4 holiday date ideas for the most romantic time of year

August 2024 · 12 minute read

If you believe the movies, the holiday season is the most romantic time of the year. But parties, shopping and family obligations can also make it the most harried and stressful. To help make the most of your limited free time, we’ve been going on dates around the D.C. area, looking for fun and romantic activities that embrace the best of the holiday season.

We’ve put together four itineraries with recommended stops, as well as optional events to explore. Feel free to reorder them — maybe you want to have dinner before hearing live music, or think an optional item sounds more to your date’s liking than one of the main destinations. No matter what you do, we hope you enjoy it.

Georgetown: Add some swing to your caroling

There’s something even more idyllic about Georgetown’s charm during the holiday season. With light-wrapped trees illuminating cobblestone streets, Christmas tunes drifting from trendy storefronts and an ice-skating rink materializing by the waterfront, the Northwest neighborhood ups its romantic allure with a festive feel. Here’s how to make the most out of an evening in Georgetown.

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Stop 1: Check a name off your gift list.

Start your evening with some (last-minute?) shopping at the Four Seasons Hotel Holiday Market. Behind a towering Christmas tree in the courtyard, covered stalls designed to look like cozy cabins house vendors selling handmade jewelry, contemporary art and other artisanal items. Grab a warm drink from the outdoor hot chocolate bar or watch a holiday-themed musical performance on the courtyard stage. And if you’re in a charitable mood this season, rest assured that a percentage of each purchase is donated to Children’s National Hospital. The market is open Fridays, Saturdays and Sundays through Dec. 18.

Four Seasons Hotel Holiday Market, 2800 Pennsylvania Ave. NW. fourseasons.com/washington. Free entry.

Optional: Get your glow on.

As you stroll, you’ll find light displays scattered throughout the commercial district. As part of the neighborhood’s seasonal Georgetown Glow event, artists from around the world have been commissioned to create five light installations, including an interactive electronic display on which your silhouette appears, a functional swing set under a glowing blue “cloud” and a field of giant glowing butterflies. Works will be on display each night from 5 to 10 p.m. through Jan. 22.

Georgetown Glow, multiple locations. Check the website’s map for details. georgetownglowdc.com. Free.

Stop 2: Catch a Christmas show at Blues Alley.

Wander down Wisconsin Avenue and duck into Blues Alley, the intimate, historic jazz club hosting holiday-themed concerts throughout the month. Christmas lights and tinsel adorn the interior, and cinnamon-scented candles line the staircase. Order from a seasonal cocktail menu and take in the swinging guitar of John Pizzarelli (Dec. 9-11), the bluesy vocals of Nicole Henry (Dec. 17-18) or the soulful saxophone of Langston Hughes II (Dec. 23).

Blues Alley, 1073 Wisconsin Ave. NW. bluesalley.com. Concert prices vary.

Stop 3: Grab a bite at D.C.’s most festive Italian restaurant.

It’s a short walk to Filomena, but take a moment before entering to admire the golden reindeer perched on its awning beside a glowing wreath and strings of baubles. As impressive as it is, the decor is nothing compared with what you’ll find inside. Pass the life-size Santa mannequin in the window and walk downstairs to be greeted by a giant nutcracker. Silver trees with white doves guard sparkly streamers, and red-and-green-striped ornaments hang from the ceiling. That’s just the front of the house. Awash in romantic red light, the dining area shows that Filomena’s staff took the words “deck the halls” to heart. The Brooklyn-style Italian menu is fit for a winter meal with hearty pasta dishes and decadent desserts (the tiramisu is a must-try). There’s an extensive wine list, but a post-dinner amaretto will add a perfectly sweet touch to the end of your evening.

Filomena Ristorante, 1063 Wisconsin Ave. NW. filomena.com. Entrees $16.99-$59.99.

National Harbor: Embrace your inner child

As we get older, we realize that many of the things we love about the holiday season, from lights to carols to snowball fights, are really for kids. But that doesn't mean adults can't join in the fun, or at least carve out their own space.

Stop 1: Take in lights, music and fireworks.

Every half-hour between sunset and 9 p.m., a voice blares from speakers near the National Harbor waterfront, warning everyone that the light show is about to begin. Now, the 60-foot LED tree overlooking National Harbor’s central plaza is already animated with falling snowflakes and twirling ornaments, so you might not think this is a big deal. But then jazzy, brass-driven seasonal music recorded by the U.S. Air Force Band reaches your ears; a blizzard of artificial snow cascades down from the roofs of adjacent buildings; and swirls of light, marching toy soldiers and spinning dreidels take over the facade of the tree for a few minutes. Even the children running around with bubble wands or climbing on “The Awakening” feel compelled to stop and watch. On Saturdays through Dec. 17, things get even more impressive, as a mini-Independence Day fireworks show erupts after the 5:30 p.m. tree lighting and everyone oohs and aahs over a barrage of red, gold and green explosions. The two-part extravaganza is over in around 10 minutes.

