Road Trip Series: How to Spend a Weekend in Pittsburgh, PA

Thank you to Visit Pittsburgh, the Ace Hotel Pittsburgh, Maggie‘s Farm Rum Distillery, Umami, and the Gateway Clipper Sightseeing Cruise for hosting us and gifting us with free products and services for this post.

Pittsburgh Road Trip
Ace Hotel – Pittsburgh Road Trip / Photo x Jessica Kelly

Just about 3 1/2 hours away from Buffalo is Pittsburgh, Pennsylvania, an area with wonderful restaurants, activities, and eclectic hotels with their own character and history. I was pleasantly surprised with the area and all there was to do and see in Pittsburgh, including an award-winning rum distillery, a beautifully lit Christmas tree, and a hotel that used to be a school. Curious about how to plan a trip of your own? Read on to discover the perfect itinerary for Pittsburgh!

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Checking into the Ace Hotel Pittsburgh

120 S Whitfield St, Pittsburgh, PA 15206 / (412) 361-3300

acehotel.com/pittsburgh

Just outside the city is the Ace Hotel. As we walked in we saw an extremely busy bar off to the right and restaurant to the left. While checking in we asked if it was mostly guests and they said a lot of locals love coming to enjoy the bar, too, with plenty of seating and the restaurant that’s run by a James Beard nominee. As were walking towards the elevator and we noticed that there’s a school like gym with a pickle ball competition going on. An interesting element… once up to our floor, we started to realize and put the pieces together that there was history within these walls. At one point it was a YMCA and at another point it was actually a school, which they carried over into the theme of the rooms. The large windows are a dead giveaway. Some rooms even have a little cubby holes. Our room had a desk and even the menu for room service resembled a notebook. I love that they took the time to tie in subtle elements of the buildings history with modern touches. Plus there are plenty of channels on the TV to fall asleep to a good movie. An added bonus! 

Ace Hotel Pittsburgh – Pittsburgh Road Trip / Photo x Jessica Kelly
Ace Hotel Pittsburgh – Pittsburgh Road Trip / Photo x Jessica Kelly
Ace Hotel Pittsburgh – Pittsburgh Road Trip / Photo x Jessica Kelly
Ace Hotel Pittsburgh - Pittsburgh Road Trip
Ace Hotel Pittsburgh – Pittsburgh Road Trip / Photo x Jessica Kelly
Ace Hotel Pittsburgh – Pittsburgh Road Trip / Photo x Jessica Kelly

 

Pittsburgh Holiday Market

Market Square, Pittsburgh, PA 15222

downtownpittsburghholidays.com/peoples-gas-holiday-market/ 

If you’re in Pittsburg during the holiday season, this is definitely an experience to add to your list. After checking in to the hotel, we made our way to Market Square where they were having the Light Up the Night event where they lit their huge Christmas tree in the center of the square. There were vendors, food trucks, fireworks, and more all celebrating the kick off to Christmas. You can go to get your picture taken with the beautiful Christmas tree, ice skate, and check out the local shops! Explore the wooden chalets in the Christmas village open daily from November 22nd – December 23rd Monday through Thursday from 11:00 a.m. – 8:00 p.m., Friday & Saturday 11:00 a.m. – 9:30 p.m., and Sunday: 11:00 a.m. – 6:00 p.m. with plenty to eat, shopping, and holiday karaoke.

Pittsburgh Road Trip / Photo x Jessica Kelly
Pittsburgh Road Trip / Photo x Jessica Kelly
Pittsburgh Road Trip / Photo x Jessica Kelly
Pittsburgh Road Trip / Photo x Jessica Kelly
Pittsburgh Road Trip / Photo x Jessica Kelly
Pittsburgh Road Trip / Photo x Jessica Kelly
Pittsburgh Road Trip / Photo x Jessica Kelly
Strip District - Pittsburgh Road Trip
Pittsburgh Road Trip / Photo x Jessica Kelly

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Grab Coffee & Breakfast

The following day we found two local coffee shops in the area walking distance from the Ace Hotel to check out for breakfast. Instead of choosing one like a normal person, we decided to scope out both! Because, when in Pittsburgh.

