Neon room at Bicycle Heaven in Pittsburgh

I love the ‘Burgh – it’s one of the most underrated cities I’ve lived in. There are so many fun things to do here no matter the season. While the majority of the year, it is either too cold, too hot and humid, too overcast, too rainy, or too snowy to do much outside, it doesn’t really matter as there are so many great things to do inside too. While I love the Three Rivers Heritage bike trail, the pretty parks, the zoo, and strolling around the many festivals taking place year-round, I don’t ever have a problem finding something to do if the weather is not perfect.

Personally, I love the change of seasons as it keeps thing interesting. One day, I can take a beautiful bike ride while it’s 80 and sunny, and on the next rainy day, I can stroll around a wonderful museum and sip coffee in a local shop.

This city offers a great mix of outdoor and indoor activities so you can mix things up a bit when the weather doesn’t cooperate. My guide will focus on a few of the best things you can do inside. Don’t let the gloom get you down – you can have fun regardless!

1. Go back in time at The Carnegie Museum of Natural History

Dinosaur at the Carnegie Museum of Natural History

Pittsburgh is home to several world-class Carnegie museums. I love strolling around The Carnegie Museum of Natural History on a rainy, gloomy day. There’s a lot to see here so you can easily kill a few hours. Plus, it connects to the beautiful art museum and your admission ticket includes entry to both.

This museum was founded by industrialist Andrew Carnegie back in 1896. Today, the impressive dinosaur exhibit is considered one of the best in the country. 75% of the fossils are original and most skeletons are real. The T-Rex is a holotype (which means it is the first specimen of a species).

You will also find 20+ dioramas showcasing wildlife in America and Africa and an incredible Hall of Minerals and Gems (seeing all the shiny gemstones never gets old!).

Note: Bank of America members get in free (as part of the Museums on Us program), the first full weekend of each month! Each person in your party needs to show their card and photo ID.

Read more about my experience at the Carnegie Museum

2. Be wowed at The Carnegie Museum of Art

The Carnegie Museum of Art in Pittsburgh

Andrew Carnegie founded this beautiful museum back in 1895. According to this NY Times article, Carnegie envisioned the collection as a showcase to the“Old Masters of tomorrow”. It is considered one of the first contemporary art museums in the country.

The collection is really impressive, and I find the architecture of the building just as incredible. The museum has expanded many times over the years and today is considered one of the best of its’ kind. I spend the most time in the incredible Hall of Architecture which spotlights 140 plaster casts of masterpieces from Greece, rome, and Egypt. On a side note, the beautiful marble in the Hall of Sculptures came from the same quarry used to build the Parthenon in Athens.

This is easily one of the most incredible art museums I’ve come across. Fortunately, I have a Bank of America card, so I can enjoy free admission once a month!

3. Go old-school gaming at Pinball Perfection

Star Wars pinball machines at Pinball Perfection in Pittsburgh

For all the old-school gamers out there, a visit to Pinball Perfection is a must. I love this place – seriously I could spend all day here. This gigantic space is filled to the brim with iconic pinball and arcade machines (it is 2 floors!).

Your admission ticket ($15) includes endless hours (it’s open between Noon and 5pm from Tuesday-Saturday) playing your favorite nostalgic games. I love the all-you-can play setup so you can stay until you get bored (it’s a great deal when it’s too cold and rainy to do much else).

So leave the phone at home and take a temporary step back into time to the 80’s. With over 300 machines, you will won’t care what is going on outside! I love the amazing selection of Star Wars & Star Trek pinball machines! On a side note, it’s always absolutely freezing in here during the winter season, so much so that I have to keep my jacket on.

4. Learn about Andy Warhol’s life & art at The Warhol Museum

Warhol Museum in Pittsburgh

Andy Warhol is amongst a handful of notable Pittsburgh celebrities. The famous pop art icon was born in a working class neighborhood here and later moved to NYC. An entire 7 floor museum (the largest museum dedicated to a single artist) chronicles his life and art work.

I recommend a visit if you are a fan of Warhol and/or modern art. As a fan of pop art, I never get bored strolling around. As a cat lover, I especially love the colorful cat exhibits.

