While there plenty going on in Williamsburg, Virginia this weekend for Valentines day, there is enough non-valentine related events to entertain even the dateless!

Crim Dell William and Mary romantic spots in Williamsburg Virginia, near Colonial Williambsburg

This weekend looks to be a typical early spring weekend in the Historic Triangle. There are plenty of outdoor events as well as indoor family activities, if a little chill isn’t in your plans..

For more details and events you can check events for any date by using our events calendar search.

Southeast Virginia Arts Fair & Colonial 1/2 Marathon

The tradition continues, on February 15th, 2020 in Williamsburg, Virginia. Colonial Sports, Inc. sponsors this historical 1/2 Marathon Run.

Half Marathon Run. Race is followed by the Southeast Virginia Arts Fest. Live Music, Beer, Food, Arts. Located at the DeWitt Wallace Decorative Arts Museum 325 Francis St. East. See you there !

Catch A Play

The Williamsburg Players are performing

By Neil Simon
Directed By Sam Miller
Showtimes: Fri. February 14th, 7pm. ~~~ Sat. February 15th, 1pm & 7pm

Simon was inspired by his experience working as the youngest staff writer on Your Show of Shows beside comic greats like Sid Caesar, Mel Brooks, and Larry Gelbart.

With comic drama, the play tells the story of a harried writing staff frantically scrambling to top each other with gags while competing for the attention of star madman “Max Prince.”

Pressure from both the network and national political environment threaten the show’s cancellation, raising the stakes and the humor ever higher as the humor rises toward a comic boiling point. MORE INFO


Dog Street Pub offers a happy hour M-F | 3-6 

$5 Eats

PUB CHIPS: thick cut steak fries topped with 
welsh rarebit cheese sauce and pancetta

HOUSE JERKY: house made beef jerky with rarebit cheese sauce 

PORK NACHOS: fried tortillas topped with marinated pulled pork, 
cheddar and BBQ Sauce

CHICKEN QUESADILLA: blackened chicken breast, peppers, 
onions and pepper jack


🍸 $5 cocktail list

🍺 Selection of Beer deals including a 20pz Imperial pint of our Alewerks & DoG Street Pub Collaboration Maizie’s ESB.

Weekend Live Music

The Deloreans at Precarious Beer Hall

For an out-of-the-ordinary Valentine option, don’t miss The Deloreans live at Precarious. This all 80’s show band from Hampton Roads, Virginia . They are a local-favorite, high-energy band offering some of your favorite retro cover tunes.

The Groove Cats at Cogan’s Deli & Sports Pub

If blues are more your thing, check out The Groove Cats who put a fresh spin on the traditional blues genre. Their style reflects a diverse combination of rock, funk, and jazz with and infectious blues groove.

John Spence at Center Street Grill

The Dog Street Boy’s John Spence will be playing live acoustically at Center Street Grill! Come out and support local music and hear your favorite tunes. More About John

Free Live Jazz at Culture Cafe
Sunday February 16th from noon til 2 pm.

Two great local artists Brandon Musko – saxophonist and Randall Lawson on keyboard both from Good Shot Judy together they promise to deliver an upbeat jazzy afternoon!

Weekend Dining in Williamsburg

Just about any restaurant could be the setting for your Valentine’s dinner, but why not splurge for something truly special?

Culture Cafe Your favorite date spot has Valentine’s Day covered from Wednesday February 12 thru Sunday February 16 with a special made for two! Pierogis and kielbasa sautéed in a red pepper coulis with mixed
greens, house made rolls and a sinful chocolate heart cake that will
start your celebration of with love ❤️  ($16 for two)!

