best winter destinations

Find sights, entertainment, food and more on Boston’s harbor. (Photo: DenisTangneyJr / E+ / Getty Images)

Tips + Trends

7 Great Winter City Breaks

Come cold-weather winter months, some cities don’t hibernate — they alight with only-in-winter activities like ice-skating rinks and WinterBrew festivals, as well as cozy igloo pop-ups. Better yet, the crowds thin out and there are deals to be found, making it easier to snag the hottest tables and tickets.


Celebrate winter at Boston Harbor’s Seaport, which has transformed 23 acres of iconic waterfront into an epicenter for all things art, culture and innovation in the city.

Alongside 100-year-old warehouses and contemporary spaces sits the seasonal (open through February) winter village, SNOWPORT, which offers a 3,000-square-foot ice rink, iceless curling, pop-up bars and dining options.

Warm up with cocktails in the heated igloos at Igloo Bar at Lookout Rooftop or fuel up for skating with a local favorite at The Waffle Cabin pop-up. Seaport is full of retail shops and also home to the city’s Institute of Contemporary Art.

New York City

best winter destinations
Try bumper cars on ice in Bryant Park. (Photo: Anadolu Agency / Getty Images)

There’s no better time to find a calmer New York City than under a blanket of snow, but if that doesn’t happen, there’s always bumper cars on ice to get you into the winter mood.

Yes, leave it to New York to transform the iconic winter pastime of ice-skating into something new and exciting. Here by popular demand, ice bumper cars is offered at Bryant Park’s Bank of America Winter Village until the end of February. For a more traditional spin around the rink, you can bring your own skates or rent them.

Get your hygge on with knitting sessions in heated igloos, or burn some calories with Exerskate, free on-ice exercise classes conducted by trained figure skaters and hockey players. Or simply take an old-school spin around NYC’s only free-admission ice-skating rink.

Washington, D.C.

While winter temps are relatively mild in Washington, D.C., (except for times when Snowpocalypse hits, that is) there are winter activities to indulge in.

After heading to the all-free museums on the National Mall, lace up your skates for a spin around the ice rink at the National Gallery of Art’s Sculpture Garden. Open until mid-March, this iconic D.C. spot is surrounded by large-scale sculptures and a lit-up garden.

Or practice your triple axel in Georgetown at Washington Harbour Ice Rink, D.C.’s largest ice-skating rink, or skate a bit off the tourist path at the Wharf’s waterfront ice rink.

If skating is not your thing, you can warm up by the Torch, the Wharf’s 14-foot, gas-powered flame, while you take in the waterfront views.


best winter destinations
Take a spin around Millennium Park. (Photo: stevegeer/iStock Unreleased)

While Chicago is known for its chilly winter temps and snow, the city’s residents don’t let winter weather keep them indoors.

One of the most quintessential winter activities here is taking a spin around Millennium Park’s ice-skating rink near the city’s iconic Cloud Gate sculpture (or “The Bean,” as its more known).

Or glide through the winding Skating Ribbon through Maggie Daley Park, under a pass of pine trees, open through March. You’ll be praying for snow so you can take a ride down the 33-foot slope on the Soldier Field Sledding Hill, but the good news is that even if nature doesn’t bring it, Chicago Park District will pump out fake snow here.

Otherwise, try snowshoeing along the nature trails on Northerly Island, a man-made peninsula that juts into Lake Michigan. No faux-snow-making here, so you’ll need at least three inches of powder for snowshoeing. Good news, that’s not a rarity in Chicago in winter.


The epicenter of winter fun in Philly can be found at Blue Cross RiverRink Winterfest, a seasonal winter park along the city’s Delaware River waterfront. Revel in the winter fun with ice-skating, fire pits, warming cabins and a kids lodge and arcade.

Sample local treats at the Franklin Fountain Confectionary Cabin or try the Lodge’s Chickie’s and Pete’s Crabfries and clam chowder. Be sure to check out the city’s other winter pop-up experience at Dilworth Park for downtown ice-skating and a stroll through twinkly lights and seasonal plant arrangements in the Wintergarden.


best winter destinations
Hit the slopes with the littles. (Photo: Don Mason / Getty Images)

Nestled in the foothills of Colorado’s Rocky Mountains, Denver is a winter lover’s paradise and offers some of the country’s best skiing, as well as the world’s largest après-ski scene.

Head to the slopes on the city’s weekend ski train, Winter Park Express, an Amtrak double-decker that takes skiers and snowboarders from downtown Union Station to Winter Park Resort in two hours.

Even if you don’t ski, there are plenty of ways to revel in winter, like taking a spin downtown at Skyline Park’s free-admission ice rink.


While Charm City usually has milder temps in winter than other northern cities, you can ice-skate at the Inner Harbor ice rink. In addition, February’s Black History Month is a great time to be in Baltimore to learn about its African American history.

Check out the permanent collection Visionary Artists of Color at American Visionary Art Museum. The National Great Blacks in Wax Museum offers events throughout February, such as documentaries and panel discussions. And in honor of Black History Month, Homewood Museum, a historical museum on the Johns Hopkins University campus, is launching a new interpretive tour and offering free admission all month.