Distance:
5.5 mile loop around Poughkeepsie, NY
Highlights:
The Walkway Over the Hudson is proudly the the world’s longest elevated pedestrian bridge. A State Historic Park, it connects Poughkeepsie, NY with Highland, NY and is also part of the Empire State Trail.
On this approximately 5-mile loop, in addition to the walkway, we’ll also cover four of the five historic districts of Poughkeepsie:
- City Downtown
- Poughkeepsie Waterfront
- Union Street Historic Neighborhood
- Southside Historic District
Consider it a high-level introduction to “The Queen City of the Hudson.”
Starting Line:
Parking at the lot across from The Academy isn’t free, but it’s easy (and it’s pretty cheap). Plus, the bathrooms inside are worth a stop to see their wacky wallpaper and neon lights.
Head north on Academy Street. You’ll pass Goodnight, Kenny—owned by the stars of HGTV’s Small Town Potential and a nominee for best bar in the Hudson Valley—on your right.
Route:
At the intersection with Cannon Street, make a left. At Market Street, make a right. You won’t be able to miss the historic Bardavon marquee on your right. It’s the oldest continuously operating theater in the state. A 1869 Opera House, the venue still attracts world class acts. We’re now in the City Downtown.
Continue on Market Street past the convention center on your left. Ahead, is the East-West Arterial. The next goal is to safely cross it to arrive at Mill House Brewing Company. However, the arterial makes that simple task challenging. Called a “modern highway project,” it essentially chops up the city into pieces that can’t cohesively be navigated on foot. Even worse, in 1966 at its time of construction, it forced the relocation of 400 families. It’s awful and frustrating.
A stop at Mill House is worth playing human Frogger across the arterial, though. They’ve pretty much won every award in the Hudson Valley—best chef, best restaurant, best bartenders, best all the things (ok, not that last one… yet).
Backtrack on the East-West Arterial, thankfully staying on the same side of the “street.” Make a right on Civic Center Plaza. In front of you is one of President Franklin D. Roosevelt’s five Dutchess County United States Post Office buildings constructed during the New Deal. The other four are in Beacon, Wappingers Falls, Rhinebeck, and Hyde Park. Built in 1937 as part of the Works Progress Administration, this huge post office features murals by Gerald Foster, Georgiana Klitgaard, and Charles Rosen.
From the post office, turn right on Washington Street cutting through the gas station parking lot. You’ll cross over the Fall Kill bridge, and then the stairway to the Walkway Over the Hudson will be on your right. There’s also a big sign on the overpass that can’t be missed. Take the stairs up to the trail.
On the Empire State Trail, head west toward the river to cross the Walkway Over the Hudson. The bridge opened to the public as a State Historic Park in 2009, and at 6,768 feet it’s the longest, elevated pedestrian bridge in the world. It definitely gets a ton of use by both tourists and locals—from dog walkers to rollerbladers, from families with strollers to bikers and runners.
That record 6,768-foot length means it’s about 1.3 miles to the plaza on the Highland side of the bridge. The plaza has public restrooms and information booths, and there are also often food trucks and coffee available. Turn around and head back over the bridge, but at the river’s edge on the Poughkeepsie side keep an eye out for the elevator instead of heading all the way back to the stairs on Washington Street.
Not only does the elevator offer a unique vantage point, but it also drops visitors off in the Poughkeepsie Waterfront district. Follow the Walkway Elevator Access Pass through Upper Landing Park, and make sure to read the placards detailing the last 300 years of the district’s history. The Mid-Hudson Discovery Museum will be in front of you. Veer around its venue space toward the water. Continue south on the riverside path through Waryas Park until its intersection with Main Street. Make a left. The Poughkeepsie train station will be on your left.
Continue up Main Street. At the intersection with South Clover Street, we’re going to make a short, worthwhile detour. In two blocks, Rosticceria Rossi & Sons will be on your left. When BuzzFeed and Yelp named the best sandwich in every state, New York’s winner wasn’t from the city; it was from this spot in Poughkeepsie’s Union Street Historic Neighborhood. (If you’re an Ed Wood—or I guess, Johnny Depp?—fan, turn the corner of Delano Street and his childhood home will be right in front of you.)
Head back to Main Street and continue up the hill away from the river. In about two blocks, Zeus Brewing Company will be on your right. This brewery is currently Poughkeepsie’s only rooftop bar, so it’s a perfect spot to sit back and literally visualize the miles you have just clocked.
Back out on Main Street, turn left and make another left onto South Bridge Street. Then, make a right on Union Street and a quick left on Jefferson Street. This will lead you into Eastman Park. On the other side of the park, make a left on Franklin Street. We’re now in the South Side Historic District with its Victorian mansion-lined streets. The estates are truly so spectacular, with gorgeous lawns and spacious front porches, that they’re used in the summer as makeshift outdoor concert venues during PorchFest.
Finish Line:
Make a left from Franklin Street back onto Academy Street. After reaching our old friend the East-West Arterial in three blocks, the parking lot will be on your left and The Academy will be on your right. If you’ve worked up an appetite, Hudson & Packard is next door. Serving Detroit-style pizza, the pizzeria won second-best pan pizza in the world at the International Pizza Expo in Las Vegas, made top 3 again in 2023 and 2024, and won Best Detroit Pizza in 2024. They’re worth the hype. Definitely make sure to check Instagram for their weekly specials.
