Enjoy a Stellar Weekend in Williamsburg: Top Things to See & Do

Enjoy a Stellar Weekend in Williamsburg: Top Things to See & Do :: I've Been Bit! Travel Blog

Williamsburg is best known to many as a historical hot spot. Many Virginians have probably visited Jamestown, Yorktown and Colonial Williamsburg (also known as the historic triangle) whether that be for school trips or a family vacation. While history buffs will be in their element as it’s home to the largest outdoor living museum in the United States, others may be quick to write it off in favour of a different destination. I’m here to share that with plenty of outdoor recreational opportunities, unique experiences and delicious eats, it’s easy to spend a wonderful weekend in Williamsburg as there is truly something for everyone.

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A Little About Williamsburg Virginia

What is now Williamsburg resides in the traditional territory of the Powhatan Confederacy who have called these lands home for over 12,000 years. It consisted of the Pamunkey, Mattaponi, Upper Mattaponi, Chickahominy, Eastern Chickahominy, Nansemond and the Rappahannock tribes. Colonization saw the upheaval of the Indigenous as English settlements had grown to overtake this area by the 1630s. Those interested in learning more can better understand the turbulent history via this timeline crafted by the National Parks Service.

Of the American colonies to exist at this point, Virginia was the largest, most populated of the American colonies and therefore the centre of culture, education and politics. As tensions between the American colonists and England grew, leaders sought a better life with the leaders of Williamsburg at the forefront. The thirteen colonies voted unanimously to declare independence from England and their ideologies for justice and liberty later became a pivotal part of the US Constitution.

Knowing just this tiny bit of information, it becomes clear why Jamestown, Yorktown and Colonial Williamsburg are such historical destinations. Not only this but Williamsburg is also home to the College of William & Mary, the second-oldest university in the United States as it was established in 1693 with Harvard as its only predecessor. 

I’m barely scratching the surface here but that’s all the more reason to plan a weekend in Williamsburg. See for yourself just how much history there is to uncover or follow along in my footsteps and uncover some of the other incredible things to do in the city!

Pedestrian Area in Colonial Williamsburg at Sunset :: I've Been Bit! Travel Blog

Pedestrian Area in Colonial Williamsburg at Sunset

Top Things to Do in Williamsburg

Before I dive in, I want to differentiate between Williamsburg and Colonial Williamsburg. It’s my understanding that Colonial Williamsburg is one of the three living history museums (with the other two being Jamestown and Yorktown) and refers to the area within Francis, Waller, Nicholson, North England, Lafayette, and Nassau Streets. Everything else outside of that is Williamsburg, though they are all often marketed together due to their close proximity to one another.

This guide will have some destinations within Colonial Williamsburg, however it has a heavy emphasis on non-historic things to do in the area. While some locations may technically be in neighbouring districts and counties, they are close enough to the border that they are often referred to as a part of Williamsburg.

Walk Around the Pedestrian-Only Duke of Gloucester

Something I love and wish more cities had are pedestrian-only thoroughfares so you can imagine how delighted I was to find the Duke of Gloucester Street! As the main artery for Colonial Williamsburg, you’ll enjoy beautiful expanses of heavily treed walkways past gorgeously maintained architecture that are a meld of old and new. It’s fascinating to see how various elements from the 1770s mix and mingle with the present day! Grab a seat at one of the many tables, enjoy a meal on one of the patios or pop into some of the local shops. You can easily spend a few hours in Merchant’s Square alone, featuring over 40 shops and restaurants bursting with that old-time charm.

While many of my readers aren’t as big of a winter nut as I am, it’s no stretch of the mind to think about how the quaint architecture of Colonial Williamsburg is straight out of a Hallmark card. With a sprinkle of snow, this whole area would be picture-perfect and I’ve been told that Williamsburg gets decked to the nines around Christmas time!

Explore The College of William & Mary’s Campus

While the eastern end of the Duke of Gloucester will have you feeling as though you stepped into the 1700s amidst live actors in costume, the western end leads you into The College of William & Mary’s Campus. I’m always so blown away by the magnificent grounds of American universities as it’s so different than us here in Canada. What a treat it must be to walk between classes past mature trees through forested walkways. My love for nature probably would have blossomed sooner!

Luckily I can enjoy it now as the campus is open for anyone to enjoy their trails. One of the campuses main features is the Sunken Gardens. Designed with 18th-century English landscape gardens as the inspiration, you’ll see sweeping lawns rather than ornamental flower beds. However, two massive Oak trees stand out on the horizon, one willow and one water, that are said to be the oldest trees on campus.

