Best Spots in Williamsburg, VA to Pop the Question this Valentine’s Day!

Love is in the air! If you’re planning to pop the big question this Valentine’s Day, Williamsburg, VA is the place to do it! Williamsburg is known for rich history,  quaint charm,  fabulous food, and quiet romance. Here are our top picks for proposal locations

Colonial Williamsburg

We recommend three different locations in the revolutionary city for the big moment:

  1. Governor’s Palace
    The Palace Green lawn right in front of the gates provides a picturesque backdrop in the middle of the town. If you prefer something more secluded and private, check out the grounds behind the palace, which offer gardens, benches, and a quiet stream.
  2. The Big Tree on Nicholson Street
    This large, beautiful tree is a well-known proposal spot for both locals and tourists alike. The tree is located on Nicholson Street right across from the George Tucker House, making it a less formal, but very special location.
  3. Carriage Rides
    CW offers horse-drawn carriage rides daily. This 15-minute ride tours all the best spots in the colonial city. Tickets can only be purchased the day of the tour, so plan to buy these tickets first thing when you get downtown before they sell-out! Don’t forget to tell your driver your plans as many of them will make a special stop for you.


Crim Dell Bridge

bridgeThis bridge is located on the College of William & Mary campus. Tucked away in the trees, this romantic spot can be easily overlooked. This bridge is well-known by locals for it’s romantic lore. Legend says that if you kiss someone on this bridge, you will become soul mates and remain forever in love. You can’t beat that for romance!


Fine Dining Restaurants

There are three restaurants we can recommend for an intimate Valentine’s Day Dinner. We recommend calling for reservations as soon as possible.

  1. The Regency Room at The Williamsburg Inn
    This 4-star restaurant will be offering a Sweetheart Valentine’s Day Dinner. This six-course meal is unbeatable and perfect for an extra special occasion.
  2. Opus 9
    Williamsburg’s finest steakhouse is offering both a Sweetheart brunch as well as killer dinner specials. When you call for your reservation, ask to sit in one of the couple’s booths in the back. These are the best tables for an intimate meal.
  3. Le Yaca
    The finest French dining in Williamsburg. They are offering a Valentine’s Day brunch menu for early in the day as well as a three-course dinner menu in the evening. This is without a doubt one of the most romantic restaurants, with intimate seating and candlelight.


Williamsburg Winery


The Williamsburg Winery offers many different tasting options and tours. The property includes The Gabriel Archer Tavern, which serves gourmet salads and sandwiches. Prepare to experience breathtaking views!


A Romantic Bed & Breakfast

Williamsburg has no shortage of quaint, cozy, and romantic bed and breakfasts in town. If you’re looking for a private proposal, this is a great way to go! If you prefer a room with a view of the city, choose one of the B&Bs downtown. If you would prefer gardens or a cute backyard, check out some a mile or so away from the city center. When you book your stay, ask about any romance packages they may be offering for the holiday and let them know you plan to propose! The innkeepers can be a great help in helping you find the perfect place on the property for the proposal and that you are undisturbed.

Horse-back Ride & Picnic Lunch at Carlton Farm Stables


If your beau loves the outdoors, Carlton Farm Stables offers horse-back rides on designated trails, perfect for everyone from beginners to experts. A proposal wont get much more outdoorsy and secluded than this. They offer a private 90-minute tour with picnic lunch included. Williamsburg residents receive a 50% discount!

Whether you are planning a grand and public proposal, or something more private, there are plenty of options here to fit any plan! If you’re going out, be sure to tell your hostess, innkeeper, concierge, or tour guide your plans! You’ll find these people are eager to make the event perfect and extra special!

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