Grandpa Joe's Candy Shop at 2124 Penn Ave. in the Strip District
Grandpa Joe's Candy Shop at 2124 Penn Ave. in the Strip District. Photo courtesy of Grandpa Joe's Candy Shop.

The Strip District is inarguably the coolest neighborhood in Pittsburgh. A mélange of markets, eclectic boutiques and charming eateries harmonize along the bustling streets, each establishment carrying a narrative of its own. 

From farm fresh produce evoking the area’s agricultural roots, to culinary-focused markets that span the globe, most businesses in the Strip are multigenerational. 

This shopping haven brings the energy on so many levels — seasoned chefs cook up stir-fries in a flaming wok in street stalls while musicians feverishly play their instruments. Many delicious aromas mingle together. 

What’s a shopping trip without a caffeine or cocktail break? Well, there are plenty of spots to unwind with a brew or two.

While this is not an exhaustive list, here are some of our favorite haunts in the Strip District.

The Olive Tap

106 19th St.

With its warm ambience and rustic wooden shelves, The Olive Tap boasts endless rows and drums of olive oil from small-batch producers based all over the world. 

There are grassy, fruity extra virgin varieties that are waiting to be mopped up with hunks of crusty bread, cooking olive oils with higher smoke points, and infused oils with herbs like rosemary and basil. 

The shop also carries delicious aged balsamic vinegar from Italy, great for revving up salads and sandwiches. 

Come here to buy quality olive oils, and stay for the unexpected olive oil master class. The focal point of Olive Tap is the tasting experience. Knowledgeable staff members guide visitors through this sensory journey, offering insights into the origins, discerning subtle differences among the different oils, harvesting and production processes, and tasting notes of each oil. 

There also are curated food baskets that would make great gifts for your gastronome friends. 

A bouquet of dried flowers in a ceramic vase
Photo courtesy of Roxanne’s Dried Flowers.

Roxanne’s Dried Flowers

2115 Penn Ave.

There’s something hopelessly romantic about Roxanne’s Dried Flowers. The shop has a decidedly Parisian vibe — and impossibly chic florals to boot. 

Roxanne’s journey is a homegrown one — it began in a Greek revival farmhouse, cultivating a love for growing flowers and crafting dried arrangements. Recognizing a shift toward environmental appreciation, she founded a shop in Pennsylvania, offering exquisite dried flowers and botanical gifts. For more than 25 years, the has shop flourished, expanding in Pittsburgh’s market district, featuring global dried blooms, custom pieces and a lush garden. 

They also have seasonal wreaths, so you don’t have to wait for Christmas to decorate your door. From budding blossoms to pumpkin patches, there’s a wreath for every season. 

Pro tip: Look out for the after-hours garden parties, which almost always feature fun floral demonstrations and sparkling wine! 

Photo courtesy of Bass & Bennett Trading Co.

Bass & Bennett Trading Co.

1900 Smallman St.

Bass & Bennett Trading Co. brings a touch of whimsy to furniture shopping. 

The use of reclaimed materials forms the soul of this establishment. There’s rosewood that’s been repurposed from ancient temple posts and reclaimed wrought iron bears witness to eras preceding the British Raj. Trestle tables, once rail sleepers crisscrossing distant lands, are ready for their second lives as workstations or coffee tables. The focal point is that most furniture here is not cookie-cutter, but rather conversation starting.  

Beyond aesthetics, Bass & Bennett takes a sustainable approach. By repurposing materials, the shop contributes to environmental conservation. Additionally, the support of local artisans ensures the continuation of traditional craftsmanship in the modern world. 

Whether you’re a history buff, an eco-warrior or just hunting for a cool coffee table, this is an interesting spot to check out. 

Photo courtesy of Pennsylvania Macaroni Company.

Pennsylvania Macaroni Company

2010-2012 Penn Ave.

Pennsylvania Macaroni Co., lovingly referred to as Penn Mac, stands as a cherished touchstone in the Strip. 

Penn Mac is a culinary gem with a rich story. Originating from a Sicilian village, the Sunseri brothers founded the business in 1902, initially focussing on crafting artisanal pasta. What began as a haven for authentic Italian pasta blossomed into an emporium of culinary treasures. The Sunseri legacy surged forward, expanding to embrace olive oils, spices, specialty foods, and an array of tantalizing Italian cheeses. 

Stroll through aisles lined with an enchanting collection of pasta, from basic spaghetti to the new trending cascatelli. Choose from glistening plump olives, marinated peppers, briny capers, and all the meat — savory slices of prosciutto and salami. Antipasto party, anyone?

In the Kitchen

1725 Penn Ave.

Founded by KC and Jim Lapiana in 2002, this specialty store is a paradise for both pro chefs and kitchen novices alike. 