Choose your own adventure as the pathways mix and mingle and soak up the sights of The College of William & Mary. Public sculptures dot the area and feel like a sort of treasure as they seem to pop out of nowhere. I highly recommend exploring the trails along the shoreline of Matoaka Lake. You’ll hardly believe you’re in the middle of a city with how peaceful the area is! Named after the true Powhatan name for who we know as “Pocahontas”, this pond was constructed around the year 1700 to power a gristmill which once stood here. 

See the Crim Dell Bridge

As I said, The College of William & Mary Campus is stunning but the crown jewel has to be the Crim Dell Bridge. While Crim Dell refers to the pond, when folks say Crim Dell, they mean the iconic wooden bridge spanning the body of water. It’s quite a beautiful sight as the rich cranberry red pops amongst the surrounding emerald foliage. 

Campus folklore states that if two people hold hands while crossing the bridge, they’ll be friends for life. However if they kiss, then they’ll be lifelong lovers. I can only imagine how many people have taken a love interest across in the hopes of an everlasting romance but there’s no denying that it’s one of the most beautiful spots in Williamsburg.

Lindsay Sitting In Front of the Crim Dell Bridge :: I've Been Bit! Travel Blog

The Crim Dell Bridge is Not to Be Missed in Williamsburg!

Take a Haunted Tour of Colonial Williamsburg

Suppose you’re like me and aren’t the biggest history buff but are still curious to know a bit more about the area’s history. In that case, I highly recommend participating in a haunted Colonial Williamsburg tour.

A great mix of then and now, follow your guide as you learn about some of Williamsburg’s notoriously haunted buildings like the Peyton Randolph House. They’ll share about the important roles the historic dwellers of these buildings played in the happenings of Williamsburg and how they continue to interact with the living to this very day. Be sure to follow your guide’s instructions to politely greet and pay your respects to characters like Gertrude Ball Daversa and Father Goodwin or you may just experience some spooky sightings!

INSIDER TIP: While there are numerous haunted tours of Williamsburg, this is the only tour that allows you to enter a handful of the most haunted buildings in the city. However if the tours are sold out, I still recommend experiencing a haunted tour so take a look at these additional options here.

If you want to dive deeper, you can always check out some of the other things to do in Colonial Williamsburg such as the art museums or the Governor’s Palace later in your visit.

Paddle Chickahominy Riverfront Park

Located approximately 20 minutes from the heart of Williamsburg, Chickahominy Riverfront Park is a great escape for nature lovers. Visitors will be treated to beautiful views of tidal streams and rivers where you’ll find a variety of marsh birds, especially during low tide when the mudflats are revealed. Birders may catch glimpses of Eastern Kingbirds, White and Red-Eyed Vireos, Great Crested Flycatchers and more.

This 140-acre park is a popular camping spot featuring two pools, playgrounds for kids, riverfront boat access and rentals. Interpretive signage within the park shares how this area was originally inhabited by the Paspahegh People as discovered by archeological digs near Jamestown. While this park is more for picnicking and play, it has a few boat launches which make it fantastic for exploring by water. Rentals are available from the park office by the hour or for the day. Rates can be found here.

From the main boat launch, you’ll paddle into Gordon Creek. These calm waters are an offshoot of the Chickahominy River and offer plenty of little nooks to explore. I loved paddling under the overhanging trees and watching for birds from the water. You can also head out onto the larger Chickahominy River and paddle under the bridge to the James River if you’re feeling adventurous! Whether you wish to paddle for an hour or a full day, there’s no shortage of possibilities for exploration.

Kayak Around Waller Mill Park

If that’s not enough, another fantastic option for paddling is Waller Miller Park. This 2,705-acre park features a 360-acre fishing reservoir and numerous options for boat rentals. Canoes and kayaks are available during the summer months while rowboats and motorized boats can be rented year round. Full details including rates for rentals can be found here.

Heavily forested shorelines make for a beautiful paddle on these calm waters. I was surprised to find a number of turtles sunbathing on some of the fallen logs which was such a treat! While it’s a common spot to fish so you will come across other boats, it’s very quiet and everyone is respectful. For anyone who’s new to paddling and looking for calm waters to get some experience, this is the perfect place! Even an experienced paddler like me enjoyed leisurely exploring the various coves and admiring the beautiful reflections off the water.