Waypoint Seafood & Grill is celebrating Valentine’s Day all weekend. Join them on the 14th for a la carte dining in a romantic setting featuring Smoked Tuna Belly Amatraciana, Wood Grilled Kobe Beef, Dark Chocolate Stout Cake, plus special romance-themed drinks. On Sunday, Feb. 16, 2020, don’t miss their Chocolate Lover’s Brunch offering crab, lobster, shrimp, and scallops plus delicious appetizers and decadent desserts. Reservations are suggested. Located at 1480 Quarterpath Road in Williamsburg, Virginia. Learn more.

Other Romantic Williamsburg Restaurants

Romantic Williamsburg Weekend

Café Provencal at the Williamsburg Winery – is offering a special menu from Feb. 14-16 2020 in honor of Valentine’s Day. The french-inspired selections include caviar, confit duck, lamb tartare, lobster tail and New York Strip. Dessert features smoked vanilla and chocolate mouse , and – of course- the wine list is spectacular. There’s no need to rush home after dinner if you chose the Valentine’s Day Escape Package at Wessex Hundred, a one-night couple’s retreat that pulls out all the stops . Enjoy a one night stay in their Tradition Room, with king-sized bed and wood-burning fireplace. The package also includes wine tasting for two, a welcome bottle of wine, artisanal chocolates, and a continental breakfast. You’ll also enjoy a $100 dinner voucher for Café Provençal for a fairytale Valentine’s Day that will not be forgotten.

Williamsburg-Themed Romance

A Ride Through History

In classic romance movies, the happy couple is often featured riding off into the sunset. Why not make this movie trope a romantic reality? A cozy and intimate horse-drawn carriage ride through Colonial Williamsburg is the ultimate in romance. Where else can you wind through quiet streets while taking in a number of 18th century living-history sites including the Capitol Building, quaint colonial taverns, and the Governor’s Palace? Carriage rides are offered daily, weather permitting, and do have limited availability.   Tickets may be purchased at the Lumber House Ticket Office (on Duke of Gloucester Street across from Palace Green), or the William Pitt Store (on the corner of Duke of Gloucester Street and Botetourt Street) on the day of use.

Tickets can also be purchased online.

Lover’s Bridge

Another uniquely-Williamsburg experience is the Crim Dell Bridge on the campus of William & Mary. With its beautiful arched walkway and ornate design, it’s not surprising that it has been nicknamed “Lover’s Bridge.” In fact, the Crim Dell is one of the most photographed spots in Williamsburg, and has frequently been ranked one of the most romantic places on a college campus in the United States. According to the myth, if you cross the bridge with the person you love – and kiss at the end – you’ll stay together forever. With its close proximity to the colonial area, it’s an easy and romantic stroll with a “wow” finish to celebrate your special relationship on Valentine’s Day – or any day!

The Crim Dell is located directly behind the historic Christopher Wren building near the beautifully landscaped Sunken Garden. It’s the perfect spot for a Valentine’s Day picnic!

Williamsburg’s Valentine’s Day Farmers Market

If you’re looking for a special gift with Williamsburg flair, be sure to stop by the Valentine’s Day Market Feb. 8 in Merchants Square. The market features over 25 local vendors with a variety of baked goods, honey, plants, kombucha, coffee, mushrooms and more. The market runs 8am-12noon.

Additional Details

Anti-Valentine’s Day Options

Here’s a Valentine’s Day celebration like no other! Who needs flowers and chocolate when you have ex’s and axes? Axe Republic, an axe throwing and entertainment establishment, invites you to bring in a picture of your ex for the bullseye. Friday, February 14, 2020 at 5 PM – 10 PM at 4919 Courthouse St. in Williamsburg’s New Town.

axe republic axe throwing entertainment venue in williamsburg virginia

For more information

Thanks for reading. All WilliamsburgVisitor.com content, articles, news updates, event calendars, Food Truck Tracker and Live Music Finder are always free!

Previous articleBusch Gardens, Water Country USA announces ‘Fun Sale’ in 2020
Next article25% Discount at Chowning’s Tavern During Colonial Williamsburg’s Colonial Fashion Days


Please enter your comment!
Please enter your name here