The Perfect 3-Day Weekend in Pittsburgh: River Kayaking, Bourbon Sipping, and Sports Galore

There’s no shortage of adventure to be had in Pittsburgh, a place that offers a surprising amount of culture, entertainment, and amenities for a midsize city of about 300,000 people. History buffs, sports fans, and foodies alike find that the 'Burgh caters to getaway enthusiasts of all kinds.

Sitting close to the western edge of Pennsylvania, the city of Pittsburgh splits into three sections where the Allegheny and Monongahela rivers converge into the Ohio River. Each of these sections—the North Side, the South Side, and Downtown (aka the Golden Triangle)—boasts its own array of districts and historic neighborhoods filled with great eateries, museums, unique attractions, and friendly locals.

These proud residents—or Yinzers, as they call themselves—know their city by many names: the “City of Champions” for its fiercely competitive and accomplished sports teams, the “Steel City” for its once prominent role in the U.S. steel industry, and the “City of Bridges” for having more bridges (446 total) than any other city in America.

Tourists from all over the country enjoy Pittsburgh for its robust arts and music scene, annual festivals, intense sporting events, and historic attractions. Whatever draws you here—a game, business, visiting friends or family—there’s a hefty list of things to see, do, and eat over a long weekend. Here’s how to squeeze as much fun as possible out of three action-packed days in Pittsburgh.

How to Get to and Around Pittsburgh

If traveling by air, you’ll land in Pittsburgh International Airport, which is about a 30-minute drive from Downtown. Because the airport has no rail connection, make plans to get a taxi, use rideshare, or rent a car if you’d like to have one for the weekend. You can still take advantage of public transportation: Pittsburgh Regional Transit (PRT) offers bus service—the 28X Airport Flyer—to and from the airport. These buses operate seven days a week, twice an hour, from 4 a.m. until midnight, and the fare is only $2.75.

While it offers more flexibility, renting a car is not necessary if you’ll be staying mostly within city limits. Besides being very walkable, Pittsburgh has an extensive bus system. Grab a day pass ($7) at local grocery store chains, or easily download the Transit app to purchase passes on your phone. There is also a light rail system (the “T”) that covers some of the southern neighborhoods, Downtown, and part of Pittsburgh’s North Side. Riding the T is free when you travel between the Downtown and North Shore areas.

When to Visit Pittsburgh

Spring and fall offer milder weather (averaging low- to mid-60s) and tend to be the best seasons to visit if you don’t like heat or cold. While summers can be humid and winter temperatures (typically from late November into March) average upper 20s to low 30s, the city stays alive with events. Come in November for the annual Light Up Night to view the Highmark Christmas Tree Lighting, watch fireworks, and ice skate at the Rink at PPG Place under the dazzling lights of a 66-foot-tall, decorated tree. From the end of May to the beginning of June, the Three Rivers Arts Festival features performing and visual arts attractions that are free to attend. And July’s Picklesburgh event is not to be missed—voted USA Today's Best Specialty Food Festival in America for three consecutive years.

Where to Stay in Pittsburgh

The Omni William Penn Hotel is a luxurious place to stay if you’re willing to shell out. Past guests have included John F. Kennedy, Dwight D. Eisenhower, and Ronald Reagan. With 23 floors and over 600 rooms, plus three restaurants and a 1920s-inspired speakeasy, this hotel lets you experience Old World style with modern amenities—plus, you’re right in the heart of Downtown.

A more affordable and under-the-radar option is the Traveler’s Rest Hotel, a unique and charming historic South Side building. Located along the Great Allegheny Passage bike trail (especially ideal for cyclists), it was originally the headquarters for the A.M. Byers Wrought Iron Pipe Co. before getting updated and renovated as a hotel in 2018. Conveniently located within walking distance of local art galleries and studios, Traveler’s Rest Hotel also provides bike storage, laundry facilities, and a kitchen and communal great room.

Where to Eat in Pittsburgh: Best Breakfast, Lunch, and Dinner

For breakfast, savor a Pittsburgh favorite: Pamela’s Diner. With four locations throughout the city, the restaurant has customers drooling for its crepe-style hotcakes and Lyonnaise potatoes. When lunchtime rolls around, get yourself to Primanti Bros. The original shop, opened in 1933, is in the Strip District—and best approached with a serious appetite. If a hefty serving of french fries stuffed directly inside your sandwich sounds appealing, you're home. For dinner, you can’t go wrong with a juicy, flame-grilled burger at Tessaro’s American Bar & Hardwood Grill in Bloomfield.

Where to Drink in Pittsburgh: Best Bars

Arsenal Cider House, lauded for its easy-to-drink ciders, is less than easy to find but well worth looking for. Make your way to the red brick house tucked in the residential neighborhood of Lawrenceville; inside, soak up the homey atmosphere with plenty of tables and a long counter for buying and sampling ciders, fruit wines, and mead—all of which are small-batch and independently crafted. When the weather is pleasant enough for sipping outside, enjoy the award-winning Archibald's Ado Semi-Sweet Modern Hard Cider in the spacious backyard, complete with twinkling string lights, games, a fire pit, and live music. For some of the city's most inventive craft cocktails, Bridges & Bourbon boasts Downtown's best whiskey lineup, along with elevated concoctions like its minty Thoroughbred (starring Wild Turkey 101) and a tasty Slice of Rye (rye, pisco, Luxardo, lime juice).

