Happy hour is great and a movie date is a tried-and-true classic, but if you’re looking for a weekend outing with a bit more excitement, those things might start to feel a bit tired. This sunny spring weather has us looking for reasons to get outdoors, and a stroll by some of Pittsburgh’s most historic mansions could be just the thing — and lucky for you, most of them are situated within walking distance of some of our favorite cocktail spots.

Highland Park

Start your tour of Highland Park’s many historic mansions with the incredible Alexander King mansion Baywood, which was built in 1880 by glass manufacturer Alexander King. Current owners Frank and Maura Brown restored the house to its original glory in 2011, and it’s worth it to walk by and see the recently unveiled red brick exterior. Make your way down Elgin Street to admire smaller but just as historic homes before turning on to Bryant Street for a bloody mary or a Belgian beer (and maybe an order of PEI mussels) at Park Bruges before setting back out on foot.

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Continue the Highland Park walking tour by gazing at homes built between 1870 and 1900 within the Highland Park Residential Historic District, which was officially listed on the National Register of Historic Places in 2007. Finally, finish it off by popping in on Altholl, the stately James Scott house, on Stanton Avenue.


Once inhabited by well-known Pittsburgh names like Carnegie, Mellon, Frick, Westinghouse and Heinz, “Millionaire’s Row” along Fifth Avenue in Shadyside is a great place to stroll past some of the most awe-inspiring mansions in the city. Once you pick your jaw up off the floor, wander through neighborhood streets with equally as impressive homes before you head over to Acorn on Walnut Street and slide up to their modern bar for a cocktail like the pear brandy and rosewater-infused Gilded Lily or the pisco-based Iggy Pop. If all of that luxury has you feeling inspired to try an equally upscale meal, the beef tenderloin for two will make you feel like you’re eating like a king (or queen).

Squirrel Hill
One of the most scenic neighborhoods from end to end, Squirrel Hill is the perfect place for a mansion stroll sans compass. Set out on Chatham University’s campus and admire the 1915 Raizman House and the 1909 Gregg House (both situated along Woodland Road).  It could be one of Pittsburgh’s most serene streets.

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Make your way up the hill on Shady Avenue and turn right onto Aylesboro Avenue, a tree-lined neighborhood street perfect for peeping on the city’s beautiful homes. You’ll find both turn-of-the-century mansions and mid-century modern estates inspired by Frank Lloyd Wright’s broad influence. Pop over one street to Forbes Avenue for a tropical-themed cocktail at Hidden Harbor before making you way down the hill toward Carnegie Mellon to check out the university’s gorgeous academic buildings and stately homes along Schenley Park.