If you wish to extend your stay, check out some of the park’s fantastic hiking trails like the Reservoir and Tower Trail or the Bayberry Nature Trail. Be sure to grab a selfie at the Virginia LoveWorks sign before you depart!

Water Reflections from a Kayak at Waller Mill Park :: I've Been Bit! Travel Blog

The Reflections from Waller Mill Park

Grab a Flight at the Virginia Beer Company

The brainchild of two College of William & Mary alumni, the Virginia Beer Company is not just a brewery but a venture in philanthropy. While their careers originally took them elsewhere, co-founders Chris and Robby stayed in touch. They were reunited as Chris moved back to Williamsburg and that brought their passion to life. While it took longer than the two had hoped as it was quite the process to convert the old building where telecommunications utility trucks were serviced, they were thrilled to open the Virginia Beer Company’s doors in 2016.

The team never stops experimenting as they brew over 150 beers in a single year. Some are flagship brews that you’ll see return again and again while others are one-shots, but the fact of the matter is there will always be something new to try whenever you visit! I highly recommend grabbing a flight so you can try a few of their brews. I had a handful while I was there and my favourites were their Crosstown Coffee Porter made with coffee beans from local shop Column15 and the One with All the Berries fruited gose crafted with blackberry, raspberry puree, blueberry and boysenberry purees. Also if Pizza Hawk is on tap during your visit, definitely ask about the story behind the name!

FUN FACT: The Virginia Beer Company crafts so many beers that they often have trouble naming them so they’ll often ask their supporters for help. 

With the mantra drink good beer, do good things, Williamsburg’s second microbrewery has no shortage of partners, making it a community leader. I’ve honestly never heard of a brewery that works with so many causes! Whether it’s with local businesses, non-profit partners or other charitable organizations, the Virginia Beer Company is happy to step up to the plate and craft a beer to support. You can check out a handful of their partners here!

Hop On a Guided Bike Tour

Cycling has never been high on my list of things to do when exploring a destination but over the past few years, I’ve embraced it more and I’m so glad I have. Otherwise, I’d miss out on incredible tours like the River to River E-Bike Tour with Williamsburg on Wheels!

Meet your guide at the Jamestown trailhead of the Virginia Capital Trail as you get set up and ready for two hours of exploration by bike! You’ll closely follow Highway 5 as you enjoy a small section of this 83-kilometre-long multi-use trail. Along the way, your guide will share fun facts and plenty of historical information about the areas you’re pedalling through such as the Battle of Green Spring, relations between the settlers and the Powhatan People, the true history behind what we know as Pocahontas, and more.

I was incredibly impressed by how much knowledge my guide William shared with me. It was fantastic to learn in-depth about the true history of the area while getting the blood flowing! Plus you’ll cross numerous boardwalks, bridges, and beautiful forests with a rest stop along the Chickahominy River Bridge. At the 9th mile marker, you’ll turn around to head back to your start point.

If two hours seems like a lot to you, you can hop on their hour long tour that takes you along the Powhatan Creek Trail. Of course, you can always explore on your own and just rent an e-bike from Williamsburg on Wheels as they offer hourly, half-day and full-day rentals.

Artisan Italian Pizza at The Social Terrace in the Williamsburg Inn :: I've Been Bit! Travel Blog

Artisan Italian Pizza at The Social Terrace in the Williamsburg Inn

Amazing Williamsburg Restaurants

With over 170 restaurants in Williamsburg, there is no shortage of dining options. However, I can confirm without a doubt that these spots have delicious eats!

The Social Terrace

On the outdoor patio of the luxurious Williamsburg Inn is where you’ll find The Social Terrace. Enjoy the stunning architecture of this historic building as you dine al fresco overlooking the gorgeous grounds of the Golden Horseshoe Golf Course. It’s casual yet classy and perfect for a weekday dinner date or celebrating a special occasion.

Their menu isn’t large which I love, especially as it offers quite a variety of flavours. However, I recommend one of their hand-crafted pizzas as they’re made with Red May Wheat Berry. This rare and historically milled flour dates back to the colonial era! I opted for their Artisan Italian pizza topped with pepperoni, sausage, and bresaola sourced from Virginia’s Chapel Hill Farms located in Berryville just east of the I-81 near Winchester. These delicious meats mix and mingle with balsamic braised onions, fresh Mozzarella and San Marzano pizza sauce with a sprinkle of basil and oregano. My mouth’s watering just thinking about it!

In case it isn’t implied, The Social Terrace is seasonal and open weather permitting.