I recommend starting on the 7th floor as the museum is organized chronologically. The section dedicated to his early life is pretty interesting, more so if you are a big Warhol fan. I also love the gift shop -you can really pick up some cool souvenirs here.

Read more about my experience exploring The Warhol. Note: This museum is also free for Bank of America cardolers on the first full weekend of each month. What a great deal!

5. Shop, dine & explore regional history at The Strip District

Heinz Center in the Strip District of Pittsburgh

This historic neighborhood was once home to many factories and steel mills. Today, you can shop at long-running ethnic grocers, pick up fresh produce, score deals on Steelers merchandise, enjoy local coffee, and dine at local restaurants. Because everything is so closely packed together, visiting is a good idea on a rainy day – just bring the umbrella.

There are a number of coffeehouses where you can escape the rain for a bit including local gems like Defer (a trendy favorite of mine) and La Prima, a notable Italian roaster serving what I think is the best overall coffee in the city. The original Primanti Brothers (known for their iconic sandwiches stacked with coleslaw and french fries) started in the Strip.

Also, I recommend anyone who wants to learn more about the city’s history to visit the Heinz Center (featuring Mr. Roger’s TV set, Heinz ketchup exhibits, and the Western PA Sports Museum).

Mr. Roger's Neighborhood set at the Heinz History Center in Pittsburgh
It was so nostalgic seeing Mr. Roger’s set!

Take a look at my guide to the best of The Strip for my breakdown on the best coffeebars, attractions, and activities in this neighborhood.

6. Escape the cold at Phipps Conservatory

Pretty gardens at Phipps Conservatory in Pittsburgh

The best time to explore the lovely gardens at this incredible conservatory is either on a gloomy overcast or cold snowy winter’s day. This green oasis is a nice cozy escape when it is too rainy or cold to do much else. I am not sure of the actual temp, but it feels about 80 degrees to me which is so nice on a frosty day.

Along with exploring 23 diverse gardens and a beautiful 14 room glasshouse, you can look forward to special seasonal displays and events. What I love most about this garden is the incorporation of mesmerizing Chihuly glass pieces throughout. I’ve been a big fan ever since visiting the Chihuly in St. Petersburg, Florida.

Since exhibiting the glass blown masterpieces by artist Dale Chihuly in 2007, Phipps continues to display some of his more incredible pieces. If your visit falls during the winter season, do book tickets to the festive Holiday Magic event.

See more of the beautiful gardens at Phipps.

7. Cozy up with a drink at Mediterra

Seasonal treats at Mediterra cafe in Sewickley, PA

Relaxing with a good cup of joe at a local coffeehouse is definitely one of the best things to do on a rainy day, and luckily the ‘Burgh is home to a fantastic array of indie coffeehouses. In fact, the city is ranks the 3rd best coffee city! I totally agree with this ranking – I love all the great coffeehouses here.

One of my local favorites is Mediterra, an upscale bakery/coffeehouse with 3 convenient locations. Mediterra serves excellent coffee (and offers refills!), bakes homemade pastries and artisan bread daily, and offers a full breakfast menu (the Shakshuka is so good!). I have a hard time going anywhere else because the food, coffee, and ambiance are all so perfect here. Basically, this is my choice unless I am headed into the city.

As for the pastries, there are almost too many to choose amongst. Go for the cinnamon roll, danish, almond bostock, or chocolate croissant. Even better, they offer seasonal pastries and drinks throughout the year – I love the Pumpkin Danish! Check out my full guide to the best pastries I’ve tried.

Note – the setting is especially gorgeous at the downtown Sewickley cafe.

8. Take a sightseeing cruise

Gateway Clipper cruise in Pittsburgh

On a rainy or cold winter’s day, a cruise really is the best way to take in the scenery. You will take in amazing views of the skyline, sports stadiums, and the Allegheny, Ohio, and Monongahela rivers. While I think the best viewpoint is from the Duquesne Incline (or better yet the free Mt. Washington overlook), a cruise is the better choice for a gloomy cold or rainy day.