150 National Plaza, National Harbor. nationalharbor.com. Free.

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Stop 2: Go for a spin.

The Capital Wheel has become a fixture along the Potomac River, and views from the top of the 180-foot-high Ferris wheel encompass Alexandria, the National Mall and far beyond. The private gondolas mean you and your date can get some one-on-one time while enjoying the lights, which seem particularly merry and bright at this time of year. Buy a combo ticket for $20, which is $5 more than the regular adult admission, and get sparkling wine or beer at the Flight Deck lounge after your ride.

141 American Way, National Harbor. thecapitalwheel.com. $11.25-$15.

Optional: Watch an ice show at the Gaylord National Resort.

This year’s holiday-themed ice show at the Gaylord National Resort is based on “A Christmas Story,” so visitors walk by oversized scenes from the film — the “fra-gee-lay” leg lamp, the pink bunny pajamas, the frozen metal pole — all hand-carved and colored from 10 million pounds of ice, kept at a chilly 9 degrees. The reason it’s optional is that it’s not cheap: Tickets start at $27.99 for kids and $36.99 for adults to walk through and take selfies. If you do go, make sure to visit the hotel’s soaring atrium to see the floating Christmas tree and holiday lights. Competitive couples can check out the new Harbor Social bar, which opened this summer and contains duckpin bowling lanes, a bocce court, shuffleboard tables and darts. Think of it as a bar Olympics.

201 Waterfront St., National Harbor. gaylordhotels.com.

Stop 3: Finish with dinner.

National Harbor’s dining scene is driven by chains. Among the standouts is Bombay Street Food 5, the latest outpost of chef Arjun Kumar Ranabhat’s collection of Indian restaurants, where keema pav, saag paneer and lamb biryani are among the recommended dishes. (Sadly for fans of other locations, the menu here lacks the fiery vindaloo and other flame-throwing dishes.) Chef Edward Lee’s Succotash, the chef’s first restaurant in the D.C. area, remains a showcase for Southern flavors: a sharing board with traditional ham, pimento cheese and pickled veggies alongside buttermilk biscuits; shrimp and grits with andouille sausage; smoked wings with white sauce. Wash that down with classic cocktails and a strong selection of bourbon and rye whiskeys. If you need a nightcap, consider the Brass Tap, which features a diverse selection of Maryland breweries among the 60 craft beer drafts, or the dark, cozy Irish Whisper pub.

Bombay Street Food 5, 151 American Way, National Harbor. bombayharbor.us. Entrees $17-$34.

Succotash, 186 Waterfront St., National Harbor. succotashrestaurant.com. Entrees $18-$49.

Westpost: Have a good time on and off the ice

Ice skating outdoors at Arlington’s Westpost is hardly a secret. The rink, which opened two decades ago, boasts that it’s the largest in Northern Virginia at 6,840 square feet. What has changed at this shopping center, formerly known as Pentagon Row, is the ice rink’s supporting cast, which now provides more appealing options for things to do once you’ve gotten off the ice.

Stop 1: Meet and greet over coffee.

Exposed brick walls, industrial-style tables and a neon sign depicting the chemical structure of caffeine are about what you’d expect from an achingly hip coffee shop. But Origin Coffee Lab, which opened in early 2021, is much more: It imports green beans from cooperatives in multiple countries, including Ethiopia and Brazil, and roasts them in the middle of its cafe. Settle in at a booth with your date and fuel up with a cup of straight coffee, which can be made via multiple processes, such as V60 and Chemex, or order a cinnamon-spiced latte or another seasonal drink. (Housemade chai lattes and loose-leaf teas are also available.)

Origin Coffee Lab and Kitchen, 1101 S. Joyce St., Arlington. origincoffeeco.com. Drinks $2.65-$4.60.

Stop 2: Lace up your skates.

Ice skating is a perfect date in chilly weather: You bundle up, hold hands and feel the chill of the wind on your cheeks while getting a light workout. While Westpost’s rink does get its share of kids, especially right after work, the oval-shaped rink is spacious enough that you don’t feel like you’re going to crash into anyone — unless you’re clinging to the walls, which tend to become congested. The rink requires advance reservations (especially if you need to reserve skates, too), which cover 80 minutes of ice time. Anyone arriving early can perch at the fire pit outside the rink’s entrance.

Pentagon Row Ice Skating Rink, 1201 S. Joyce St., Arlington. pentagonrowskating.com. Skating $10-$11; skate rental $6.

Stop 3: Take time to relax.