Berret’s Seafood Restaurant

Located within Merchant’s Square, Berret’s Seafood Restaurant was once a gas station and is now a fantastic restaurant with a beautiful outdoor patio. It’s said to be one of the best seafood restaurants in the city as they source the freshest seafood regionally from the York and James Rivers and the Chesapeake Bay as much as possible. If you’re not a fan of seafood, they have a variety of land-based proteins that are just as high in quality.

While I’m sure their dinner menu is fantastic, my visit had me enjoying a meal from their brunch menu. When I saw their flash-fried crab cakes and poached eggs, I knew I had to have it. Three cheese grits are shaped into patties and crowned with a slice of Virginia Ham, fresh tomatoes, poached eggs and Hollandaise sauce. Accompanied by sausages from Edwards Smokehouse in Surry and their incredible crab cakes, this is a protein-heavy meal with so many incredible flavours. It’s practically a bougie Eggs Benedict and after a very early morning of travel, it was exactly what I needed to start my adventures in Williamsburg!

Amber Ox Public House

The fantastic live music on their bustling patio was what drew me to the Amber Ox Public House. Their menu is a nod to classic Southern fare but with their contemporary twists. Every dish highlights the regionally sourced ingredients from several local farmers and producers to utilize whatever may be in season during your visit. 

What’s great about their menu is that you can opt for smaller, shareable plates or a larger main course. While a number of their big plates look delicious like the diver scallops and duck breast, I was very curious about their public house poutine. As a Canadian, I typically have a rule that I only have poutine in Quebec because I’m 99% of the time disappointed, however seeing as Amber Ox actually had cheese curds listed, I was curious. Their fries are delicious and the poutine is topped with shredded pork, pickled cabbage, crema and a chile chimichurri. I honestly thought of it more as decked-out fries rather than a poutine but it’s definitely delicious!

If you visit during their Tiki Mondays as I did, make sure you snag an order of the chargrilled oysters. They’re topped with smoked clam and bacon butter, nauc chom and lemon oil. It might sound like a weird combination but they’re incredibly delicious. Just don’t eat the salt and spices on the plate as it’s meant only as a garnish. Yes, I learned the hard way.

SOMETHING TO NOTE: The Amber Ox enforces what they call a universal hospitality charge as their way of providing a living wage for their employees. Most living wage employers I’ve had the pleasure of dining at incorporate this into their food pricing rather than tacking on a percentage at the end so it seemed strange to me to do so in the form of a mandatory 20% tip, but this could be common practice elsewhere.

Charly’s Airport Restaurant

As soon as I heard there was a restaurant where you can watch planes land and depart, I knew I had to check it out and Charly’s did not disappoint! It’s definitely a popular spot for families but it makes sense considering my inner child was certainly giddy!

A staple of Williamsburg for almost 30 years, this simple, no-frills restaurant has delicious comfort food and plenty of aviation memorabilia. While you can grab a table inside, outside is where the action is as you soak up the sun and get a perfect view of the runway. As their website says “you won’t find a better lunch show in town” and they are right!

Sandwiches are the bread and butter of their menu (sorry, not sorry for that pun) with everything served on their homemade bread baked fresh daily. While I was tempted to go southern with the Kitty Hawk, I decided some comfort food was in order and had Charly’s Famous Cheese Melt aka a grilled cheese. You can add bacon and tomato which you can bet I did and upgraded my side to a cup of their seafood bisque which was perfect for dipping the sandwich in. I satisfied my southern cravings with a sweet tea to round out my meal.

Charly’s is typically only open for lunch but they also do dinner Friday evenings featuring live music on the patio. This spot already is a vibe but to add some golden hour colours and local talent to it would take the whole experience to the next level!

Pierce’s Pitt Bar-B-Que

Long gone are the days when Pierce’s Pitt was just a walk-up stand along the side of State Highway Route 168 selling barbecue sandwiches. Now you’ll find a bold building boasting their signature orange and yellow colours. 

As the name says, southern-style barbecue is exactly what you’ll find on the menu. To be honest, I was a little overwhelmed by the options but I’m happy I decided on the Super Doc Sandwich. Six ounces of slow-cooked pulled pork is smothered in “Doc” Pierce’s original barbecue sauce and layered with cheese, diced onions and their homemade slaw as everything is deliciously sandwiched in a freshly baked six inch sub roll. They do not skimp on the toppings as this sandwich was absolutely bursting!

