Ask an Insider: Winter Date Ideas in Alexandria

Are you looking for a cozy spot to cuddle up with your partner on a date night this winter? Named the “#3 Most Romantic City in the U.S.” in 2017 by, Alexandria, Virginia, located just outside of Washington, D.C. is known as one of the top spots in the region to take a date. With Old Town’s colonial architecture, cobblestone streets, historic charm, and walkable downtown filled with independent restaurants and bars, it’s easy to stroll and find a hidden gem where you can unwind, enjoy a drink and take in live music nearly every night of the week. Resist the urge to hibernate and get outside with these top winter date ideas provided by those in the know.

Dr. Andy Baldwin
“The Bachelor,” Season 10

King Street Stroll Under the Stars

IMG_8819v2-3_Masonic_Temple_dusk_holiday_lights_CREDIT_Matt_Chenet_for_Visit_Alexandria_2100x1400_300_RGBImage Credit: Matt Chenet for Visit Alexandria 

U.S. Navy Dr. Andy Baldwin knows a thing or two about impressing a date. As the bachelor of the 10th season of the reality dating show “The Bachelor” he went on his share of romantic excursions. Though he’s not handing out roses on national television anymore, when he wants to impress a date this Alexandria resident says it has to start with a stroll on King Street.

“Winter is a magical time in Old Town,” Andy says. “My favorite thing to do with my date is to stroll King Street in the evening, cuddle up and take in the view of tree lights all the way down to the George Washington Masonic National Memorial.”

While strolling under the stars Andy suggests stopping for hot chocolate at Killer ESP or coffee at Misha’s Coffee, having oysters and a beer at Hank’s Oyster Bar, ducking into an antique shop or watching street performers at the waterfront.

Spooks & Sparks

Carlyle_House_with_Ghost_Tour_credit_Richard_Nowitz-3Image Credit: Richard Nowitz

Another way to take in the beauty of Alexandria at night is by going on an Alexandria Original Ghost & Graveyard Tour that leaves from the Alexandria Visitor Center. “I learned so much about Alexandria history and the city’s graveyards, it was like a step back in time,” Andy says. “My date and I loved it.”

Rebecca Cooper
Restaurant and Retail Reporter, Washington Business Journal

Lunch Date at Restaurant Eve

Restaurant_Eve_CREDIT_Restaurant_Eve2 smallerImage Credit: Restaurant Eve

As a Washington Business Journal reporter who covers the D.C.-area dining scene, Alexandria resident Rebecca Cooper knows all about the region’s hottest restaurants. For a perfect lunch date spot, or if you want to treat yourself, she suggests the “lickity split lunch” at Restaurant Eve. Tucked away just off King Street, Restaurant Eve is a beautiful, acclaimed restaurant that is one of the city’s finest dining establishments—even President Obama and Michelle Obama dined there for their 19th wedding anniversary. At the helm is three-time James Beard Best Chef Mid-Atlantic nominee Chef Cathal Armstrong.

“Val, the lunchtime bartender, is a true pro, and Cathal Armstrong is sure to be cooking up something warm and comforting in the winter months,” says Rebecca. “At $15 for two courses, it’s a steal.”

Art & Artfully-Crafted Cocktails

volas_Hi-TideLounge2_JeremyBrandt-VorelImage Credit: Jeremy Brandt-Vorel for Vola’s Dockside Grill and Hi-Tide Lounge

When winter kicks into high gear Rebecca satisfies her desire to wander in Old Town by heading to the Torpedo Factory Art Center with her husband and checking out what the more than 80 artists who have studios there are working on. With three stories featuring artists who work in a range of mediums from painting to ceramics to stained glass, as well as seven galleries, there is plenty to see.

“The newly opened Hi-Tide Lounge in the building makes for a great next stop,” says Rebecca. “What better way to transport yourself to paradise when it’s freezing out than with tiki drinks?”