Celebrate surviving skating and soothe any bumps and bruises at one of the recent arrivals to Arlington’s dining scene. Mattie and Eddie’s, which took over the old Siné Irish Pub space last year, is a cozy, low-lit space filled with high-backed “snug” booths, banquettes and a bar area with comfortable drink rails. Thursdays through Saturdays, there’s live music on a small stage — mostly Irish troubadours performing raucous singalongs and tender ballads — while customers sip Guinness and share snacks like cheese on toast and sausage rolls. (Mattie and Eddie’s, from veteran Irish chef Cathal Armstrong, made Tom Sietsema’s fall 2022 dining guide for good reason.) The second option is very different: Nighthawk Pizza, from the team behind Aslin Beer Co. and chef Johnny Spero, is a bright game room that takes its decor inspiration from 1980s neon and skateboard designs. The sprawling space is filled with gleaming picnic tables, video game cabinets, piles of board games and large TVs. While garlic cheesy bread and poutine feature on the menu, focus on the slices, whether thin-crust, New York-style triangles or thick Detroit-style blocks, paired with Aslin’s signature hazy IPAs, fruited sours or more traditional German lagers. Ask about the limited-release beers, and consider getting a crowler to go.

Mattie and Eddie’s, 1301 S. Joyce St., Arlington. mattieandeddies.com. Appetizers $7-$20; Guinness $8.50.

Nighthawk Pizza, 1201 S. Joyce St., Arlington. nighthawkbrewery.co. Pizzas $16-$28, slices $5-$6; beers $7-$9.

Stop 4: Finish with cocktails and a game.

Bun’d Up’s terrific gua bao and rice bowls earned the food truck a loyal following, and it can now be found in three bricks-and-mortar locations, including at Westpost. But the destination here isn’t the Bun’d Up counter, as fun as the table tennis might look: Head to the back, where the Sparrow Room awaits. The centerpiece is a trio of mah-jongg tables, which can be reserved with tiles and a dedicated server. Don’t know how to play? There are twice-monthly beginner lessons. But you don’t have to play to enjoy the atmosphere: Sparrow Room has a comfortable and classy vibe, with thick carpet, cabinets filled with plants and large fans hanging on the walls. The cocktail menu includes inventive and tasty twists on classics, such as the Sparrow Sling, a Singapore Sling with litchi and Thai basil syrup, and a daiquiri starring chrysanthemum-infused rum. There’s also a short-and-sweet vegetarian-friendly menu with chow mein, cabbage spring rolls and mapo tofu.

1201 S. Joyce St., Arlington. sparrowroom.com. Cocktails $14; food $8-$25.

Woodley Park/Adams Morgan: Celebrate the season with a light display

The National Zoo’s ZooLights appears on many Washingtonians’ holiday must lists. But in mostly residential Woodley Park, a stroll through the displays can be challenging to expand into a fully fledged date. Here’s an itinerary to warm up an evening that centers on an outdoor walk.

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Optional: Warm up with a hot drink.

Regular visitors to the zoo know how pricey refreshments can get there. If you take the subway to Woodley Park, stop by Petit Monde Café, a renovated rowhouse across Connecticut Avenue from the exit. Expect Christmas music jingling in the decorated shop, and grab a warm coffee or hot chocolate to take with you during your zoo stroll.

Petit Monde Café, 2653 Connecticut Ave. NW. petitmondedc.com. Warm drinks $2.69-$5.49.

Stop 1: Take in a light show.

Returning for the first year since 2019, ZooLights is a D.C. holiday staple. This year, 500,000 LED lights hang from trees and illuminate walkways. Animals won’t be on display, but don’t miss the glowing three-dimensional animatronics in the shape of Siberian tigers and rhinoceroses — animals you won’t see live at the zoo during viewing hours. Festive tunes by local musicians drift from a tented performance area each night. The display is popular with families, and there’s usually stroller traffic, so plan your visit after bedtime. Note that entry is free but reserved passes are required.

Smithsonian National Zoological Park, 3001 Connecticut Ave. NW. nationalzoo.si.edu.

Stop 2: Dine at New Heights.

Head down Connecticut Avenue and hang a left on Calvert Street for some modern American cuisine at the simple yet elegant New Heights. Stop at the spacious bar, which specializes in gin drinks, before heading upstairs to a dining room that overlooks treetops. Chef Jose Molina, formerly of the Graham hotel in Georgetown, delivers specialties like a kale and mushroom paella, which food critic Tom Sietsema called “required eating.” Take an after-dinner stroll across the Duke Ellington Memorial Bridge to your next stop.

New Heights, 2317 Calvert St. NW. newheightsrestaurant.com. Entrees $18-$42.

Stop 3: Finish with a holiday-themed nightcap.

Adams Morgan is known for its nightlife, but Miracle’s holiday pop-up at Death Punch bar brings a decidedly festive flair to the strip of bars and clubs on 18th Street. Red, green and gold balloons hang from nearly every inch of ceiling; an animatronic Santa dances at the far end in front of dangling lights; and a nutcracker counts down the days until Christmas. On a recent weekend, two screens played both “Home Alone” movies. Grab a spiked chai served in a “carol barrel” mug or try a shot, depending on your mood: bourbon and cinnamon if you’re feeling naughty; rum, peppermint tea and chocolate if you’re feeling nice. Be sure to make a reservation in advance as long lines of Santa hats stretch down the block.

Miracle at Death Punch, 2321 18th St. NW. deathpunchbar.com. Cocktails $16; shots $10.

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