I have to say though, the hardest part was choosing my sides. I really wanted one of everything but that’s a little much for just one gal so I landed on the baked beans made with hot dogs and their iconic barbecue sauce and southern-style collards as locally sourced greens are simmered with butter with Pierce’s own spice blend from the Spice & Tea Exchange in Williamsburg and ham hocks. Both were out of this world, especially paired with a big cup of sweet tea!

Why the two Ts you may ask? It was the original sign painter’s mistake but he wanted an extra $20 to make the change. In the early days with no extra money to spare, the double Ts stuck and has stayed the same ever since!

Interior of the Safari Tents by Timberline Glamping Company :: I've Been Bit! Travel Blog

Inside One of the Timberline Glamping Co’s Safari Tents

Where to Stay in Williamsburg

There is a plethora of possibilities when it comes to hotels in Williamsburg. You can spoil yourself with one of the historic options within Colonial Williamsburg such as the Griffin Hotel, the Williamsburg Lodge or the iconic Williamsburg Inn. All three are within walking distance of several of the aforementioned points of interest such as the Duke of Gloucester Street, Market Square and the haunted tours. I always love being able to get a break from the car and stretch the legs. However, there’s another option located 20 minutes from Colonial Williamsburg for those who love the outdoors like me.

Remember how I mentioned Chickahominy Riverfront Park earlier? In 2023, Timberline Glamping Co set up some super cool safari tents and I’m obsessed! They have six tents available in two configurations: the Double Safari Tents feature two queen beds and the Deluxe Safari Tents which have a king bed and two sets of bunk beds. 

I had the pleasure of staying in double safari tent #104 and the first thing I noticed was how much space I had! Inside you’ll find a Keurig coffee maker, mini-refrigerator, a diffuser with essential oils made special for Timberline, a heating/AC unit and plenty of outlets to keep your electronics charged. They didn’t skimp out on the decor as you’ll find plenty of adorable items such as a pegboard sign and strings of Edison lights that add to the ambiance. Between the fresh air and their incredibly cozy beds, you’ll sleep deeply with the rustling leaves and slight splash of Gordon Creek as your soundscape. 

Each tent also features its own patio facing the water with two Muskoka chairs, a charcoal grill complete with a cooking grate, a picnic table and a hammock which is perfect for relaxing on those hot summer days in Virginia! For those wondering, the tents are all located just steps from the comfort station which has three toilets and three showers for all campers to use.

Sound like the perfect Williamsburg getaway to you? Then don’t delay and book your glamping tent now as they sell out quickly! If you do find they’re unavailable for your dates, you can always see what hotels in Williamsburg are available during your travel dates.

Front of the Williamsburg Inn with Reflection in the Pond Water :: I've Been Bit! Travel Blog

Reflections of the Williamsburg Inn

Things to Know for Your Weekend in Williamsburg

Have I convinced you to plan a getaway to Williamsburg? That’s what I like to hear! Check out these popular questions and things to know about visiting so you can make the most of your Williamsburg weekend.

How do I get to Williamsburg Virginia?

Located just one hour from Norfolk International Airport, head west along Interstate 64 for approximately one hour. While you can get there by bus or train, I highly recommend renting a car from the airport as this is the most direct way to travel and allows you the freedom to explore the gems surrounding Williamsburg that I’ve highlighted in this post.

What is Williamsburg VA known for?

Williamsburg has made a name for itself as the centre of preservation of America’s colonial history largely due to the not-for-profit The Colonial Williamsburg Foundation. As one of the United States’ top public universities, The College of William & Mary has largely contributed to the city’s prowess as well.

When is the best time to visit Williamsburg?

The summer months can be quite a scorcher and the abundance of tourists can potentially impact your visit. In my opinion, the best time to visit would be in either spring or fall as you have a combination of great weather and many of the attractions are still fully operational. My visit was the perfect balance of comfortable weather and a lack of crowds so I highly recommend visiting in the latter half of May for your Williamsburg vacation.

What’s parking like in Williamsburg?

There is ample parking in Williamsburg, whether that be street parking or in designated lots. Many have a two-hour time limit but signage will dictate any limitations. Also, some lots (especially on the College of William & Mary Campus) will require you to use the Passport Parking app. You can always park for free at the Colonial Williamsburg Visitors Centre.

Looking to Extend Your Visit to Virginia?
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While this article was crafted in partnership with Visit Williamsburg and Visit Virginia, all of the content and opinions outlined here are, as always, honest and speak to my personal experience.

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