Zeke’s Coffee – Pittsburgh Road Trip / Photo x Jessica Kelly
Zeke’s Coffee – Pittsburgh Road Trip / Photo x Jessica Kelly
Zeke’s Coffee – Pittsburgh Road Trip / Photo x Jessica Kelly

Zeke’s Coffee Pittsburgh

6015 Penn Ave, Pittsburgh, PA 15206 / (412) 670-6231

zekescoffeepgh.com 

If you’re into sweets or giant bagels in the morning, Zeke’s has some wonderful pastry options and great lattes like their lavender latte! They even had some surprisingly tasty gluten-free, vegan apple cider doughnut… almost makes it sound healthy!

Adda Coffee & Tea House – Pittsburgh Road Trip / Photo x Jessica Kelly
Adda Coffee & Tea House- Pittsburgh Road Trip / Photo x Jessica Kelly

Adda Coffee & Tea House

200 S Highland Ave, Pittsburgh, PA 15206 / (412) 404-8403

addacoffeehouse.com 

Adda was more my style with food. They had a blue smoothie made with house made cashew mylk, blue majik, spirulina, dates, vanilla, coconut oil, pink himalayan sea salt and a teahouse vibe that was really cool. I love the teal features and decor. Very cute! Plus my smoothie tasted like liquid oatmeal cookies… can’t go wrong with that.

 

Adda Coffee & Tea House Pittsburgh Road Trip / Photo x Jessica Kelly
Adda Coffee & Tea House – Pittsburgh Road Trip / Photo x Jessica Kelly

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Duquesne Incline

1197 W Carson St, Pittsburgh, PA 15219

duquesneincline.org 

This is a must for first-time visitors! The inclined railway station open back in 1877 and is a staple landmark in the Pittsburgh area where you can ride to the top and get amazing views of the city after exiting the cable car. You can even explore underneath to see how the cable cars run while learning a little bit about the history of the incline while you’re there. It’s simply one of the best views you’ll get off the downtown area at one of the few remaining inclines in the country.

Duquesne InclinePittsburgh Road Trip / Photo x Jessica Kelly
Duquesne Incline – Pittsburgh Road Trip / Photo x Jessica Kelly
Duquesne Incline – Pittsburgh Road Trip / Photo x Jessica Kelly
Strip District - Pittsburgh Road Trip
Duquesne Incline – Pittsburgh Road Trip / Photo x Jessica Kelly
Strip District - Pittsburgh Road Trip
Pittsburgh Road Trip / Photo x Jessica Kelly

Explore the Strip District

The strip district in Pittsburgh is a neighborhood with vibrant shops, food markets, and grocers with bustling restaurants and street art lining the roads. Any souvenir you could ever want you’ll find throughout the streets in the food markets are full of cheeses, meats, pastas, candies, and so much more. Check out the shops like DiAnoia’s or the The PA Market to get delicious pizza at Romulus Pizza al Taglio and explore the wine library. D Polish Deli, Sunseri’s, and the Pennsylvania Macaroni Company (Penn Mac) all come highly rated! The Penn Mac has an incredible selection of fresh cheeses, meats, salami, abruzzese sausage swirled with juicy flavorful fat, salted fish, italian imports, pasta, cookies, candies, and more! Pick up some Pittsburg pickles loaded with mustard seed and celery seed from Stamoolis Brothers and don’t forget to make a quick stop at Pittsburgh Popcorn to grab some bags to bring home. They even have flavors like Thanksgiving stuffing, cheddar, raspberry chocolate, and more! If you’re in need of some home decor, check out JTHN. Moran Woodworks for home goods. Fragrant flower stands and bakery tables with fresh pastries and chocolates line the street with pretty much anything your heart desires. I definitely could’ve spent all day here!

Strip District – Pittsburgh Road Trip / Photo x Jessica Kelly
Strip District – Pittsburgh Road Trip / Photo x Jessica Kelly
Strip District – Pittsburgh Road Trip / Photo x Jessica Kelly
Strip District – Pittsburgh Road Trip / Photo x Jessica Kelly
Strip District – Pittsburgh Road Trip / Photo x Jessica Kelly
Strip District - Pittsburgh Road Trip
Strip District – Pittsburgh Road Trip / Photo x Jessica Kelly
Strip District - Pittsburgh Road Trip
Strip District – Pittsburgh Road Trip / Photo x Jessica Kelly
Strip District - Pittsburgh Road Trip
Strip District – Pittsburgh Road Trip / Photo x Jessica Kelly
Strip District - Pittsburgh Road Trip
Strip District – Pittsburgh Road Trip / Photo x Jessica Kelly
Strip District - Pittsburgh Road Trip
Strip District – Pittsburgh Road Trip / Photo x Jessica Kelly
Strip District - Pittsburgh Road Trip
Strip District – Pittsburgh Road Trip / Photo x Jessica Kelly

