5 Charming Valentine’s Day Locations in Williamsburg, Virginia


Williamsburg, Virginia has no shortage of charming, romantic spots. If you’re looking for a special place to take your sweetie for a picnic, dinner, or perhaps, to pop the question, we’ve listed a few of our favorite charming areas in Williamsburg, Virginia for Valentine’s Day.

The Crim Dell Bridge
The College of Williams & Mary

Charming Valentine’s Day Locations Williamsburg VA

The campus of The College of William & Mary is nothing if not charming. As the second oldest college in the United States, founded in 1693, there is no lack of beautiful architecture, amazing history, and especially hidden romantic spots. The most famous and romantic is the Crim Dell Bridge.

What’s so special about this spot?

This bridge is stretched over a charming wooded lily pond, out of sight from tourists and students. In addition to its stunning location, the bridge also carries an interesting legend.

The Romantic Legend of Crim Dell Bridge

According to legend, if you walk across the bridge with your significant other and kiss in the middle, you are destined to be together forever. However, the legend also states that if the relationship does not work out, the couple must revisit the bridge and break the spell by tossing one of the two into the pond.

So before you go, make sure it’s with someone special!

The Big Tree on Nicholson Street
Historic Colonial Williamsburg

Charming Valentine’s Day Locations Williamsburg VA

You can find this charming site in the center of beautiful historic downtown Williamsburg.
This amazing tree stands 61 feet tall and spans 119ft around, providing lovely shade and some romantic privacy.

According to the Daily Press, oak trees were very important to early colonists, as they served to provide much of their needs and wants. Its wood provided warmth in the winter, the shelter and comfort of their homes, and prosperity as they sold the lumber back in England.

What makes this tree so romantic today?

This oak tree symbolizes the promise that the couple will keep each other warm, provide safe shelter and comfort, as well as the promise of prosperity in their new life together. Because of this tradition, the tree is a well-known proposal spot for both locals and tourists alike.

Quite romantic!!

The tree is located on Nicholson Street right across from the George Tucker House, making it a less formal, but very special location.

Historic Williamsburg Carriage Rides
Historic Colonial Williamsburg

Charming Valentine’s Day Locations Williamsburg VA

As you walk through Colonial Williamsburg, you’ll no doubt see the horse drawn carriage rides that tour the city.

Need we say more?

There is no more iconic way to show love and invite romance than with a charming carriage ride. And a carriage ride through the historic streets of 1700s Colonial Williamsburg is special enough to rival even the most romantic movie scene.

How can you get one?

Tickets to ride are open to everyone, however, you cannot schedule them ahead of time. To make your reservation, you must go to the ticket counter the day-of to buy your tickets. Tickets can be bought at the Lumber Yard in Colonial Williamsburg. We recommend getting there early, especially on Valentine’s Day, as they tend to fill up quickly! The ticket counter opens at 9am!

Click here for more information about booking Colonial Williamsburg carriage rides.

The Fat Canary Restaurant
Patrick Henry Square

Charming Valentine’s Day Locations Williamsburg VA

If you plan to stay in the downtown district and are looking for a romantic restaurant for dinner, we can think of none better than The Fat Canary.

Our reasons?

  • They have some of the best food in Williamsburg! They offer a wide variety of entree choices, including salmon, duck, and prime rib. And don’t get us started on their desserts!
  • They have a romantic location and atmosphere. Quiet tables, dimmed lighting, and lovely music makes this an extra special location.
  • The staff will make it extra special. If you are celebrating an anniversary or perhaps even proposing, let the hostess know when you make your reservation! They bring out free dessert or a bottle of champagne to take home. They also do a special keepsake menu personalized just for you!

Williamsburg Winery
Wessex Hundred Estate

Charming Valentine’s Day Locations Williamsburg VA

If you want to head outside the downtown district and get some fresh air, the Williamsburg Winery is another charming and romantic place to visit. Spanning hundreds of acres, the rolling green hills and grape vineyards serve as the perfect backdrop to any romantic occasion, especially Valentine’s Day!

What is there to do?

The winery offers many wine tastings and tours, every half an hour, as well as, special reserve wine tastings that are by reservation only. In addition, they also have a lovely tavern on the property serving gourmet salads and sandwiches.

As you can see, there is no shortage of charming Valentine’s Day Locations in Williamsburg, Virginia! How about you? Did your favorite spot make the list?


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