On a narrated sightseeing cruise, you can take great pictures and learn more about the city, all in a cozy, warm setting. Gateway Clipper offers a variety of cruise options including special dinner buffet and holiday rides. We too a fun Halloween themed cruise where the boat was decked out and they played some spooky music. We mainly took the ride for the views, but the extra activities were a nice bonus.

9. Tour the world’s largest bicycle museum

Pee-Wee Herman's bike at the Bicycle Heaven museum in Pittsburgh

A browse through the world’s largest bicycle shop and museum is a great stop on a cold or overcast day. Bike afficianotos will have a field day checking out all the rarities on display at Bicycle Heaven. This was my first stop after moving to this city and I’ve been back so many times because it is so quirky and cool. It used to be free but they now charge $15 per person as a result of massive flooding damage.

If you really like old bikes, you could spend some time exploring here as there are over 6000 bikes on display. I love visiting all these weird places like this museum. It’s so fun to seek out these retro attractions that are few and far between today!

The highlight here is the collection of Bowden Space Landers (the first fiberglass bike) which today can be worth upwards of $40,000! To date, 30 have been found including 17 at this museum. For the movie buffs out there, they have Pee Wee Herman’s famous ride, along with classic bikes from E.T., The Monkees, Happy Days, and more.

I really loved the Neon Sprocket room and all the fun vintage throwbacks to the past.

Check out more unique rides at this crazy museum!

More indoor fun in the ‘Burgh

The Living Dead Museum at the Monroeville Mall
The Living Dead Museum at Monroeville Mall

*See a movie. This is always a great go-to option on a rainy or cold day. Cinemark North Hills and Cinema Robinson both offer matinee deals.

*Walk around a mall. My favorite big mall is The Mall at Robinson. For movie buffs, Monroeville Mall is a fun pick as it was used for Dawn of the Dead filming. This is one of those old malls that has a lot of weird and random stores. It’s dark inside and a little eerie and that’s why I love it.

*Visit cats for a good cause. Cat cafes are seemingly popping up everywhere. The concept is simple – you pay a small fee to observe cats (which are all available for adoption). I recently adopted this adorable orange tabby from the wonderful Kitty Cat Queen Rescue.

*Check out the local food scene. It’s not my kind of city for food as vegetarian options are limited. However, The Steel City is known for a lot of food, from iconic stacked sandwiches, to “the Pittsburgh salad,” to pierogies. Check out my guide to the best restaurants in the ‘Burgh. I recommend this cozy Irish pub in the Mexican War Streets called Monterey Pub. It’s been around for a long time – it’s so cozy inside and the food is great! It’s the perfect choice on a rainy day.

Primanti Brothers sandwich in Pittsburgh, PA
The iconic Primanti sandwich stacked with coleslaw and fries!
Great Fish and Chips at Monterey Pub in Pittsburgh
Fish and Chips at Monterey

*Stroll around the National Aviary. I find it a bit small and overpriced, yet worth a look if you love birds and the weather is bad. It’s located in the Mexican War Streets neighborhood. I recommend pairing a visit here with Commonplace Coffee – one of my favorite cozy local shops.

Flamingos at The National Aviary in Pittsburgh
Flamingos at the Aviary
Brick walls at Commonplace coffee in the Mexican War Streets of Pittsburgh
Commonplace is a cozy historic space to spend time on a rainy day

*See a show. The Cultural District is home to several theaters including the Benedum Center featuring Broadway productions. There really is no bad seat in the house here. Update: I recently saw a wonderful production of the Nutcracker here for Christmas.

View from the balcony at the Benedum Center in Pittsburgh
Our view: not too bad considering our tickets were only 30 bucks!

*Go bowling. You will find lots of alleys around the metro, both casual and upscale. I like AMF in Mt. Lebanon.

Bowling at AMF in Mt. Lebanon, PA

*Spend the day reading at The Carnegie Library. This is a gorgeous building to catch up on the latest novel on a gloomy day.

*See a hockey game. Cheer on the Penguins at the PPG Arena.

*Go ice skating. This city is home to some amazing outdoor rinks. Fortunately, if it rains you are not out of luck. Indoor options include Ice Castle and Mt. Lebanon Ice Center.