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Randyland

1501 Arch St, Pittsburgh, PA 15212

randy.land 

I will admit, going into Randyland with no real idea of what the point of it is can be a little overwhelming. This art museum in Pittsburgh was created by folk artist Randy Gilson after he purchased the building at auction for just $10,000. He wasn’t sure what to do with the place at first, but often thought that too many people think with their brains and not their hearts, so he chose to let that lead him and created colorful murals, gardens, and art installations and objects that were vividly colored and bright to bring joy to locals and visitors. The property became a place where he could let his creative side flourish. All of the bricks on the property were collected from houses in the neighborhood that were torn down because he has the title peoples energies and believes that the stories will live on if the bricks are involved in his art. He created an oasis for people to feel like they could be themselves and be goofy, taking pictures and exploring the art for what it is. Now people come from all over to see his work!

Randyland - Pittsburgh Road Trip
Randyland – Pittsburgh Road Trip / Photo x Jessica Kelly
Randyland - Pittsburgh Road Trip
Randyland – Pittsburgh Road Trip / Photo x Jessica Kelly
Randyland - Pittsburgh Road Trip
Randyland – Pittsburgh Road Trip / Photo x Jessica Kelly
Randyland - Pittsburgh Road Trip
Randyland – Pittsburgh Road Trip / Photo x Jessica Kelly
Randyland - Pittsburgh Road Trip
Randyland – Pittsburgh Road Trip / Photo x Jessica Kelly
Randyland - Pittsburgh Road Trip
Randyland – Pittsburgh Road Trip / Photo x Jessica Kelly
Randyland - Pittsburgh Road Trip
Randyland – Pittsburgh Road Trip / Photo x Jessica Kelly
Randyland - Pittsburgh Road Trip
Randyland – Pittsburgh Road Trip / Photo x Jessica Kelly
Randyland - Pittsburgh Road Trip
Randyland – Pittsburgh Road Trip / Photo x Jessica Kelly

Maggie’s Farm Rum Distillery

3212a Smallman St, Pittsburgh, PA 15201 / (412) 709-6480

maggiesfarmrum.com 

Maggie’s is a little difficult to find, but once we did we were greeted by friendly staff and a cute bar overlooking the backdrop of the distillery. Even though they’re only been making rum for just six years so far, they’ve received over 90 awards for their products, making them the most awarded rum distillery in the US. With everything from white rum and flavored rums to spiced and dark rums or liquors, there’s something for everyone to enjoy here. Each bottle has its own unique pungent flavor and story behind it. Like the local coffee shop called Common Place that makes a blend just for them to use for the rum or that they don’t filter the rum because they believe it strips the flavor and aroma.

The story behind the incredible flavor in Maggie’s Farm Falernum Liqueur is another unusual one! When I tried this I couldn’t even believe it was alcoholic let alone 50 proof. I’m kind of a wuss when it comes to things without chasers. This has such intense notes of ginger and lime, the flavor was just absolutely incredible on its own without even being mixed with anything. They explained that so much lime zest has to go into the distilling process to give it this flavor that they actually will schedule lime zesting parties for two hours. They have 30 spots available and invite the public to claim a ticket. They have 30 people come in and zest as many limes as they can in two hours as they serve them cocktails on the house. I believe that’s definitely a fair trade!

Maggie's Farm Rum Distillery - Pittsburgh Road Trip
Maggie’s Farm Rum Distillery – Pittsburgh Road Trip / Photo x Jessica Kelly
Maggie's Farm Rum Distillery - Pittsburgh Road Trip
Maggie’s Farm Rum Distillery -Pittsburgh Road Trip / Photo x Jessica Kelly
Maggie's Farm Rum Distillery - Pittsburgh Road Trip
Maggie’s Farm Rum Distillery -Pittsburgh Road Trip / Photo x Jessica Kelly

 

The Church Brew Works

3525 Liberty Ave, Pittsburgh, PA 15201 / (412) 688-8200

churchbrew.com 

The city is full of historical buildings, one of which is this former church that is now housing a brewery where you can get a selection of different beers, pizzas, bratwurst, pretzels, and more! The actual area where they make the beer is even at the altar, making this extremely unique venue one to say “thank you, Jesus!” for. Even the seating area in the dining room includes some of the old pews. I’ve been suggesting that they put beer in the holy water hand dippers, but have yet to see that added.

