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Walking the Walk(way)



Did you know that the largest pedestrian walkway in the world sits in Poughkeepsie (and Highland), New York? Built on Poughkeepsie-Highland Railroad Bridge that was originally constructed in 1889, The Walkway Over the Hudson sits 212 feet above the Hudson River and spans 1.28 miles across with sweeping views of the river itself and the Catskills in the distance.


The Walkway presents a relatively easy stroll; you're not here for a challenge, it's about the scenery and experience. The biggest issue for most is the lack of cover in hot weather and strong winds even when it may be still elsewhere. I recommend starting and ending on the Poughkeepsie side because of more parking options and better post-walk food and drink options.


Address: 61 Parker Avenue in Poughkeepsie, New York (There's free parking in Pulaski Park [162 Washington Street] about 0.2 miles from the Walkway's Washington Street Stairs entrance, and along Brookside Avenue between Washington Street and Garden Street.)


Après Walk Food + Drink

  • Lolita's Pizza - 129 Washington Street, Poughkeepsie, NY, 12601 - Lolita's has some of the best pizza and pasta in town. Everything on the menu is a hit, but my personal go-tos are the kale caesar salad, Alabama white BBQ wings, lumache, and the meatball parm pizza. Learn more.

  • Millhouse Brewing Company - 289 Mill Street, Poughkeepsie, NY, 12601 - An institution unto itself, Millhouse Brewing features refined American fare and house brewed beers to write home about. I'd go for the buffalo fried Brussels sprouts alone. Learn more.

  • Hudson & Packard - 29 Academy St, Poughkeepsie, NY, 12601 - Look, we like pizza in Poughkeepsie, ok? This Detroit-style pizza with "crust you can trust" tastes like it's right out of the Motor City. You can't go wrong here either: start with the caesar salad and tuck into a classic like the Cutlass Supreme or a newer model like the Firebird (essentially a buffalo chicken pie). Learn more.

  • Sundaze Smash Burgers - 33 Academy Street, Poughkeepsie, NY 12601 - You want the OG and seasoned fries. Full stop. Learn more.

  • Goodnight Kenny - 27 Academy Street. Poughkeepsie, NY 12601 - Great cocktails and great vibes in a great neighborhood bar. Learn more.

  • King's Court Brewing Company - 40 Cannon Street, Poughkeepsie, NY, 12601 - Award-winning beers across the style spectrum in a laid-back, family-friendly spot. Learn more.

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