Isle of Wight Historic Homes Tour in Virginia

Several years ago, when I was new to Virginia, I learned about the state-wide Historic Garden Week. I love gorgeous gardens, as well as lovely historic homes. Plus I thought I could learn a thing or two about the Commonwealth of Virginia, its history, and gorgeous gardening by checking out a few of the tours. Over the years, I’ve had a chance to travel the state for Virginia’s Historic Garden Week and have loved every minute of these adventures.

Garden Club of Virginia Historic Garden Week Dates

• 2025 Historic Garden Week Dates – April 26 – May 3, 2025
• 2026 Historic Garden Week Dates – April 18 – 25, 2026
• 2027 Historic Garden Week Dates – April 17 – 24, 2027

Did you know that Virginia Historic Garden Week began way back in 1927! Wow! How many fund-raisers do you know of that have been around nearly a century? I’d say that’s quite a legacy. Add to that the fact that all tour proceeds fund the restoration and preservation of many of Virginia’s historic public gardens and landscapes, a research fellowship program, and a new partnership with Virginia State Parks.

I wanted to see one of the first tours of the week to get a taste of what could be ahead so I’d know how to plan. I live in Hampton Roads, so I chose the Isle of Wight Tour on Saturday. It’s an area that I hadn’t visited yet, which was an added bonus. Rain was threatening, but I decided to take a chance anyway since I knew that at least some of the tour would be inside.

Pro Tip – Buy Tickets in Advance

I neglected to buy my ticket in advance online, so I stopped at the Tour Headquarters located in front of Boykin’s Tavern. Note: If you wait until the day of the tour, you’ll pay a higher ticket price. Usually $5 more than the online price. Not a huge deal, but just wanted you to be aware.

Now, remember, I was a “historic garden tour” virgin, so I was expecting tours of historic gardens. Silly me. The Isle of Wight tour didn’t include any grand gardens per se, although I learned later that many regions include spectacular gardens in their tours as well.

Each region and year is different. Mainly historical homes with lovely floral arrangements sprinkled both inside and out. Creative and talented gardeners from the sponsoring garden clubs nearby contributed the floral arrangements. Several members of the garden clubs volunteered at each location to help with logistics, too. In most cases, there was a host(ess) in each room of the house and outside to answer questions or share about items of interest.

Don’t get me wrong, I was a little puzzled by this, but not really too disappointed since I was able to see seven unique properties, including many historic homes, dozens of gorgeous floral arrangements, and even learn a few things that I wasn’t expecting.

No Photography Inside the Historic Homes

I learned that no photography is allowed inside the homes. Of course, this makes perfect sense since this is someone’s private space and there could be valuable items that they don’t want to be published for the whole world to see. It does, however, make it a little more difficult for a post like this one.

I had so much fun that I could go on and on about each site, but to keep things simple, here are the locations in the order that I visited, with a tidbit about each one. When you’re finished with the list, click on the last photo to get to the photo album and more details.

Where to stay near Virginia’s Historic Homes

One of the fun parts about traveling from out of state or heading to a different region beyond where you live is that you can find some amazing historical lodging near these Virginia historic homes. I highly recommend searching on either Booking.com [below] or VRBO (Vacation Rentals by Owner) to find boutique hotels, unique historical inns, and other one-of-a-kind lodging near your home tour destinations all over the state. Virginia is packed with amazing historic homes and lodgings, sometimes dating back to the 1700s.

Isle of Wight Historic Homes & Tour Stops

Boykins Tavern in Isle of Wight, Virginia

This building (circa 1790) once stood next to the Isle of Wight County courthouse and served staff and visitors to the busy public house for many years. The tavern houses architectural facets that are rare in rural Virginia. Boykins Tavern also played a significant role in both the Revolutionary and the Civil Wars. 

During my tour, local historian Albert P. Burckard portrayed the original owner, Major Francis Boykin and greeted guests, answered questions, and shared historical insights about the tavern.

Check the Isle of Wight County Museum webpage here to see about various tours of the tavern that may be available throughout the year.

Davis Day House in Smithfield, Virginia

(c. 1850) – The original home was built in 1809. Two additional wings were recently added that are a gorgeous complement to the original structure. In addition to a gorgeous home and expansive grounds, the owners of this property raise prize-winning Gypsy Vanner horses. I had the chance to see these magnificent steeds courtesy of Mokete’s Village, their family business.

Six Oaks – Historic Home in Smithfield

(c. 1750) – This quaint Tidewater cottage included a staircase painted to look like book spines with titles, authors, and all. There was also a small flower garden on-site with a helpful volunteer to answer questions.

Saint Luke’s Church in Smithfield

This amazing church dates all the way back to 1632 before the birth of our nation. It’s the oldest Anglo church in Virginia, which is saying a lot, since many early European settlers made their home in this state/commonwealth. I found gorgeous stained glass, an intricate rafter ceiling, and a knowledgeable tour guide, Collin, who made this stop so memorable. They also have a variety of opportunities for volunteering if you’re so inclined.

St. Luke’s Historic Church & Museum – 14477 Benns Church Blvd, Smithfield, VA 23430

Oak Level/Young House in Smithfield

Isle of Wight County was one of the original shires, or counties, first enumerated in 1634 in America. The present name was given in 1637. Work on the Young family’s historic home began in 1768.

The Young family has lived in this historic home for generations. Many of the men in this family served as County Clerk over a 118-year span from the late 1700s to the early 1900s. Elizabeth Bennett Young, the wife of Deputy Clerk Francis Young, is credited with removing and burying all the county records for safekeeping during the Revolutionary War. Her husband was away serving in the Army at the time. She kept them buried until after the surrender at Yorktown.

During the Civil War, Randall Booth removed and protected the county records. Randall was an enslaved man, owned by N.P. Young, who was the County Clerk in 1862. Randall was honored for his service to the people of Isle of Wight County in preserving those important documents. The records room in the courthouse is now named after Mr. Booth.

You can read more about the Young family and the people who protected these documents in the History of Isle of Wight County here. Because of these heroic actions, Isle of Wight County records are some of the oldest in the nation, dating back to the 1600s. These documents provide valuable information to historians, genealogists, and more.

Darden Homestead in Windsor, Virginia

(1850) – Homeowner William (Billy) Bell was kind enough to share his process for smoking ham. He allowed guests to take in the wonderful sights and scents of his smokehouse.

Colonel Thomas Darden Home in Windsor

The Thomas Darden home was built in 1834. What a treat to have one of the family members on site to answer questions. Hannah Wise shared personal stories from her experiences at this historic home as a child. She also confirmed that she painted the lovely expansive murals on the walls of the entry hall in 1986.

These are just a few of the unique glimpses you’ll see into these interesting and beautiful historic homes in Virginia.

Find Out More About Historic Garden Week

As I mentioned, each year and region is unique with the chance to tour different properties. You can find out more about the historic homes, gardens, and other locations for this year and how to get tickets by visiting their website here.

Thanks for joining me for a lovely day. By the way, the rain only fell when I was inside a restaurant taking a lunch break, so that worked out well. You may also enjoy these other posts about the dozens of historic homes and gardens open for Virginia’s Historic Garden Week here.

Have you ever done a Historic Home or Garden Tour in Virginia? If so, I’d love to hear about your favorites so I can try to catch them in the future.