room, and outdoor sports courts for tennis, pickleball or volleyball. 

• 1 bathing suit 
• 1 pair of sneakers 
• 1 pair of hiking boots 
• 1 pair of sunglasses 

Tip #2 – Plan Family Fun Activities 

Since there are so many seasonal activities, I like to check out what festivities will occur during our vacations. In autumn, I can count on finding pumpkin-carving events, hayrides, and corn mazes.  

Autumn is a time for harvesting and the time to check out local farmer’s markets. We let the kids each pick out one piece of produce to prepare back at the in-suite kitchen. Not only are the markets a fun place to visit with the family, but they also help my kids try new things!

In my own personal opinion, food festivals are the best festivals. They are delicious and quite memorable. Sitting banquet-style at picnic tables, we feast on new dishes and get to know our fellow festival-goers surrounded by plates and smiles!

The cooler nights are perfect in front of a fire, and some parks host free or low-cost admission for community campfire socials. We bring marshmallows, chocolate, and graham crackers to make s’mores with other families. If we can’t find a campfire, we’ve used the resort’s barbeque grills instead. Nothing gets between my kids and a sweet treat. 

There are also nearby local attractions that are open during the fall months. My kids love seeing the switch theme parks make from their standard appearance to spooky and scary like Colonial Williamsburg running ghost tours. Busch Gardens® Williamsburg turns into Howl-o-Scream with nightly attractions like escape rooms, haunted houses, and themed live shows. It’s a popular pick for families with older kids and teens. 

Since the resort has all the amenities of home with the bonus of onsite amenities like horseshoe pit, The Pantry (which is their snack/sundry shop), a spa, and children’s playground, my wife and I flip a coin for who gets the afternoon off for some seasonal spirits. Our Williamsburg resort is near wine festivals and craft brews events, which are fun for learning about local wineries and breweries. 

Our fall vacations at Vacation Village at Williamsburg are the best! They are affordable and memorable. The amenities at the resort keep our expenses low, and the changing of scenery is unforgettable.

• By Jorge Valentino, a long time owner of Vacation Village Resorts