Afternoon ice skating at Millennium Park in Chicago

Ice skating has always been one of my favorite winter pastimes. It’s fun, a great workout, festive, and in many cases really affordable. In the past, skating rinks were more common in big cities, primarily cold weather destinations. Today, you can find rinks everywhere; even many warm weather havens like Vegas, Phoenix, and Santa Monica are getting in on the action. I’ve always wanted to skate amongst the cacti and palms at the Fairmont Princess and Scottsdale so hopefully I’ll get to cross that one off my bucket list soon.

Whether you are an avid skater or a newbie, skating is a great way to burn calories, get into the fresh air, and have some fun! It’s often hard to stick to a regular exercise routine during the long and bleak winter season. I find that skating is a wonderful way to motivate yourself to get off the couch. Not only is it an absolute blast, it’s also relatively affordable compared to most big city activities (esp if you have your own skates). After being cooped up for months on end, skating can help break up the monotony of the season.

Rink at Rockefeller
The iconic rink at Rockefeller is amazing: but also super pricey with a long wait!

I love skating so much that I bought my own pair of skates. I make it a point to check out new rinks anytime I travel and even specifically plan daytrips just to check out a great one. My guide will highlight a few of my recommended favorites to add to your bucket list. I hope to add more in the future!

1. Wollman

Ice skating at the Central Park Wollman rink in NYC
  • Location: Central Park in Manhattan
  • Opening Date: 1950
  • Dates: October to March
  • Pricing: $16-40 per adult (depending on date), $11 for seniors and kids, $12 skate rental. Cash only.
  • Highlight: Iconic NYC tourist destination due to its’ presence in various media, most notably Home Alone 2 and Serendipity.

Skating at the famous Wollman Rink in Manhattan is not cheap. In fact, it is one of the most expensive skating experiences on this list. Despite the cost, skating within one of America’s most picturesque urban parks is an unparalleled experience. The natural setting, which feels miles away from the concrete jungle, makes up for the hefty fees in my experience. As a big movie buff, I can’t help but think of memorable movie scenes from Serendipity and Home Alone 2 while skating about.

At a massive 30,000 acres, this rink is so much grander than the miniscule Rockefeller rink, which is also much pricier ($65+ as of 2025) and oftentimes hard to get into (on busy days, the wait can be several hours!). Skating in Central Park has long been a favorite winter pastime of both locals and tourists, well before the media coverage. In fact, local NY skaters used the pond for decades before the official opening in 1950. After moving to Philly, I just knew I had to cross this one off my bucket list.

The views are incredible with beautiful trees and high rise buildings creating a picture-perfect serene urban setting. Central Park is such a gorgeous place and I really loved the winter ambiance and festive flair in the air.

Winter in NYC is such an incredible experience. In addition to several ice rinks, there are tons of holiday festivities to enjoy. You can check out my New York Christmas guide for my bucket list ideas.

2. Riverrink

Riverrink in Philadelphia, Pennsylvania
  • Location: Old City Philadelphia
  • Opening Date: 1994
  • Dates: Late November – early March
  • Pricing: $5 admission, $12 skate rental
  • Highlight: Great views of the Delaware River

Although it does not receive nearly as much press as the nearby New York rinks, Philly’s picturesque seasonal rink along the Delaware River is one of my favorites. Rarely do you find a rink that looks out upon the water, and for this reason alone I place it near the top of my list. You can also see the beautiful Benjamin Franklin bridge in the background. I like to skate in the early morning hours to practice new moves and skills without tons of crowds and loud music. The ice is zambonied after each session for the smoothest conditions. If you have ever skated on an unmaintained rink before then I don’t need to tell you how frustrating skating on a rough rink can be.

Skating here is pretty cheap (just 5 bucks if you have your own skates). In addition to skating, there is a free festival called Winterfest. In addition to enjoying the pretty lights and ambiance, you can cozy up by a firepit, sip hot cocoa, and even roast marshmallows. Even better, after your session you can walk a few blocks down the street and take in the historical sights of Old City, “the birthplace of America.” Be on the lookout for special events particularly the annual New Year’s Eve skate featuring a prime view of the riverfront fireworks.