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The Church Brew Works - Pittsburgh Road Trip
The Church Brew Works – Pittsburgh Road Trip / Photo x Jessica Kelly
The Church Brew Works - Pittsburgh Road Trip
The Church Brew Works – Pittsburgh Road Trip / Photo x Jessica Kelly
The Church Brew Works - Pittsburgh Road Trip
The Church Brew Works – Pittsburgh Road Trip / Photo x Jessica Kelly

Dinner at Umami

202 38th St, Pittsburgh, PA 15201 / (412) 224-2354

umamipgh.com 

Up two flights of stairs in a discreet building is a contemporary Japanese restaurant serving street food and sushi. The vibe was loud and funky with bright red lights and music blasting, but not too loud that you couldn’t talk to each other. The open kitchen allowed you to watch the chefs firing up the grill and charring the different kabobs. We enjoyed an order of the Yuzu deviled eggs with yuzu kosho (a Japanese seasoning paste made from yuzu peep, salt, and chili peppers), togarashi (Japanese spice mixture), compressed nori to start followed by a selection of tender marbled Wagyu beef tenderloin, bacon quail egg, crispy chicken skin, and juicy Pork belly charred on the grill. Following that, a dish of whole, sliced squid with a thick, salty soy sauce slathered on top and a festive Electric Dragon cocktail on the side. The drink, garnished with a flower and mini umbrella, is made with Aperol, Blanco Tequila, pepper, Thai basil, lime, chili shrub, and saline. The whole meal was absolutely incredible!

Umami - Pittsburgh Road Trip
Umami – Pittsburgh Road Trip / Photo x Jessica Kelly
Umami - Pittsburgh Road Trip
Umami – Pittsburgh Road Trip / Photo x Jessica Kelly
Umami - Pittsburgh Road Trip
Umami – Pittsburgh Road Trip / Photo x Jessica Kelly
Umami - Pittsburgh Road Trip
Umami – Pittsburgh Road Trip / Photo x Jessica Kelly
Umami – Pittsburgh Road Trip / Photo x Jessica Kelly
Umami – Pittsburgh Road Trip / Photo x Jessica Kelly
Umami - Pittsburgh Road Trip
Umami – Pittsburgh Road Trip / Photo x Jessica Kelly
Pittsburgh Road Trip
Umami – Pittsburgh Road Trip / Photo x Jessica Kelly
Pittsburgh Road Trip
Umami – Pittsburgh Road Trip / Photo x Jessica Kelly

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The Abbey on Butler Street

4635 Butler St #2906, Pittsburgh, PA 15201 / (412) 682-0200

theabbeyonbutlerstreet.com 

After dinner, we took a short drive to the Abbey. Since I’m learning that Pittsburgh seems to love turning old buildings into new concepts, instantly a bar that used to be a funeral home grabbed my attention. You can definitely tell by the exterior of the building what the history of it was, and the inside gives off vibes of almost a church type dim lighting with huge light fixtures. I absolutely loved the drinks! I tried the Spicy Dirty Pickle made with jalapeño infused Tito’s Vodka, pickle juice, and salty olive juice. I generally love these flavors anyway, especially a really good extra dirty martini, but even if you’re not partial to the saltiness in your drinks this was a very subtle flavor, making it accommodating to a wider range of people. It has a soft flavor of bread and butter pickles with a strong fresh cucumber finish and just a very slight saltiness with a tiny kick from the jalapeño.

The Abbey on Butler Street
The Abbey on Butler Street – Pittsburgh Road Trip / Photo x Jessica Kelly
The Abbey on Butler Street - Pittsburgh Road Trip
The Abbey on Butler Street – Pittsburgh Road Trip Pittsburgh Road Trip / Photo x Jessica Kelly

Brunch at Ace at the Whitfield

whitfieldpgh.com 

The Whitfield restaurant was absolutely packed and I quickly learned why. The leaders of the restaurant are James Beard award nominated chef’s Bethany Zozula and Casey Renee. Even brunch was absolutely incredible! We tried the fresh fruit and the pastrami hash for with a runny, sunny side up egg and salt and vinegar chips along with perfectly cooked steak and eggs with flaky shards of salt and soft boiled eggs for served with fries and béarnaise sauce with a buttermilk biscuit with raspberry jam and butter. My mouth is watering just thinking about the steak and how perfectly cooked it was, medium rare and full of flavor drenched and creamy yolk and béarnaise. I highly recommend enjoying at least one meal here!