Don't Miss: Top Attraction in Pittsburgh

You haven’t had the full Pittsburgh experience until you’ve ridden the Inclines. There are two options available: the Duquesne Incline and the Monongahela (Mon) Incline. These little-cable-cars-that-still-could slowly ascend the side of Mount Washington so you can enjoy stunning views of the city skyline and Pittsburgh’s iconic three rivers. While the Mon Incline is a steeper climb, the Duquesne Incline offers a longer and ultimately higher ride. Just do both. Ride one incline up the mountain, and take the other down.

Savvy Tip for Visitors to Pittsburgh

You won’t need a pocket translator when visiting the Steel City, but prepare to hear some “Pittsburghese,” the efficient and unique dialect of the region. Exchange your “y’all” for “yinz” and you’re one step closer to blending in.

Pack your best walking shoes. While the Three Rivers Heritage Trail and parts of central Pittsburgh are relatively flat, this is a city both renowned and notorious for its hills. In fact, it has more stairs than any other U.S. city—nearly 800 sets of city-owned steps. And, because it follows the topography of the land rather than a grid system, Pittsburgh is not always intuitive to navigate. Open yourself up to adventure and don’t fear getting a little lost.

Things to Do in Pittsburgh Over Three Days

Day 1: Explore the Triangle, Picnic in the Park, and See a Show

Dedicate your first day in Pittsburgh to exploring the “Golden Triangle” that is Downtown. Start in the Strip District to devour an early breakfast of thin, crispy hotcakes at Pamela’s Diner. Take some time to check out the shops here and in neighboring Lawrenceville, referred to as the “Brooklyn of Pittsburgh.” This trendy neighborhood frequently hosts the city’s major arts events and is a hotspot for shopping and dining.

After a full morning of hoofing it around town, order one of the famous Primanti Bros. sandwiches to go and have a delectable picnic at Point State Park. Perfectly situated at the confluence of the city's three rivers, the park features a beautiful fountain, museums, and an access point to the Three Rivers Heritage Trail.

Continue your exploration of Downtown by walking around the Cultural District, where you can find (and catch a show at) most of the performing arts venues in the area—including Heinz Hall, the Benedum, the Pittsburgh Public Theater, and Arcade Comedy Theater. In the evening, return to the Strip District to dine at Penn Avenue Fish Company, where seafood lovers can enjoy dishes ranging from sushi to swordfish. For a change of scenery, head east to the Squirrel Hill neighborhood for a mouthwatering meal at the Taiwanese noodle house Everyday Noodles. Cap it off with a sweet treat at Dave & Andy's Homemade Ice Cream.

Day 2: Ride the River, Savor the South Side, and Feel the Incline

Today, Pittsburgh's historic and lively South Side is on the agenda. Start with brunch at Oak Hill Post, where everything is made in house and served by friendly staff. The menu is full of winners, but the breakfast burrito and smash burger on a biscuit are fan favorites. Then, head over to Pittsburgh Boat Rental and experience the thrill of riding the rivers via kayak or pontoon. Or, break out of city limits and drive an hour to Fallingwater to see the famous Frank Lloyd Wright architectural wonder (make reservations in advance) and hike its on-site trails.

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Don't forget about those iconic inclines—an essential activity when visiting Pittsburgh. Station Square in the South Shore is where to purchase your fare, board a cable car up Mount Washington via the Mon Incline, and snap some photos of the city at the top. Take the Duquesne Incline down for the best of both worlds (or vice versa).

For dinner, head to the festive and very filling Hofbrauhaus for Bavarian favorites. The German brewery hosts lively evenings in its music-filled main hall where you're encouraged to dance on the tabletops. If that's not you, the rear balcony overlooking the river is a peaceful spot to dig into your schnitzel. End the evening at either Acacia, a hidden gem with delicious craft cocktails, or the MilkShake Factory if you prefer imbibing a rich and creamy dessert instead. For devoted ice cream connoisseurs, Page’s Dairy Mart is a beloved South Side institution since 1951—and it won't be closing for the season until mid-October.

Day 3: Museum Hop, Enter Burger Heaven, and Catch a Game

There’s plenty of fun to be had in the city's North Side, particularly for sports fans and art enthusiasts. Your first stop is Commonplace Coffee in the Mexican War Streets neighborhood for a hot drink and breakfast sandwich. While in this historic district, look around and admire the impressive architecture. Deutschland is another historic neighborhood in the North Side with unique older buildings that architecture aficionados will appreciate.

If quirky art is your thing, don’t miss Randyland, a colorful, open-air museum that is free to the public. Just down the street is Mattress Factory, a contemporary art museum with provocative and immersive art exhibits. Another installation worth visiting is the interactive Troy Hill Art Houses, where you can book a free tour to wander through abandoned homes that have been transformed into eccentric, total-structure art pieces.

When hunger hits, go down to the North Shore district for lunch. You’ll be in burger heaven at Burgatory, or you can peruse Federal Galley, which houses four restaurant concepts under one roof for a variety of food and drink options. If you still haven’t had enough art for one day, view the world's largest collection of Warhol art at the Andy Warhol Museum.

Last but certainly not least, if it’s a sporting event you're after, you’re definitely in the right place. The North Shore is home to many of Pittsburgh’s stadiums and arenas, including the Steelers’ Acrisure Stadium and the Pirates' PNC Park. Since these stadiums double as music venues, this is also the place to catch a concert. Afterward, toast to three great days in Pittsburgh at Max’s Allegheny Tavern, a cozy eatery that serves authentic German food and beer, and will inspire your next trip. In the City of Champions, there's always a reason to return.