Philly is a really underrated winter and holiday travel destination. While living here, I discovered that it can easily compete with the big guns like NYC and Chicago in terms of festive events, museums, and tourist attractions. Check out my winter travel guide for details.

Ice skating at the National Gallery of Art Sculpture Garden in Washington D.C.
  • Location: Capitol Hill, Washington D.C.
  • Opening date: 1999
  • Dates: Late November – early March
  • Pricing: $15 adults, $12 kids 12 and under, $6 skate rental
  • Highlight: Unique historical vibe in the nation’s capital

One of the most unique places I’ve skated at was the National Gallery of Art rink in D.C. Despite it’s super cool location, it sees little traffic, thus making it a great place to skate in peace without noisy crowds. What really sets this rink apart from others is its’ unique historical setting. The stately National Archives building in the backdrop gives it a unique historical touch. Where else can you say that you skated amongst the building which houses the nation’s founding documents? By night the rink transforms into a romantic wonderland with twinkling lights, making it one of the city’s top romantic date night locations.

I first checked out this rink on a winter vacation and came back several times as I loved the historic setting. This rink is located adjacent to The National Gallery of Art, which I highly recommend checking out if you are into art. On a side note, all Smithsonians museums are fabulous and well worth a visit. Note they are massive so you are going to need more than a single trip to cover them all.

D.C. is a surprisingly fantastic winter vacation destination. I’ve visited numerous times during the spring and winter and I actually prefer the low-key vibe during the colder months. It’s so much more personal to explore the monuments in peace and the Smithsonian’s are not nearly as crowded. The addition of so many festive (and free) holiday attractions is another bonus.

4. Frog Pond

Frog Pond ice rink in Boston Common
  • Location: Boston
  • Opening Date: 1997
  • Dates: mid November – march
  • Pricing: $12 admission (over 58 inches), $18 skate rentals for adults, $12 for kids
  • Highlight: Located in America’s oldest public park

By summer, The Boston Common Frog Pond is a spray pool. By winter, the pond transforms into a beautiful ice rink. While it’s hard to take a break from all the wonderful historical attractions this incredible city has to offer, skating is a fun side activity during the holiday season. Skating here on Christmas Eve is one of my best holiday memories. I love that the Pond is located nearby so many historic sites as well as holiday attractions like the city tree. It’s touristy, but Cheers is a fun dinner choice and I also recommend a plate of lobster ravioli at Giacomo’s.

The twinkly lights and views of the park and skyline create a winning romantic ambiance. I love skating here during the day to take in the beautiful cityscapes. Recently USA Today ranked the rink as the second best in North America. Being located amidst America’s oldest park and just a stone’s throw away from so much history, this ranking is well justified in my opinion. After your skating session, I recommend warming up with a hot coffee at nearby Thinking Cup, one of the city’s best roasters.

5. Millennium Park

NIght ice skating at Millennium Park in Chicago
  • Location: Chicago
  • Opening Date: 2001
  • Dates: mid November – late February
  • Pricing: Free admission with your own skates Mon-Thurs and the first session on weekends (other sessions are $5). If you don’t have your own skates, admission plus skates is $17 on weekdays & $21 on weekends.
  • Highlight: The most magnificent skyline views and great views of the city tree and the famous “Bean”

Chicago’s Millennium Park is home to one of the most picturesque urban ice rinks in the country. While attempting to stay on your feet, you will take in views of the iconic cityscape that the city is so famous for. I love that you can see the gorgeous Christmas tree in the background and also the famous Cloud Gate “Bean” reflective sculpture. The views are beyond fabulous, day or night. Skating can break up the monotony of those cold dark winter days which are pretty frequent here in the upper Midwest.

What’s even more fabulous is that admission is free, so if you have your own skates, skating will not cost you a dime on weekdays. Of course, while you are here you will have to check out the famous Cloud Gate aka as “The Bean” sculpture. This award-winning artistic piece by British artist Anish Kapoor is one of the city’s most popular attractions. Even though I grew up in the city, I still love coming back and taking fun reflective photos.

Chicago is one of my favorite places to be during the winter season. In addition to Millennium Park, you have the Maggie Daley ribbon rink and a whole lineup of holiday attractions. Check out my Chi-town winter travel guide for full details.