Catering to a diverse culinary community, the shop’s curated selection boasts top tier cookware, precision cutlery and innovative gadgets. If you like delegating tasks to technology, there are nifty kitchen appliances to be found.  

Beyond tools, explore gourmet foods and chic homeware. Whether you’re flipping pancakes or crafting a complex soufflé — you’ll find all the tools you need here. 

And they also carry gourmet foods from around the world and stylish homeware, too.

While we’ll take any excuse to stroll around the Strip, their online shop delivers to your doorstep if you can’t drop by.

Spicy Pickle cotton candy from Grandpa Joe's
Would you try spicy pickle cotton candy? Photo courtesy of Grandpa Joe’s Candy Shop.

As a child, Grandpa Joe’s Candy Shop founder and CEO Christopher Beers was inspired to get into the candy business by “Charlie And the Chocolate Factory.” In fact, Grandpa Joe’s Candy Shop is named after the iconic character who accompanies Charlie to the chocolate factory. 

It wouldn’t be a stretch to say that Beers built a candy oasis of his own. At Grandpa Joe’s, you can unleash your inner Willy Wonka with its unbeatable deal: If the lid shuts, it’s yours for just $5. No weight limits, no candy boundaries. 

Specializing in resurrecting long-lost childhood candies, the knowledgeable staff effortlessly deciphers candy lingo and nicknames. If it’s still being manufactured, Grandpa Joe’s is bound to have it. 

Soda lovers will appreciate the collection of old fashioned glass bottle sodas — more than 250 soda varieties, with a selection ranging from national chart toppers to cherished regional classics. 

There are some pretty unique gifts too. From funky socks to boundary-pushing gag gifts, the store caters to the quirkiest of tastes. Searching for a horse head squirrel feeder or a towel proclaiming “Rock out with your crock out?!” Look no further. For collectors, Funko POP figurines are a standout, accompanied by an array of toys and trending items.

Need a caffeine boost while walking around the Strip? Allegheny Coffee & Tea Exchange is a java gem. 

This shop boasts an impressive selection of the finest coffees and teas from around the world. With beans roasted on-site in small batches, their coffee is as fresh as it gets. Craving nitro coffee on tap? They’ve got six rotating options — grab a cup or a growler to go! Seasonal lattes and cold brews cater to hot days. 

The self-serve coffee bean wonderland boasts 40-50 barrels of flavors, such as Highlander Grogg, Salted Caramel and many more. 

This spot’s got a traditional coffee shop vibe, complete with pastries and cookies to munch on.

Yinzers in the Burgh

2127 Penn Ave.

Yinzers in the Burgh is like a Pittsburgh enthusiast’s treasure trove. From snazzy black-and-gold sports gear to clever tees flaunting local slang, they’ve got clothes that scream Steel City pride. 

Expect an eclectic range of clothing, memorabilia, souvenirs and gifts that pay homage to the city in this nostalgia wonderland. Walls adorned with vintage photos and signed sports gear take you on a time-traveling tour of Pittsburgh’s finest moments. 

If you’re hunting for one-of-a-kind gifts, they’ve got quirky souvenirs like Pittsburgh Pirates mini bats and Steelers hip flask collectibles. 

The staff? Total Pittsburgh pros.

Photo courtesy of love, Pittsburgh.

Love, Pittsburgh 

1728 Penn Ave.

Love, Pittsburgh’s Strip District location is a vibrant hub celebrating local creativity. You’ll find something for everyone — including grandma and your friend’s new baby. 

With a commitment to supporting the local creative community, the shop showcases more than 120 Pittsburgh-based artists. Discover hand-poured candles, jewelry that screams “Steel City chic,” cute baby Steelers onesies, and mugs for cozy Yinzer mornings. For the fashion-forward, there are T-shirts and bags that blend style with a touch of hometown pride. 

Psst! Don’t miss the quirky limited-edition treasures that capture the city’s vibe.

Pennsylvania Libations

​​2103 Penn Ave.

Pennsylvania Libations is a revolutionary “sip before you shop” concept in the Keystone State. With a nod to the homegrown, it boasts the state’s most extensive selection of locally-crafted spirits, wines, ciders, meads and beers. 

Christian Simmons, the brains behind the operation, took the business all the way from his humble broker beginnings to a chic Strip District destination. Step inside and find distinctive “made in PA” producers. You won’t just shop; you’ll sample your heart out before you buy. 

While local libations steal the show, this is more than your run-of-the-mill liquor store. Pennsylvania Libations also helps bars jazz up their drinks and crafts custom sips for events. And its mixologists bring the party to private bashes. 


Aakanksha Agarwal is a wine, travel and lifestyle writer from India. Formerly a Bollywood stylist, she now resides in Pittsburgh, embracing full-time writing while juggling family life and indulging in her passions for cuisine, literature and wanderlust.