Discover Day Trips from Williamsburg

Whether it be exploring Virginia’s first colony at Jamestown, spending a day swimming and enjoying the historic charm and culture of Yorktown, or getting out in nature on a working farm along the James River dating back to the early 1600s, these day trips from Williamsburg showcase the best sightseeing in the area surrounding Williamsburg.

Our historic Williamsburg bed and breakfast is just an easy drive away from all of them, so stay in our Jamestown or Yorktown suite and then plan day trips to both!


Jamestown – A Trip Back in Time to the First Virginia Settlement

Jamestown Settlement sign for the parking area.There are two parks at Jamestown. We recommend you start at the original site at Historic Jamestowne, where English settlers established their first permanent Virginia colony in 1607.  Here, history is preserved in statues, monuments, and the old 17th-century Church Tower, while also coming alive in the ongoing archaeological digs in the area. Take the scenic 10-mile route on the Colonial National Historical Parkway, which crosses College Creek, a great place to pull over and enjoy the waterside views.

Explore the indoor exhibits like the Archaearium Museum and the Inside the Vault tour, where you get an up-close look at the 4 million and counting artifacts discovered at the site over the last several decades. During the summer of 2023, a team of archaeology students will be unearthing even more pottery, glass, and other centuries-old artifacts during an active dig on a James Fort well, so you’ll see historical discoveries happening in real time.
Near the digs, you will see the Hunt Shrine, a tribute to the colony’s first Anglican pastor depicting what a service looked like in 1607. The evolution of the church is shown through the marked location of the 1608 church where Pocahontas married John Rolfe and through a creative reimagining of the old brick church, the site of the first Representative Government in America. The Captain John Smith statue is a towering and impossible-to-miss 20-foot tall monument to the seafaring captain and leader of the first colonists.

Finish your visit with a drive around the Island. Take the 3-mile or the 5-mile loop highlighted on this Jamestown Island map, where you’ll drive through the marshes and preserved natural habitat.

Before crossing the isthmus to the island, you will see a sign “Glasshouse of 1608”. We recommend you stop and see the glassblowing exhibit; also a great place to purchase gifts “with a story.”

Next door to the Island is Jamestown Settlement, a recreation of the original fort, ships, and Indian lodges. The experience is a mix of indoor exhibits and outdoor activities – during the earlier part of the day, when it’s not too hot, tour the outdoor sites.


It’s genuinely unique to step on board exact replicas of the three ships – Susan Constant, Godspeed, and Discovery – that brought the group of 105 settlers to Virginia. Like Colonial Williamsburg, this part of the Jamestown Settlement is a living history museum, so costumed interpreters will guide you through the ship’s tight quarters, regale you with stories of the 4-month journey, and give you a realistic glimpse at what their epic voyage was like.
Native American interpreters give regular demonstrations on life in the Virginia woods; inside the fort, costumed interpreters give demonstrations at the armory. All of the exhibits are very hands-on for children.

Yorktown – Swimming, Riverside Charm, and Weekly Events All Summer

The riverwalk in Yorktown.Take another day trip to Yorktown, just 12 miles in the other direction on the Historical Parkway and right on the water of the York River on the north side of the Virginia peninsula.

For history lovers, Yorktown has two museums. The Revolutionary War Museum has numerous hands-on experiences for kids. The 4-D theaters are a must as you travel back to the last hours of the Battle of Yorktown.

After the museum, download the National Park Service app for the driving tour of the Battlefields. This fascinating tour takes you beyond the fields into the nearby forest where the preparations for the battle took place. Stop at the Moore House, where the treaty ended the Revolutionary War.

While you stroll through the small historic area, look for the Nelson House, embedded with cannonballs from the battle.

If you’re visiting during the summer and want to spend a day in the water, Yorktown Beach is a great place to swim near Williamsburg. The calm, pleasant-temp water, sandy shores, and protected swimming area make it perfect for adults and kids. Walk the rustic wooden pier (which is also a great place to drop a fishing line) and take in panoramic views of the wide span of the York River as it feeds into the larger Chesapeake Bay, one of the sources of Virginia’s legendary and delicious oysters.

As you stroll along the Yorktown Riverwalk pedestrian path, a mile-long flat and accessible paved walkway passing the downtown district’s shops and restaurants, grab some locally-sourced clams, oysters, shrimp, gumbo, or one of five burgers at the Yorktown Pub along Water Street. If you visit on a Saturday, check out the Yorktown Market Days, which runs from April to November and features food trucks, local artisans, and a lively farmers-market-by-the-water ambiance. Don’t miss the Sounds of Summer concert series, when local bands play in Yorktown every Thursday night from June through early August – it’s a family-friendly atmosphere at the Riverwalk Landing, so set up a blanket on the grass, get food and drinks from the local vendors, and enjoy the free tunes.


An Afternoon at Chippokes – Explore the History and Trails on a Centuries-Old Farm

Take another day trip to Chippokes State Park, a 1,400-acre plantation full of history and nature trails. It’s on the other side of the James River, so it involves a fun and free ride aboard the Jamestown-Scotland ferry, doable by either car or bike. Chippokes Park takes its name from a Native American chief named Choapoke and has been a working farm for over 400 years, going through various iterations since the time of the first settlers (Captain William Powell established the plantation in 1619), through the Civil War, and into modern times, still being farmed and housing farm animals today.

Start with a free, self-guided tour of the Farm and Forestry Museum, which has artifacts showing what daily life and farm work were like throughout the centuries at Chippokes before modern tools changed the landscape. Check out the antebellum mansion, outbuildings (including slave quarters, an up-close glimpse of a brutal chapter of our nation’s past), and the twelve miles of connected trails throughout the sprawling property – it’s a place where Virginia’s natural beauty and fascinating history are equally impressive.

Stay with us, where your day trips from Williamsburg will be scenic, fun, and full of history!

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