15 Reasons to Visit Pittsburgh in January – Enjoying Winter

Published by Jeremy. Last Updated on November 23, 2023.

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Winter is in full gear in January in Pittsburgh, which means it is time to either embrace the season or rush to a museum or favorite libation spot to stay warm inside.

No matter which you pick, there are many great things to do in Pittsburgh in January- so check out the following options to get a few ideas on where to start!


Cocktail at Grapperia in Pittsburgh

Kick off the New Year in style with one of Lawrenceville's trendiest bars- Grapperia!

This bar celebrates the European spirit known as Grappa (one of our favorite spirits), made from fermenting the skins and seeds of grapes after the winemaking process is complete.

Grapperia has more of this spirit than any bar in the city, and perhaps even the entire country, so if you're looking to try something different you most certainly won't be let down here.

Looking for more while in Lawrenceville? Why not have dinner at Piccolo Forno, Umami, or possibly take in a movie at Row House Cinema.

Mattress Factory

Mattress Factory in Pittsburgh

Pittsburgh's contemporary art museum, Mattress Factory, is a hard one to describe as the art can be all over the place. One room is a mirrored hall with hundreds of polka dots that go on for infinity. Another is pitch black to give you sensory deprivation. Yet another may contain a rotating exhibit made entirely out of cardboard, concrete, or some other unusual medium.

That's the fun thing about contemporary art as there is no one style that fits the mold, and this North Side museum does a great job showcasing a blend of permanent and rotating attractions that will have you coming back time and time again.

Looking for more while in the North Side? Check out Randyland, Commonplace Coffee, or read our North Side neighborhood guide for more recommendations!

Tubing at Boyce Park

Tubing at Boyce Park

You don't have to drive all the way out into the mountains to enjoy Pittsburgh activities during the winter. Allegheny County's Boyce Park offers their own dedicated skiing, snowboarding, and snow tubing hills during the winter months- perfect for those who want to get outside without the drive!

Although we advocate going to proper mountains for skiing and snowboarding, the snow tubing hills at Boyce Park makes for a great afternoon out in town when snow is on the ground.

Looking for more while in the East Side of the city? On your way back in stop in Squirrel Hill to check out Commonplace Coffee or Independent Brewing Company, or if you're back early enough, have a late brunch at Square Cafe in East Liberty!

Pittsburgh Winery

Barrels at Pittsburgh Winery

Pittsburgh Winery is one of the most interesting in the city, mostly because they import all of their grapes from famous wine regions from around the world! This means they offer wines that are strikingly different from most in western Pennsylvania, and are quite good at what they do. Be sure to visit on a Friday or Saturday from 6-8pm for their happy hour specials.

Have more time in the Strip District? Check out Kaya or Primanti Brothers if you're looking for a meal, or to continue the fun head to Maggie's Farm Rum just a few blocks down the road!

Clemente Museum

Clemente Museum

Out of all of the Pittsburgh Pirates baseball players to ever play for the team, there is none with a more famous history than Roberto Clemente. This local baseball icon had an incredible run with the Pirates before his untimely death in 1972 at the age of 38. To honor the legacy of one of the greats, the Roberto Clemente Museum in Lawrenceville opened. This one covers a wide spectrum of Clemente's history and is a must visit for sports fans and non-sports fans alike.

This one is only open for private visits, so you must call ahead for a tour.

Want to spend more time in Lawrenceville? Grab a coffee at Espresso a Mano or a local beer at Industry Public House!

Winter Activities at Nemacolin Woodlands

Nemacolin Resort

When we get out, we try to stay close to Pittsburgh. But when we suggest you drive out of the city for an experience, there is often a good reason. The winter activities at the Nemacolin Woodlands resorts are one such reason as this property is home to dog sledding, cross-country skiing, snowshoeing, tubing, and a whole lot more (dog sledding on select weekends only).

So if you are wanting to embrace all things winter, especially in the great outdoors, a trip to Nemacolin may be for you!

Looking for a meal while at Nemacolin? Be sure to get reservations at Aqueous if you are staying overnight!

Apis Meadery

Apis Meadery

If you've never tried mead (or enjoy it frequently like us), then a visit to Apis Meadery in Carnegie is a must on a night out. This one focuses on all things mead- fermented honey for those who are not familiar with this drink. The mead at Apis is on the lighter side and their numerous fruit flavors are reminiscent of fruit wines with a honey touch. Be sure to try the spicy ones if they are available!

