For years, we had heard stories about the insane bike race known as the Dirty Dozen.
Riders from all over come together to ride a baker's dozen of Pittsburgh's steepest streets, and is an event that even us as bicycle enthusiasts hesitate over the insanity of it all.
In 2025, I finally got a chance to check out part of this ride, at the incredibly steep Canton Avenue leg of the race, and wanted to share more about what you can expect when taking this ride in!
There are many reasons to love the holiday season in Pittsburgh, and perhaps one of the most amazing ones is your ability to see many beautiful Christmas lights all over the region.
From the holiday displays downtown, to the many drive-thru light shows, and more, there really is no shortage of impressive Christmas lights in Pittsburgh. So in this one, we wanted to curate all the best places where you can see holiday lights and decorations in the region!
Note: Many of the experiences below are drive-thru light displays such that you can enjoy the holiday lights and decorations from the comfort of your own car. However, we felt we would be doing you a disservice if we didn't mention a few other light viewing opportunities that take place outside of your car as well!
Who doesn't love a great discount? Naturally, the Black Friday to Cyber Monday shopping weekend presents a wealth of shopping opportunities with discounted prices.
Naturally, Pittsburgh businesses and attractions are getting in on the Black Friday celebration as well.
So in this one, we thought we would share some of the best deals that we see popping up on our feeds to help you get the most out of exploring the city. From annual memberships and season passes to special releases at area breweries and distilleries, we've found some gems!
When it comes to holiday festivities, one of the best places in Pittsburgh to visit is Phipps Conservatory. Their winter flower show, which typically begins before Thanksgiving and runs until early January, is a celebration of the holiday season with festive art pieces, an array of gorgeous winter flowers, and some of the most beautifully decorated Christmas trees in Pittsburgh.
The 2025-2026 flower show is themed Holiday Magic and takes an elegant look at all things Christmas. With traditional decorations and subtle design elements, this one is simply beautiful.
As members of the conservatory, we got the chance to visit early in the season (running until January 4th, 2026) and wanted to share a few of our favorite rooms here!
In Pittsburgh, the start of the holiday season is not ambiguous.
It is not after Halloween when department stores put out Christmas decorations (or do they do it before now?). It is not the day after Thanksgiving that many traditionally observe. It is also not the first snow sighting, December 1st, the fall time change, or any other arbitrary benchmark.
This one particular instance should not be up for debate, as the start of the Christmas season in Pittsburgh is Light Up Night- the Saturday before Thanksgiving.
In this guide, we want to share some of our favorite tips on how to get the most out of what is perhaps our favorite annual event in Pittsburgh!
Note: In 2025, Light Up Night will have some slightly modified event locations due to the on-going construction in Market Square. While this article is meant to be somewhat static year-to-year, we've noted some variations for 2025's festivities in this one.
Do you love sandwiches? We know the answer is yes, but we feel like we have to ask anyway.
Since you likely fall into this category, we're just going to cut to the chase and tell you that you need to make it over to the North Side to check out their annual sandwich week- taking place starting October 27th in 2025.
This annual event challenges all North Side restaurants to showcase a special sandwich for the week and throw down against each other for a judged event at The Priory Hotel to kick off the festivities.
We were invited to check out the opening night party in 2025 as guest judges and were able to get a sneak peek at some of the creations.
This is one party you don't want to miss in future years!
Phipps Conservatory is known for being one of the largest botanical gardens in the region, and also for its seasonal flower shows that are truly events not to be missed.
For 2025's Fall Flower Show, Phipps is heading to Asia with the theme Visions of Japan. With some elegant and intentional designs, this one will delight with imagery of the fall and harvest in East Asia.
As with all of our show reviews, we're not going to share every room in the Conservatory (you'll have to visit yourself to see them all!). Instead, we're going to feature a few of our favorite rooms from the show to highlight a cross-section of the displays!
We are fortunate to have so many talented artists in the Pittsburgh area. With these artists come the art shows, and there are truly a number of excellent events to enjoy throughout the year.
One annual event that has become one of our favorites is A Fair in the Park by the Craftmen's Guild of Pittsburgh. This one showcases 80+ artists (many of whom are local members of the guild) with a variety of mediums, with the stunning Mellon Park as the backdrop for three days every September.
A stroll around the park while shopping for art on a nice late-summer's day? It really is hard to beat that one- if you can get parking at least.
We have a soft spot for all things Oktoberfest, and after getting to enjoy the celebration in Munich for its wild party, we love checking out all of the Pittsburgh Oktoberfest celebrations that take place throughout September (and spill into October).
As there are no shortage of events taking place in breweries and other public places, we thought we would share a few of the top Oktoberfest events you may want to consider. Prost!
Note: This article features a mix of Oktoberfest celebrations that have been announced in 2025 as well as celebrations that took place last year that we hope are returning this year. These will be noted in each section.
The Teetotal Initiative helps individuals in the greater Pittsburgh area sustain sobriety, and is a great organization for those who are sober and sober curious.
One part of their work is to help encourage restaurants and bars to offer non-alcoholic mocktails on their menus and have options for everyone.
The Pittsburgh Mocktail Mixer brought all of these components together for a fundraiser for the organization while showcasing the local mocktail scene with a friendly competition to find the best Mocktail in Pittsburgh!
We were guests of the Teetotal Initiative for the first-ever mixer, and share more about what it was like in this review!