Winter Fun in Pittsburgh: 10 Things to Do & See
Disclaimer: We are not paid to promote any restaurant, hotel, activity, product, or attraction. All opinions are subjective and based on our personal experience. Your experience may be different.
Special holiday events in the ‘Burgh
I love attending festive winter and Christmas attractions wherever I am currently living. It’s no New York or Chicago for sure, but I was impressed with the Burgh’s lineup of holiday activities.
From special holiday plays, to a German inspired shopping village in the heart of downtown, to a gingerbread display now in its’ 20th season, a few spirited holiday events will help to brighten up the dreary December skies. And as I mentioned earlier, the ice rinks are awesome and abundant! Shown in this pic is the Santas Around the World exhibit at PPG Place downtown (next to the ice rink). This is a pretty unique find where you can learn about how other countries around the world view Santa.

General indoors winter fun
In addition to the activities listed above, all the regular fun indoor activities like bowling, movie theaters, and malls that you find in any major city can be enjoyed. Here are a few of my recommendations.

The Mall at Robinson – Best mall in the area. I love the central Starbucks location and local gems including the I Made It Market store. It’s festively decorated around the holiday season which is a nice bonus.
Monroeville Mall – Dawn of the Dead filmed here – there is a museum on-site if you are interested. Although a bit outdated and run down, the mall is home to a number of unique stores including Pearl of the Orient. I found a really cool elephant themed water fountain here as well as some eclectic knick knacks.
AMF Mt. Lebanon – Nice basic bowling alley which doesn’t get overcrowded. Great weekly specials.
AMC Waterfront 22/Cinemark Robinson Township – Decent matinee rates. Lots of restaurants in both areas so you do not have to dive around. Personally, I love Choolaah in Robinson.
Dave and Busters (Homestead) – Great location in the Waterfront mall.
Winter recreation

Besides enjoying the many ice rinks in and around the city, skiing and snow tubing are popular ways to enjoy the snowy season in Pennsylvania. Boyce Park is located just a half hour outside of the city and features the only downhill skiing in Allegheny County.
What will the weather be like?

Temps from December-March average in the 20’s-40’s. Skies are typically overcast and rain and/or snow are common. Definitely prepare with a heavy jackets, hats, gloves, and winter boots, especially if you will be walking around in the cold for lengthy periods.
Where to stay?

Downtown, the Omni William Penn and Kimpton Hotel Monaco are excellent luxury choices within walking distance of many theaters and restaurants. Cheaper hotel rates can be found in suburbs outside of the city (Moon Township near the airport is a good choice). I love the holiday decor at the Omni and The Terrace Room is a beautiful place for breakfast (just skip the buffet and order from the menu). It’s also walkable to the ice rink and the theater district which is convenient.
Local dining/shopping options

While I wouldn’t say this is the best food city, I managed to find a few gems here and there. A few great places to shop/dine without ending driving around aimlessly for hours on end:
Downtown Sewickley – Charming Main St. home to many local businesses. Mediterra is an excellent choice for breakfast. I always order the shakshuka if I am not enjoying one of their top notch pastries.

Downtown Mt. Lebanon – Home to many unique businesses including cafes, coffeehouses, record stores, and more. Check out Orbis Caffe (serving great coffee), Sesame Inn (delicious Chinese),and Badamo (best pizza in the Burgh). Update: Badamo has moved to the Dormont area – yes, it’s worth the drive!

Shadyside – Walnut St. is a dense shopping area home to a mix of national chains like Lululemon and Starbucks and independent businesses. Grab a specialty espresso at Coffee Tree Roasters and treat yourself to lunch at Mercurio (they serve delicious wood fired pizza and gelato!).

Tip: Plan your day out on a Sunday or during the evening hours. All street parking is free on Sundays and Monday-Saturdays after 6pm. Parking is quite expensive (ranging from $1.50-4 per hour) and can add up fast if you are driving to multiple destinations.