Seeking more while in Carnegie? Head to Riley's Pour House or make the short trip to Heidelberg to visit Insurrection Brewery for more local beverages!

Trundle Manor

Trundle Manor

Do you love the offbeat, macabre, steampunk, or the just plain weird? If you said yes to any of these, a visit to Trundle Manor is for you!

This house is the private residence of Mr. Arm and his lovely wife Velda von Minx- two local artists who have what is perhaps the most unusual collection in the city ranging from fetal animals in jars to death rays on the ceiling, and everything in between. An appointment is required to visit.

On your way back into Pittsburgh stop at D's Six Pack and Dogz or Biddle's Escape for a quick bite to eat or coffee, or perhaps head over to Squirrel Hill for a meal at Chengdu Gourmet!

The Phipps Orchid and Tropical Bonsai Show

Orchids at Phipps

If you are in need of warmer thoughts this January, take a trip to Phipps Conservatory for their annual Orchid and Tropical Bonsai Show which starts on January 14th in 2023! This year's theme is Origin Stories and will delight you with how these two popular plants came to be. We expect it to be quite colorful as always!

The Troy Hill Art Houses

Out of respect to the owner of The Troy Hill Art Houses, I'm really not supposed to even be writing about these private collections in Troy Hill. What are they? We can't say- you'll just have to make an appointment to each of the three homes find out for yourself. Trust us when we say that you won't regret it. (Tour is available for those 16+ with advanced registration only).

Stay in Troy Hill for a bite to eat at Scratch Food & Beverage!

Hitchhiker Brewing

Hitchhiker Brewing Company

As frequent travelers, we love the name of Hitchhiker Brewing– something we found ourselves doing more often than we'd like to admit when abroad.

This brewery's taprooms in Mount Lebanon and Sharpsburg feature a strong rotating tap list with many seasonal specials, meaning you will find yourself returning time and time again throughout the year. So whether you're looking for a stout, a flavored IPA with lactose, a fruited sour, or more, this one has you covered.

Be sure to check out their food truck schedule for a great bite while you're there!

Bicycle Heaven and Johnny Angel's

Things to Do in Pittsburgh - Bicycle Heaven

You should make a return trip to the North Side to check out Bicycle Heaven– what is claimed to be the largest bicycle museum and store in the country (and possibly the world). This multi-level store features numerous showrooms of the most unusual and rarest bicycles on the planet (which, in many cases, they have duplicates of). Whatever you do, do not miss their upstairs rooms which are the very best.

Afterward, check out Johnny Angel's Ginchy Stuff located right next door- a music museum dedicated to Johnny's impressive 50-year career as a local Pittsburgh musician.

For more things to do in the North Side, why not grab a drink at Southern Tier or, if the weather is nice, take a stroll along the North Shore River Trail?

Try a New Spot During Pittsburgh Restaurant Week

Pittsburgh Restaurant Week

Pittsburgh Restaurant Week takes place a couple of times each year, and the winter edition of this one is on January 9th-15th in 2023. This one features over 30 participating restaurants with menu specials, including a few of our favorites like The Porch and Station taking part.

So if you need an excuse to go out and try a new restaurant, this is it.

Downtown Gallery Crawl

Wood Street Galleries

Every quarter the Cultural Trust in downtown Pittsburgh hosts a gallery crawl where the public and private art galleries scattered throughout downtown open up for one fun evening. As these galleries are typically not open late, this event is the perfect opportunity to explore a side of downtown you may not normally see!

In January 2023, the downtown gallery crawl takes place on the 27th starting at 5:30pm.

In need of a reservation for a great downtown restaurant while visiting the gallery crawl? Click the previous link to check out some of our favorites!

Heinz History Center

Heinz History Center in Pittsburgh, PA

When it comes to museums about Pittsburgh and Western Pennsylvania, there is none more inspiring than the Heinz History Center– a six-floor beast of a museum that covers every aspect of Pittsburgh's history from its early days as a colony (where it even hosted George Washington on several occasions) to modern industries, inventions, and entertainment (they even have the set of Mr. Roger's Neighborhood!).

If you've ever wanted to learn more about how Pittsburgh came to be the city we all know and love, this one is a must-visit.

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