Mellenie Runion
Owner, Truly-Life

Neighborhood Bites & The Birchmere

Birchmere_1_CREDIT_R_Kennedy_for_Visit_Alexandria smallerImage credit: R Kennedy for Visit Alexandria

If you or your date is a music lover, Del Ray resident and owner of Truly-Life Eco Gifts Mellenie Runion suggests heading to The Birchmere, which is celebrating more than 50 years in Alexandria. This legendary music hall has welcomed musicians like Johnny Cash and Ray Charles and still offers a mix of legends and rising stars in an intimate setting. Before the concert, she suggests grabbing a bite at RT’s Restaurant, a nearby neighborhood favorite featuring New Orleans-style classics, and enjoying a cocktail and dessert during the show.

Matthew Stensrud
Chair, Alexandria Commission for the Arts

Down-to-Earth Date Night in Del Ray

COURTESY GREG POWERS (42)Image Credit: Greg Powers for No. 9 Lounge

For those wanting to explore a different side of town, Matthew Stensrud suggests heading to his neighborhood of Del Ray for a down-to-earth flavor of Alexandria. “One of my favorite spots to go to with my partner is The Sushi Bar, an adults-only restaurant nestled between Pork Barrel BBQ and Holy Cow on Mt. Vernon Avenue in the heart of Del Ray.” With a modern feel and dim lighting, it’s perfect for intimate conversation. Matthew says the Baby Octopus Salad is a must-try appetizer.

After dinner, Matthew suggests strolling down Mt. Vernon Avenue and stopping in the Majestic Lounge, a neighborhood bar tucked behind Evening Star. Known for its local flavor, grab one of the many beers on tap or enjoy a specialty crafted cocktail. Open Wednesday through Saturday, the No. 9 Lounge upstairs is a great place to hear live music or shoot some pool.

Brooke Sydnor Curran
Founder and CEO, RunningBrooke

 Miles & Mimosas

Del_Ray_Cafe_CREDIT_K_Summerer_for_Visit_AlexandriaImage Credit: K Summerer for Visit Alexandria

If you’re a marathon runner like Brooke Sydnor Curran, whose nonprofit RunningBrooke benefits Alexandria’s at-risk children, you may want to opt for a more active date. Her hands-down favorite wintertime date begins with a long run starting in Old Town past historic buildings and down cobblestone streets, up and through Jones Point Park, and down the Mt. Vernon Trail. “Along the way, there is always tons of wildlife, including a bald eagle nest, greenery, marshes and beautiful scenery,” she says.

After your run, head to brunch at Fontaine Caffe & Crêperie in Old Town for Vanilla Brioche French Toast and a Bloody Mary a la Fontaine. Or, if you end your date in Del Ray, indulge in a Crôque Monsieur or Smoked Salmon Eggs Benedict at Del Ray Café.

Chris Van Orden
Marketing and Outreach Manager, Port City Brewing Company 

Morning Cup of Joe


Weekend ritual ☕️One of my Central Perks — I love @swingscoffee

A photo posted by Alice Wang (@alicelily) on


There are plenty of great coffee spots in Alexandria, but when Chris Van Orden and his wife who live in D.C. come to Alexandria they make a day of it. To start, they visit Swing’s Coffee Roasters’ Del Ray Coffee Bar for a coffee and a pastry. “We typically let the barista choose which beans to use for a pour over,” Chris says. “Last time, we enjoyed a rich, fruity cup of Java Honey with pain au chocolate.”

Pizza & Pints

Port City Brewing Company is an artisanal brewery in Alexandria producing a line of hand made, great quality and locally crafted ales for the DC and Mid-Atlantic market. Virginia Tourism Corporation, www.Virginia.orgImage Credit: Sarah Hauser for Virginia Tourism Corporation

Next, like Rebecca, Chris suggests heading to the Torpedo Factory Art Center to check out local artists at work (don’t miss the handmade jewelry!) before heading up King Street to Pizzeria Paradiso for some of the region’s best pies. “We’re vegetarians, so we appreciate having so many options,” he says. “The expertly curated beer list doesn’t hurt either.”

Before heading back to the District, Chris says they stop at his stomping grounds, Port City Brewing Company, one of the best small breweries in the U.S., for one of the tasting room events like the upcoming pairing event with Undone Chocolate on Valentine’s Day.

Want even more date ideas? Visit

Header Image Credit: M Enriquez for Visit Alexandria