Brunch at Ace at the Whitfield - Pittsburgh Road Trip
Brunch at Ace at the Whitfield – Pittsburgh Road Trip / Photo x Jessica Kelly
Brunch at Ace at the Whitfield - Pittsburgh Road Trip
Brunch at Ace at the Whitfield – Pittsburgh Road Trip / Photo x Jessica Kelly
Brunch at Ace at the Whitfield - Pittsburgh Road Trip
Brunch at Ace at the Whitfield – Pittsburgh Road Trip / Photo x Jessica Kelly
Brunch at Ace at the Whitfield - Pittsburgh Road Trip
Brunch at Ace at the Whitfield – Pittsburgh Road Trip / Photo x Jessica Kelly
Brunch at Ace at the Whitfield - Pittsburgh Road Trip
Brunch at Ace at the Whitfield – Pittsburgh Road Trip / Photo x Jessica Kelly
Brunch at Ace at the Whitfield - Pittsburgh Road Trip
Brunch at Ace at the Whitfield – Pittsburgh Road Trip / Photo x Jessica Kelly

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Brunch at Ace at the Whitfield - Pittsburgh Road Trip
Brunch at Ace at the Whitfield – Pittsburgh Road Trip / Photo x Jessica Kelly
Brunch at Ace at the Whitfield - Pittsburgh Road Trip
Brunch at Ace at the Whitfield – Pittsburgh Road Trip / Photo x Jessica Kelly
Brunch at Ace at the Whitfield - Pittsburgh Road Trip
Brunch at Ace at the Whitfield – Pittsburgh Road Trip / Photo x Jessica Kelly
Brunch at Ace at the Whitfield - Pittsburgh Road Trip
Brunch at Ace at the Whitfield – Pittsburgh Road Trip / Photo x Jessica Kelly
Brunch at Ace at the Whitfield - Pittsburgh Road Trip
Brunch at Ace at the Whitfield – Pittsburgh Road Trip / Photo x Jessica Kelly

Gateway Clipper Sightseeing Cruise 

350 W Station Square Dr, Pittsburgh, PA 15219

gatewayclipper.com / gatewayclipper.com/holiday-cruises

The Gateway Clipper Sightseeing Cruises find ways for you to enjoy the boat and being out on the water even in the colder months. They do really amazing kid friendly boat rides with Santa and holiday themes throughout the month of December along with adult Christmas themed and dinner cruises! There’s even the highly anticipated New Year’s Eve dinner cruise and a Valentine’s Day cruise mid February. Check out their website for details and to book your tickets!

Gateway Clipper Sightseeing Cruise - Pittsburgh Road Trip
Gateway Clipper Sightseeing Cruise – Pittsburgh Road Trip / Photo x Jessica Kelly
Gateway Clipper Sightseeing Cruise - Pittsburgh Road Trip
Gateway Clipper Sightseeing Cruise – Pittsburgh Road Trip / Photo x Jessica Kelly
Gateway Clipper Sightseeing Cruise - Pittsburgh Road Trip
Gateway Clipper Sightseeing Cruise – Pittsburgh Road Trip / Photo x Jessica Kelly
Gateway Clipper Sightseeing Cruise - Pittsburgh Road Trip
Gateway Clipper Sightseeing Cruise – Pittsburgh Road Trip / Photo x Jessica Kelly
Jessica Kelly
Author: Jessica Kelly

Jess is a freelance writer and photographer with a focus on food, travel, and entertainment living in Buffalo. Her work has appeared in over 10 different local publications in WNY, the Huffington Post, Dame Traveler, Insider, Wine Enthusiast, Kitchn, AAA World Magazine, and Thrillist. She's a self-proclaimed bloody mary connoisseur, obsessed with all things Buffalo, the Real Housewives of EVERYTHING, horror movies, vintage cookbooks, coffee, and food markets. Follow her crazy adventures and countless food pictures on Instagram @Adventures.Are.Waiting!

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